Showing metabocard for Dehydroandrosterone (BMDB0005962)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:19:24 UTC
Update Date2020-04-22 15:16:36 UTC
BMDB IDBMDB0005962
Secondary Accession Numbers
  • BMDB05962
Metabolite Identification
Common NameDehydroandrosterone
DescriptionDehydroandrosterone 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, dehydroandrosterone is considered to be a steroid. Based on a literature review a small amount of articles have been published on Dehydroandrosterone.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3a-Hydroxy-5-androsten-17-oneHMDB
3a-Hydroxy-androst-5-en-17-oneHMDB
Androst-5-en-3a-ol-17-oneHMDB
D5-Androstene-3a-ol-17-oneHMDB
IsoandrostenoloneHMDB
AndrostenoloneMeSH, HMDB
DehydroisoandrosteroneMeSH, HMDB
5 Androsten 3 beta hydroxy 17 oneMeSH, HMDB
5 Androsten 3 ol 17 oneMeSH, HMDB
5-Androsten-3-ol-17-oneMeSH, HMDB
DHEAMeSH, HMDB
DehydroepiandrosteroneMeSH, HMDB
5-Androsten-3-beta-hydroxy-17-oneMeSH, HMDB
PrasteroneMeSH, HMDB
Prasterone, 3 alpha isomerMeSH, HMDB
Prasterone, 3 alpha-isomerMeSH, HMDB
Chemical FormulaC19H28O2
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
IUPAC Name(1S,2R,5R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one
Traditional Namedehydroandrosterone
CAS Registry Number2283-82-1
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+/m1/s1
InChI KeyFMGSKLZLMKYGDP-HKQXQEGQSA-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-alpha-hydroxysteroid
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 - 150 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability33.96 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, Positivesplash10-08pl-0290000000-e7c57e64082ba630bb86View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001m-1069000000-c5bd759bc6149ac932eaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0090000000-a667a243a4d1f4d5e402View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0290000000-03f40d327c70daf5361aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-3590000000-254aaa59cce970705502View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-8b01497a25c81d375b42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-41c2d6ae909fbc17a1bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-2090000000-5e1c69e4cc1018242a56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0090000000-4960bda663b1d44029e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-72a131a47792264b8104View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ds-0960000000-d3247804f790527b1237View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-327ab298a3612249a230View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0005962
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023792
KNApSAcK IDNot Available
Chemspider ID118560
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDehydroepiandrosterone
METLIN IDNot Available
PubChem Compound134506
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceButenandt, Adolf; Dannenbaum, Hans; Hanisch, Gunter; Kudszus, Helmut. Dehydroandrosterone. Z. physiol. Chem. (1935), 237 57-74.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available