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Record Information
Version3.6
Creation Date2009-07-25 00:10:16 UTC
Update Date2013-02-09 00:29:34 UTC
HMDB IDHMDB12941
Secondary Accession NumbersNone
Metabolite Identification
Common NameEstrone-2,3-quinone
DescriptionEstrogen 2,3- and 3,4-quinones are reactive species toward nucleophiles and Michael acceptors. As such, they can bind to DNA and induce cellular damages.Tumors may arise in cells covalently damaged by the free radicals or by the quinones and stimulated to proliferate by hormone receptor-mediated. processes. This hypothesis is supported by the correlation between quinone formation, 8-hydroxylation of guanine bases of DNA and tumor incidence of 4- versus 2-hydroxylated estrogen metabolites. Moreover, estrone-3,4-quinone, but not. estrone-2,3-quinone, induced liver tumors in mice.
Structure
Thumb
Synonyms
  1. Catecholestrogen quinone
Chemical FormulaC18H20O3
Average Molecular Weight284.3496
Monoisotopic Molecular Weight284.141244506
IUPAC Name(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,6-diene-4,5,14-trione
Traditional IUPAC Name(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,6-diene-4,5,14-trione
CAS Registry Number40551-33-5
SMILES
C[C@]12CCC3C(CCC4=CC(=O)C(=O)C=C34)C1CCC2=O
InChI Identifier
InChI=1S/C18H20O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14H,2-7H2,1H3/t11?,12?,14?,18-/m0/s1
InChI KeyWFPLOQDPWXNOST-PEDDLLMLSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassKetosteroids
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
Substituents
  • Benzoquinone
  • Cyclohexane
  • Decaline
  • Ketone
  • Sesquiterpene Backbone
Direct ParentKetosteroids
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • 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 solubility0.041 g/LALOGPS
logP2.62ALOGPS
logP3.43ChemAxon
logS-3.8ALOGPS
pKa (strongest acidic)18.39ChemAxon
pKa (strongest basic)-7.5ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count0ChemAxon
polar surface area51.21ChemAxon
rotatable bond count0ChemAxon
refractivity80.7ChemAxon
polarizability31.26ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
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 IDFDB029219
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12941
Metagene LinkHMDB12941
METLIN IDNot Available
PubChem Compound53481559
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a sulfatase activity.
Gene Name:
GSTT2
Uniprot ID:
P0CG29
Molecular weight:
Not Available