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Record Information
Version2.0
Created at2020-11-23 19:40:22 UTC
Updated at2021-08-12 19:52:08 UTC
NP-MRD IDNP0002785
Secondary Accession NumbersNone
Natural Product Identification
Common NameAndrosterone
Provided ByBMRBBMRB logo
DescriptionAndrosterone, also known as androkinine, 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. Androsterone exists in all living organisms, ranging from bacteria to humans. In humans, androsterone is involved in the androstenedione metabolism pathway. Androsterone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Androsterone is found in Homo sapiens, Mus musculus and Streptomyces nigra. It was first documented in 1979 (PMID: 158859). Based on a literature review a significant number of articles have been published on Androsterone (PMID: 10625505) (PMID: 17984079) (PMID: 3802509) (PMID: 6211346).
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-oneMeSH, HMDB
3 alpha Hydroxy 5 alpha androstan 17 oneMeSH, HMDB
5 alpha Androstan 3 alpha ol 17 oneMeSH, HMDB
5 alpha-Androstan-3 alpha-ol-17-oneMeSH, HMDB
EpiandrosteroneMeSH, HMDB
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
AndrosteroneHMDB
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-oneGenerator, HMDB
5alpha-Androstan-17-one-3alpha-olGenerator, HMDB
5alpha-Androstan-3alpha-ol-17-oneGenerator, HMDB
Chemical FormulaC19H30O2
Average Mass290.4403 Da
Monoisotopic Mass290.22458 Da
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 NumberNot Available
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, acetone, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, acetone, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, acetone, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Streptomyces nigraLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
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
HMDB IDHMDB0000031
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021881
KNApSAcK IDNot Available
Chemspider ID5668
KEGG Compound IDC00523
BioCyc IDANDROSTERONE
BiGG ID35244
Wikipedia LinkAndrosterone
METLIN ID2797
PubChem Compound5879
PDB IDNot Available
ChEBI ID16032
Good Scents IDNot Available
References
General References
  1. Kim YS, Zhang H, Kim HY: Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. Anal Biochem. 2000 Jan 15;277(2):187-95. [PubMed:10625505 ]
  2. Muller L, Phillipou G: Quantification of 5 alpha- and 5 beta-androstanediols in urine by gas chromatography-mass spectrometry. Clin Chem. 1987 Feb;33(2 Pt 1):256-60. [PubMed:3802509 ]
  3. Schonberger W, Benes P, Morsches B, Zabel B, Scheidt E: [Improvement in the longitudinal growth in Ullrich-Turner syndrome with oxandrolone. Function of urinary excretion of steroid hormones]. Dtsch Med Wochenschr. 1982 Jul 2;107(26):1008-11. doi: 10.1055/s-2008-1070063. [PubMed:6211346 ]
  4. Labows JN, Preti G, Hoelzle E, Leyden J, Kligman A: Steroid analysis of human apocrine secretion. Steroids. 1979 Sep;34(3):249-58. doi: 10.1016/0039-128x(79)90077-1. [PubMed:158859 ]