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5alpha-Androst-16-en-3-one (FDB012796)

Record Information
Version1.0
Creation date2010-04-08 22:10:22 UTC
Update date2019-11-26 03:07:37 UTC
Primary IDFDB012796
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5alpha-Androst-16-en-3-one
Description5alpha-Androst-16-en-3-one, also known as 3-keto-5alpha,16-androstene or androstenone, 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. 5alpha-Androst-16-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number18339-16-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not 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
Polarizability32.86 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H28O
IUPAC name2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-one
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
InChI KeyHFVMLYAGWXSTQI-UHFFFAOYSA-N
Isomeric SMILESCC12CCC3C(CCC4CC(=O)CCC34C)C1CC=C2
Average Molecular Weight272.425
Monoisotopic Molecular Weight272.214015518
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
  • 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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 83.77%; H 10.36%; O 5.87%DFC
Melting PointMp 140-141°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]17D +38 (c, 2.08 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5alpha-Androst-16-en-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-0290000000-c34aa5054883b3ad13e6Spectrum
Predicted GC-MS5alpha-Androst-16-en-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5alpha-Androst-16-en-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5alpha-Androst-16-en-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-574fd253156e121ac1442017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fs-1290000000-172e066e35f7e2baa99f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r1-3390000000-2d9bdf5fda43f59c87992017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-304bb54718cd6d863ae82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-32310c650985124416672017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-3090000000-e87d431cebc617fdf93d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-3a6e962fc715b278f2ef2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ac1-1690000000-5ae3fcb24c1f192a2d9a2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9500000000-8c58bc20cd3b71173cdf2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-c4728b358ec3c0d7d18c2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-c4728b358ec3c0d7d18c2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-0190000000-6f1fcb32aa48f1b823fd2021-10-12View Spectrum
NMRNot Available
ChemSpider ID78208
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID86705
Pubchem Substance IDNot Available
ChEBI ID37894
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34406
CRC / DFC (Dictionary of Food Compounds) IDHLQ23-G:HLD08-S
EAFUS IDNot Available
Dr. Duke ID5-ALPHA-ANDROST-16-EN-3-ONE
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 / Bioactivities
DescriptorIDDefinitionReference
pheromone26013 A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).