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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-04-12 17:03:26 UTC
Update Date2017-12-07 01:55:33 UTC
HMDB IDHMDB0005896
Secondary Accession Numbers
  • HMDB05896
Metabolite Identification
Common Name4-Hydroxyestradiol
Description4-Hydroxyestradiol, also known as 3,4,17beta-estriol or 4OHE2, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. 4-Hydroxyestradiol is considered to be a practically insoluble (in water) and relatively neutral molecule. 4-Hydroxyestradiol has been found in human hepatic tissue tissue, and has also been primarily detected in urine. Within the cell, 4-hydroxyestradiol is primarily located in the membrane (predicted from logP) and cytoplasm.
Structure
Thumb
Synonyms
ValueSource
1,3,5[10]-Estratriene-3,4,17beta-triolHMDB
3,4,17beta-EstriolHMDB
3,4,17beta-Trihydroxy-1,3,5[10]-estratrieneHMDB
4,17 Dihydroxy estradiolHMDB
4-Hydroxy-17beta-estradiolHMDB
4-Hydroxy-estradiolHMDB
4-Hydroxyestradiol-17 betaHMDB
4-Hydroxyestradiol-17betaHMDB
4-OH-EstradiolHMDB
4OHE2HMDB
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
IUPAC Name(14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,6,14-triol
Traditional Name(14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,6,14-triol
CAS Registry Number5976-61-4
SMILES
C[C@]12CCC3C(CCC4=C3C=CC(O)=C4O)C1CC[C@@H]2O
InChI Identifier
InChI=1S/C18H24O3/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/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11?,12?,14?,16-,18-/m0/s1
InChI KeyQOZFCKXEVSGWGS-JNYWYMJGSA-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
  • 3-hydroxysteroid
  • 4-hydroxysteroid
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.066 g/LALOGPS
logP3.34ALOGPS
logP3.44ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.69ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.89 m³·mol⁻¹ChemAxon
Polarizability32.83 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, Positivesplash10-0adr-2490000000-3aa4258bafb58fa45700View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-002u-1002900000-9d2df63f119c9dbf0962View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0090000000-ed24fd96ce297ed99b3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0690000000-235f4fdeb530ba151b7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-7590000000-d4d1f4c9d17256df8044View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-aff5ef70c0e417742016View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-e8909947f3f0e44912b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-0090000000-dc9ec3182d5ff0ec464aView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023787
KNApSAcK IDNot Available
Chemspider ID23205091
KEGG Compound IDC14209
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44348689
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available