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Showing Compound Androsterone (FDB021881)

Record Information
Version1.0
Creation date2011-09-21 00:04:27 UTC
Update date2015-10-09 22:30:01 UTC
Primary IDFDB021881
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAndrosterone
DescriptionAndrosterone is an inactive breakdown metabolite of testosterone, the product of a reaction mediated by the enzyme oxidative 17beta-hydroxysteroid dehydrogenase (EC 1.1.1.51, 17beta-HSD). Androsterone is also can be metabolized from other adrenal androgens such as dehydroepiandrosterone, dihydrotestosterone or androstenedione, and is considered an inactive end product; however, it can be a physiological effector in its own right. Androsterone might be converted back to dihydrotestosterone. Humans (and other primates) are unique among mammals in having high levels of circulating androsterone glucuronide, a process that is the major role uridine-diphospho-glucuronosyltransferase (EC 2.4.1.17, UGT) enzymes for glucuronidation of steroid metabolism in humans. Conjugation of androsterone is a pathway found in all vertebrates and is widely recognized that the liver is a major site of glucuronidation; however it is now clear that extrahepatic tissues are also involved in the conjugation of compounds to which these tissues are exposed. High levels of androsterone glucuronide found in the human prostate, breast cyst fluid and ovary follicular fluid suggest that glucuronidation of 5alpha-reduced C19 steroids occurs in these tissues as well. In doping control, the ratio of androsterone/etiocholanone provides valuable information that allows the assignment of a urine specimen to a particular person or the identification of urine samples with identical steroid profiles; this is particularly important to detect attempts of urine manipulation including urine alteration and substitution. (PMID: 9188497, 17017935, 14643063, 12943709, 9699884, 17260133) [HMDB]
CAS Number53-41-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3alpha,5alpha)-3-Hydroxy-androstan-17-oneHMDB
(3R,5S,8R,9S,10S,13S,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-oneHMDB
3-alpha-Hydroxy-17-androstanoneHMDB
3-alpha-Hydroxy-5-alpha-androstan-17-oneHMDB
3-alpha-Hydroxy-5-alpha-androstane-17-oneHMDB
3-alpha-Hydroxy-5alpha-androstan-17-oneHMDB
3-alpha-Hydroxyetioallocholan-17-oneHMDB
3-Epihydroxyetioallocholan-17-oneHMDB
3-Hydroxy-(3-alpha,5-alpha)-androstan-17-oneHMDB
3-Hydroxyandrostan-17-oneHMDB
3a-Hydroxyetioallocholan-17-oneHMDB
3alpha-Hydroxy-17-androstanoneHMDB
3alpha-Hydroxy-5alpha-androstan-17-oneHMDB
3alpha-Hydroxyetioallocholan-17-oneHMDB
5-alpha-Androstan-3-alpha-ol-17-oneHMDB
5-alpha-Androstane-3alpha-ol-17-oneHMDB
5-alpha-AndrosteroneHMDB
5a-Androstan-3a-ol-17-oneHMDB
5a-Androstane-3a-ol-17-oneHMDB
5a-AndrosteroneHMDB
5alpha-Androstane-3alpha-ol-17-oneHMDB
5alpha-AndrosteroneHMDB
AndrokinineHMDB
Androstanon-3-alpha-ol-17-oneHMDB
AndrotineHMDB
Atromide iciHMDB
cis-AndrosteroneHMDB
(3alpha,5alpha)-3-hydroxy-Androstan-17-onehmdb
(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-onehmdb
3-alpha-hydroxy-5alpha-Androstan-17-onehmdb
3-hydroxy-(3-alpha,5-alpha)-Androstan-17-onehmdb
Androsteronehmdb
Atromide ICIhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0064 g/LALOGPS
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
Polarizability34.7 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H30O2
IUPAC name(1S,2S,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
InChI IdentifierInChI=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-XYQQMQERSA-N
Isomeric SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(O)CC[C@]12C
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
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
  • 17-oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAndrosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03ea-0390000000-17f2f9f14aa5e282a19aSpectrum
Predicted GC-MSAndrosterone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-2169000000-bf71d6f9c1a2a4af0d20Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0190000000-c78d6bb7b08e2a97f5ccSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0390000000-a2a8c979727ec005be63Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01rw-2890000000-de73b07d88fdae4d011aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-9e9f9de3b33af0311acdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-fe9d47d83cd24c9d3a15Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-2190000000-513ad65531fff88b9f69Spectrum
NMRNot Available
ChemSpider ID23931264
ChEMBL IDNot Available
KEGG Compound IDC00523
Pubchem Compound ID12306765
Pubchem Substance IDNot Available
ChEBI ID16032
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00031
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35244
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAndrosterone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B10UGT2B10P36537
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 2B15UGT2B15P54855
UDP-glucuronosyltransferase 2A1UGT2A1Q9Y4X1
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-8UGT1A8Q9HAW9
UDP-glucuronosyltransferase 1-3UGT1A3P35503
UDP-glucuronosyltransferase 1-10UGT1A10Q9HAW8
UDP-glucuronosyltransferase 2B17UGT2B17O75795
UDP-glucuronosyltransferase 1-6UGT1A6P19224
UDP-glucuronosyltransferase 1-5UGT1A5P35504
UDP-glucuronosyltransferase 2B11UGT2B11O75310
UDP-glucuronosyltransferase 1-7UGT1A7Q9HAW7
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
Androgen receptorARP10275
Bile salt sulfotransferaseSULT2A1Q06520
Dehydrogenase/reductase SDR family member 9DHRS9Q9BPW9
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference