(1S,7R)-4-oxo-3-{[(4S)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methyl}-10-oxa-3-azatricyclo[5.2.1.01,5]dec-8-ene-6-carboxylic acid

• ChemBase ID: 119553
• Molecular Formular: C19H23NO4
• Molecular Mass: 329.39022
• Monoisotopic Mass: 329.16270822
• SMILES: C12[C@]3(O[C@H](C2C(=O)O)C=C3)CN(C1=O)CC1=CC[C@@H](C(=C)C)CC1
• Canonical SMILES: CC(=C)[C@H]1CCC(=CC1)CN1C[C@@]23C(C1=O)C([C@@H](O3)C=C2)C(=O)O
• InChI: InChI=1S/C19H23NO4/c1-11(2)13-5-3-12(4-6-13)9-20-10-19-8-7-14(24-19)15(18(22)23)16(19)17(20)21/h3,7-8,13-16H,1,4-6,9-10H2,2H3,(H,22,23)/t13-,14-,15?,16?,19-/m1/s1
• InChIKey: GHIGRDADUISATB-AAERBBOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,7R)-4-oxo-3-{[(4S)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methyl}-10-oxa-3-azatricyclo[5.2.1.0^1,^5]dec-8-ene-6-carboxylic acid
• IUPAC Traditional name: (1S,7R)-4-oxo-3-{[(4S)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methyl}-10-oxa-3-azatricyclo[5.2.1.0^1,^5]dec-8-ene-6-carboxylic acid
• Synonyms: (3aS,6R)-1-oxo-2-(((S)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl)-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic acid

Database IDs

• PubChem SID: 162107660
• PubChem CID: 16394586

CALCULATED PROPERTIES

• Acid pKa: 4.1596694
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.25622085
• LogD (pH = 7.4): -1.4473411
• Log P: 1.6131476
• Molar Refractivity: 89.9452 cm^3
• Polarizability: 34.518562 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true