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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:24 UTC
Update Date2020-04-23 20:52:50 UTC
HMDB IDHMDB0002984
Secondary Accession Numbers
  • HMDB02984
Metabolite Identification
Common Name11-Hydroxyandrosterone
DescriptionOriginates from androsterone. A steroid hormone with weak androgenic activity. It is made in the liver from the metabolism of testosterone. The consumption of large amounts of celery can cause an increase in the production of this hormone in males. Androsterone has pheromonic properties.
Structure
Data?1582752260
Synonyms
ValueSource
11beta-HydroxyandrosteroneKegg
11b-HydroxyandrosteroneGenerator
11Β-hydroxyandrosteroneGenerator
11-beta-HydroxyandrosteroneHMDB
11-Hydroxy-androsteroneHMDB
11-HydroxyetiocholanoloneHMDB
11beta-Hydroxy-androsteroneHMDB
11 beta-HydroxyandrosteroneHMDB
11 beta-Hydroxyandrosterone, (3alpha,5alpha)-isomerHMDB
11 beta-Hydroxyandrosterone, (3alpha,5alpha,11alpha)-isomerHMDB
11 beta-Hydroxyandrosterone, (3alpha,5beta)-isomerHMDB
11 beta-Hydroxyandrosterone, (3alpha,5beta,11alpha)-isomerHMDB
11 beta-Hydroxyandrosterone, (3alpha,5beta,11beta)-isomerHMDB
11 beta-Hydroxyandrosterone, (3beta,5alpha,11beta)-isomerHMDB
11 beta-Hydroxyandrosterone, (3beta,5beta,11beta)-isomerHMDB
11 beta-HydroxyetiocholanoloneHMDB
3alpha,11beta-Dihydroxy-5beta-androstan-17-oneHMDB
Chemical FormulaC19H30O3
Average Molecular Weight306.4397
Monoisotopic Molecular Weight306.219494826
IUPAC Name(1S,2S,5R,7S,10S,11S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one
Traditional Name11-hydroxyandrosterone
CAS Registry Number57-61-4
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h11-15,17,20-21H,3-10H2,1-2H3/t11-,12+,13-,14-,15-,17+,18-,19-/m0/s1
InChI KeyPIXFHVWJOVNKQK-PTXZMSDUSA-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
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.4ALOGPS
logP2.46ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)14.89ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.4 m³·mol⁻¹ChemAxon
Polarizability35.22 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fs-0490000000-845f1333bf38189468d4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0019-1646900000-5f3db467d73d551ea523Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0092000000-7ee9333f2ca834b6dc41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059i-0190000000-ce3d130e38421477defcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-4290000000-29cdb28119cfafcfecccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0049000000-0583782d3fbeec16854dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0097000000-81d91167799b4dbad7ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01rf-3090000000-758543fa8bec7808bdcfSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Ovary
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.15 (0.11-0.15) umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected and Quantified0.069 (0.047-0.088) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified0.000073 +/- 0.000028 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified0.00013 +/- 0.000093 umol/mmol creatinineAdult (>18 years old)FemaleStress urinary incontinence details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB023089
    KNApSAcK IDNot Available
    Chemspider ID8461834
    KEGG Compound IDC14606
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID3178
    PubChem Compound10286365
    PDB IDNot Available
    ChEBI ID34350
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceKlyne, W.; Ridley, Sheila. Urinary steroids and related compounds. I. 11-Substituted derivatives of androsterone. Journal of the Chemical Society (1956), 4825-8.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Pucsok JM, Gyore I, Hollosi I, Soos E, Ali Ghasemi NR, Frenkl R: Urine steroid profile of judo competitors affected by acute physical exercises. J Chromatogr Sci. 2005 Sep;43(8):438-40. [PubMed:16212787 ]
    2. Ball KD, Levell MJ, Pickup ME: The effect of ibuprofen on the excretion of steroid metabolites. Clin Chim Acta. 1982 Sep 1;124(1):23-9. [PubMed:7127837 ]
    3. Norli HR, Esbensen K, Westad F, Birkeland KI, Hemmersbach P: Chemometric evaluation of urinary steroid profiles in doping control. J Steroid Biochem Mol Biol. 1995 Jul;54(1-2):83-8. [PubMed:7632620 ]
    4. Akgun S, Ertel NH, Imperato-McGinley J, Sayli BS, Shackleton C: Familial male pseudohermaphroditism due to 5-alpha-reductase deficiency in a Turkish village. Am J Med. 1986 Aug;81(2):267-74. [PubMed:3740084 ]
    5. Vierhapper H, Nowotny P, Waldhausl W: Stimulation of gonadal steroid synthesis by chronic excess of adrenocorticotropin in patients with adrenocortical insufficiency. J Clin Invest. 1986 Apr;77(4):1063-70. [PubMed:3007576 ]