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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:14:47 UTC
Update Date2022-03-07 02:54:05 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-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 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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140 - 141 °CNot Available
Boiling Point371.00 to 372.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility3.16 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.568 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-197.56230932474
DeepCCS[M+Na]+173.03130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5alpha-Androst-16-en-3-one[H][C@@]12CC=C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C2165.3Standard polar33892256
5alpha-Androst-16-en-3-one[H][C@@]12CC=C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C2270.3Standard non polar33892256
5alpha-Androst-16-en-3-one[H][C@@]12CC=C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C2320.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5alpha-Androst-16-en-3-one,1TMS,isomer #1C[C@@]12C=CC[C@H]1[C@@H]1CC[C@H]3CC(O[Si](C)(C)C)=CC[C@]3(C)[C@H]1CC22386.6Semi standard non polar33892256
5alpha-Androst-16-en-3-one,1TMS,isomer #1C[C@@]12C=CC[C@H]1[C@@H]1CC[C@H]3CC(O[Si](C)(C)C)=CC[C@]3(C)[C@H]1CC22204.9Standard non polar33892256
5alpha-Androst-16-en-3-one,1TMS,isomer #2C[C@@]12C=CC[C@H]1[C@@H]1CC[C@H]3C=C(O[Si](C)(C)C)CC[C@]3(C)[C@H]1CC22375.0Semi standard non polar33892256
5alpha-Androst-16-en-3-one,1TMS,isomer #2C[C@@]12C=CC[C@H]1[C@@H]1CC[C@H]3C=C(O[Si](C)(C)C)CC[C@]3(C)[C@H]1CC22232.3Standard non polar33892256
5alpha-Androst-16-en-3-one,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC=C[C@@]4(C)CC[C@@H]32)C12642.4Semi standard non polar33892256
5alpha-Androst-16-en-3-one,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC=C[C@@]4(C)CC[C@@H]32)C12405.0Standard non polar33892256
5alpha-Androst-16-en-3-one,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC=C[C@@]4(C)CC[C@@H]3[C@@]2(C)CC12621.1Semi standard non polar33892256
5alpha-Androst-16-en-3-one,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC=C[C@@]4(C)CC[C@@H]3[C@@]2(C)CC12440.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androst-16-en-3-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 10V, Positive-QTOFsplash10-00di-0190000000-de4dfd97d926ab07b89b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 20V, Positive-QTOFsplash10-05fr-1290000000-6f5b179317e592e831742016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 40V, Positive-QTOFsplash10-1029-3590000000-72a108ce86fc26b6dd662016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 10V, Negative-QTOFsplash10-00di-0090000000-aa03a22349c3b98dd5ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 20V, Negative-QTOFsplash10-00di-0090000000-767700b9189fcf71f4da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 40V, Negative-QTOFsplash10-052f-4190000000-9f20045d168687f5cc802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 10V, Negative-QTOFsplash10-00di-0090000000-c4728b358ec3c0d7d18c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 20V, Negative-QTOFsplash10-00di-0090000000-c4728b358ec3c0d7d18c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 40V, Negative-QTOFsplash10-00xr-0090000000-41f1062cc2af3d0c4a1e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 10V, Positive-QTOFsplash10-00di-0090000000-b64fbd7855590abc7a522021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 20V, Positive-QTOFsplash10-06xt-1960000000-db209cc7fc98d53c0afb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androst-16-en-3-one 40V, Positive-QTOFsplash10-0059-6900000000-2ff94cac50baf33126d12021-09-25Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1211791
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.