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Showing Compound 7b-Hydroxydehydroepiandrosterone (FDB023384)

Record Information
Version1.0
Creation date2011-09-21 00:29:07 UTC
Update date2015-07-21 06:57:40 UTC
Primary IDFDB023384
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number2487-48-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted 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
Chemical FormulaC19H28O3
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS7b-Hydroxydehydroepiandrosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03g0-0390000000-5b84fc74cc8c3d885c1bSpectrum
Predicted GC-MS7b-Hydroxydehydroepiandrosterone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-1735900000-cde53af4934fd251f9d9Spectrum
Predicted GC-MS7b-Hydroxydehydroepiandrosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0092000000-003d307a3c381597e38b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0190000000-7563041720b7687053892017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-3190000000-8012f9fad41969d73d462017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-3459db2d82d83321802f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0098000000-6a1aaf578c3c1719798a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-2090000000-85d4a8001358a115f59b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-93986d59045cc7fce5512021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-8b3060136e49afe5a3362021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy0-0093000000-e42b11a1c3c059294db32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0069000000-61a09d88b13611d21a892021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-1981000000-b0f1410f207bdaec9fa12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05dl-3910000000-4b2efd9d887548375fc02021-09-24View Spectrum
NMRNot Available
ChemSpider ID7993704
ChEMBL IDCHEMBL1082098
KEGG Compound IDNot Available
Pubchem Compound ID9817954
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04624
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference