(2S)-2-[(R)-carboxy[2-(thiophen-2-yl)acetamido]methyl]-5-methyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

• ChemBase ID: 1996
• Molecular Formular: C14H16N2O5S2
• Molecular Mass: 356.41724
• Monoisotopic Mass: 356.05006362
• SMILES: S1CC(=C(C(=O)O)N[C@@H]1[C@@H](C(=O)O)NC(=O)Cc1cccs1)C
• Canonical SMILES: O=C(N[C@@H]([C@@H]1SCC(=C(N1)C(=O)O)C)C(=O)O)Cc1cccs1
• InChI: InChI=1S/C14H16N2O5S2/c1-7-6-23-12(16-10(7)13(18)19)11(14(20)21)15-9(17)5-8-3-2-4-22-8/h2-4,11-12,16H,5-6H2,1H3,(H,15,17)(H,18,19)(H,20,21)/t11-,12-/m0/s1
• InChIKey: JRYZEMHNDUZNMI-RYUDHWBXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(R)-carboxy[2-(thiophen-2-yl)acetamido]methyl]-5-methyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• IUPAC Traditional name: (2S)-2-[(R)-carboxy[2-(thiophen-2-yl)acetamido]methyl]-5-methyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• Synonyms: Hydrolyzed Cephalothin

Database IDs

• PubChem SID: 46508343; 160965451
• PubChem CID: 5288660

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6170366
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.045579
• LogD (pH = 7.4): -5.2939696
• Log P: 1.0226307
• Molar Refractivity: 85.9456 cm^3
• Polarizability: 33.05874 Å^3
• Polar Surface Area: 115.73 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.83
• LOG S: -3.98
• Solubility (Water): 3.74e-02 g/l

DETAILS

DrugBank - DB02247

Drug information: experimental