Record Information
Version1.0
Creation date2010-04-08 22:04:29 UTC
Update date2019-11-26 02:54:35 UTC
Primary IDFDB000246
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-S-Glutathionyl caftaric acid
Description2-s-glutathionyl caftaric acid is a member of the class of compounds known as oligopeptides. Oligopeptides are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. 2-s-glutathionyl caftaric acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 2-s-glutathionyl caftaric acid can be found in common grape, grape wine, and vinegar, which makes 2-s-glutathionyl caftaric acid a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
2-S-Glutathionyl caftarateGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP-1.1ALOGPS
logP-4.6ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)1.67ChemAxon
pKa (Strongest Basic)8.92ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area320.41 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity137.38 m³·mol⁻¹ChemAxon
Polarizability56.6 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC23H27N3O15S
IUPAC name2-{[(2E)-3-(2-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
InChI IdentifierInChI=1S/C23H27N3O15S/c24-10(21(35)36)3-5-13(28)26-11(20(34)25-7-14(29)30)8-42-19-9(1-4-12(27)16(19)32)2-6-15(31)41-18(23(39)40)17(33)22(37)38/h1-2,4,6,10-11,17-18,27,32-33H,3,5,7-8,24H2,(H,25,34)(H,26,28)(H,29,30)(H,35,36)(H,37,38)(H,39,40)/b6-2+
InChI KeyFRUUTAANUZUTPG-QHHAFSJGSA-N
Isomeric SMILESNC(CCC(=O)NC(CSC1=C(\C=C\C(=O)OC(C(O)C(O)=O)C(O)=O)C=CC(O)=C1O)C(=O)NCC(O)=O)C(O)=O
Average Molecular Weight617.537
Monoisotopic Molecular Weight617.116287899
Classification
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • Pentacarboxylic acid or derivatives
  • Glutamine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Cinnamic acid ester
  • Cinnamic acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cysteine or derivatives
  • Coumaric acid or derivatives
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Aryl thioether
  • Thiophenol ether
  • Catechol
  • Styrene
  • Phenol
  • Beta-hydroxy acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Sugar acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkylarylthioether
  • Fatty acid ester
  • Alpha-hydroxy acid
  • Fatty amide
  • Fatty acyl
  • Hydroxy acid
  • Benzenoid
  • Monosaccharide
  • N-acyl-amine
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Organooxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Primary amine
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-4411696000-7d36b29438beacf2bed7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9202330000-8ee1a43a6e86ea0dbe4dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9221000000-c4480624c637a8c55984Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00yi-2312291000-ef2b1fca5415640378a0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0015-4596450000-7e7e4c9f0f9d29d1da9dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4592100000-bae959e051ff91c3be08Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID477
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.