(2R,3R,6S,7R)-3-[(acetyloxy)methyl]-7-[(6R)-6-(2-aminoacetamido)-6-carboxyhexanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid

• ChemBase ID: 4063
• Molecular Formular: C19H28N4O9S
• Molecular Mass: 488.51202
• Monoisotopic Mass: 488.1576995
• SMILES: CC(=O)OC[C@@H]1CS[C@H]2[C@H](NC(=O)CCCC[C@@H](NC(=O)CN)C(=O)O)C(=O)N2[C@H]1C(=O)O
• Canonical SMILES: CC(=O)OC[C@@H]1CS[C@@H]2N([C@H]1C(=O)O)C(=O)[C@H]2NC(=O)CCCC[C@H](C(=O)O)NC(=O)CN
• InChI: InChI=1S/C19H28N4O9S/c1-9(24)32-7-10-8-33-17-14(16(27)23(17)15(10)19(30)31)22-12(25)5-3-2-4-11(18(28)29)21-13(26)6-20/h10-11,14-15,17H,2-8,20H2,1H3,(H,21,26)(H,22,25)(H,28,29)(H,30,31)/t10-,11-,14-,15-,17+/m1/s1
• InChIKey: JDAREAJBQYNCGO-GYOFPWAWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,6S,7R)-3-[(acetyloxy)methyl]-7-[(6R)-6-(2-aminoacetamido)-6-carboxyhexanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,6S,7R)-3-[(acetyloxy)methyl]-7-[(6R)-6-(2-aminoacetamido)-6-carboxyhexanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid
• Synonyms: (6r,7r)-3-[(Acetyloxy)Methyl]-7-{[(6s)-6-(Glycylamino)-7-Oxido-7-Oxoheptanoyl]Amino}-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]Octane-2-Carboxylate

Database IDs

• PubChem SID: 160967497; 46504718
• PubChem CID: 46936986; 46936987

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.0213876
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -6.4457064
• LogD (pH = 7.4): -8.008023
• Log P: -4.90816
• Molar Refractivity: 111.3012 cm^3
• Polarizability: 44.656773 Å^3
• Polar Surface Area: 205.43 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.47
• LOG S: -2.52
• Solubility (Water): 1.69e+00 g/l

DETAILS

DrugBank - DB04488

Drug information: experimental