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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:14:47 UTC
Update Date2020-05-13 16:19:11 UTC
HMDB IDHMDB0034406
Secondary Accession Numbers
  • HMDB34406
Metabolite Identification
Common Name5alpha-Androst-16-en-3-one
Description5alpha-Androst-16-en-3-one, also known as androstenone, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favour the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, 5alpha-androst-16-en-3-one is considered to be a steroid lipid molecule. 5alpha-androst-16-en-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5alpha-Androst-16-en-3-one is found in animal foods and causes boar taint in pigmeat product.
Structure
Data?1589386751
Synonyms
ValueSource
AndrostenoneChEBI
5a-Androst-16-en-3-oneGenerator
5Α-androst-16-en-3-oneGenerator
Androst-16-en-3-oneMeSH
5 alpha-Androst-16-en-3-oneMeSH
AEON steroidMeSH
Androst-16-en-3-one, (5beta)-isomerMeSH
(5alpha)-Androst-16-en-3-oneHMDB
(5α)-Androst-16-en-3-oneHMDB
16,(5alpha)-Androsten-3-oneHMDB
16,(5α)-Androsten-3-oneHMDB
5alpha-Androst-16-en-3-oneHMDB
5alpha-Androst-16-ene-3-oneHMDB
5alpha-AndrostenoneHMDB
5α-Androst-16-ene-3-oneHMDB
5α-AndrostenoneHMDB
Chemical FormulaC19H28O
Average Molecular Weight272.432
Monoisotopic Molecular Weight272.214015522
IUPAC Name(1S,2S,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-one
Traditional Name(1S,2S,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-one
CAS Registry Number18339-16-7
SMILES
[H][C@@]12CC=C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13,15-17H,4-8,10-12H2,1-2H3/t13-,15-,16-,17-,18-,19-/m0/s1
InChI KeyHFVMLYAGWXSTQI-QYXZOKGRSA-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-5-alpha-steroid
  • Oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140 - 141 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00021 g/LALOGPS
logP4.62ALOGPS
logP4.28ChemAxon
logS-6.1ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.2 m³·mol⁻¹ChemAxon
Polarizability32.94 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-de4dfd97d926ab07b89bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-1290000000-6f5b179317e592e83174Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1029-3590000000-72a108ce86fc26b6dd66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-aa03a22349c3b98dd5ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-767700b9189fcf71f4daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-4190000000-9f20045d168687f5cc80Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012796
KNApSAcK IDNot Available
Chemspider ID5254715
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAndrostenone
METLIN IDNot Available
PubChem Compound6852393
PDB IDNot Available
ChEBI ID37894
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.