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Showing Compound 16alpha-Hydroxyandrost-4-ene-3,17-dione (FDB024076)

Record Information
Version1.0
Creation date2011-09-21 00:39:30 UTC
Update date2015-07-21 06:57:59 UTC
Primary IDFDB024076
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name16alpha-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 lipid molecule. 16a-Hydroxyandrost-4-ene-3,17-dione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number63-02-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
4-Androsten-16alpha-ol-3,17-dioneChEBI
4-Androsten-16a-ol-3,17-dioneGenerator
4-Androsten-16α-ol-3,17-dioneGenerator
16alpha-Hydroxyandrost-4-ene-3,17-dioneHMDB
16alpha-HydroxyandrostenedioneHMDB
16-Hydroxyandrost-4-en-3,17-dioneHMDB
16 alpha-Hydroxyandrost-4-en-3,17-dioneHMDB
16-Hydroxyandrost-4-en-3,17-dione, (16alpha)-isomerHMDB
16-Hydroxyandrost-4-en-3,17-dione, (16beta)-isomerHMDB
16alpha-OHADHMDB
16a-Hydroxyandrost-4-ene-3,17-dioneGenerator
16Α-hydroxyandrost-4-ene-3,17-dioneGenerator
16α-hydroxyandrost-4-ene-3,17-dioneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.067 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H26O3
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight302.4079
Monoisotopic Molecular Weight302.188194698
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-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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS16alpha-Hydroxyandrost-4-ene-3,17-dione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-0190000000-333d436ce8b783dec900Spectrum
Predicted GC-MS16alpha-Hydroxyandrost-4-ene-3,17-dione, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ldj-1029000000-d779bb8112f47f4675a3Spectrum
Predicted GC-MS16alpha-Hydroxyandrost-4-ene-3,17-dione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyandrost-4-ene-3,17-dione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0169000000-552881f7e148e949c2d52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fi9-0191000000-5bba772cd2498247059b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldl-3390000000-dcf95e7ad7d31a7b23452017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-0e8dc36bc54906d11cd22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0029000000-e08d062d1b3fb4e552672017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bo-1090000000-86e6dcdcc4e4babac09e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0049000000-79630e98940a556508ff2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114s-0972000000-fef31191241a5fee6d7a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r7-1910000000-e9b6c3405a956f7823012021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-4360bacaf95498925fe52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0039000000-479f11c50b787985f7d52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0091000000-9edb0c3dd24f9aa0965b2021-09-23View Spectrum
NMRNot Available
ChemSpider ID389474
ChEMBL IDCHEMBL1908014
KEGG Compound IDC05140
Pubchem Compound ID440574
Pubchem Substance IDNot Available
ChEBI ID27582
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06774
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
FoodReference
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