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Record Information
Version3.6
Creation Date2007-04-12 17:02:56 UTC
Update Date2016-02-11 01:07:19 UTC
HMDB IDHMDB05895
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Hydroxyestrone
Description4-Hydroxyestrone is metabolite originating from 17beta-estradiol, and is reported as carcinogenic and have ability to initiate cancer.
Structure
Thumb
Synonyms
ValueSource
1,3,5(10)-Estratriene-3,4-diol-17-oneHMDB
3,4-Dihydroxy-1,3,5(10)-estratrien-17-oneHMDB
3,4-Dihydroxy-estra-1,3,5(10)-trien-17-oneHMDB
3,4-Dihydroxyestra-1,3,5(10)-trien-17-oneHMDB
4-Hydroxy catechol estrogenHMDB
4OHEsHMDB
Estra-1,3,5(10)-triene-3,4-diol-17-oneHMDB
Chemical FormulaC18H22O3
Average Molecular Weight286.3655
Monoisotopic Molecular Weight286.15689457
IUPAC Name(15R)-5,6-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one
Traditional Name(15R)-5,6-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one
CAS Registry Number3131-23-5
SMILES
C[C@@]12CCC3C(CCC4=C3C=CC(O)=C4O)C1CCC2=O
InChI Identifier
InChI=1S/C18H22O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,19,21H,2-3,5,7-9H2,1H3/t11?,12?,14?,18-/m1/s1
InChI KeyInChIKey=XQZVQQZZOVBNLU-KQWCVQSUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • 4-hydroxysteroid
  • 3-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1,2-diphenol
  • Benzenoid
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
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 Solubility0.026 mg/mLALOGPS
logP3ALOGPS
logP4.01ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.69ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.06 m3·mol-1ChemAxon
Polarizability32.18 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00332
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023786
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05895
Metagene LinkHMDB05895
METLIN IDNot Available
PubChem Compound53477797
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available