(1R,11S)-8-oxo-3,14-dioxa-7-azatetracyclo[9.2.1.01,9.02,7]tetradec-12-ene-10-carboxylic acid

• ChemBase ID: 119551
• Molecular Formular: C12H13NO5
• Molecular Mass: 251.23532
• Monoisotopic Mass: 251.07937252
• SMILES: [C@@]123C(C(=O)N4C1OCCC4)C([C@H](O2)C=C3)C(=O)O
• Canonical SMILES: OC(=O)C1[C@H]2C=C[C@]3(C1C(=O)N1C3OCCC1)O2
• InChI: InChI=1S/C12H13NO5/c14-9-8-7(10(15)16)6-2-3-12(8,18-6)11-13(9)4-1-5-17-11/h2-3,6-8,11H,1,4-5H2,(H,15,16)/t6-,7?,8?,11?,12+/m0/s1
• InChIKey: IUOYQEHMOHDDDU-VHZGTCFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,11S)-8-oxo-3,14-dioxa-7-azatetracyclo[9.2.1.0^1,^9.0^2,^7]tetradec-12-ene-10-carboxylic acid
• IUPAC Traditional name: (1R,11S)-8-oxo-3,14-dioxa-7-azatetracyclo[9.2.1.0^1,^9.0^2,^7]tetradec-12-ene-10-carboxylic acid
• Synonyms: (8S,10aR)-6-oxo-2,3,4,6,6a,7,8,10b-octahydro-8,10a-epoxy[1,3]oxazino[2,3-a]isoindole-7-carboxylic acid

Database IDs

• PubChem SID: 162107984
• PubChem CID: 16394584

CALCULATED PROPERTIES

• Acid pKa: 3.9130788
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -2.2702253
• LogD (pH = 7.4): -3.8839188
• Log P: -0.6771336
• Molar Refractivity: 58.629 cm^3
• Polarizability: 22.963358 Å^3
• Polar Surface Area: 76.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true