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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:10:16 UTC
Update Date2022-03-07 02:51:27 UTC
HMDB IDHMDB0012941
Secondary Accession Numbers
  • HMDB12941
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
Data?1582753079
Synonyms
ValueSource
Catecholestrogen quinoneHMDB
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 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
Description 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
  • 2-oxosteroid
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 Area51.21 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.7 m³·mol⁻¹ChemAxon
Polarizability31.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.32931661259
DarkChem[M-H]-162.68531661259
DeepCCS[M-2H]-203.82930932474
DeepCCS[M+Na]+179.21330932474
AllCCS[M+H]+169.032859911
AllCCS[M+H-H2O]+165.732859911
AllCCS[M+NH4]+172.132859911
AllCCS[M+Na]+173.032859911
AllCCS[M-H]-175.132859911
AllCCS[M+Na-2H]-174.832859911
AllCCS[M+HCOO]-174.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Estrone-2,3-quinoneC[C@]12CCC3C(CCC4=CC(=O)C(=O)C=C34)C1CCC2=O3380.8Standard polar33892256
Estrone-2,3-quinoneC[C@]12CCC3C(CCC4=CC(=O)C(=O)C=C34)C1CCC2=O2443.0Standard non polar33892256
Estrone-2,3-quinoneC[C@]12CCC3C(CCC4=CC(=O)C(=O)C=C34)C1CCC2=O2881.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Estrone-2,3-quinone,1TMS,isomer #1C[C@]12CCC3C4=CC(=O)C(=O)C=C4CCC3C1CC=C2O[Si](C)(C)C2797.2Semi standard non polar33892256
Estrone-2,3-quinone,1TMS,isomer #1C[C@]12CCC3C4=CC(=O)C(=O)C=C4CCC3C1CC=C2O[Si](C)(C)C2521.1Standard non polar33892256
Estrone-2,3-quinone,1TMS,isomer #1C[C@]12CCC3C4=CC(=O)C(=O)C=C4CCC3C1CC=C2O[Si](C)(C)C3303.1Standard polar33892256
Estrone-2,3-quinone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=CC(=O)C(=O)C=C4C3CC[C@]12C3024.8Semi standard non polar33892256
Estrone-2,3-quinone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=CC(=O)C(=O)C=C4C3CC[C@]12C2722.4Standard non polar33892256
Estrone-2,3-quinone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=CC(=O)C(=O)C=C4C3CC[C@]12C3501.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Estrone-2,3-quinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-0590000000-8c8c122e6d9b125e2f7f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estrone-2,3-quinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estrone-2,3-quinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 10V, Negative-QTOFsplash10-001i-0090000000-b52ab2d316b4a1905ea32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 20V, Negative-QTOFsplash10-001i-0090000000-875af10e53aa400e62ab2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 40V, Negative-QTOFsplash10-0lg0-0090000000-11e6d40e9af6a58763282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 10V, Negative-QTOFsplash10-001i-0090000000-78a425e25a58a7330ede2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 20V, Negative-QTOFsplash10-001i-0090000000-1cce43a24f2838cc95572021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 40V, Negative-QTOFsplash10-0fai-0190000000-a9d81c8838a462df3bcc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 10V, Positive-QTOFsplash10-000i-0090000000-3640f8d8cf7d729317852017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 20V, Positive-QTOFsplash10-05n0-0290000000-ac6ebae2649658cc06a12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 40V, Positive-QTOFsplash10-0udi-5590000000-bf0202392e0921e342652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 10V, Positive-QTOFsplash10-000i-0090000000-8cb5c211dee4a6b288ac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 20V, Positive-QTOFsplash10-02t9-1590000000-ed6a18c605a9e5c85c552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone-2,3-quinone 40V, Positive-QTOFsplash10-004r-3920000000-f3aa5a90c960a060e7b02021-09-24Wishart LabView Spectrum
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
FooDB IDFDB029219
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481559
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE5252
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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