(2R,4R)-2-[(1S)-2-[(2R)-2-amino-2-carboxyethoxy]-1-[(2,6-dimethoxyphenyl)formamido]-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 2181
• Molecular Formular: C20H27N3O9S
• Molecular Mass: 485.50808
• Monoisotopic Mass: 485.14680046
• SMILES: COc1cccc(OC)c1C(=O)N[C@H]([C@@H]1N[C@H](C(=O)O)C(C)(C)S1)C(=O)OC[C@@H](N)C(=O)O
• Canonical SMILES: COc1cccc(c1C(=O)N[C@H]([C@@H]1N[C@@H](C(S1)(C)C)C(=O)O)C(=O)OC[C@H](C(=O)O)N)OC
• InChI: InChI=1S/C20H27N3O9S/c1-20(2)14(18(27)28)23-16(33-20)13(19(29)32-8-9(21)17(25)26)22-15(24)12-10(30-3)6-5-7-11(12)31-4/h5-7,9,13-14,16,23H,8,21H2,1-4H3,(H,22,24)(H,25,26)(H,27,28)/t9-,13-,14-,16-/m1/s1
• InChIKey: GFYFFUGNPVBDAK-APGPQJPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R)-2-[(1S)-2-[(2R)-2-amino-2-carboxyethoxy]-1-[(2,6-dimethoxyphenyl)formamido]-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: (2R,4R)-2-[(1S)-2-[(2R)-2-amino-2-carboxyethoxy]-1-[(2,6-dimethoxyphenyl)formamido]-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• Synonyms: Methicillin Acyl-Serine

Database IDs

• PubChem SID: 160965634; 46506281
• PubChem CID: 46936386; 46936385

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.0204146
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.6624365
• LogD (pH = 7.4): -5.5942407
• Log P: -4.5751634
• Molar Refractivity: 115.0294 cm^3
• Polarizability: 45.887478 Å^3
• Polar Surface Area: 186.51 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.85
• LOG S: -2.74
• Solubility (Water): 9.49e-01 g/l

DETAILS

DrugBank - DB02443

Drug information: experimental