(2R,3S)-2,3-bis({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy})pentanedioic acid

• ChemBase ID: 5945
• Molecular Formular: C23H20O10
• Molecular Mass: 456.3989
• Monoisotopic Mass: 456.10564684
• SMILES: c1cc(O)ccc1/C=C/C(=O)O[C@@H](CC(=O)O)[C@H](C(=O)O)OC(=O)/C=C/c1ccc(O)cc1
• Canonical SMILES: Oc1ccc(cc1)/C=C/C(=O)O[C@H]([C@@H](OC(=O)/C=C/c1ccc(cc1)O)CC(=O)O)C(=O)O
• InChI: InChI=1S/C23H20O10/c24-16-7-1-14(2-8-16)5-11-20(28)32-18(13-19(26)27)22(23(30)31)33-21(29)12-6-15-3-9-17(25)10-4-15/h1-12,18,22,24-25H,13H2,(H,26,27)(H,30,31)/b11-5+,12-6+/t18-,22+/m0/s1
• InChIKey: VJLMRHSHSNLOGC-NOPZTHQXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2,3-bis({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy})pentanedioic acid
• IUPAC Traditional name: (2R,3S)-2,3-bis({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy})pentanedioic acid
• Synonyms: 2-DEOXY-3,4-BIS-O-[3-(4-HYDROXYPHENYL)PROPANOYL]-L-THREO-PENTARIC ACID

Database IDs

• PubChem SID: 99444793; 160969370
• PubChem CID: 11669698

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.1702378
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.18078524
• LogD (pH = 7.4): -2.982893
• Log P: 3.7166743
• Molar Refractivity: 113.9349 cm^3
• Polarizability: 43.75606 Å^3
• Polar Surface Area: 167.66 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.54
• LOG S: -4.2
• Solubility (Water): 2.87e-02 g/l

DETAILS

DrugBank - DB08322

Drug information: experimental