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Record Information
Version3.6
Creation Date2013-04-09 21:20:03 UTC
Update Date2016-02-11 07:57:37 UTC
HMDB IDHMDB60019
Secondary Accession NumbersNone
Metabolite Identification
Common NameSinapinic acid-O-glucuronide isomer
DescriptionSinapinic acid-O-glucuronide isomer is a conjugate of Sinapinic acid and glucuronide. A glucuronide, also known as glucuronoside, is any substance produced by linking glucuronic acid to another substance via a glycosidic bond. The glucuronides belong to the glycosides. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H20O11
Average Molecular Weight400.3341
Monoisotopic Molecular Weight400.100561482
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(\C=C\C(=O)O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)=CC(OC)=C1O
InChI Identifier
InChI=1S/C17H20O11/c1-25-8-5-7(6-9(26-2)11(8)19)3-4-10(18)27-17-14(22)12(20)13(21)15(28-17)16(23)24/h3-6,12-15,17,19-22H,1-2H3,(H,23,24)/b4-3+/t12-,13-,14+,15-,17+/m0/s1
InChI KeyInChIKey=YAIVMBWMHPRYKU-VKAIBYOUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • Hydroxycinnamic acid glycoside
  • O-cinnamoyl glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Phenylpropene
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • Phenol
  • Fatty acid ester
  • Beta-hydroxy acid
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Polyol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
OriginNot Available
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
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
Water Solubility3.41 mg/mLALOGPS
logP-0.01ALOGPS
logP-0.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area172.21 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity90.27 m3·mol-1ChemAxon
Polarizability38.25 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60019
Metagene LinkHMDB60019
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J: Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal Chem. 2012 Aug 21;84(16):7263-71. doi: 10.1021/ac3017339. Epub 2012 Aug 2. [22827565 ]