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Record Information
Version1.0
Creation Date2016-09-30 22:18:41 UTC
Update Date2020-03-18 18:12:23 UTC
BMDB IDBMDB0000031
Secondary Accession Numbers
  • BMDB00031
Metabolite Identification
Common NameAndrosterone
DescriptionAndrosterone, also known as androkinine or atromide ici, 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, androsterone is considered to be a steroid lipid molecule. Androsterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
(3alpha,5alpha)-3-Hydroxyandrostan-17-oneChEBI
3-Epihydroxyetioallocholan-17-oneChEBI
3alpha-Hydroxy-5alpha-androstan-17-oneChEBI
3alpha-Hydroxyetioallocholan-17-oneChEBI
5alpha-Androstane-3alpha-ol-17-oneChEBI
5alpha-AndrosteroneChEBI
AndrokinineChEBI
AndrotineChEBI
cis-AndrosteroneChEBI
(3a,5a)-3-Hydroxyandrostan-17-oneGenerator
(3Α,5α)-3-hydroxyandrostan-17-oneGenerator
3a-Hydroxy-5a-androstan-17-oneGenerator
3Α-hydroxy-5α-androstan-17-oneGenerator
3a-Hydroxyetioallocholan-17-oneGenerator
3Α-hydroxyetioallocholan-17-oneGenerator
5a-Androstane-3a-ol-17-oneGenerator
5Α-androstane-3α-ol-17-oneGenerator
5a-AndrosteroneGenerator
5Α-androsteroneGenerator
3-alpha-Hydroxy-5-alpha-androstan-17-oneHMDB
3 alpha Hydroxy 5 alpha androstan 17 oneHMDB
5 alpha Androstan 3 alpha ol 17 oneHMDB
5 alpha-Androstan-3 alpha-ol-17-oneHMDB
EpiandrosteroneHMDB
3-alpha-Hydroxy-17-androstanoneHMDB
3-alpha-Hydroxy-5-alpha-androstane-17-oneHMDB
3-alpha-Hydroxy-5alpha-androstan-17-oneHMDB
3-alpha-Hydroxyetioallocholan-17-oneHMDB
3-Hydroxy-(3-alpha,5-alpha)-androstan-17-oneHMDB
3-Hydroxyandrostan-17-oneHMDB
3alpha-Hydroxy-17-androstanoneHMDB
5-alpha-Androstan-3-alpha-ol-17-oneHMDB
5-alpha-Androstane-3alpha-ol-17-oneHMDB
5-alpha-AndrosteroneHMDB
Androstanon-3-alpha-ol-17-oneHMDB
Atromide iciHMDB
3Α-hydroxy-17-androstanoneHMDB
3Α-hydroxy-5α-androstane-17-oneHMDB
5Α-androstan-17-one-3α-olHMDB
5Α-androstan-3α-ol-17-oneHMDB
3alpha-Hydroxy-5alpha-androstane-17-oneHMDB
5alpha-Androstan-17-one-3alpha-olHMDB
5alpha-Androstan-3alpha-ol-17-oneHMDB
AndrosteroneHMDB
Chemical FormulaC19H30O2
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
IUPAC Name(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
Traditional Name(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
CAS Registry Number481-29-8
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1
InChI KeyQGXBDMJGAMFCBF-HLUDHZFRSA-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-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.71ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.81 m³·mol⁻¹ChemAxon
Polarizability34.56 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-056u-6920000000-1d886b76fe1f65860afbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-00al-9820000000-321baddda5ac4f8adaa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0090000000-42eb8c941695a061666dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0290000000-1a37c17eb6ea7be9211cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06u7-2790000000-d6e7cebd4af538181f77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-9e9f9de3b33af0311acdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-5ba62f51f815ded16002View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-2190000000-513ad65531fff88b9f69View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Intestine
  • Most Tissues
  • Primarily Liver
  • Prostate
  • Testes
PathwaysNot Available
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 IDFDB021881
KNApSAcK IDNot Available
Chemspider ID5668
KEGG Compound IDC00523
BioCyc IDNot Available
BiGG ID35244
Wikipedia LinkAndrosterone
METLIN ID2797
PubChem Compound5879
PDB IDNot Available
ChEBI ID16032
References
Synthesis ReferenceMarker, Russell E. Androsterone. Journal of the American Chemical Society (1935), 57 1755-6.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available