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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 17:45:27 UTC
HMDB IDHMDB0000550
Secondary Accession Numbers
  • HMDB00550
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
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-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 16-alpha-hydroxysteroid
  • 16-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    System process:

Role

Industrial application:

Biological role:

  Molecular messenger:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.84 m³·mol⁻¹ChemAxon
Polarizability35.87 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-0090000000-92a740780401e8faa587View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-1013980000-19f683f12fe72ee4fbe8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0194000000-011fe8294b03cd99c307View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0291000000-93f8ce400365e9f77412View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-106r-4790000000-f11bb35212636b0fc7cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0039000000-42eb9903da1420867cd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0098000000-b323ec779ce3d7281f9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-0190000000-357cc1f239acaff5ed32View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
    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 ]