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Record Information
Version3.6
Creation Date2006-05-22 15:12:24 UTC
Update Date2016-02-11 01:05:56 UTC
HMDB IDHMDB02984
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
11beta-HydroxyandrosteroneKegg
11b-HydroxyandrosteroneGenerator
11β-hydroxyandrosteroneGenerator
11-beta-HydroxyandrosteroneHMDB
11-Hydroxy-androsteroneHMDB
11-HydroxyetiocholanoloneHMDB
11beta-Hydroxy-androsteroneHMDB
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 KeyInChIKey=PIXFHVWJOVNKQK-PTXZMSDUSA-N
Chemical Taxonomy
DescriptionThis compound 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-alpha-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.4 m3·mol-1ChemAxon
Polarizability35.22 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Gonads
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023089
KNApSAcK IDNot Available
Chemspider ID8461834
KEGG Compound IDC14606
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02984
Metagene LinkHMDB02984
METLIN ID3178
PubChem Compound10286365
PDB IDNot Available
ChEBI 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. 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. [3740084 ]
  2. 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. [16212787 ]
  3. 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. [7127837 ]
  4. 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. [7632620 ]
  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. [3007576 ]