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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 02:49:00 UTC

HMDB ID

HMDB0000253

Secondary Accession Numbers

HMDB00253

Metabolite Identification

Common Name

Pregnenolone

Description

Pregnenolone is a derivative of cholesterol, the product of cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1. This reaction consists of three consecutive monooxygenations, a 22-hydroxylation, a 20-hydroxylation, and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum, and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted into pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell, angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and many steps in the transport to the inner membrane. Thus, it exerts a powerful control over the use of cholesterol for aldosterone production (PMID: 17222962 , 15823613 , 16632873 , 15134809 ).

Structure

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

  Mrv1652305271900262D          

 26 29  0  0  1  0            999 V2000
   -1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435   -1.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4290   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7144    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2134   -0.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6984    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4685    1.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754    2.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9164    2.4775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  9  1  0  0  0  0
 22 16  1  0  0  0  0
 11  8  1  0  0  0  0
 11 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16  7  1  0  0  0  0
 14  5  1  0  0  0  0
 14  1  1  0  0  0  0
  8  9  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  2  0  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  3 26  1  1  0  0  0
 22 10  1  6  0  0  0
 11 12  1  6  0  0  0
 19 13  1  1  0  0  0
 14 15  1  1  0  0  0
 16 17  1  1  0  0  0
 18 23  1  1  0  0  0
 19 18  1  0  0  0  0
 21 20  1  0  0  0  0
 18 21  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  2  0  0  0  0
M  END

HMDB0000253
     RDKit          3D
Pregnenolone
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.9957   -0.2681   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054    0.0711   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    0.7658   -1.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -0.4433    0.0063 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6667    0.0621    1.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018    0.5651    1.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4075   -0.1353    0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0163    0.3226    0.8327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7109    0.1085    2.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065    0.5472    1.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268    0.4477    0.8177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1354    0.9131    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9786   -0.1566   -0.0007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3535    0.2929   -1.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -1.4312   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9766   -1.2413   -0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1086   -0.1085   -0.4095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0902    0.9668   -1.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7062   -0.6095   -0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0068   -0.7834   -1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721   -0.9798   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1204    0.0206   -0.4036 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0943    1.3798   -1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376    0.1365   -1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2022    0.2460    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1380   -1.3616   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -1.5507   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3986    0.8867    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101   -0.7813    2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    1.6533    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.1258    2.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4204   -1.2135    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747    1.3685    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -0.9783    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1668    0.7366    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759    0.9771    2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6048    1.0411    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2360    1.9040    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9156   -0.3729    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5526    1.2579   -1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7660   -2.3026   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7735   -1.5448    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -1.0430   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4040   -2.1893   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2230    0.5085   -2.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    1.6248   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002    1.6161   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -1.5889    0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027    0.0163   -2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241   -1.7151   -1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9029   -0.8566   -2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -2.0340   -1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924    2.0106   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009    1.2713   -2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081    1.8455   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  1
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

  Mrv1652305271900262D          

 26 29  0  0  1  0            999 V2000
   -1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435   -1.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4290   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7144    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2134   -0.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6984    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4685    1.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754    2.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9164    2.4775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  9  1  0  0  0  0
 22 16  1  0  0  0  0
 11  8  1  0  0  0  0
 11 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16  7  1  0  0  0  0
 14  5  1  0  0  0  0
 14  1  1  0  0  0  0
  8  9  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  2  0  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  3 26  1  1  0  0  0
 22 10  1  6  0  0  0
 11 12  1  6  0  0  0
 19 13  1  1  0  0  0
 14 15  1  1  0  0  0
 16 17  1  1  0  0  0
 18 23  1  1  0  0  0
 19 18  1  0  0  0  0
 21 20  1  0  0  0  0
 18 21  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000253

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1

> <INCHI_KEY>
ORNBQBCIOKFOEO-QGVNFLHTSA-N

> <FORMULA>
C21H32O2

> <MOLECULAR_WEIGHT>
316.4776

> <EXACT_MASS>
316.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.08645703431432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
3.581358452666668

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.403038799839706

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972432940071755

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
93.7567

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000253
     RDKit          3D
Pregnenolone
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.9957   -0.2681   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054    0.0711   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    0.7658   -1.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -0.4433    0.0063 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6667    0.0621    1.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018    0.5651    1.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4075   -0.1353    0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0163    0.3226    0.8327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7109    0.1085    2.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065    0.5472    1.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268    0.4477    0.8177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1354    0.9131    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9786   -0.1566   -0.0007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3535    0.2929   -1.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -1.4312   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9766   -1.2413   -0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1086   -0.1085   -0.4095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0902    0.9668   -1.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7062   -0.6095   -0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0068   -0.7834   -1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721   -0.9798   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1204    0.0206   -0.4036 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0943    1.3798   -1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376    0.1365   -1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2022    0.2460    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1380   -1.3616   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -1.5507   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3986    0.8867    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101   -0.7813    2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    1.6533    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.1258    2.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4204   -1.2135    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747    1.3685    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -0.9783    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1668    0.7366    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759    0.9771    2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6048    1.0411    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2360    1.9040    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9156   -0.3729    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5526    1.2579   -1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7660   -2.3026   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7735   -1.5448    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -1.0430   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4040   -2.1893   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2230    0.5085   -2.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    1.6248   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002    1.6161   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -1.5889    0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027    0.0163   -2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241   -1.7151   -1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9029   -0.8566   -2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -2.0340   -1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924    2.0106   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009    1.2713   -2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081    1.8455   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  1
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       4.132   2.016   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.608   3.480   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.114   3.801   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.577   4.625   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   14    2                                                       
CONECT    2    1    3                                                       
CONECT    3    4    2   26                                                  
CONECT    4    5    3                                                       
CONECT    5   14    4    6                                                  
CONECT    6    7    5                                                       
CONECT    7   16    6                                                       
CONECT    8   11    9                                                       
CONECT    9   19    8                                                       
CONECT   10   22                                                            
CONECT   11    8   14   16   12                                             
CONECT   12   11                                                            
CONECT   13   19                                                            
CONECT   14   11    5    1   15                                             
CONECT   15   14                                                            
CONECT   16   22   11    7   17                                             
CONECT   17   16                                                            
CONECT   18   23   19   21                                                  
CONECT   19    9   13   18   22                                             
CONECT   20   21   22                                                       
CONECT   21   20   18                                                       
CONECT   22   16   10   19   20                                             
CONECT   23   18   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0000253
HETATM    1  C1  UNL     1       5.996  -0.268  -0.410  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.605   0.071  -0.793  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.425   0.766  -1.759  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.500  -0.443   0.006  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.667   0.062   1.444  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.302   0.565   1.870  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.407  -0.135   0.902  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.016   0.323   0.833  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.711   0.108   2.173  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.107   0.547   1.976  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.727   0.448   0.818  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.135   0.913   0.709  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.979  -0.157  -0.001  1.00  0.00           C  
HETATM   14  O2  UNL     1      -5.353   0.293  -1.241  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.184  -1.431  -0.004  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.977  -1.241  -0.895  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.109  -0.109  -0.409  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.090   0.967  -1.466  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.706  -0.610  -0.151  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.007  -0.783  -1.442  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.472  -0.980  -1.360  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.120   0.021  -0.404  1.00  0.00           C  
HETATM   23  C21 UNL     1       2.094   1.380  -1.002  1.00  0.00           C  
HETATM   24  H1  UNL     1       6.738   0.137  -1.131  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.202   0.246   0.563  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.138  -1.362  -0.246  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.502  -1.551  -0.035  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.399   0.887   1.503  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.010  -0.781   2.087  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.225   1.653   1.870  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.109   0.126   2.891  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.420  -1.213   1.155  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.175   1.369   0.586  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.656  -0.978   2.456  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.167   0.737   2.902  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.676   0.977   2.807  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.605   1.041   1.715  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.236   1.904   0.226  1.00  0.00           H  
HETATM   39  H16 UNL     1      -5.916  -0.373   0.565  1.00  0.00           H  
HETATM   40  H17 UNL     1      -5.553   1.258  -1.203  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.766  -2.303  -0.310  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.774  -1.545   1.042  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.380  -1.043  -1.921  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.404  -2.189  -0.987  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.223   0.509  -2.485  1.00  0.00           H  
HETATM   46  H23 UNL     1      -2.965   1.625  -1.319  1.00  0.00           H  
HETATM   47  H24 UNL     1      -1.200   1.616  -1.426  1.00  0.00           H  
HETATM   48  H25 UNL     1      -0.778  -1.589   0.363  1.00  0.00           H  
HETATM   49  H26 UNL     1      -0.203   0.016  -2.195  1.00  0.00           H  
HETATM   50  H27 UNL     1      -0.424  -1.715  -1.916  1.00  0.00           H  
HETATM   51  H28 UNL     1       1.903  -0.857  -2.378  1.00  0.00           H  
HETATM   52  H29 UNL     1       1.718  -2.034  -1.061  1.00  0.00           H  
HETATM   53  H30 UNL     1       2.892   2.011  -0.546  1.00  0.00           H  
HETATM   54  H31 UNL     1       2.201   1.271  -2.107  1.00  0.00           H  
HETATM   55  H32 UNL     1       1.108   1.846  -0.859  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5   22   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   22   32
CONECT    8    9   19   33
CONECT    9   10   34   35
CONECT   10   11   11   36
CONECT   11   12   17
CONECT   12   13   37   38
CONECT   13   14   15   39
CONECT   14   40
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   19
CONECT   18   45   46   47
CONECT   19   20   48
CONECT   20   21   49   50
CONECT   21   22   51   52
CONECT   22   23
CONECT   23   53   54   55
END

HMDB0000253
     RDKit          3D
Pregnenolone
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.9957   -0.2681   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054    0.0711   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    0.7658   -1.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -0.4433    0.0063 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6667    0.0621    1.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018    0.5651    1.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4075   -0.1353    0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0163    0.3226    0.8327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7109    0.1085    2.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065    0.5472    1.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268    0.4477    0.8177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1354    0.9131    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9786   -0.1566   -0.0007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3535    0.2929   -1.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -1.4312   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9766   -1.2413   -0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1086   -0.1085   -0.4095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0902    0.9668   -1.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7062   -0.6095   -0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0068   -0.7834   -1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721   -0.9798   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1204    0.0206   -0.4036 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0943    1.3798   -1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376    0.1365   -1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2022    0.2460    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1380   -1.3616   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -1.5507   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3986    0.8867    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101   -0.7813    2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    1.6533    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.1258    2.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4204   -1.2135    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747    1.3685    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -0.9783    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1668    0.7366    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759    0.9771    2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6048    1.0411    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2360    1.9040    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9156   -0.3729    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5526    1.2579   -1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7660   -2.3026   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7735   -1.5448    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -1.0430   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4040   -2.1893   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2230    0.5085   -2.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    1.6248   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002    1.6161   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -1.5889    0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027    0.0163   -2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241   -1.7151   -1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9029   -0.8566   -2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -2.0340   -1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924    2.0106   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009    1.2713   -2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081    1.8455   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  1
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3BETA)-3-HYDROXYPREGN-5-en-20-one	ChEBI
3beta-Hydroxypregn-5-en-20-one	ChEBI
5-Pregnen-3beta-ol-20-one	ChEBI
(3b)-3-HYDROXYPREGN-5-en-20-one	Generator
(3Β)-3-hydroxypregn-5-en-20-one	Generator
3b-Hydroxypregn-5-en-20-one	Generator
3Β-hydroxypregn-5-en-20-one	Generator
5-Pregnen-3b-ol-20-one	Generator
5-Pregnen-3β-ol-20-one	Generator
5-Pregnen-3-beta-ol-20-one	HMDB
5 Pregnen 3 beta ol 20 one	HMDB

Chemical Formula

C₂₁H₃₂O₂

Average Molecular Weight

316.4776

Monoisotopic Molecular Weight

316.240230268

IUPAC Name

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

Traditional Name

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

CAS Registry Number

145-13-1

SMILES

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

InChI Identifier

InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1

InChI Key

ORNBQBCIOKFOEO-QGVNFLHTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:16581 )
20-oxo steroid (CHEBI:16581 )
C21-steroid (CHEBI:16581 )
Pregnane and derivatives [Fig] (C01953 )
Progestagens (C01953 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030088 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 11739473)
Cerebrospinal Fluid (CSF) (PMID: 10625505)

Organ substructure

Adrenal cortex (HMDB: HMDB0000253)

Organ

Gland

Adrenal Gland (HMDB: HMDB0000253)

Cell

Neuron (HMDB: HMDB0000253)
Nerve cell (HMDB: HMDB0000253)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000253)
Mitochondrion (HMDB: HMDB0000253)

Source

Exogenous

Exogenous (HMDB: HMDB0000253)

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)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0000253)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Steroidogenesis (HMDB: HMDB0000253)

Disease pathway

Physiological pathway

Aldosterone from Steroidogenesis (PathBank: SMP0121126)

Role

Biological role

Human metabolite (HMDB: HMDB0000253)

Industrial application

Pharmaceutical industry

Biomarker

Congenital Adrenal Insufficiency with 46,XY Sex Reversal (MarkerDB: MDB00000123)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	192 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0071 mg/mL at 37 °C	Not Available
LogP	4.22	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	182.862	30932474
[M+H]+	MetCCS_train_pos	173.981	30932474
[M+H]+	Not Available	177.248	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001969

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	4.06	ALOGPS
logP	3.58	ChemAxon
logS	-4.4	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	1	ChemAxon
Refractivity	93.76 m³·mol⁻¹	ChemAxon
Polarizability	38.09 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
AllCCS	[M+H]+	181.924	32859911
AllCCS	[M-H]-	186.891	32859911
DeepCCS	[M-2H]-	211.737	30932474
DeepCCS	[M+Na]+	186.193	30932474
AllCCS	[M+H]+	181.9	32859911
AllCCS	[M+H-H2O]+	179.1	32859911
AllCCS	[M+NH4]+	184.5	32859911
AllCCS	[M+Na]+	185.3	32859911
AllCCS	[M-H]-	186.9	32859911
AllCCS	[M+Na-2H]-	187.3	32859911
AllCCS	[M+HCOO]-	188.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pregnenolone	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2458.5	Standard polar	33892256
Pregnenolone	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2676.1	Standard non polar	33892256
Pregnenolone	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2842.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pregnenolone,1TMS,isomer #1	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2784.7	Semi standard non polar	33892256
Pregnenolone,1TMS,isomer #2	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2807.5	Semi standard non polar	33892256
Pregnenolone,1TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2789.1	Semi standard non polar	33892256
Pregnenolone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2839.4	Semi standard non polar	33892256
Pregnenolone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2805.5	Standard non polar	33892256
Pregnenolone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3134.7	Standard polar	33892256
Pregnenolone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2812.9	Semi standard non polar	33892256
Pregnenolone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2793.5	Standard non polar	33892256
Pregnenolone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3225.7	Standard polar	33892256
Pregnenolone,1TBDMS,isomer #1	CC(=O)[C@H]1CC[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	3018.6	Semi standard non polar	33892256
Pregnenolone,1TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3063.7	Semi standard non polar	33892256
Pregnenolone,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3056.2	Semi standard non polar	33892256
Pregnenolone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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	3331.9	Semi standard non polar	33892256
Pregnenolone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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	3291.2	Standard non polar	33892256
Pregnenolone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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	3374.6	Standard polar	33892256
Pregnenolone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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	3331.6	Semi standard non polar	33892256
Pregnenolone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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	3283.9	Standard non polar	33892256
Pregnenolone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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	3438.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Pregnenolone GC-MS (1 MEOX; 1 TMS)	splash10-0fic-5910000000-4b4de0891180a420522a	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Pregnenolone EI-B (Non-derivatized)	splash10-05o0-2982000000-90eb349ceb4f7cdf4bf0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pregnenolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pregnenolone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pregnenolone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pregnenolone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pregnenolone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pregnenolone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pregnenolone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-6920000000-2b11c86505b10fe4485f	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 10V, Positive-QTOF	splash10-00kb-0195000000-742fffef9b8fa170f05e	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 20V, Positive-QTOF	splash10-00kb-0391000000-7f19b3f9aed012b1e539	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 40V, Positive-QTOF	splash10-0kbo-3390000000-f6f0115bbcd9afb5ddb9	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 10V, Negative-QTOF	splash10-014i-0039000000-5c36ec019f325626a9b6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 20V, Negative-QTOF	splash10-014i-0089000000-99239f61c3086ee3d434	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 40V, Negative-QTOF	splash10-0592-1090000000-66cb81b0a398e104af3c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 10V, Negative-QTOF	splash10-014i-0009000000-be6e06313d0abca8e664	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 20V, Negative-QTOF	splash10-014j-0059000000-29a13c8b5bcf95bf2c0e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 40V, Negative-QTOF	splash10-00ls-0091000000-ceb36b1daa98969bf576	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 10V, Positive-QTOF	splash10-014i-0069000000-4c14a1135d3725f8f03a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 20V, Positive-QTOF	splash10-05mk-0591000000-a85817c6a0529a583cdf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregnenolone 40V, Positive-QTOF	splash10-0a4i-2920000000-465c7c1e069f6588a706	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Mitochondria
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Adrenal Cortex
Adrenal Gland
Brain
Kidney
Neuron
Ovary
Placenta
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Steroidogenesis
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency		Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH		Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency		Not Available
17-alpha-hydroxylase deficiency (CYP17)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00474-0.0632 uM	Newborn (0-30 days old)	Female	Normal	18182448	details
Blood	Detected and Quantified	0.00186 +/- 0.00090 uM	Adult (>18 years old)	Female	Normal	11739473	details
Blood	Detected and Quantified	0.00083 +/- 0.00080 uM	Adult (>18 years old)	Both	Normal	12215085	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22944140	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22944140	details
Blood	Detected and Quantified	0.00424 +/- 0.00236 uM	Adult (>18 years old)	Female	Normal	11739473	details
Blood	Detected and Quantified	0.0147 +/- 0.0084 uM	Adult (>18 years old)	Female	Normal	11739473	details
Blood	Detected and Quantified	0.0429 +/- 0.0325 uM	Adult (>18 years old)	Female	Normal	11739473	details
Blood	Detected and Quantified	0.0573 +/- 0.0133 uM	Adult (>18 years old)	Female	Normal	11739473	details
Blood	Detected and Quantified	0.00985 +/- 0.00851 uM	Adult (>18 years old)	Female	Normal	11739473	details
Blood	Detected and Quantified	0.00373 +/- 0.00214 uM	Adult (>18 years old)	Female	Normal	11739473	details
Blood	Detected and Quantified	0.00168 +/- 0.00137 uM	Adult (>18 years old)	Female	Normal	11739473	details
Blood	Detected and Quantified	0.00088 +/- 0.00062 uM	Adult (>18 years old)	Female	Normal	12215085	details
Blood	Detected and Quantified	0.00054 +/- 0.00033 uM	Adult (>18 years old)	Female	Normal	12215085	details
Blood	Detected and Quantified	0.013 +/- 0.0027 uM	Adult (>18 years old)	Both	Normal	10625505	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00013 (0.000082-0.00019) uM	Adult (>18 years old)	Both	Normal	10625505	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	0.00401 uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	18182448	details
Blood	Detected and Quantified	0.00082 +/- 0.00071 uM	Adult (>18 years old)	Female	Premenstrual dysphoric disorder (follicular stage of menstrual cycle)	12215085	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Schizophrenia	22944140	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Schizophrenia	22944140	details
Blood	Detected and Quantified	0.0423 +/- 0.0130 uM	Adult (>18 years old)	Female	Prepartum depression	11739473	details
Blood	Detected and Quantified	0.0684 +/- 0.0222 uM	Adult (>18 years old)	Female	Prepartum depression	11739473	details
Blood	Detected and Quantified	0.00974 +/- 0.00371 uM	Adult (>18 years old)	Female	Postpartum depression	11739473	details
Blood	Detected and Quantified	0.00209 +/- 0.00090 uM	Adult (>18 years old)	Female	Postpartum depression	11739473	details
Blood	Detected and Quantified	0.00179 +/- 0.00108 uM	Adult (>18 years old)	Female	Premenstrual dysphoric disorder (mid luteal stage of menstrual cycle)	12215085	details
Blood	Detected and Quantified	0.00169 +/- 0.00107 uM	Adult (>18 years old)	Female	Premenstrual dysphoric disorder (late luteal stage of menstrual cycle)	12215085	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00003510 +/- 0.00002656 uM	Adult (>18 years old)	Not Specified	Leuprolide acetate-induced hypogonadism	16585475	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00005312 +/- 0.00004775 uM	Adult (>18 years old)	Not Specified	Leuprolide acetate-induced hypogonadism with testosterone replacment	16585475	details

Associated Disorders and Diseases

Disease References

Premenstrual dysphoric disorder
Epperson CN, Haga K, Mason GF, Sellers E, Gueorguieva R, Zhang W, Weiss E, Rothman DL, Krystal JH: Cortical gamma-aminobutyric acid levels across the menstrual cycle in healthy women and those with premenstrual dysphoric disorder: a proton magnetic resonance spectroscopy study. Arch Gen Psychiatry. 2002 Sep;59(9):851-8. [PubMed:12215085 ]
Prepartum depression
Pearson Murphy BE, Steinberg SI, Hu FY, Allison CM: Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. J Clin Endocrinol Metab. 2001 Dec;86(12):5981-7. [PubMed:11739473 ]
Postpartum depression
Pearson Murphy BE, Steinberg SI, Hu FY, Allison CM: Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. J Clin Endocrinol Metab. 2001 Dec;86(12):5981-7. [PubMed:11739473 ]
Schizophrenia
Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
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 ]

Associated OMIM IDs

181500 (Schizophrenia)
613743 (Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete)

External Links

DrugBank ID

DB02789

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00047082

Chemspider ID

8611

KEGG Compound ID

C01953

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pregnenolone

METLIN ID

Not Available

PubChem Compound

8955

PDB ID

Not Available

ChEBI ID

16581

Food Biomarker Ontology

Not Available

VMH ID

PRGNLONE

MarkerDB ID

MDB00000123

Good Scents ID

Not Available

References

Synthesis Reference

Shingate, Bapurao B.; Hazra, Braja G.; Pore, Vandana S.; Gonnade, Rajesh G.; Bhadbhade, Mohan M. Stereoselective syntheses of 20-epi cholanic acid derivatives from 16-dehydropregnenolone acetate. Tetrahedron (2007), 63(25), 5622-5635.

Material Safety Data Sheet (MSDS)

Not Available

General References

Kim YS, Zhang H, Kim HY: Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. Anal Biochem. 2000 Jan 15;277(2):187-95. [PubMed:10625505 ]
Schoneshofer M, Weber B: Specific estimation of fifteen unconjugated, non-metabolized steroid hormones in human urine. J Steroid Biochem. 1983 Jan;18(1):65-73. [PubMed:6865405 ]
Morfin R, Young J, Corpechot C, Egestad B, Sjovall J, Baulieu EE: Neurosteroids: pregnenolone in human sciatic nerves. Proc Natl Acad Sci U S A. 1992 Aug 1;89(15):6790-3. [PubMed:1386671 ]
Eriksson CJ, Widenius TV, Leinonen P, Harkonen M, Ylikahri RH: Inhibition of testosterone biosynthesis by ethanol: relation to the pregnenolone-to-testosterone pathway. FEBS Lett. 1984 Jul 9;172(2):177-82. [PubMed:6540203 ]
George MS, Guidotti A, Rubinow D, Pan B, Mikalauskas K, Post RM: CSF neuroactive steroids in affective disorders: pregnenolone, progesterone, and DBI. Biol Psychiatry. 1994 May 15;35(10):775-80. [PubMed:8043707 ]
Hill M, Lukac D, Lapcik O, Sulcova J, Hampl R, Pouzar V, Starka L: Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects. Clin Chem Lab Med. 1999 Apr;37(4):439-47. [PubMed:10369116 ]
Diallo S, Lecanu L, Greeson J, Papadopoulos V: A capillary gas chromatography/mass spectrometric method for the quantification of hydroxysteroids in human plasma. Anal Biochem. 2004 Jan 1;324(1):123-30. [PubMed:14654054 ]
Saenger P, Klonari Z, Black SM, Compagnone N, Mellon SH, Fleischer A, Abrams CA, Shackelton CH, Miller WL: Prenatal diagnosis of congenital lipoid adrenal hyperplasia. J Clin Endocrinol Metab. 1995 Jan;80(1):200-5. [PubMed:7829612 ]
Meloun M, Hill M, Militky J, Kupka K: Analysis of large and small samples of biochemical and clinical data. Clin Chem Lab Med. 2001 Jan;39(1):53-61. [PubMed:11256802 ]
Lykkesfeldt G, Nielsen MD, Lykkesfeldt AE: Placental steroid sulfatase deficiency: biochemical diagnosis and clinical review. Obstet Gynecol. 1984 Jul;64(1):49-54. [PubMed:6234482 ]
Hill M, Havlikova H, Vrbikova J, Kancheva R, Kancheva L, Pouzar V, Cerny I, Starka L: The identification and simultaneous quantification of 7-hydroxylated metabolites of pregnenolone, dehydroepiandrosterone, 3beta,17beta-androstenediol, and testosterone in human serum using gas chromatography-mass spectrometry. J Steroid Biochem Mol Biol. 2005 Jul;96(2):187-200. [PubMed:15908198 ]
Weusten JJ, Smals AG, Hofman JA, Kloppenborg PW, Benraad TJ: Early time sequence in pregnenolone metabolism to testosterone in homogenates of human and rat testis. Endocrinology. 1987 May;120(5):1909-13. [PubMed:3569120 ]
Doouss TW, Skinner SJ, Couch RA: Synthesis of dehydroepiandrosterone and dehydroepiandrosterone sulphate by the human adrenal. J Endocrinol. 1975 Jul;66(1):1-12. [PubMed:126268 ]
Nishida S, Matsumura S, Horino M, Matsuki M, Oyama H, Tenku A, Kakita K, Tanaka H, Omukai Y: Dexamethasone suppressibility of plasma pregnenolone or dehydroepiandrosterone in gonadectomized patients. Steroids. 1979 Oct;34(4):471-6. [PubMed:229589 ]
Pearson Murphy BE, Steinberg SI, Hu FY, Allison CM: Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. J Clin Endocrinol Metab. 2001 Dec;86(12):5981-7. [PubMed:11739473 ]
Ahboucha S, Pomier-Layrargues G, Mamer O, Butterworth RF: Increased levels of pregnenolone and its neuroactive metabolite allopregnanolone in autopsied brain tissue from cirrhotic patients who died in hepatic coma. Neurochem Int. 2006 Sep;49(4):372-8. Epub 2006 Mar 24. [PubMed:16563564 ]
Tuckey RC: Progesterone synthesis by the human placenta. Placenta. 2005 Apr;26(4):273-81. [PubMed:15823613 ]
Storbeck KH, Swart P, Swart AC: Cytochrome P450 side-chain cleavage: insights gained from homology modeling. Mol Cell Endocrinol. 2007 Feb;265-266:65-70. Epub 2007 Jan 12. [PubMed:17222962 ]
Patte-Mensah C, Kibaly C, Boudard D, Schaeffer V, Begle A, Saredi S, Meyer L, Mensah-Nyagan AG: Neurogenic pain and steroid synthesis in the spinal cord. J Mol Neurosci. 2006;28(1):17-31. [PubMed:16632873 ]
Capponi AM: The control by angiotensin II of cholesterol supply for aldosterone biosynthesis. Mol Cell Endocrinol. 2004 Mar 31;217(1-2):113-8. [PubMed:15134809 ]

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

Pregnenolone + Phosphoadenosine phosphosulfate → 3beta-Hydroxypregn-5-en-20-one sulfate + Adenosine 3',5'-diphosphate	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

Pregnenolone + Oat gum → 3beta-Hydroxypregn-5-en-20-one sulfate + Water	details

Enzyme Details

3. Cholesterol side-chain cleavage enzyme, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:: CYP11A1
Uniprot ID:: P05108
Molecular weight:: 60101.87

Reactions

Cholesterol + reduced adrenal ferredoxin + Oxygen → Pregnenolone + 4-Methylpentanal + oxidized adrenal ferredoxin + Water	details
20a,22b-Dihydroxycholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion → 4-Methylpentanal + Pregnenolone + Water + Oxidized adrenal ferredoxin	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

Pregnenolone + Reduced acceptor + Oxygen → 17a-Hydroxypregnenolone + Acceptor + Water	details

Enzyme Details

5. 25-hydroxycholesterol 7-alpha-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP7B1
Uniprot ID:: O75881
Molecular weight:: 58255.325

Reactions

Pregnenolone + NADPH + Hydrogen Ion + Oxygen → 7alpha-Hydroxypregnenolone + NADP + Water	details

Enzyme Details

6. 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

Pregnenolone + NAD → Progesterone + NADH + Hydrogen Ion	details

Enzyme Details

7. 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

Pregnenolone + NAD → Progesterone + NADH + Hydrogen Ion	details

Enzyme Details

8. Cytochrome P450 21-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: P450-CYP21B
Uniprot ID:: Q16874
Molecular weight:: 56000.9

Enzyme Details

9. Cytochrome P450, family 21, subfamily A, polypeptide 2

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP21A2
Uniprot ID:: Q08AG9
Molecular weight:: 55972.9

Enzyme Details

10. Steroid 21-hydroxylase

General function:: Not Available
Specific function:: Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:: CYP21A2
Uniprot ID:: P08686
Molecular weight:: 56000.94

Reactions

Pregnenolone + Reduced acceptor + Oxygen → 21-Hydroxypregnenolone + Acceptor + Water	details

Showing metabocard for Pregnenolone (HMDB0000253)

MOL for HMDB0000253 (Pregnenolone)

3D MOL for HMDB0000253 (Pregnenolone)

3D SDF for HMDB0000253 (Pregnenolone)

3D-SDF for HMDB0000253 (Pregnenolone)

PDB for HMDB0000253 (Pregnenolone)

3D PDB for HMDB0000253 (Pregnenolone)

SMILES for HMDB0000253 (Pregnenolone)

INCHI for HMDB0000253 (Pregnenolone)

Structure for HMDB0000253 (Pregnenolone)

3D Structure for HMDB0000253 (Pregnenolone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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