(2S,4S)-2-[(1S)-2-[(2R)-2-amino-2-carboxyethoxy]-2-oxo-1-(2-phenylacetamido)ethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 2677
• Molecular Formular: C19H25N3O7S
• Molecular Mass: 439.4827
• Monoisotopic Mass: 439.14132116
• SMILES: CC1(C)S[C@H](N[C@H]1C(=O)O)[C@@H](NC(=O)Cc1ccccc1)C(=O)OC[C@@H](N)C(=O)O
• Canonical SMILES: O=C(N[C@H]([C@H]1N[C@H](C(S1)(C)C)C(=O)O)C(=O)OC[C@H](C(=O)O)N)Cc1ccccc1
• InChI: InChI=1S/C19H25N3O7S/c1-19(2)14(17(26)27)22-15(30-19)13(18(28)29-9-11(20)16(24)25)21-12(23)8-10-6-4-3-5-7-10/h3-7,11,13-15,22H,8-9,20H2,1-2H3,(H,21,23)(H,24,25)(H,26,27)/t11-,13-,14+,15+/m1/s1
• InChIKey: USNINKBPBVKHHZ-RZFFKMDDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-2-[(1S)-2-[(2R)-2-amino-2-carboxyethoxy]-2-oxo-1-(2-phenylacetamido)ethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: (2S,4S)-2-[(1S)-2-[(2R)-2-amino-2-carboxyethoxy]-2-oxo-1-(2-phenylacetamido)ethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• Synonyms: Penicillin G Acyl-Serine

Database IDs

• PubChem SID: 160966126; 46509100
• PubChem CID: 46936542; 46936541

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.3424679
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.17344
• LogD (pH = 7.4): -5.1766896
• Log P: -4.11155
• Molar Refractivity: 106.1544 cm^3
• Polarizability: 42.80238 Å^3
• Polar Surface Area: 168.05 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.78
• LOG S: -2.83
• Solubility (Water): 7.03e-01 g/l

DETAILS

DrugBank - DB02968

Drug information: experimental