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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (3) Show 9 proteins XML

enzymes (6)transporters (3) Show 9 proteins

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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:59 UTC

HMDB ID

HMDB0000077

Secondary Accession Numbers

HMDB00077

Metabolite Identification

Common Name

Dehydroepiandrosterone

Description

Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue, and the brain. DHEA is structurally similar to and is a precursor of, androstenedione, testosterone, estradiol, estrone, and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate or DHEA-S) before secretion. DHEA-S is the sulfated version of DHEA; this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEA-S with levels that are about 300 times higher than free DHEA. Blood measurements of DHEA-S/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEA-S.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000077
     RDKit          3D
Dehydroepiandrosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.7875    0.1894   -1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937    0.6234   -0.0001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9123    1.8657    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4957    1.6798   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499    0.4258    0.2241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7516   -0.7895    0.1280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0782   -1.9921    0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -1.9136    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -0.9674    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5964   -0.9638    0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1358    0.3507    0.7088 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2732    0.7035    0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086    1.4592    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    1.3198   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3929    0.1313   -0.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0846   -0.3122   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122   -0.4554    0.8577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0207   -1.5378    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656   -0.8149    0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0403    0.6177    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7602    1.5383    0.8078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216   -0.9102   -1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    0.5902   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323    0.6367   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365    2.7059   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555    2.1606    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920    2.5411    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    1.8276   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    0.5132    1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627   -0.9531   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3436   -2.8698    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4821   -2.2484    1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122   -2.7323    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100   -1.1239   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572   -1.7553    0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000    0.2745    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0795    0.7007    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4629    1.4051    1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6553    2.4295    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151    1.1167   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729    2.2389   -0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.3490   -2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -0.2462   -2.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.3356   -2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581    0.0052    1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876   -1.9685    1.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9021   -2.3211    0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8331   -1.1927   -0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9911   -0.9691    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END

  Mrv1652303182019232D          

 24 27  0  0  0  0            999 V2000
 9999.306610000.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.447910001.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4479 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1658 9998.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.733710000.1945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0216 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5937 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8792 9999.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8792 9998.5410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5937 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.734610001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.020110000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0201 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7346 9999.3746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3067 9999.3661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3067 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0212 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7357 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.233810000.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.449210000.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4491 9999.7871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2337 9999.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.718610000.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.488710001.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  9  4  1  1  0  0  0
  7 15  1  0  0  0  0
 10 16  1  0  0  0  0
 15  1  1  1  0  0  0
 13 15  1  0  0  0  0
 18 14  1  0  0  0  0
 14  5  1  1  0  0  0
 13  6  1  6  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  2  0  0  0  0
 11 20  1  0  0  0  0
 14 21  1  0  0  0  0
 20  2  1  1  0  0  0
 21  3  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000077

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1

> <INCHI_KEY>
FMGSKLZLMKYGDP-USOAJAOKSA-N

> <FORMULA>
C19H28O2

> <MOLECULAR_WEIGHT>
288.4244

> <EXACT_MASS>
288.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.099316668638735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
3.361705055333334

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.957705855663583

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.204289505502594

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972434077338853

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
84.65889999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000077
     RDKit          3D
Dehydroepiandrosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.7875    0.1894   -1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937    0.6234   -0.0001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9123    1.8657    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4957    1.6798   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499    0.4258    0.2241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7516   -0.7895    0.1280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0782   -1.9921    0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -1.9136    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -0.9674    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5964   -0.9638    0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1358    0.3507    0.7088 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2732    0.7035    0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086    1.4592    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    1.3198   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3929    0.1313   -0.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0846   -0.3122   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122   -0.4554    0.8577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0207   -1.5378    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656   -0.8149    0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0403    0.6177    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7602    1.5383    0.8078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216   -0.9102   -1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    0.5902   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323    0.6367   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365    2.7059   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555    2.1606    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920    2.5411    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    1.8276   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    0.5132    1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627   -0.9531   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3436   -2.8698    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4821   -2.2484    1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122   -2.7323    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100   -1.1239   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572   -1.7553    0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000    0.2745    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0795    0.7007    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4629    1.4051    1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6553    2.4295    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151    1.1167   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729    2.2389   -0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.3490   -2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -0.2462   -2.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.3356   -2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581    0.0052    1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876   -1.9685    1.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9021   -2.3211    0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8331   -1.1927   -0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9911   -0.9691    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0    8665.3728667.030   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3698669.361   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0    8669.3698664.725   0.000  0.00  0.00           H+0
HETATM    4  O   UNK     0    8661.3768663.164   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8668.0368667.030   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.7078664.725   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8664.0428666.253   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.7088665.483   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.7088663.943   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.0428663.173   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.0388668.579   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.7048667.809   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.7048666.269   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.0388665.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.3738665.483   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.3738663.943   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8666.7068663.173   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8668.0408663.943   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.8368668.285   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.3728667.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.3728666.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.8368665.793   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.7418667.039   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8671.3128669.750   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4    9                                                            
CONECT    5   14                                                            
CONECT    6   13                                                            
CONECT    7    8   15                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    4                                                  
CONECT   10    9   16                                                       
CONECT   11   12   20                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15    6                                             
CONECT   14   13   18    5   21                                             
CONECT   15   16    7    1   13                                             
CONECT   16   15   17   10                                                  
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   20   23   24                                                  
CONECT   20   19   21   11    2                                             
CONECT   21   20   22   14    3                                             
CONECT   22   21   23                                                       
CONECT   23   19   22                                                       
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0000077
HETATM    1  C1  UNL     1      -2.788   0.189  -1.446  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.694   0.623  -0.000  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.912   1.866   0.197  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.496   1.680  -0.243  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.150   0.426   0.224  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.752  -0.790   0.128  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.078  -1.992   0.691  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.400  -1.914   0.698  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.114  -0.967   0.131  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.596  -0.964   0.185  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.136   0.351   0.709  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.273   0.704   0.007  1.00  0.00           O  
HETATM   13  C12 UNL     1       3.109   1.459   0.590  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.319   1.320  -0.674  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.393   0.131  -0.585  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.085  -0.312  -1.989  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.012  -0.455   0.858  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.021  -1.538   0.927  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.366  -0.815   0.804  1.00  0.00           C  
HETATM   20  C19 UNL     1      -4.040   0.618   0.568  1.00  0.00           C  
HETATM   21  O2  UNL     1      -4.760   1.538   0.808  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.922  -0.910  -1.527  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.952   0.590  -2.017  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.732   0.637  -1.855  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.337   2.706  -0.417  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.955   2.161   1.249  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.092   2.541   0.188  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.458   1.828  -1.339  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.448   0.513   1.288  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.963  -0.953  -0.962  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.344  -2.870   0.046  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.482  -2.248   1.704  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.912  -2.732   1.231  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.010  -1.124  -0.831  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.957  -1.755   0.863  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.400   0.275   1.789  1.00  0.00           H  
HETATM   37  H16 UNL     1       6.080   0.701   0.602  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.463   1.405   1.473  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.655   2.430   0.547  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.015   1.117  -1.519  1.00  0.00           H  
HETATM   41  H20 UNL     1       1.773   2.239  -0.927  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.721  -1.349  -2.043  1.00  0.00           H  
HETATM   43  H22 UNL     1       2.053  -0.246  -2.566  1.00  0.00           H  
HETATM   44  H23 UNL     1       0.381   0.336  -2.510  1.00  0.00           H  
HETATM   45  H24 UNL     1      -1.758   0.005   1.821  1.00  0.00           H  
HETATM   46  H25 UNL     1      -2.988  -1.969   1.968  1.00  0.00           H  
HETATM   47  H26 UNL     1      -2.902  -2.321   0.162  1.00  0.00           H  
HETATM   48  H27 UNL     1      -4.833  -1.193  -0.121  1.00  0.00           H  
HETATM   49  H28 UNL     1      -4.991  -0.969   1.703  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   17   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   15   29
CONECT    6    7   17   30
CONECT    7    8   31   32
CONECT    8    9    9   33
CONECT    9   10   15
CONECT   10   11   34   35
CONECT   11   12   13   36
CONECT   12   37
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16
CONECT   16   42   43   44
CONECT   17   18   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   21
END

HMDB0000077
     RDKit          3D
Dehydroepiandrosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.7875    0.1894   -1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937    0.6234   -0.0001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9123    1.8657    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4957    1.6798   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499    0.4258    0.2241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7516   -0.7895    0.1280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0782   -1.9921    0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -1.9136    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -0.9674    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5964   -0.9638    0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1358    0.3507    0.7088 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2732    0.7035    0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086    1.4592    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    1.3198   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3929    0.1313   -0.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0846   -0.3122   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122   -0.4554    0.8577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0207   -1.5378    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656   -0.8149    0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0403    0.6177    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7602    1.5383    0.8078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216   -0.9102   -1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    0.5902   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323    0.6367   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365    2.7059   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555    2.1606    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920    2.5411    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    1.8276   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    0.5132    1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627   -0.9531   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3436   -2.8698    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4821   -2.2484    1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122   -2.7323    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100   -1.1239   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572   -1.7553    0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000    0.2745    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0795    0.7007    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4629    1.4051    1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6553    2.4295    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151    1.1167   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729    2.2389   -0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.3490   -2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -0.2462   -2.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.3356   -2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581    0.0052    1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876   -1.9685    1.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9021   -2.3211    0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8331   -1.1927   -0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9911   -0.9691    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-BETA-HYDROXY-5-androsten-17-one	ChEBI
3beta-Hydroxyandrost-5-en-17-one	ChEBI
Dehydroisoandrosterone	ChEBI
DHA	ChEBI
DHEA	ChEBI
Intrarosa	ChEBI
Prasterone	ChEBI
Biolaif	Kegg
3-b-HYDROXY-5-androsten-17-one	Generator
3-Β-hydroxy-5-androsten-17-one	Generator
3b-Hydroxyandrost-5-en-17-one	Generator
3Β-hydroxyandrost-5-en-17-one	Generator
(+)-Dehydroisoandrosterone	HMDB
(3-beta)-3-Hydroxyandrost-5-en-17-one	HMDB
(3beta)-3-Hydroxy-androst-5-en-17-one	HMDB
(3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-one	HMDB
17-Chetovis	HMDB
17-Hormoforin	HMDB
3-beta-Hydroxyandrost-5-en-17-one	HMDB
3b-Hydroxy-D5-androsten-17-one	HMDB
3beta-Hydroxy-5-androsten-17-one	HMDB
3beta-Hydroxy-androst-5-en-17-one	HMDB
3beta-Hydroxy-D5-androsten-17-one	HMDB
5,6-Dehydroisoandrosterone	HMDB
5,6-Didehydroisoandrosterone	HMDB
5-Androsten-3-beta-ol-17-one	HMDB
5-Androsten-3b-ol-17-one	HMDB
5-Androsten-3beta-ol-17-one	HMDB
5-Dehydro-epiandrosterone	HMDB
5-Dehydroepiandrosterone	HMDB
Andrestenol	HMDB
Androst-5-ene-3b-ol-17-one	HMDB
Androst-5-ene-3beta-ol-17-one	HMDB
Androsten-3beta-ol-17-one	HMDB
Androstenolone	HMDB
Astenile	HMDB
D5-Androsten-3b-ol-17-one	HMDB
D5-Androsten-3beta-ol-17-one	HMDB
Deandros	HMDB
Dehydro-epi-androsterone	HMDB
Diandron	HMDB
Diandrone	HMDB
Hydroxyandrostenone	HMDB
Prasterona	HMDB
Prasteronum	HMDB
Prestara	HMDB
Psicosterone	HMDB
trans-Dehydroandrosterone	HMDB
Prasterone, 3 alpha-isomer	HMDB
5 Androsten 3 beta hydroxy 17 one	HMDB
5-Androsten-3-beta-hydroxy-17-one	HMDB
5 Androsten 3 ol 17 one	HMDB
Prasterone, 3 alpha isomer	HMDB
5-Androsten-3-ol-17-one	HMDB
EM-760Dehydroandrosterone	HMDB

Chemical Formula

C₁₉H₂₈O₂

Average Molecular Weight

288.4244

Monoisotopic Molecular Weight

288.20893014

IUPAC Name

(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

Traditional Name

(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

CAS Registry Number

53-43-0

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1

InChI Key

FMGSKLZLMKYGDP-USOAJAOKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Oxosteroid
17-oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:28689 )
17-oxo steroid (CHEBI:28689 )
androstanoid (CHEBI:28689 )
C19 steroids (androgens) and derivatives (C01227 )
Androstane and derivatives (C01227 )
Androgens (C01227 )
C19 steroids (androgens) and derivatives (LMST02020021 )

Ontology

Not Available

Adipose tissue (HMDB: HMDB0000077)

Epithelium

Epidermis (HMDB: HMDB0000077)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000077)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 14625002)
Saliva (PMID: 6210977)
Cerebrospinal Fluid (CSF) (PMID: 1620285)

Organ substructure

Adrenal cortex (HMDB: HMDB0000077)

Organ

Gland

Adrenal Gland (HMDB: HMDB0000077)

Cell

Fibroblasts (HMDB: HMDB0000077)
Neuron (HMDB: HMDB0000077)

Hematocyte

Platelet (HMDB: HMDB0000077)

Excreta

Biofluid or Excreta

Urine (PMID: 15560936)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000077)

Tissue substructure

Muscle (HMDB: HMDB0000077)

Source

Exogenous

Exogenous (HMDB: HMDB0000077)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0000077)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Androgen and Estrogen Metabolism (HMDB: HMDB0000077)

Disease pathway

17-beta Hydroxysteroid Dehydrogenase III Deficiency (HMDB: HMDB0000077)
Aromatase Deficiency (PathBank: SMP0120848)

Role

Biological role

Human metabolite (HMDB: HMDB0000077)
Androgen (HMDB: HMDB0000077)

Industrial application

Pharmaceutical industry

Biomarker

Lipoid Congenital Adrenal Hyperplasia (MarkerDB: MDB00000041)
Antley Bixler Syndrome With Genital Anomalies And Disordered Steroidogenesis (MarkerDB: MDB00000041)
21-hydroxylase deficiency (MarkerDB: MDB00000041)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140 - 141 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.064 mg/mL	Not Available
LogP	3.23	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	175.343	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000178

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	3.53	ALOGPS
logP	3.36	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.66 m³·mol⁻¹	ChemAxon
Polarizability	34.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	205.122	30932474
DeepCCS	[M+Na]+	179.579	30932474
AllCCS	[M+H]+	174.7	32859911
AllCCS	[M+H-H2O]+	171.6	32859911
AllCCS	[M+NH4]+	177.6	32859911
AllCCS	[M+Na]+	178.5	32859911
AllCCS	[M-H]-	178.5	32859911
AllCCS	[M+Na-2H]-	178.6	32859911
AllCCS	[M+HCOO]-	178.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydroepiandrosterone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2511.7	Standard polar	33892256
Dehydroepiandrosterone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2480.2	Standard non polar	33892256
Dehydroepiandrosterone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2617.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydroepiandrosterone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O	2604.0	Semi standard non polar	33892256
Dehydroepiandrosterone,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2619.5	Semi standard non polar	33892256
Dehydroepiandrosterone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2643.4	Semi standard non polar	33892256
Dehydroepiandrosterone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2554.7	Standard non polar	33892256
Dehydroepiandrosterone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2939.8	Standard polar	33892256
Dehydroepiandrosterone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C1	2860.0	Semi standard non polar	33892256
Dehydroepiandrosterone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2894.9	Semi standard non polar	33892256
Dehydroepiandrosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3170.3	Semi standard non polar	33892256
Dehydroepiandrosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2831.4	Standard non polar	33892256
Dehydroepiandrosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3188.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dehydroepiandrosterone GC-MS (1 MEOX; 1 TMS)	splash10-004i-4920000000-9dc14963a290268534b8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dehydroepiandrosterone GC-MS (1 TMS)	splash10-004i-3910000000-2bbc760dbeb7f9f1ebfc	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dehydroepiandrosterone EI-B (Non-derivatized)	splash10-0abi-1790000000-52f5e67bc4d1fab73561	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-6940000000-948ad487c238d48aa9be	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-qTof , Positive-QTOF	splash10-022a-1229000000-5fc1bd40299ad859ad1c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOF	splash10-0fk9-0190000000-66ac82624767dc6821e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOF	splash10-0w90-1690000000-b3a231fc509b7a34e09c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOF	splash10-08gj-1930000000-309dc082cc36ec9dcd8c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOF	splash10-06sj-2910000000-378638f2a861c948f79d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOF	splash10-0536-3900000000-72e80e1a07c4d3a40a7a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOF	splash10-0036-4900000000-26c8272483a80d1b5eab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone , positive-QTOF	splash10-000i-0290000000-1a3588ca5d5bacb9ad30	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone , positive-QTOF	splash10-0bta-3920000000-2df257db43df6cc86570	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone 90V, Positive-QTOF	splash10-0036-4900000000-a5988c20b9c2dcaaa0b0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone 75V, Positive-QTOF	splash10-0536-3900000000-9a88dec56cfcb5147a12	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone 45V, Positive-QTOF	splash10-08gj-1930000000-7cae68c709391babec19	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone 60V, Positive-QTOF	splash10-06sj-2910000000-370c122c31de467a2a1f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone 35V, Positive-QTOF	splash10-05d1-0930000000-890b3cea5a94fdd69458	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone 30V, Positive-QTOF	splash10-0w90-0690000000-cd7d0ebd514f0a8966d6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dehydroepiandrosterone 15V, Positive-QTOF	splash10-0fk9-0190000000-8d6dc67ca77600c3affa	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroepiandrosterone 10V, Positive-QTOF	splash10-00dr-0090000000-89da8cb383a0718d9033	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroepiandrosterone 20V, Positive-QTOF	splash10-00dr-0390000000-e6efd70cef2520255bf5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroepiandrosterone 40V, Positive-QTOF	splash10-0udm-4690000000-e304b251e97b02f672ad	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroepiandrosterone 10V, Positive-QTOF	splash10-00dr-0090000000-89da8cb383a0718d9033	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroepiandrosterone 20V, Positive-QTOF	splash10-00dr-0390000000-e6efd70cef2520255bf5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroepiandrosterone 40V, Positive-QTOF	splash10-0udm-4690000000-e304b251e97b02f672ad	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroepiandrosterone 10V, Negative-QTOF	splash10-000i-0090000000-7498c93972acc3c16404	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroepiandrosterone 20V, Negative-QTOF	splash10-000i-0090000000-d3ddffc56e91bed39fc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroepiandrosterone 40V, Negative-QTOF	splash10-052f-2190000000-15aba54ba135047ffe9a	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2018-06-19	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Saliva
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Brain
Epidermis
Fibroblasts
Kidney
Liver
Neuron
Ovary
Placenta
Platelet
Prostate
Skeletal Muscle
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Androgen and Estrogen Metabolism
17-Beta Hydroxysteroid Dehydrogenase III Deficiency		Not Available
Aromatase deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00173-0.0264 uM	Newborn (0-30 days old)	Female	Normal	18182448	details
Blood	Detected and Quantified	0.00225-0.0433 uM	Newborn (0-30 days old)	Female	Normal	18182448	details
Blood	Detected and Quantified	0.020 +/- 0.011 uM	Adult (>18 years old)	Male	Normal	17185878	details
Blood	Detected and Quantified	0.0153 +/- 0.00763 uM	Adult (>18 years old)	Female	Normal	11826238	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.001 (0.00034-0.0017) uM	Children (1-13 years old)	Female	Normal	14625002	details
Blood	Detected and Quantified	0.0087 (0.0035-0.013) uM	Adult (>18 years old)	Female	Normal	14625002	details
Blood	Detected and Quantified	0.0146 +/- 0.00451 uM	Adult (>18 years old)	Female	Normal	7951484	details
Blood	Detected and Quantified	0.023 (0.005-0.042) uM	Adult (>18 years old)	Both	Normal	The Merck Manual,...	details
Blood	Detected and Quantified	0.000700-0.0204 uM	Infant (0-1 year old)	Not Specified	Normal	16439592	details
Blood	Detected and Quantified	0.00295 +/- 0.00319 uM	Children (1-13 years old)	Both	Normal	26079780	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00101 (0.00002-0.002) uM	Adult (>18 years old)	Not Specified	Normal	1620285	details
Saliva	Detected and Quantified	0.0033 (0.0024-0.0090) uM	Adult (>18 years old)	Both	Normal	6210977	details
Urine	Detected and Quantified	0.0022 (0.0006-0.0273) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	23159298	details
Urine	Detected and Quantified	0.10 (0.066-0.17) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11085621	details
Urine	Detected and Quantified	0.022 (0.017-0.041) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11085621	details
Urine	Detected and Quantified	0.13 +/- 0.057 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15560936	details
Urine	Detected and Quantified	0.0016 +/- 0.00026 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15249323	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00250-0.00284 uM	Adult (>18 years old)	Female	21-hydroxylase deficiency	11826238	details
Blood	Detected and Quantified	0.0103 +/- 0.0100 uM	Newborn (0-30 days old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00520 +/- 0.00740 uM	Children (1-13 years old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.052 uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.653 uM	Adolescent (13-18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00157-0.385 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.0226-0.407 uM	Newborn (0-30 days old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00150 +/- 0.00120 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.0120 +/- 0.00700 uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.0140 +/- 0.00700 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00800 +/- 0.0100 uM	Infant (0-1 year old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	<0.00003 uM	Adult (>18 years old)	Female	Lipoid Adrenal Hyperplasia	9077535	details
Blood	Detected and Quantified	<0.00003 uM	Adolescent (13-18 years old)	Female	Lipoid Adrenal Hyperplasia	9077535	details
Blood	Detected and Quantified	0.0184-0.0333 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	7951484	details
Blood	Detected and Quantified	0.00240-0.00830 uM	Infant (0-1 year old)	Both	Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis	16439592	details
Blood	Detected and Quantified	0.0016 uM	Children (1-13 years old)	Female	Aromatase deficiency	9177373	details
Blood	Detected and Quantified	0.0448 +/- 0.0655 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Blood	Detected and Quantified	0.00246 +/- 0.00350 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Blood	Detected and Quantified	0.00101 uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	18182448	details
Blood	Detected and Quantified	0.0042 uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	18182448	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00114 +/- 0.000630 uM	Adult (>18 years old)	Not Specified	Leuprolide acetate-induced hypogonadism	16585475	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00127 +/- 0.00128 uM	Adult (>18 years old)	Not Specified	Leuprolide acetate-induced hypogonadism with testosterone replacment	16585475	details
Urine	Detected and Quantified	0.00032 +/- 0.000065 umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	15249323	details
Urine	Detected and Quantified	0.00066 +/- 0.00021 umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	15249323	details
Urine	Detected and Quantified	0.00034 +/- 0.000078 umol/mmol creatinine	Adult (>18 years old)	Both	Systemic lupus erythematosus (SLE)	15249323	details
Urine	Detected and Quantified	0.0011 +/- 0.00026 umol/mmol creatinine	Adult (>18 years old)	Both	Systemic lupus erythematosus (SLE)	15249323	details

Associated Disorders and Diseases

Disease References

Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ] Lutfallah C, Wang W, Mason JI, Chang YT, Haider A, Rich B, Castro-Magana M, Copeland KC, David R, Pang S: Newly proposed hormonal criteria via genotypic proof for type II 3beta-hydroxysteroid dehydrogenase deficiency. J Clin Endocrinol Metab. 2002 Jun;87(6):2611-22. doi: 10.1210/jcem.87.6.8615. [PubMed:12050224 ] Benkert AR, Young M, Robinson D, Hendrickson C, Lee PA, Strauss KA: Severe Salt-Losing 3beta-Hydroxysteroid Dehydrogenase Deficiency: Treatment and Outcomes of HSD3B2 c.35G>A Homozygotes. J Clin Endocrinol Metab. 2015 Aug;100(8):E1105-15. doi: 10.1210/jc.2015-2098. Epub 2015 Jun 16. [PubMed:26079780 ]
Aromatase deficiency
Mullis PE, Yoshimura N, Kuhlmann B, Lippuner K, Jaeger P, Harada H: Aromatase deficiency in a female who is compound heterozygote for two new point mutations in the P450arom gene: impact of estrogens on hypergonadotropic hypogonadism, multicystic ovaries, and bone densitometry in childhood. J Clin Endocrinol Metab. 1997 Jun;82(6):1739-45. doi: 10.1210/jcem.82.6.3994. [PubMed:9177373 ]
21-Hydroxylase deficiency
Gmyrek GA, New MI, Sosa RE, Poppas DP: Bilateral laparoscopic adrenalectomy as a treatment for classic congenital adrenal hyperplasia attributable to 21-hydroxylase deficiency. Pediatrics. 2002 Feb;109(2):E28. [PubMed:11826238 ]
Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis
Fukami M, Hasegawa T, Horikawa R, Ohashi T, Nishimura G, Homma K, Ogata T: Cytochrome P450 oxidoreductase deficiency in three patients initially regarded as having 21-hydroxylase deficiency and/or aromatase deficiency: diagnostic value of urine steroid hormone analysis. Pediatr Res. 2006 Feb;59(2):276-80. doi: 10.1203/01.pdr.0000195825.31504.28. [PubMed:16439592 ]
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
Kim CJ, Lin L, Huang N, Quigley CA, AvRuskin TW, Achermann JC, Miller WL: Severe combined adrenal and gonadal deficiency caused by novel mutations in the cholesterol side chain cleavage enzyme, P450scc. J Clin Endocrinol Metab. 2008 Mar;93(3):696-702. doi: 10.1210/jc.2007-2330. Epub 2008 Jan 8. [PubMed:18182448 ]
Lipoid Congenital Adrenal Hyperplasia
Fujieda K, Tajima T, Nakae J, Sageshima S, Tachibana K, Suwa S, Sugawara T, Strauss JF 3rd: Spontaneous puberty in 46,XX subjects with congenital lipoid adrenal hyperplasia. Ovarian steroidogenesis is spared to some extent despite inactivating mutations in the steroidogenic acute regulatory protein (StAR) gene. J Clin Invest. 1997 Mar 15;99(6):1265-71. doi: 10.1172/JCI119284. [PubMed:9077535 ]
Rheumatoid arthritis
Straub RH, Weidler C, Demmel B, Herrmann M, Kees F, Schmidt M, Scholmerich J, Schedel J: Renal clearance and daily excretion of cortisol and adrenal androgens in patients with rheumatoid arthritis and systemic lupus erythematosus. Ann Rheum Dis. 2004 Aug;63(8):961-8. [PubMed:15249323 ]

Associated OMIM IDs

201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
613546 (Aromatase deficiency)
201910 (21-Hydroxylase deficiency)
201750 (Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis)
613743 (Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete)
201710 (Lipoid Congenital Adrenal Hyperplasia)
180300 (Rheumatoid arthritis)

External Links

DrugBank ID

DB01708

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021808

KNApSAcK ID

Not Available

Chemspider ID

8036443

KEGG Compound ID

C01227

BioCyc ID

3-BETA-HYDROXYANDROST-5-EN-17-ONE

BiGG ID

37131

Wikipedia Link

Dehydroepiandrosterone

METLIN ID

5133

PubChem Compound

5881

PDB ID

Not Available

ChEBI ID

28689

Food Biomarker Ontology

Not Available

VMH ID

DHEA

MarkerDB ID

MDB00000041

Good Scents ID

Not Available

References

Synthesis Reference

Nguyen Xuan Cuong; Nguyen Van Dan. Synthesis of dehydroepiandrosterone (DHA) from 16-dehydropregnenolone acetate (DPA). Tap Chi Duoc Hoc (1983), (4), 12-14.

Material Safety Data Sheet (MSDS)

Not Available

General References

Schwarz S, Pohl P: Steroid hormones and steroid hormone binding globulins in cerebrospinal fluid studied in individuals with intact and with disturbed blood-cerebrospinal fluid barrier. Neuroendocrinology. 1992 Feb;55(2):174-82. [PubMed:1620285 ]
Robinzon B, Michael KK, Ripp SL, Winters SJ, Prough RA: Glucocorticoids inhibit interconversion of 7-hydroxy and 7-oxo metabolites of dehydroepiandrosterone: a role for 11beta-hydroxysteroid dehydrogenases? Arch Biochem Biophys. 2003 Apr 15;412(2):251-8. [PubMed:12667489 ]
Rao MS, Subbarao V, Yeldandi AV, Reddy JK: Hepatocarcinogenicity of dehydroepiandrosterone in the rat. Cancer Res. 1992 May 15;52(10):2977-9. [PubMed:1316232 ]
Saruc M, Yuceyar H, Ayhan S, Turkel N, Tuzcuoglu I, Can M: The association of dehydroepiandrosterone, obesity, waist-hip ratio and insulin resistance with fatty liver in postmenopausal women--a hyperinsulinemic euglycemic insulin clamp study. Hepatogastroenterology. 2003 May-Jun;50(51):771-4. [PubMed:12828082 ]
Bamberg E, Aichinger A, Mitteregger G: In vitro metabolism of dehydroepiandrosterone and testosterone by canine hair follicle cells. Vet Dermatol. 2004 Feb;15(1):19-24. [PubMed:14989701 ]
Gordon GB, Bush TL, Helzlsouer KJ, Miller SR, Comstock GW: Relationship of serum levels of dehydroepiandrosterone and dehydroepiandrosterone sulfate to the risk of developing postmenopausal breast cancer. Cancer Res. 1990 Jul 1;50(13):3859-62. [PubMed:2141293 ]
Weill-Engerer S, David JP, Sazdovitch V, Liere P, Schumacher M, Delacourte A, Baulieu EE, Akwa Y: In vitro metabolism of dehydroepiandrosterone (DHEA) to 7alpha-hydroxy-DHEA and Delta5-androstene-3beta,17beta-diol in specific regions of the aging brain from Alzheimer's and non-demented patients. Brain Res. 2003 Apr 18;969(1-2):117-25. [PubMed:12676372 ]
Finlay EM, Morton MS, Gaskell SJ: Identification and quantification of dehydroepiandrosterone sulphate in saliva. Steroids. 1982 Jan;39(1):63-71. [PubMed:6210977 ]
Uzieblo-Zyczkowska B, Sidlo E, Stelmaszuk T: [Dehydroepiandrosterone (DHEA)--slows down the aging process?]. Pol Merkur Lekarski. 2005 Dec;19(114):831-4. [PubMed:16521435 ]
Prost O, Nicollier M, Laurent R, Adessi GL: Estrone- and dehydroepiandrosterone-sulfatase activities in human female epidermis. Arch Dermatol Res. 1985;277(3):195-200. [PubMed:3160310 ]
Friess E, Schiffelholz T, Steckler T, Steiger A: Dehydroepiandrosterone--a neurosteroid. Eur J Clin Invest. 2000 Dec;30 Suppl 3:46-50. [PubMed:11281367 ]
Hakkinen A, Pakarinen A, Hannonen P, Kautiainen H, Nyman K, Kraemer WJ, Hakkinen K: Effects of prolonged combined strength and endurance training on physical fitness, body composition and serum hormones in women with rheumatoid arthritis and in healthy controls. Clin Exp Rheumatol. 2005 Jul-Aug;23(4):505-12. [PubMed:16095120 ]
Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. [PubMed:14625002 ]
Kim SB, Hill M, Kwak YT, Hampl R, Jo DH, Morfin R: Neurosteroids: Cerebrospinal fluid levels for Alzheimer's disease and vascular dementia diagnostics. J Clin Endocrinol Metab. 2003 Nov;88(11):5199-206. [PubMed:14602750 ]
Chalbot S, Morfin R: Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives. Drug Metab Dispos. 2005 Apr;33(4):563-9. Epub 2005 Jan 13. [PubMed:15650074 ]
Miller KK, Cai J, Ripp SL, Pierce WM Jr, Rushmore TH, Prough RA: Stereo- and regioselectivity account for the diversity of dehydroepiandrosterone (DHEA) metabolites produced by liver microsomal cytochromes P450. Drug Metab Dispos. 2004 Mar;32(3):305-13. [PubMed:14977864 ]
Martina V, Benso A, Gigliardi VR, Masha A, Origlia C, Granata R, Ghigo E: Short-term dehydroepiandrosterone treatment increases platelet cGMP production in elderly male subjects. Clin Endocrinol (Oxf). 2006 Mar;64(3):260-4. [PubMed:16487434 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

Phosphoadenosine phosphosulfate + Dehydroepiandrosterone → Adenosine 3',5'-diphosphate + Dehydroepiandrosterone sulfate	details

Enzyme Details

2. Steryl-sulfatase

General function:: Involved in catalytic activity
Specific function:: Conversion of sulfated steroid precursors to estrogens during pregnancy.
Gene Name:: STS
Uniprot ID:: P08842
Molecular weight:: 65491.72

Reactions

Dehydroepiandrosterone sulfate + Water → Dehydroepiandrosterone + Oat gum	details
Dehydroepiandrosterone sulfate + Water → Dehydroepiandrosterone + Oat gum	details

Enzyme Details

3. Cholesterol 7-alpha-monooxygenase

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:: CYP7A1
Uniprot ID:: P22680
Molecular weight:: 57660.155

Reactions

Dehydroepiandrosterone + Oxygen + NADPH + Hydrogen Ion → 7a-Hydroxydehydroepiandrosterone + NADP + Water	details

Enzyme Details

4. Steroid 17-alpha-hydroxylase/17,20 lyase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:: CYP17A1
Uniprot ID:: P05093
Molecular weight:: 57369.995

Reactions

17a-Hydroxypregnenolone + Reduced acceptor + Oxygen → Dehydroepiandrosterone + Acetic acid + Acceptor + Water	details

Enzyme Details

5. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:: HSD3B1
Uniprot ID:: P14060
Molecular weight:: 42251.25

Reactions

Dehydroepiandrosterone + NAD → Androstenedione + NADH + Hydrogen Ion	details

Enzyme Details

6. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:: HSD3B2
Uniprot ID:: P26439
Molecular weight:: 42051.845

Reactions

Dehydroepiandrosterone + NAD → Androstenedione + NADH + Hydrogen Ion	details

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B3

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:: SLCO1B3
Uniprot ID:: Q9NPD5
Molecular weight:: 77402.2

Enzyme Details

2. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

Enzyme Details

3. Solute carrier family 22 member 7

General function:: Involved in transmembrane transport
Specific function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular weight:: 60025.0

Showing metabocard for Dehydroepiandrosterone (HMDB0000077)

MOL for HMDB0000077 (Dehydroepiandrosterone)

3D MOL for HMDB0000077 (Dehydroepiandrosterone)

3D SDF for HMDB0000077 (Dehydroepiandrosterone)

3D-SDF for HMDB0000077 (Dehydroepiandrosterone)

PDB for HMDB0000077 (Dehydroepiandrosterone)

3D PDB for HMDB0000077 (Dehydroepiandrosterone)

SMILES for HMDB0000077 (Dehydroepiandrosterone)

INCHI for HMDB0000077 (Dehydroepiandrosterone)

Structure for HMDB0000077 (Dehydroepiandrosterone)

3D Structure for HMDB0000077 (Dehydroepiandrosterone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters