(1R,4S,7aS)-4-methoxy-1-[(2E)-1-oxobut-2-en-2-yl]-2,4,5,6,7,7a-hexahydro-1H-isoindole-3-carboxylic acid

• ChemBase ID: 5738
• Molecular Formular: C14H19NO4
• Molecular Mass: 265.30496
• Monoisotopic Mass: 265.13140809
• SMILES: C/C=C(/C=O)\[C@@H]1NC(=C2[C@@H]1CCC[C@@H]2OC)C(=O)O
• Canonical SMILES: CO[C@H]1CCC[C@H]2C1=C(N[C@H]2/C(=C\C)/C=O)C(=O)O
• InChI: InChI=1S/C14H19NO4/c1-3-8(7-16)12-9-5-4-6-10(19-2)11(9)13(15-12)14(17)18/h3,7,9-10,12,15H,4-6H2,1-2H3,(H,17,18)/b8-3-/t9-,10-,12-/m0/s1
• InChIKey: ZYKSDPVHVMSKIL-IIHMJNQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,7aS)-4-methoxy-1-[(2E)-1-oxobut-2-en-2-yl]-2,4,5,6,7,7a-hexahydro-1H-isoindole-3-carboxylic acid
• IUPAC Traditional name: (3R,3aS,7S)-7-methoxy-3-[(2E)-1-oxobut-2-en-2-yl]-3,3a,4,5,6,7-hexahydro-2H-isoindole-1-carboxylic acid
• Synonyms: (1R,4S,7AS)-1-(1-FORMYLPROP-1-EN-1-YL)-4-METHOXY-2,4,5,6,7,7A-HEXAHYDRO-1H-ISOINDOLE-3-CARBOXYLIC ACID

Database IDs

• PubChem SID: 160969165; 99444581
• PubChem CID: 46937125

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.2724147
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.62962615
• LogD (pH = 7.4): -2.3615158
• Log P: 0.6229417
• Molar Refractivity: 71.6331 cm^3
• Polarizability: 27.032013 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.65
• LOG S: -2.3
• Solubility (Water): 1.34e+00 g/l

DETAILS

DrugBank - DB08110

Drug information: experimental