(2R)-5-(2-methoxy-2-oxoethyl)-2-[(1R)-2-oxo-1-[2-(thiophen-2-yl)acetamido]ethyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

• ChemBase ID: 3128
• Molecular Formular: C16H18N2O6S2
• Molecular Mass: 398.45392
• Monoisotopic Mass: 398.06062831
• SMILES: S1CC(=C(C(=O)O)N[C@H]1[C@@H](C=O)NC(=O)Cc1cccs1)CC(=O)OC
• Canonical SMILES: COC(=O)CC1=C(N[C@H](SC1)[C@H](NC(=O)Cc1cccs1)C=O)C(=O)O
• InChI: InChI=1S/C16H18N2O6S2/c1-24-13(21)5-9-8-26-15(18-14(9)16(22)23)11(7-19)17-12(20)6-10-3-2-4-25-10/h2-4,7,11,15,18H,5-6,8H2,1H3,(H,17,20)(H,22,23)/t11-,15-/m1/s1
• InChIKey: UUWFGEKEQSCSMB-IAQYHMDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-5-(2-methoxy-2-oxoethyl)-2-[(1R)-2-oxo-1-[2-(thiophen-2-yl)acetamido]ethyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• IUPAC Traditional name: (2R)-5-(2-methoxy-2-oxoethyl)-2-[(1R)-2-oxo-1-[2-(thiophen-2-yl)acetamido]ethyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• Synonyms: Cephalothin Group

Database IDs

• PubChem SID: 46506959; 160966572
• PubChem CID: 46936680

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7631059
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.603602
• LogD (pH = 7.4): -3.1447108
• Log P: 0.13423537
• Molar Refractivity: 96.0557 cm^3
• Polarizability: 37.08457 Å^3
• Polar Surface Area: 121.8 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.77
• LOG S: -4.16
• Solubility (Water): 2.79e-02 g/l

DETAILS

DrugBank - DB03450

Drug information: experimental