(2S,3S,4S,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 130196
• Molecular Formular: C14H13BrClNO7
• Molecular Mass: 422.61252
• Monoisotopic Mass: 420.95639144
• SMILES: Brc1ccc2c(c(O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c[nH]2)c1Cl
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](Oc2c[nH]c3c2c(Cl)c(cc3)Br)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C14H13BrClNO7/c15-4-1-2-5-7(8(4)16)6(3-17-5)23-14-11(20)9(18)10(19)12(24-14)13(21)22/h1-3,9-12,14,17-20H,(H,21,22)/t9-,10-,11+,12-,14+/m0/s1
• InChIKey: DHJFFLKPAYHPHU-BYNIDDHOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 5-Bromo-4-chloro-3-indolyl-β-D-glucuronide; X-Gluc

Database IDs

• CAS Number: 18656-89-8
• PubChem SID: 162224480
• PubChem CID: 2733579
• Chemspider ID: 2015360
• Wikipedia Title: X-Gluc

CALCULATED PROPERTIES

• Acid pKa: 2.9452777
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.3187351
• LogD (pH = 7.4): -2.2872984
• Log P: 1.1934463
• Molar Refractivity: 83.5648 cm^3
• Polarizability: 34.665928 Å^3
• Polar Surface Area: 132.24 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true