(7S)-2-(carboxyformamido)-7-{[(1,1-dioxo-1$l^{6},2-benzothiazol-3-yl)oxy]methyl}-4H,5H,7H-thieno[2,3-c]pyran-3-carboxylic acid

• ChemBase ID: 2540
• Molecular Formular: C18H14N2O9S2
• Molecular Mass: 466.44176
• Monoisotopic Mass: 466.01407204
• SMILES: O1[C@H](c2c(CC1)c(c(s2)NC(=O)C(=O)O)C(=O)O)COC1=NS(=O)(=O)c2c1cccc2
• Canonical SMILES: OC(=O)C(=O)Nc1sc2c(c1C(=O)O)CCO[C@H]2COC1=NS(=O)(=O)c2c1cccc2
• InChI: InChI=1S/C18H14N2O9S2/c21-14(18(24)25)19-16-12(17(22)23)9-5-6-28-10(13(9)30-16)7-29-15-8-3-1-2-4-11(8)31(26,27)20-15/h1-4,10H,5-7H2,(H,19,21)(H,22,23)(H,24,25)/t10-/m0/s1
• InChIKey: MDYIGSPVMWSFEZ-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S)-2-(carboxyformamido)-7-{[(1,1-dioxo-1$l^{6},2-benzothiazol-3-yl)oxy]methyl}-4H,5H,7H-thieno[2,3-c]pyran-3-carboxylic acid
• IUPAC Traditional name: (7S)-2-(carboxyformamido)-7-{[(1,1-dioxo-1$l^{6},2-benzothiazol-3-yl)oxy]methyl}-4H,5H,7H-thieno[2,3-c]pyran-3-carboxylic acid
• Synonyms: 7-(1,1-Dioxo-1h-Benzo[D]Isothiazol-3-Yloxymethyl)-2-(Oxalyl-Amino)-4,7-Dihydro-5h-Thieno[2,3-C]Pyran-3-Carboxylic Acid

Database IDs

• PubChem SID: 46504664; 160965990
• PubChem CID: 446871

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8844026
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -2.7455347
• LogD (pH = 7.4): -4.5259237
• Log P: 2.2900596
• Molar Refractivity: 106.067 cm^3
• Polarizability: 40.646194 Å^3
• Polar Surface Area: 168.66 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.81
• LOG S: -4.31
• Solubility (Water): 2.26e-02 g/l

DETAILS

DrugBank - DB02827

Drug information: experimental