2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 169647
• Molecular Formular: C25H27ClN2O8
• Molecular Mass: 518.94348
• Monoisotopic Mass: 518.14559351
• SMILES: c1(ccc2c(c1)c(c(n2C(=O)c1ccc(cc1)Cl)C)CC(=O)N[C@H]1[C@H]([C@@H]([C@@H](O[C@@H]1O)CO)O)O)OC
• Canonical SMILES: OC[C@@H]1O[C@H](O)[C@H]([C@H]([C@@H]1O)O)NC(=O)Cc1c2cc(OC)ccc2n(c1C)C(=O)c1ccc(cc1)Cl
• InChI: InChI=1S/C25H27ClN2O8/c1-12-16(10-20(30)27-21-23(32)22(31)19(11-29)36-25(21)34)17-9-15(35-2)7-8-18(17)28(12)24(33)13-3-5-14(26)6-4-13/h3-9,19,21-23,25,29,31-32,34H,10-11H2,1-2H3,(H,27,30)/t19-,21-,22-,23-,25+/m1/s1
• InChIKey: LGAJOMLFGCSBFF-OLXDQKQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-N-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: 2-[[[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl]amino]-2-deoxy-α-D-Glucopyranose; α-Glucametacine; α-Glucamethacin; α-Indomethacin Glucosamide; α-Glucametacin

Database IDs

• CAS Number: 871014-84-5
• PubChem SID: 162263779
• PubChem CID: 13111987

CALCULATED PROPERTIES

• Acid pKa: 11.441243
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.5324452
• LogD (pH = 7.4): 0.53240824
• Log P: 0.53244567
• Molar Refractivity: 129.1916 cm^3
• Polarizability: 51.61975 Å^3
• Polar Surface Area: 150.48 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G412800

A nonsteroidal antiinflammatory analgesic. An indomethacin conjugates with D-glucosamine was prepared for reducing ulcerogenic potency, increasing the bioavailability of indomethacin and exerting the coordinative effects on osteoarthritis.

REFERENCES

• Mizuma, T., et al.: Biochem. Pharmacol., 43, 2037 (1992)
• Giraud, I., et al.: Bioconjugate Chem., 11, 212 (1992)
• Reginster, J., et al.: Lancet, 357, 251 (1992)