(1S,7R)-4-oxo-3-(pyridin-2-ylmethyl)-10-oxa-3-azatricyclo[5.2.1.01,5]dec-8-ene-6-carboxylic acid

• ChemBase ID: 121687
• Molecular Formular: C15H14N2O4
• Molecular Mass: 286.28266
• Monoisotopic Mass: 286.09535694
• SMILES: C12[C@]3(O[C@H](C2C(=O)O)C=C3)CN(C1=O)Cc1ncccc1
• Canonical SMILES: OC(=O)C1[C@@H]2C=C[C@@]3(C1C(=O)N(C3)Cc1ccccn1)O2
• InChI: InChI=1S/C15H14N2O4/c18-13-12-11(14(19)20)10-4-5-15(12,21-10)8-17(13)7-9-3-1-2-6-16-9/h1-6,10-12H,7-8H2,(H,19,20)/t10-,11?,12?,15-/m1/s1
• InChIKey: XSEHIJHACSPQOL-TVRADYJESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162216040
• PubChem CID: 16394735

CALCULATED PROPERTIES

• Acid pKa: 3.5928223
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -2.0127685
• LogD (pH = 7.4): -3.5359945
• Log P: -1.0386732
• Molar Refractivity: 71.885 cm^3
• Polarizability: 27.90567 Å^3
• Polar Surface Area: 79.73 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true