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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:48:59 UTC
HMDB IDHMDB0000077
Secondary Accession Numbers
  • HMDB00077
Metabolite Identification
Common NameDehydroepiandrosterone
DescriptionDehydroepiandrosterone (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
Data?1582752111
Synonyms
ValueSource
3-BETA-HYDROXY-5-androsten-17-oneChEBI
3beta-Hydroxyandrost-5-en-17-oneChEBI
DehydroisoandrosteroneChEBI
DHAChEBI
DHEAChEBI
IntrarosaChEBI
PrasteroneChEBI
BiolaifKegg
3-b-HYDROXY-5-androsten-17-oneGenerator
3-Β-hydroxy-5-androsten-17-oneGenerator
3b-Hydroxyandrost-5-en-17-oneGenerator
3Β-hydroxyandrost-5-en-17-oneGenerator
(+)-DehydroisoandrosteroneHMDB
(3-beta)-3-Hydroxyandrost-5-en-17-oneHMDB
(3beta)-3-Hydroxy-androst-5-en-17-oneHMDB
(3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-oneHMDB
17-ChetovisHMDB
17-HormoforinHMDB
3-beta-Hydroxyandrost-5-en-17-oneHMDB
3b-Hydroxy-D5-androsten-17-oneHMDB
3beta-Hydroxy-5-androsten-17-oneHMDB
3beta-Hydroxy-androst-5-en-17-oneHMDB
3beta-Hydroxy-D5-androsten-17-oneHMDB
5,6-DehydroisoandrosteroneHMDB
5,6-DidehydroisoandrosteroneHMDB
5-Androsten-3-beta-ol-17-oneHMDB
5-Androsten-3b-ol-17-oneHMDB
5-Androsten-3beta-ol-17-oneHMDB
5-Dehydro-epiandrosteroneHMDB
5-DehydroepiandrosteroneHMDB
AndrestenolHMDB
Androst-5-ene-3b-ol-17-oneHMDB
Androst-5-ene-3beta-ol-17-oneHMDB
Androsten-3beta-ol-17-oneHMDB
AndrostenoloneHMDB
AstenileHMDB
D5-Androsten-3b-ol-17-oneHMDB
D5-Androsten-3beta-ol-17-oneHMDB
DeandrosHMDB
Dehydro-epi-androsteroneHMDB
DiandronHMDB
DiandroneHMDB
HydroxyandrostenoneHMDB
PrasteronaHMDB
PrasteronumHMDB
PrestaraHMDB
PsicosteroneHMDB
trans-DehydroandrosteroneHMDB
Prasterone, 3 alpha-isomerHMDB
5 Androsten 3 beta hydroxy 17 oneHMDB
5-Androsten-3-beta-hydroxy-17-oneHMDB
5 Androsten 3 ol 17 oneHMDB
Prasterone, 3 alpha isomerHMDB
5-Androsten-3-ol-17-oneHMDB
EM-760DehydroandrosteroneHMDB
Chemical FormulaC19H28O2
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
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 Number53-43-0
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 KeyFMGSKLZLMKYGDP-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140 - 141 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.064 mg/mLNot Available
LogP3.23HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available175.343http://allccs.zhulab.cn/database/detail?ID=AllCCS00000178
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP3.53ALOGPS
logP3.36ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.66 m³·mol⁻¹ChemAxon
Polarizability34.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-205.12230932474
DeepCCS[M+Na]+179.57930932474
AllCCS[M+H]+174.732859911
AllCCS[M+H-H2O]+171.632859911
AllCCS[M+NH4]+177.632859911
AllCCS[M+Na]+178.532859911
AllCCS[M-H]-178.532859911
AllCCS[M+Na-2H]-178.632859911
AllCCS[M+HCOO]-178.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dehydroepiandrosterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C2511.7Standard polar33892256
Dehydroepiandrosterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C2480.2Standard non polar33892256
Dehydroepiandrosterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C2617.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dehydroepiandrosterone,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2604.0Semi standard non polar33892256
Dehydroepiandrosterone,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2619.5Semi standard non polar33892256
Dehydroepiandrosterone,2TMS,isomer #1C[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)C2643.4Semi standard non polar33892256
Dehydroepiandrosterone,2TMS,isomer #1C[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)C2554.7Standard non polar33892256
Dehydroepiandrosterone,2TMS,isomer #1C[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)C2939.8Standard polar33892256
Dehydroepiandrosterone,1TBDMS,isomer #1CC(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)C12860.0Semi standard non polar33892256
Dehydroepiandrosterone,1TBDMS,isomer #2CC(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@]12C2894.9Semi standard non polar33892256
Dehydroepiandrosterone,2TBDMS,isomer #1CC(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@]12C3170.3Semi standard non polar33892256
Dehydroepiandrosterone,2TBDMS,isomer #1CC(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@]12C2831.4Standard non polar33892256
Dehydroepiandrosterone,2TBDMS,isomer #1CC(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@]12C3188.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Dehydroepiandrosterone GC-MS (1 MEOX; 1 TMS)splash10-004i-4920000000-9dc14963a290268534b82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dehydroepiandrosterone GC-MS (1 TMS)splash10-004i-3910000000-2bbc760dbeb7f9f1ebfc2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dehydroepiandrosterone EI-B (Non-derivatized)splash10-0abi-1790000000-52f5e67bc4d1fab735612017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroepiandrosterone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-6940000000-948ad487c238d48aa9be2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-qTof , Positive-QTOFsplash10-022a-1229000000-5fc1bd40299ad859ad1c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOFsplash10-0fk9-0190000000-66ac82624767dc6821e52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOFsplash10-0w90-1690000000-b3a231fc509b7a34e09c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOFsplash10-08gj-1930000000-309dc082cc36ec9dcd8c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOFsplash10-06sj-2910000000-378638f2a861c948f79d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOFsplash10-0536-3900000000-72e80e1a07c4d3a40a7a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone LC-ESI-QFT , positive-QTOFsplash10-0036-4900000000-26c8272483a80d1b5eab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone , positive-QTOFsplash10-000i-0290000000-1a3588ca5d5bacb9ad302017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone , positive-QTOFsplash10-0bta-3920000000-2df257db43df6cc865702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone 90V, Positive-QTOFsplash10-0036-4900000000-a5988c20b9c2dcaaa0b02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone 75V, Positive-QTOFsplash10-0536-3900000000-9a88dec56cfcb5147a122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone 45V, Positive-QTOFsplash10-08gj-1930000000-7cae68c709391babec192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone 60V, Positive-QTOFsplash10-06sj-2910000000-370c122c31de467a2a1f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone 35V, Positive-QTOFsplash10-05d1-0930000000-890b3cea5a94fdd694582021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone 30V, Positive-QTOFsplash10-0w90-0690000000-cd7d0ebd514f0a8966d62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dehydroepiandrosterone 15V, Positive-QTOFsplash10-0fk9-0190000000-8d6dc67ca77600c3affa2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroepiandrosterone 10V, Positive-QTOFsplash10-00dr-0090000000-89da8cb383a0718d90332016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroepiandrosterone 20V, Positive-QTOFsplash10-00dr-0390000000-e6efd70cef2520255bf52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroepiandrosterone 40V, Positive-QTOFsplash10-0udm-4690000000-e304b251e97b02f672ad2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroepiandrosterone 10V, Positive-QTOFsplash10-00dr-0090000000-89da8cb383a0718d90332016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroepiandrosterone 20V, Positive-QTOFsplash10-00dr-0390000000-e6efd70cef2520255bf52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroepiandrosterone 40V, Positive-QTOFsplash10-0udm-4690000000-e304b251e97b02f672ad2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroepiandrosterone 10V, Negative-QTOFsplash10-000i-0090000000-7498c93972acc3c164042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroepiandrosterone 20V, Negative-QTOFsplash10-000i-0090000000-d3ddffc56e91bed39fc42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroepiandrosterone 40V, Negative-QTOFsplash10-052f-2190000000-15aba54ba135047ffe9a2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2018-06-19Wishart LabView 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
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00173-0.0264 uMNewborn (0-30 days old)Female
Normal
details
BloodDetected and Quantified0.00225-0.0433 uMNewborn (0-30 days old)Female
Normal
details
BloodDetected and Quantified0.020 +/- 0.011 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0153 +/- 0.00763 uMAdult (>18 years old)FemaleNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.001 (0.00034-0.0017) uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified0.0087 (0.0035-0.013) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0146 +/- 0.00451 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.023 (0.005-0.042) uMAdult (>18 years old)BothNormal
    • The Merck Manual,...
details
BloodDetected and Quantified0.000700-0.0204 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified0.00295 +/- 0.00319 uMChildren (1-13 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00101 (0.00002-0.002) uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified0.0033 (0.0024-0.0090) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0022 (0.0006-0.0273) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified0.10 (0.066-0.17) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.022 (0.017-0.041) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.13 +/- 0.057 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0016 +/- 0.00026 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00250-0.00284 uMAdult (>18 years old)Female21-hydroxylase deficiency details
BloodDetected and Quantified0.0103 +/- 0.0100 uMNewborn (0-30 days old)Not Specified
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.00520 +/- 0.00740 uMChildren (1-13 years old)Not Specified
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.052 uMAdult (>18 years old)Male
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.653 uMAdolescent (13-18 years old)Male
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.00157-0.385 uMChildren (1-13 years old)Both
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.0226-0.407 uMNewborn (0-30 days old)Both
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.00150 +/- 0.00120 uMChildren (1-13 years old)BothAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.0120 +/- 0.00700 uMAdult (>18 years old)MaleAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.0140 +/- 0.00700 uMAdult (>18 years old)FemaleAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.00800 +/- 0.0100 uMInfant (0-1 year old)Not SpecifiedAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified<0.00003 uMAdult (>18 years old)FemaleLipoid Adrenal Hyperplasia details
BloodDetected and Quantified<0.00003 uMAdolescent (13-18 years old)FemaleLipoid Adrenal Hyperplasia details
BloodDetected and Quantified0.0184-0.0333 uMAdult (>18 years old)Female
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.00240-0.00830 uMInfant (0-1 year old)Both
Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis
details
BloodDetected and Quantified0.0016 uMChildren (1-13 years old)Female
Aromatase deficiency
details
BloodDetected and Quantified0.0448 +/- 0.0655 uMChildren (1-13 years old)Both
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.00246 +/- 0.00350 uMChildren (1-13 years old)Both
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.00101 uMNewborn (0-30 days old)Female
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
details
BloodDetected and Quantified0.0042 uMNewborn (0-30 days old)Female
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00114 +/- 0.000630 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00127 +/- 0.00128 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism with testosterone replacment details
UrineDetected and Quantified0.00032 +/- 0.000065 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
UrineDetected and Quantified0.00066 +/- 0.00021 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
UrineDetected and Quantified0.00034 +/- 0.000078 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
UrineDetected and Quantified0.0011 +/- 0.00026 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
Associated Disorders and Diseases
Disease References
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
  1. 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 ]
  2. 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 ]
  3. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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)
DrugBank IDDB01708
Phenol Explorer Compound IDNot Available
FooDB IDFDB021808
KNApSAcK IDNot Available
Chemspider ID8036443
KEGG Compound IDC01227
BioCyc ID3-BETA-HYDROXYANDROST-5-EN-17-ONE
BiGG ID37131
Wikipedia LinkDehydroepiandrosterone
METLIN ID5133
PubChem Compound5881
PDB IDNot Available
ChEBI ID28689
Food Biomarker OntologyNot Available
VMH IDDHEA
MarkerDB IDMDB00000041
Good Scents IDNot Available
References
Synthesis ReferenceNguyen 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)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. Finlay EM, Morton MS, Gaskell SJ: Identification and quantification of dehydroepiandrosterone sulphate in saliva. Steroids. 1982 Jan;39(1):63-71. [PubMed:6210977 ]
  9. 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 ]
  10. 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 ]
  11. Friess E, Schiffelholz T, Steckler T, Steiger A: Dehydroepiandrosterone--a neurosteroid. Eur J Clin Invest. 2000 Dec;30 Suppl 3:46-50. [PubMed:11281367 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  19. 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 ]
  20. 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 ]
  21. 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 ]
  22. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

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 sulfatedetails
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 gumdetails
Dehydroepiandrosterone sulfate + Water → Dehydroepiandrosterone + Oat gumdetails
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 + Waterdetails
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 + Waterdetails
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 Iondetails
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 Iondetails

Transporters

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
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
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