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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-03-02 21:25:58 UTC
HMDB IDHMDB00550
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Androstenetriol
Description5-Androstenetriol is a metabolite of dehydroepiandrosterone (DHEA) found in normal urine in healthy subjects during growth (PMID 15671100 ), and is one of the markers that reflects the changes of the adrenarche process in boys and girls (Adrenarche is the adrenal glands maturaty).
Structure
Thumb
Synonyms
ValueSource
5-Androstene-3 beta,16 alpha,17 beta-triolMeSH
5-Androstene-3,16,17-triolMeSH
Chemical FormulaC19H30O3
Average Molecular Weight306.4397
Monoisotopic Molecular Weight306.219494826
IUPAC Name(1S,2R,5S,10R,11S,13R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol
Traditional Name5-androstenetriol
CAS Registry Number4150-30-5
SMILES
[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-17,20-22H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,17-,18-,19-/m0/s1
InChI KeyGUGSXATYPSGVAY-DHKQUUGRSA-N
Chemical Taxonomy
ClassificationNot classified
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
  • Cytoplasm
  • Extracellular
  • Membrane
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 Solubility0.19 mg/mLALOGPS
logP2.17ALOGPS
logP1.72ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.84 m3·mol-1ChemAxon
Polarizability35.87 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
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.098 (0.092-0.12) umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected and Quantified0.068 (0.041-0.18) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    Abnormal Concentrations
    Not Available
    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 IDFDB022110
    KNApSAcK IDNot Available
    Chemspider ID7993771
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB00550
    Metagene LinkHMDB00550
    METLIN ID5534
    PubChem Compound9818021
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceHuffman, Max N. Steroid esters from steroid ethers. (1952), US 2585553 19520212 CAN 46:52034 AN 1952:52034
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Grondal S, Eriksson B, Hagenas L, Werner S, Curstedt T: Steroid profile in urine: a useful tool in the diagnosis and follow up of adrenocortical carcinoma. Acta Endocrinol (Copenh). 1990 May;122(5):656-63. [PubMed:2141212 ]
    2. Remer T, Boye KR, Hartmann MF, Wudy SA: Urinary markers of adrenarche: reference values in healthy subjects, aged 3-18 years. J Clin Endocrinol Metab. 2005 Apr;90(4):2015-21. Epub 2005 Jan 25. [PubMed:15671100 ]