(1S,7R)-3-{[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl}-4-oxo-10-oxa-3-azatricyclo[5.2.1.01,5]dec-8-ene-6-carboxylic acid

• ChemBase ID: 119552
• 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]2C([C@@H]1C2)(C)C
• Canonical SMILES: OC(=O)C1[C@@H]2C=C[C@@]3(C1C(=O)N(C3)CC1=CC[C@@H]3C[C@H]1C3(C)C)O2
• InChI: InChI=1S/C19H23NO4/c1-18(2)11-4-3-10(12(18)7-11)8-20-9-19-6-5-13(24-19)14(17(22)23)15(19)16(20)21/h3,5-6,11-15H,4,7-9H2,1-2H3,(H,22,23)/t11-,12-,13+,14?,15?,19+/m0/s1
• InChIKey: KFWIQRFOCDYDRG-JANDRBAJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,7R)-3-{[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl}-4-oxo-10-oxa-3-azatricyclo[5.2.1.0^1,^5]dec-8-ene-6-carboxylic acid
• IUPAC Traditional name: (1S,7R)-3-{[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl}-4-oxo-10-oxa-3-azatricyclo[5.2.1.0^1,^5]dec-8-ene-6-carboxylic acid
• Synonyms: (3aS,6R)-2-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic acid

Database IDs

• PubChem SID: 162107659
• PubChem CID: 16394585

CALCULATED PROPERTIES

• Acid pKa: 3.989199
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.32485896
• LogD (pH = 7.4): -1.9702367
• Log P: 1.1949964
• Molar Refractivity: 88.1872 cm^3
• Polarizability: 34.045444 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true