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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:55 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
SynonymsNot Available
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 KeyInChIKey=GUGSXATYPSGVAY-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
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
  • 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 QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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. [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. [15671100 ]