2-Methoxyestrone 3-glucuronide (CHEM022528)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:38:38 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022528
Identification
Common Name2-Methoxyestrone 3-glucuronide
ClassSmall Molecule
Description2-Methoxyestrone 3-glucuronide belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. 2-Methoxyestrone 3-glucuronide exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. In cattle, 2-methoxyestrone 3-glucuronide is involved in the metabolic pathway called the estrone metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Methoxyestrone-3-glucuronideHMDB
2-Methoxyestrone-3-glucuronosideHMDB
Chemical FormulaC24H32O8
Average Molecular Mass448.506 g/mol
Monoisotopic Mass448.210 g/mol
CAS Registry Number25577-70-2
IUPAC Name(1S,10R,11S,15S)-4-methoxy-15-methyl-5-{[(2R,3R,4S,5S,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-14-one
Traditional Name2-methoxyestrone 3-glucuronide
SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC(OC)=C(O[C@@H]4O[C@H](O)[C@@H](O)[C@H](O)[C@H]4O)C=C3CC[C@@]21[H]
InChI IdentifierInChI=1S/C24H32O8/c1-24-8-7-12-13(15(24)5-6-18(24)25)4-3-11-9-17(16(30-2)10-14(11)12)31-23-21(28)19(26)20(27)22(29)32-23/h9-10,12-13,15,19-23,26-29H,3-8H2,1-2H3/t12-,13+,15-,19-,20-,21+,22-,23+,24-/m0/s1
InChI KeyCLTGLDLWQUZPJU-OOJOVCNMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal glycosides
Alternative Parents
Substituents
  • Steroidal glycoside
  • Estrane-skeleton
  • 17-oxosteroid
  • Oxosteroid
  • Phenolic glycoside
  • Phenanthrene
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Anisole
  • Alkyl aryl ether
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Ketone
  • Hemiacetal
  • Secondary alcohol
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Ether
  • Polyol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP1.35ALOGPS
logP2.15ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)11.22ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity112.76 m³·mol⁻¹ChemAxon
Polarizability47.84 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0540-3209700000-d504a2d881fecd8e301dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fdk-5301059000-d19e016743262b62828aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uea-0147900000-c8ee73190a7419a9accfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0598100000-967a4d153722a30a4258Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-2593000000-3dfa7e273de68159e94aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3254900000-e6c085524ee01c2217edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-1191100000-5b289634c2bcd286514bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-2090000000-4c116f4b415ad809d5b8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004482
FooDB IDFDB023375
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID7062
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17216256
ChEBI IDNot Available
PubChem Compound ID22833612
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6.
2. Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9.