Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 22:31:57 UTC
Update Date2022-09-22 18:34:18 UTC
HMDB IDHMDB0004624
Secondary Accession Numbers
  • HMDB04624
Metabolite Identification
Common Name7b-Hydroxydehydroepiandrosterone
Description7b-Hydroxydehydroepiandrosterone is one of the major metabolites of dehydroepiandrosterone. Dehydroepiandrosterone (DHEA) is a precursor of testosterone. DHEA) is 7a-hydroxylated by the cytochrome P450 7B1 (CYP7B1) in the human brain and liver. This produces 7a-hydroxy-DHEA that is a substrate for 11b-hydroxysteroid dehydrogenase type 1 (11b-HSD1) which exists in the same tissues and carries out the inter-conversion of 7a- and 7b-hydroxy-DHEA through a 7-oxo-intermediary. Both 7a-hydroxy-DHEA and 7b-hydroxy-DHEA competitively inhibited the cortisol oxidation, 7b-hydroxy-DHEA being seven times more potent in humans. Distinct species-specific routes of metabolism of DHEA and the interconversion of its metabolites obviate extrapolation of animal studies to humans. (PMID: 17467270 , 12667489 ).
Structure
Data?1582752309
Synonyms
ValueSource
(3b,7b)-3,7-Dihydroxy-androst-5-en-17-oneHMDB
3b,7b-Dihydroxy-5-androsten-17-oneHMDB
3b,7b-Dihydroxy-5-androstene-17-oneHMDB
3b,7b-Dihydroxy-androst-5-en-17-oneHMDB
3b,7b-Dihydroxy-ost-5-en-17-oneHMDB
7-b-OH-DHEAHMDB
7-beta-OH-DHEAHMDB
7b-Hydroxy dehydroepiandrosteroneHMDB
7b-Hydroxy-dheaHMDB
Androst-5-ene-3b,7b-diol-17-oneHMDB
7-Hydroxydehydroepiandrosterone, (3beta)-isomerMeSH, HMDB
7beta-OH-DHEAMeSH, HMDB
7beta-HydroxydehydroepiandrosteroneMeSH, HMDB
7 alpha-HydroxydehydroepiandrosteroneMeSH, HMDB
7-Hydroxydehydroepiandrosterone, (3beta,7beta)-isomerMeSH, HMDB
7-HydroxydehydroepiandrosteroneMeSH, HMDB
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(1S,2R,5S,9R,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one
Traditional Name7b-Hydroxy-DHEA
CAS Registry Number2487-48-1
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)C=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15-,17-,18-,19-/m0/s1
InChI KeyOLPSAOWBSPXZEA-GCNMQWDSSA-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
  • 7-hydroxysteroid
  • 7-alpha-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
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point213 - 215 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.84ALOGPS
logP2.21ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.1 m³·mol⁻¹ChemAxon
Polarizability35 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.65431661259
DarkChem[M-H]-165.6931661259
DeepCCS[M-2H]-206.4730932474
DeepCCS[M+Na]+181.17330932474
AllCCS[M+H]+177.432859911
AllCCS[M+H-H2O]+174.432859911
AllCCS[M+NH4]+180.232859911
AllCCS[M+Na]+181.032859911
AllCCS[M-H]-180.532859911
AllCCS[M+Na-2H]-180.632859911
AllCCS[M+HCOO]-180.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7b-Hydroxydehydroepiandrosterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)C=C2C[C@@H](O)CC[C@]12C2704.9Standard polar33892256
7b-Hydroxydehydroepiandrosterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)C=C2C[C@@H](O)CC[C@]12C2693.3Standard non polar33892256
7b-Hydroxydehydroepiandrosterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)C=C2C[C@@H](O)CC[C@]12C2823.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7b-Hydroxydehydroepiandrosterone,1TMS,isomer #1C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)[C@@H](O[Si](C)(C)C)C=C1C[C@@H](O)CC[C@@]13C2735.6Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,1TMS,isomer #2C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)[C@@H](O)C=C1C[C@@H](O[Si](C)(C)C)CC[C@@]13C2723.8Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,1TMS,isomer #3C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2O[Si](C)(C)C)[C@@H](O)C=C1C[C@@H](O)CC[C@@]13C2702.2Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,2TMS,isomer #1C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)[C@@H](O[Si](C)(C)C)C=C1C[C@@H](O[Si](C)(C)C)CC[C@@]13C2689.5Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,2TMS,isomer #2C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=C1C[C@@H](O)CC[C@@]13C2731.3Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,2TMS,isomer #3C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2O[Si](C)(C)C)[C@@H](O)C=C1C[C@@H](O[Si](C)(C)C)CC[C@@]13C2717.5Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,3TMS,isomer #1C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=C1C[C@@H](O[Si](C)(C)C)CC[C@@]13C2673.4Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,3TMS,isomer #1C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=C1C[C@@H](O[Si](C)(C)C)CC[C@@]13C2714.7Standard non polar33892256
7b-Hydroxydehydroepiandrosterone,3TMS,isomer #1C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=C1C[C@@H](O[Si](C)(C)C)CC[C@@]13C2967.2Standard polar33892256
7b-Hydroxydehydroepiandrosterone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C=C2C[C@@H](O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@@H]212993.6Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=C[C@H](O)[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C12993.5Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=C[C@@H]3O2994.4Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C13211.5Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=C[C@@H]3O[Si](C)(C)C(C)(C)C3278.4Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)CC1=C[C@@H]3O3249.1Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)CC1=C[C@@H]3O[Si](C)(C)C(C)(C)C3385.4Semi standard non polar33892256
7b-Hydroxydehydroepiandrosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)CC1=C[C@@H]3O[Si](C)(C)C(C)(C)C3106.5Standard non polar33892256
7b-Hydroxydehydroepiandrosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)CC1=C[C@@H]3O[Si](C)(C)C(C)(C)C3264.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7b-Hydroxydehydroepiandrosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g0-0390000000-5b84fc74cc8c3d885c1b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7b-Hydroxydehydroepiandrosterone GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1735900000-cde53af4934fd251f9d92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7b-Hydroxydehydroepiandrosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 10V, Positive-QTOFsplash10-00kr-0092000000-003d307a3c381597e38b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 20V, Positive-QTOFsplash10-0ap0-0190000000-7563041720b7687053892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 40V, Positive-QTOFsplash10-0a6u-3190000000-8012f9fad41969d73d462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 10V, Negative-QTOFsplash10-0udi-0049000000-3459db2d82d83321802f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 20V, Negative-QTOFsplash10-0udr-0098000000-6a1aaf578c3c1719798a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 40V, Negative-QTOFsplash10-059f-2090000000-85d4a8001358a115f59b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 10V, Negative-QTOFsplash10-0udi-0009000000-93986d59045cc7fce5512021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 20V, Negative-QTOFsplash10-0udi-0019000000-8b3060136e49afe5a3362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 40V, Negative-QTOFsplash10-0uy0-0093000000-e42b11a1c3c059294db32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 10V, Positive-QTOFsplash10-0a4i-0069000000-61a09d88b13611d21a892021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 20V, Positive-QTOFsplash10-0670-1981000000-b0f1410f207bdaec9fa12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7b-Hydroxydehydroepiandrosterone 40V, Positive-QTOFsplash10-05dl-3910000000-4b2efd9d887548375fc02021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023384
KNApSAcK IDNot Available
Chemspider ID7993704
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9817954
PDB IDNot Available
ChEBI ID712193
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferencePouzar, Vladimir; Slavikova, Tereza; Cerny, Ivan. On Steroids. 387. Synthesis of (19E)-3b,7b-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, new hapten for 7b-hydroxydehydroepiandrosterone (3b,7b-dihydroxyandrost-5-en-17-one). Collection of Czechoslovak Chemical Communications (1997), 62(1), 109-123.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hennebert O, Chalbot S, Alran S, Morfin R: Dehydroepiandrosterone 7alpha-hydroxylation in human tissues: possible interference with type 1 11beta-hydroxysteroid dehydrogenase-mediated processes. J Steroid Biochem Mol Biol. 2007 May;104(3-5):326-33. Epub 2007 Mar 24. [PubMed:17467270 ]
  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 ]