(2S,3S,4S)-4-[(2E,4E,6S)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid

• ChemBase ID: 2565
• Molecular Formular: C15H21NO6
• Molecular Mass: 311.33034
• Monoisotopic Mass: 311.1368874
• SMILES: C[C@@H](/C=C/C=C(\C)/[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O)C(=O)O
• Canonical SMILES: OC(=O)C[C@H]1[C@H](CN[C@@H]1C(=O)O)/C(=C/C=C/[C@@H](C(=O)O)C)/C
• InChI: InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4+/t9-,10-,11+,13-/m0/s1
• InChIKey: VZFRNCSOCOPNDB-AJKFJWDBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S)-4-[(2E,4E,6S)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: @domoic acid
• Synonyms: Domoic Acid

Database IDs

• CAS Number: 14277-97-5
• PubChem SID: 46505755; 160966015
• PubChem CID: 17753955

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.6822767
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -3.7643077
• LogD (pH = 7.4): -7.298631
• Log P: -1.7909644
• Molar Refractivity: 79.034 cm^3
• Polarizability: 30.324715 Å^3
• Polar Surface Area: 123.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.23
• LOG S: -2.61
• Solubility (Water): 7.59e-01 g/l

DETAILS

DrugBank - DB02852

Drug information: experimental