(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[N-(5-methyl-1,2-oxazol-3-yl)4-amino(2H4)benzenesulfonamido]oxane-2-carboxylic acid

• ChemBase ID: 178001
• Molecular Formular: C16H19N3O9S
• Molecular Mass: 429.40176
• Monoisotopic Mass: 429.0842002
• SMILES: c1(ccc(cc1)N)S(=O)(=O)N([C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)c1noc(c1)C
• Canonical SMILES: OC(=O)[C@@H]1O[C@H]([C@H]([C@H]([C@@H]1O)O)O)N(S(=O)(=O)c1ccc(cc1)N)c1noc(c1)C
• InChI: InChI=1S/C16H19N3O9S/c1-7-6-10(18-28-7)19(29(25,26)9-4-2-8(17)3-5-9)15-13(22)11(20)12(21)14(27-15)16(23)24/h2-6,11-15,20-22H,17H2,1H3,(H,23,24)/t11-,12-,13+,14-,15+/m0/s1
• InChIKey: BLFOMTRQSZIMKK-SBJFKYEJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[N-(5-methyl-1,2-oxazol-3-yl)4-amino(^2H₄)benzenesulfonamido]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[N-(5-methyl-1,2-oxazol-3-yl)4-amino(^2H₄)benzenesulfonamido]oxane-2-carboxylic acid
• Synonyms: 1-[[(4-Aminophenyl-d4)sulfonyl](5-methyl-3-isoxazolyl)amino]-1-deoxy-β-D-glucopyranuronic Acid; Sulfamethoxazole-d4 N1-Glucuronide; Sulfisomezole-d4 N1-Glucuronide; Glucu-SFM-d4; Sulfamethoxazole-d4 β-D-Glucuronide

Database IDs

• PubChem SID: 164233911
• PubChem CID: 71752292

CALCULATED PROPERTIES

• Acid pKa: 3.3209472
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.271885
• LogD (pH = 7.4): -4.507643
• Log P: -1.3049074
• Molar Refractivity: 96.922 cm^3
• Polarizability: 37.894966 Å^3
• Polar Surface Area: 196.65 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off White to Pale Yellow Solid
• Melting Point: >190°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S699137

The main labelled metabolite of Sulfamethoxazole.

REFERENCES

• Altenburger, R., et al.: Environ. Toxicol. Chem., 19, 2341 (2000)
• Pascoe, R., et al.: Anal. Chem., 73, 6014 (2000)
• Zhaohua, H., et al.: Eur. J. Med. Chem., 36, 863 (2000)