Showing metabocard for 7b-Hydroxydehydroepiandrosterone (BMDB0004624)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:50 UTC
Update Date2020-04-22 15:13:54 UTC
BMDB IDBMDB0004624
Secondary Accession Numbers
  • BMDB04624
Metabolite Identification
Common Name7b-Hydroxydehydroepiandrosterone
Description7b-Hydroxydehydroepiandrosterone 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. Thus, 7b-hydroxydehydroepiandrosterone is considered to be a steroid. Based on a literature review very few articles have been published on 7b-Hydroxydehydroepiandrosterone.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point213 - 215 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g0-0390000000-5b84fc74cc8c3d885c1bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1735900000-cde53af4934fd251f9d9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0092000000-003d307a3c381597e38bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0190000000-7563041720b768705389View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-3190000000-8012f9fad41969d73d46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-3459db2d82d83321802fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0098000000-6a1aaf578c3c1719798aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-2090000000-85d4a8001358a115f59bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-93986d59045cc7fce551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-8b3060136e49afe5a336View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy0-0093000000-e42b11a1c3c059294db3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0069000000-61a09d88b13611d21a89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-1981000000-b0f1410f207bdaec9fa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05dl-3910000000-4b2efd9d887548375fc0View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004624
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
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 ReferencesNot Available