(2S,3S,4S,5R,6R)-6-[(3-carboxy-4-hydroxyphenyl)amino]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 172794
• Molecular Formular: C13H15NO9
• Molecular Mass: 329.2595
• Monoisotopic Mass: 329.07468107
• SMILES: c1c(ccc(c1C(=O)O)O)N[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](Nc2ccc(c(c2)C(=O)O)O)O[C@H]([C@H]1O)C(=O)O
• InChI: InChI=1S/C13H15NO9/c15-6-2-1-4(3-5(6)12(19)20)14-11-9(18)7(16)8(17)10(23-11)13(21)22/h1-3,7-11,14-18H,(H,19,20)(H,21,22)/t7-,8-,9+,10-,11+/m0/s1
• InChIKey: JWCIKZBPGKBTKY-QUARPLMYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(3-carboxy-4-hydroxyphenyl)amino]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(3-carboxy-4-hydroxyphenyl)amino]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: N-β-D-Glucopyranosyl-5-amino-2-hydroxybenzoic Acid; N-β-D-Glucopyranosyl-5-aminosalicylic Acid; N-β-D-Glucuronide-5-ASA; Mesalazine N-β-D-Glucuronide

Database IDs

• PubChem SID: 164228704
• PubChem CID: 71750021

CALCULATED PROPERTIES

• Acid pKa: 2.844918
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -4.876623
• LogD (pH = 7.4): -7.3782315
• Log P: -0.6442662
• Molar Refractivity: 73.0184 cm^3
• Polarizability: 28.200518 Å^3
• Polar Surface Area: 176.78 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M258110

A metabolite of Mesalazine (M258100).