(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-methyl-1,1-dioxo-3-[(pyridin-2-yl)carbamoyl]-2H-1λ6,2-benzothiazin-4-yl}oxy)oxane-2-carboxylic acid

• ChemBase ID: 176796
• Molecular Formular: C21H21N3O10S
• Molecular Mass: 507.47054
• Monoisotopic Mass: 507.09476489
• SMILES: c1cccc2c1C(=C(N(S2(=O)=O)C)C(=O)Nc1ncccc1)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC2=C(C(=O)Nc3ccccn3)N(C)S(=O)(=O)c3c2cccc3)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H21N3O10S/c1-24-13(19(28)23-12-8-4-5-9-22-12)17(10-6-2-3-7-11(10)35(24,31)32)33-21-16(27)14(25)15(26)18(34-21)20(29)30/h2-9,14-16,18,21,25-27H,1H3,(H,29,30)(H,22,23,28)/t14-,15-,16+,18-,21+/m0/s1
• InChIKey: KDCQAKWMMCEUEI-DQSYDGHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-methyl-1,1-dioxo-3-[(pyridin-2-yl)carbamoyl]-2H-1λ^6,2-benzothiazin-4-yl}oxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-methyl-1,1-dioxo-3-[(pyridin-2-yl)carbamoyl]-1λ^6,2-benzothiazin-4-yl}oxy)oxane-2-carboxylic acid
• Synonyms: 2-Methyl-1,1-dioxido-3-[(2-pyridinylamino)carbonyl]-2H-1,2-benzothiazin-4-yl β-D-Glucopyranosiduronic Acid; 2-Methyl-3-[(2-pyridinylamino)carbonyl]-2H-1,2-benzothiazin-4-yl β-D-Glucopyranosiduronic Acid S,S-Dioxide; Piroxicam O-β-D-Glucuronide

Database IDs

• CAS Number: 108929-12-0
• PubChem SID: 164232706
• PubChem CID: 71751702

CALCULATED PROPERTIES

• Acid pKa: 2.6784046
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -3.5367737
• LogD (pH = 7.4): -4.475381
• Log P: -2.2512305
• Molar Refractivity: 119.3242 cm^3
• Polarizability: 46.361332 Å^3
• Polar Surface Area: 195.82 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P510010

A metabolite of the cyclooxygenase inhibitor Piroxicam (P510010).

REFERENCES

• Richardson, C.J. et al.: Eur. J. Clin. Pharmacol., 32, 89 (1987)