(1S,4R,7aR)-4-butoxy-1-[(2R)-1-oxobutan-2-yl]-2,4,5,6,7,7a-hexahydro-1H-isoindole-3-carboxylic acid

• ChemBase ID: 5737
• Molecular Formular: C17H27NO4
• Molecular Mass: 309.40058
• Monoisotopic Mass: 309.19400835
• SMILES: CCCCO[C@@H]1CCC[C@@H]2C1=C(C(=O)O)N[C@@H]2[C@@H](CC)C=O
• Canonical SMILES: CCCCO[C@@H]1CCC[C@@H]2C1=C(N[C@@H]2[C@H](C=O)CC)C(=O)O
• InChI: InChI=1S/C17H27NO4/c1-3-5-9-22-13-8-6-7-12-14(13)16(17(20)21)18-15(12)11(4-2)10-19/h10-13,15,18H,3-9H2,1-2H3,(H,20,21)/t11-,12+,13+,15+/m0/s1
• InChIKey: WRBRCIHZCYLBFW-KYEXWDHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4R,7aR)-4-butoxy-1-[(2R)-1-oxobutan-2-yl]-2,4,5,6,7,7a-hexahydro-1H-isoindole-3-carboxylic acid
• IUPAC Traditional name: (3S,3aR,7R)-7-butoxy-3-[(2R)-1-oxobutan-2-yl]-3,3a,4,5,6,7-hexahydro-2H-isoindole-1-carboxylic acid
• Synonyms: (1S,4R,7AR)-4-BUTOXY-1-[(1R)-1-FORMYLPROPYL]-2,4,5,6,7,7A-HEXAHYDRO-1H-ISOINDOLE-3-CARBOXYLIC ACID

Database IDs

• PubChem SID: 99444580; 160969164
• PubChem CID: 46937124

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.466975
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.0160192
• LogD (pH = 7.4): -0.7472578
• Log P: 2.096453
• Molar Refractivity: 84.6308 cm^3
• Polarizability: 32.778732 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.45
• LOG S: -3.18
• Solubility (Water): 2.06e-01 g/l

DETAILS

DrugBank - DB08109

Drug information: experimental