Androstenone (CHEM017625)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:30:08 UTC
Update Date2016-11-09 01:15:38 UTC
Accession NumberCHEM017625
Identification
Common NameAndrostenone
ClassSmall Molecule
DescriptionAn androstanoid that is 5alpha-androst-16-ene substituted by an oxo group at position 3. It is a steroid pheromone found in high concentrations in the saliva of male pigs,.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AndrostenoneChEBI
5a-Androst-16-en-3-oneGenerator
5Α-androst-16-en-3-oneGenerator
Androst-16-en-3-oneHMDB
5 alpha-Androst-16-en-3-oneHMDB
AEON steroidHMDB
Androst-16-en-3-one, (5beta)-isomerHMDB
(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-ene-3-oneHMDB
5alpha-AndrostenoneHMDB
5Α-androst-16-ene-3-oneHMDB
5Α-androstenoneHMDB
5alpha-Androst-16-en-3-oneHMDB
Chemical FormulaC19H28O
Average Molecular Mass272.432 g/mol
Monoisotopic Mass272.214 g/mol
CAS Registry Number18339-16-7
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-c4728b358ec3c0d7d18cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-c4728b358ec3c0d7d18cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-0090000000-41f1062cc2af3d0c4a1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-b64fbd7855590abc7a52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06xt-1960000000-db209cc7fc98d53c0afbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0059-6900000000-2ff94cac50baf33126d1Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034406
FooDB IDFDB012796
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAndrostenone
Chemspider ID5254715
ChEBI ID37894
PubChem Compound ID6852393
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14568564
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15013816
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18359508
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18684314
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21862238
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23611883
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24184511
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24239507
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=4462588
10. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
11. 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.
12. 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.
13. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
14. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
15. The lipid handbook with CD-ROM