methyl (2R,3R,4R,5S,6S)-3,4,5-tris(acetyloxy)-6-(5-{2-[4-({2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl}methyl)phenyl]phenyl}-2H-1,2,3,4-tetrazol-2-yl)oxane-2-carboxylate

• ChemBase ID: 171741
• Molecular Formular: C38H44N6O10
• Molecular Mass: 744.79016
• Monoisotopic Mass: 744.31189164
• SMILES: c1c(ccc(c1)c1ccccc1c1nn(nn1)[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)CN1C(=O)C2(N=C1CCCC)CCCC2
• Canonical SMILES: CCCCC1=NC2(C(=O)N1Cc1ccc(cc1)c1ccccc1c1nnn(n1)[C@H]1O[C@H](C(=O)OC)[C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)CCCC2
• InChI: InChI=1S/C38H44N6O10/c1-6-7-14-29-39-38(19-10-11-20-38)37(49)43(29)21-25-15-17-26(18-16-25)27-12-8-9-13-28(27)34-40-42-44(41-34)35-32(53-24(4)47)30(51-22(2)45)31(52-23(3)46)33(54-35)36(48)50-5/h8-9,12-13,15-18,30-33,35H,6-7,10-11,14,19-21H2,1-5H3/t30-,31-,32+,33-,35+/m1/s1
• InChIKey: UKSGMKYWGKQGGT-LTZUXGGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3R,4R,5S,6S)-3,4,5-tris(acetyloxy)-6-(5-{2-[4-({2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl}methyl)phenyl]phenyl}-2H-1,2,3,4-tetrazol-2-yl)oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,3R,4R,5S,6S)-3,4,5-tris(acetyloxy)-6-(5-{2-[4-({2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl}methyl)phenyl]phenyl}-1,2,3,4-tetrazol-2-yl)oxane-2-carboxylate
• Synonyms: 1-[5-[4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl][1,1'-biphenyl]-2-yl]-2H-tetrazol-2-yl]-1-deoxy-β-D-glucopyranuronic Acid Methyl Ester 2,3,4-Triacetate; Irbesartan N-β-D-2,3,4-Tri-O-acetyl-glucuronide Methyl Ester

Database IDs

• CAS Number: 224170-69-8
• PubChem SID: 164227651
• PubChem CID: 71749530

CALCULATED PROPERTIES

• H Acceptors: 10
• H Donor: 0
• LogD (pH = 5.5): 4.848003
• LogD (pH = 7.4): 4.865288
• Log P: 4.8655124
• Molar Refractivity: 211.6852 cm^3
• Polarizability: 76.230606 Å^3
• Polar Surface Area: 190.7 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - I751020

An intermediate in the production of Irbesartan metabolites

REFERENCES

• Perrier, L., et al.: J. Pharmacol. Exp. Ther., 271, 91 (1994)
• Wexler, R., et al.: J. Med. Chem., 39, 625 (1994)