Showing metabocard for 16a-Hydroxyandrost-4-ene-3,17-dione (BMDB0006774)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:56 UTC
Update Date2020-04-22 15:18:34 UTC
BMDB IDBMDB0006774
Secondary Accession Numbers
  • BMDB06774
Metabolite Identification
Common Name16a-Hydroxyandrost-4-ene-3,17-dione
Description16a-Hydroxyandrost-4-ene-3,17-dione, also known as 4-androsten-16alpha-ol-3,17-dione or 16alpha-ohad, 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, 16a-hydroxyandrost-4-ene-3,17-dione is considered to be a steroid. Based on a literature review a significant number of articles have been published on 16a-Hydroxyandrost-4-ene-3,17-dione.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-Androsten-16alpha-ol-3,17-dioneChEBI
4-Androsten-16a-ol-3,17-dioneGenerator
4-Androsten-16α-ol-3,17-dioneGenerator
16 alpha-Hydroxyandrost-4-en-3,17-dioneMeSH
16-Hydroxyandrost-4-en-3,17-dioneMeSH
16-Hydroxyandrost-4-en-3,17-dione, (16alpha)-isomerMeSH
16-Hydroxyandrost-4-en-3,17-dione, (16beta)-isomerMeSH
16alpha-OHADMeSH
16alpha-Hydroxyandrost-4-ene-3,17-dioneHMDB
16alpha-HydroxyandrostenedioneMeSH, HMDB
16a-Hydroxyandrost-4-ene-3,17-dioneGenerator
16Α-hydroxyandrost-4-ene-3,17-dioneGenerator
Chemical FormulaC19H26O3
Average Molecular Weight302.4079
Monoisotopic Molecular Weight302.188194698
IUPAC Name(1S,2R,10R,11S,13R,15S)-13-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione
Traditional Name4-androsten-16α-ol-3,17-dione
CAS Registry Number63-02-5
SMILES
[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H26O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h9,13-16,21H,3-8,10H2,1-2H3/t13-,14+,15+,16-,18+,19+/m1/s1
InChI KeySSBCZTXGVMMZOT-NBBHSKLNSA-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-oxo-delta-4-steroid
  • 3-oxosteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.32ALOGPS
logP3.06ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)13.38ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.1 m³·mol⁻¹ChemAxon
Polarizability33.99 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, Positivesplash10-006x-0190000000-333d436ce8b783dec900View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ldj-1029000000-d779bb8112f47f4675a3View 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, Positivesplash10-0udi-0169000000-552881f7e148e949c2d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fi9-0191000000-5bba772cd2498247059bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldl-3390000000-dcf95e7ad7d31a7b2345View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-0e8dc36bc54906d11cd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0029000000-e08d062d1b3fb4e55267View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bo-1090000000-86e6dcdcc4e4babac09eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0049000000-79630e98940a556508ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114s-0972000000-fef31191241a5fee6d7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r7-1910000000-e9b6c3405a956f782301View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-4360bacaf95498925fe5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0039000000-479f11c50b787985f7d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0091000000-9edb0c3dd24f9aa0965bView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006774
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024076
KNApSAcK IDNot Available
Chemspider ID389474
KEGG Compound IDC05140
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440574
PDB IDNot Available
ChEBI ID27582
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available