2-{[3-(3-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-4,5-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

• ChemBase ID: 127614
• Molecular Formular: C23H27N3O15S
• Molecular Mass: 617.53658
• Monoisotopic Mass: 617.11628818
• SMILES: Oc1cc(cc(c1O)SCC(NC(=O)CCC(N)C(=O)O)C(=O)NCC(=O)O)/C=C/C(=O)OC(C(=O)O)C(O)C(=O)O
• Canonical SMILES: OC(=O)CNC(=O)C(NC(=O)CCC(C(=O)O)N)CSc1cc(/C=C/C(=O)OC(C(C(=O)O)O)C(=O)O)cc(c1O)O
• InChI: InChI=1S/C23H27N3O15S/c24-10(21(35)36)2-3-14(28)26-11(20(34)25-7-15(29)30)8-42-13-6-9(5-12(27)17(13)32)1-4-16(31)41-19(23(39)40)18(33)22(37)38/h1,4-6,10-11,18-19,27,32-33H,2-3,7-8,24H2,(H,25,34)(H,26,28)(H,29,30)(H,35,36)(H,37,38)(H,39,40)
• InChIKey: GYXGDEQYOIGEEQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[3-(3-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-4,5-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
• IUPAC Traditional name: 2-{[3-(3-{[2-(4-amino-4-carboxybutanamido)-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}-4,5-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
• Synonyms: GRP; GRP1; 2-S-glutathionyl caftaric acid; Grape reaction product

Database IDs

• PubChem SID: 162221932
• PubChem CID: 71308212
• Wikipedia Title: Grape_reaction_product

CALCULATED PROPERTIES

• Acid pKa: 1.6792915
• H Acceptors: 15
• H Donor: 10
• LogD (pH = 5.5): -10.341405
• LogD (pH = 7.4): -14.225209
• Log P: -4.5888066
• Molar Refractivity: 137.376 cm^3
• Polarizability: 53.77485 Å^3
• Polar Surface Area: 320.41 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false