Showing metabocard for 7a-Hydroxydehydroepiandrosterone (BMDB0004611)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:47 UTC
Update Date2020-04-22 15:13:54 UTC
BMDB IDBMDB0004611
Secondary Accession Numbers
  • BMDB04611
Metabolite Identification
Common Name7a-Hydroxydehydroepiandrosterone
Description7a-Hydroxydehydroepiandrosterone, also known as 7alpha-OH-dhea or 3b,7a-dihydroxy-5-androstene-17-one, 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, 7a-hydroxydehydroepiandrosterone is considered to be a steroid. Based on a literature review a significant number of articles have been published on 7a-Hydroxydehydroepiandrosterone.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta,7alpha)-3,7-Dihydroxyandrost-5-en-17-oneChEBI
3beta,7alpha-Dihydroxy-5-androstene-17-oneChEBI
3beta,7alpha-Dihydroxyandrost-5-en-17-oneChEBI
7alpha-Hydroxy-dheaChEBI
7alpha-OH-DHEAChEBI
(3b,7a)-3,7-Dihydroxyandrost-5-en-17-oneGenerator
(3Β,7α)-3,7-dihydroxyandrost-5-en-17-oneGenerator
3b,7a-Dihydroxy-5-androstene-17-oneGenerator
3Β,7α-dihydroxy-5-androstene-17-oneGenerator
3b,7a-Dihydroxyandrost-5-en-17-oneGenerator
3Β,7α-dihydroxyandrost-5-en-17-oneGenerator
7a-Hydroxy-dheaGenerator
7Α-hydroxy-dheaGenerator
7a-OH-DHEAGenerator
7Α-OH-dheaGenerator
7-HydroxydehydroepiandrosteroneMeSH
7beta-HydroxydehydroepiandrosteroneMeSH
7-Hydroxydehydroepiandrosterone, (3beta)-isomerMeSH
7beta-OH-DHEAMeSH
7 alpha-HydroxydehydroepiandrosteroneMeSH
7-Hydroxydehydroepiandrosterone, (3beta,7beta)-isomerMeSH
(-)-7a-HydroxydehydroepiandrosteroneHMDB
(3b,7a)-3,7-Dihydroxy-androst-5-en-17-oneHMDB
3b,7a-Dihydroxy-5-androsten-17-oneHMDB
3b,7a-Dihydroxy-androst-5-en-17-oneHMDB
7-a-OH-DHEAHMDB
7-alpha-OH-DHEAHMDB
7a-HydroxydehydroisoandrosteroneHMDB
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(1S,2R,5S,9S,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one
Traditional Name7β-oh-dhea
CAS Registry Number53-00-9
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-JIEICEMKSA-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
  • 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 Point182 - 183 °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
Polarizability34.78 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, Positivesplash10-003r-5204900000-bdb069dd8202b45f9ea3View 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 IDHMDB0004611
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023382
KNApSAcK IDNot Available
Chemspider ID58963
KEGG Compound IDC18045
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link7alpha-Hydroxy-DHEA
METLIN IDNot Available
PubChem Compound65517
PDB IDNot Available
ChEBI ID712194
References
Synthesis ReferenceIshidate, Morizo; Okada, Masashi. Steroids. (1963), 2 pp. JP 38023170 19631031 Showa. CAN 60:12972 AN 1964:12972
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available