Human Metabolome Database Version 3.5

Showing metabocard for Estrone-2,3-quinone (HMDB12941)

Record Information
Version 3.5
Creation Date 2009-07-24 18:10:16 -0600
Update Date 2013-02-08 17:29:34 -0700
HMDB ID HMDB12941
Secondary Accession Numbers None
Metabolite Identification
Common Name Estrone-2,3-quinone
Description Estrogen 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
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Synonyms
  1. Catecholestrogen quinone
Chemical Formula C18H20O3
Average Molecular Weight 284.3496
Monoisotopic Molecular Weight 284.141244506
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 Number 40551-33-5
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 Key WFPLOQDPWXNOST-PEDDLLMLSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Ketosteroids
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
Substituents
  • Benzoquinone
  • Cyclohexane
  • Decaline
  • Ketone
  • Sesquiterpene Backbone
Direct Parent Ketosteroids
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.041 g/L ALOGPS
LogP 2.62 ALOGPS
LogP 3.43 ChemAxon
LogS -3.84 ALOGPS
pKa (strongest acidic) 18.39 ChemAxon
pKa (strongest basic) -7.5 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 51.21 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 80.7 ChemAxon
Polarizability 31.26 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029219
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12941 Link_out
Metagene Link HMDB12941 Link_out
METLIN ID Not Available
PubChem Compound 53481559 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Glutathione S-transferase theta-2
Reactions: Not Available
Gene Name: GSTT2
Uniprot ID: P0CG29 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA