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

• ChemBase ID: 6230
• Molecular Formular: C14H14N2O5S2
• Molecular Mass: 354.40136
• Monoisotopic Mass: 354.03441356
• SMILES: S1CC(=C)[C@@H](C(=O)O)N=C1[C@@H](C(=O)O)NC(=O)Cc1cccs1
• Canonical SMILES: O=C(N[C@@H](C1=N[C@@H](C(=C)CS1)C(=O)O)C(=O)O)Cc1cccs1
• InChI: InChI=1S/C14H14N2O5S2/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/h2-4,10-11H,1,5-6H2,(H,15,17)(H,18,19)(H,20,21)/t10-,11-/m0/s1
• InChIKey: VBBNCGUNWSPHOY-QWRGUYRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-2-[(R)-carboxy[2-(thiophen-2-yl)acetamido]methyl]-5-methylidene-5,6-dihydro-4H-1,3-thiazine-4-carboxylic acid
• IUPAC Traditional name: (4S)-2-[(R)-carboxy[2-(thiophen-2-yl)acetamido]methyl]-5-methylidene-4,6-dihydro-1,3-thiazine-4-carboxylic acid
• Synonyms: 2-[CARBOXY-(2-THIOPHEN-2-YL-ACETYLAMINO)-METHYL]-5-METHYLENE-5,6-DIHYDRO-2H-[1,3]THIAZINE-4-CARBOXYLIC ACID

Database IDs

• PubChem SID: 99445094; 160969655
• PubChem CID: 46937164

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6158335
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.7566334
• LogD (pH = 7.4): -4.999348
• Log P: 1.34835
• Molar Refractivity: 83.8949 cm^3
• Polarizability: 32.66954 Å^3
• Polar Surface Area: 116.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.07
• LOG S: -3.82
• Solubility (Water): 5.34e-02 g/l

DETAILS

DrugBank - DB08623

Drug information: experimental