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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-13 17:34:05 UTC
Update Date2019-11-12 17:21:15 UTC
HMDB IDHMDB0127973
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-[4-(3-carboxyoxiran-2-yl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Description6-[4-(3-carboxyoxiran-2-yl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 6--3,4,5-trihydroxyoxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-(4-hydroxy-3-methoxyphenyl)oxirane-2-carboxylic acid. 6-[4-(3-carboxyoxiran-2-yl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This aromatic-OH-glucuronidation occurs in humans. It is generated by UDP-glucuronosyltransferase 1-1 (P22309) enzyme via an aromatic-OH-glucuronidation reaction.
Structure
Data?1563875329
Synonyms
ValueSource
6-[4-(3-Carboxyoxiran-2-yl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Chemical FormulaC16H18O11
Average Molecular Weight386.309
Monoisotopic Molecular Weight386.0849114
IUPAC Name6-[4-(3-carboxyoxiran-2-yl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-[4-(3-carboxyoxiran-2-yl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=CC(=C1)C1OC1C(O)=O
InChI Identifier
InChI=1S/C16H18O11/c1-24-7-4-5(11-13(26-11)15(22)23)2-3-6(7)25-16-10(19)8(17)9(18)12(27-16)14(20)21/h2-4,8-13,16-19H,1H3,(H,20,21)(H,22,23)
InChI KeyWVSFYKLBJZEZAN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hexose monosaccharide
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • O-glycosyl compound
  • Methoxyphenol
  • Phenol ether
  • Phenoxy compound
  • Styrene
  • Methoxybenzene
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Beta-hydroxy acid
  • Alkyl aryl ether
  • Pyran
  • Monosaccharide
  • Benzenoid
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Oxane
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Ether
  • Carboxylic acid
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.5ALOGPS
logP-0.98ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.74ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area175.51 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity81.61 m³·mol⁻¹ChemAxon
Polarizability35.64 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0bt9-4161079000-15bb147a59bf3fefc5c6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0cfr-9247000000-7007e106dd219612eb49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02tc-0549000000-6d80ff5d4ff7d1c02a09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-0941000000-f1b9756d45facadc0d88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-0910000000-5dc6b2600751387b1366Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-1349000000-51930906fe6bdea3acf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05mo-2956000000-8d9c073cacba57b230a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-2940000000-11b500af1e79ac97587aSpectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131834354
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.