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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 19:39:59 UTC
Update Date2020-05-11 16:41:42 UTC
HMDB IDHMDB0004482
Secondary Accession Numbers
  • HMDB0154676
  • HMDB04482
Metabolite Identification
Common Name2-Methoxyestrone 3-glucuronide
Description2-Methoxyestrone 3-glucuronide belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. Thus, 2-methoxyestrone 3-glucuronide is considered to be a steroid conjugate lipid molecule. 2-Methoxyestrone 3-glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Methoxyestrone 3-glucuronide is a natural human metabolite of 2-methoxyestrone generated in the liver by UDP glucuronosyltransferase. 2-Methoxyestrone is a metabolite of 2-hydroxyestrone (a nonuterotrophic metabolite of estradiol). Glucuronidation is used to assist in the excretion of toxic substances, drugs, or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.
Structure
Data?1589215302
Synonyms
ValueSource
2-MeOE1 3gChEBI
2-Methoxyestrone 3-beta-D-glucuronideChEBI
2-Methoxyestrone 3-beta-glucuronideChEBI
2-Methoxyestrone 3-glucosiduronic acidChEBI
2-Methoxyestrone 3-glucuronosideChEBI
2-Methoxyestrone 3-O-(beta-D-glucuronic acid)ChEBI
2-Methoxyestrone 3-O-glucuronideChEBI
2-Methoxyestrone-3-glucuronideChEBI
2-Methoxyestrone 3-b-D-glucuronideGenerator
2-Methoxyestrone 3-β-D-glucuronideGenerator
2-Methoxyestrone 3-b-glucuronideGenerator
2-Methoxyestrone 3-β-glucuronideGenerator
2-Methoxyestrone 3-glucosiduronateGenerator
2-Methoxyestrone 3-O-(b-D-glucuronate)Generator
2-Methoxyestrone 3-O-(b-D-glucuronic acid)Generator
2-Methoxyestrone 3-O-(beta-D-glucuronate)Generator
2-Methoxyestrone 3-O-(β-D-glucuronate)Generator
2-Methoxyestrone 3-O-(β-D-glucuronic acid)Generator
2-Methoxyestrone 3-glucuronideHMDB
2-Methoxyestrone glucosiduronateHMDB
Chemical FormulaC25H32O9
Average Molecular Weight476.522
Monoisotopic Molecular Weight476.20463261
IUPAC Name3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-4-methoxy-15-methyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid
Traditional Name3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-4-methoxy-15-methyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid
CAS Registry Number25577-70-2
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(OC)=C3
InChI Identifier
InChI=1S/C25H32O9/c1-25-8-7-12-13(15(25)5-6-18(25)26)4-3-11-9-17(16(32-2)10-14(11)12)33-24-21(29)19(27)20(28)22(34-24)23(30)31/h9-10,12-13,15,19-22,24,27-29H,3-8H2,1-2H3,(H,30,31)/t12-,13+,15-,19-,20-,21+,22-,24+,25-/m0/s1
InChI KeyNZTHZDNDYACBSX-FJNWEKAQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroid glucuronide conjugates
Alternative Parents
Substituents
  • Steroid-glucuronide-skeleton
  • Estrane-skeleton
  • 17-oxosteroid
  • Oxosteroid
  • Fatty acyl glycoside
  • Phenolic glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • 1-o-glucuronide
  • O-glucuronide
  • Phenanthrene
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Anisole
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Fatty acyl
  • Oxane
  • Pyran
  • Benzenoid
  • Hydroxy acid
  • Monosaccharide
  • Ketone
  • Secondary alcohol
  • Acetal
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Organoheterocyclic compound
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point254.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP1.87ALOGPS
logP2.2ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area142.75 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity117.56 m³·mol⁻¹ChemAxon
Polarizability50 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FooDB IDFDB023375
      KNApSAcK IDNot Available
      Chemspider ID391376
      KEGG Compound IDC11132
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound443077
      PDB IDNot Available
      ChEBI ID37450
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not 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. [PubMed:10997942 ]
      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. [PubMed:16598814 ]

      Only showing the first 10 proteins. There are 22 proteins in total.

      Enzymes

      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
      Gene Name:
      UGT2B28
      Uniprot ID:
      Q9BY64
      Molecular weight:
      38742.9
      Reactions
      2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
      Gene Name:
      UGT2B4
      Uniprot ID:
      P06133
      Molecular weight:
      60512.035
      Reactions
      2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
      Gene Name:
      UGT1A4
      Uniprot ID:
      P22310
      Molecular weight:
      60024.535
      Reactions
      2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT2B10
      Uniprot ID:
      P36537
      Molecular weight:
      60773.485
      Reactions
      2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
      Gene Name:
      UGT2B7
      Uniprot ID:
      P16662
      Molecular weight:
      60720.15
      Reactions
      2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
      Gene Name:
      UGT2B15
      Uniprot ID:
      P54855
      Molecular weight:
      61035.815
      Reactions
      2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
      Gene Name:
      UGT2A1
      Uniprot ID:
      Q9Y4X1
      Molecular weight:
      60771.605
      Reactions
      2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
      Gene Name:
      UGT1A1
      Uniprot ID:
      P22309
      Molecular weight:
      59590.91
      Reactions
      2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
      Gene Name:
      UGT1A9
      Uniprot ID:
      O60656
      Molecular weight:
      59940.495
      Reactions
      2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A8
      Uniprot ID:
      Q9HAW9
      Molecular weight:
      59741.035
      Reactions
      2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails

      Only showing the first 10 proteins. There are 22 proteins in total.