(2S,3S,4S,5R,6R)-6-{[(1R)-3-cyano-3-(4-{2-[(pyridin-4-ylmethyl)amino]pyridine-3-amido}phenyl)cyclopentyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 170132
• Molecular Formular: C30H31N5O8
• Molecular Mass: 589.59584
• Monoisotopic Mass: 589.21726298
• SMILES: c1c(ccc(c1)NC(=O)c1cccnc1NCc1ccncc1)C1(CC[C@H](C1)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C#N
• Canonical SMILES: N#CC1(CC[C@H](C1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)c1ccc(cc1)NC(=O)c1cccnc1NCc1ccncc1
• InChI: InChI=1S/C30H31N5O8/c31-16-30(10-7-20(14-30)42-29-24(38)22(36)23(37)25(43-29)28(40)41)18-3-5-19(6-4-18)35-27(39)21-2-1-11-33-26(21)34-15-17-8-12-32-13-9-17/h1-6,8-9,11-13,20,22-25,29,36-38H,7,10,14-15H2,(H,33,34)(H,35,39)(H,40,41)/t20-,22+,23+,24-,25+,29-,30?/m1/s1
• InChIKey: PSKAPWHLYYIXRO-QMXDASEZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(1R)-3-cyano-3-(4-{2-[(pyridin-4-ylmethyl)amino]pyridine-3-amido}phenyl)cyclopentyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(1R)-3-cyano-3-(4-{2-[(pyridin-4-ylmethyl)amino]pyridine-3-amido}phenyl)cyclopentyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: rel-(1R,3R)]-3-Cyano-3-[4-[[[2-[(4-pyridinylmethyl)amino]-3-pyridinyl]carbonyl]amino]phenyl]cyclopentyl β-D-Glucopyranosiduronic Acid; cis-3-Hydroxyapatinib β-O-Glucuronide; rac cis-3-Hydroxy Apatinib 3-O-β-D-Glucuronide

Database IDs

• CAS Number: 1376331-61-1
• PubChem SID: 164226042
• PubChem CID: 71748822

CALCULATED PROPERTIES

• Acid pKa: 3.068353
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -0.31095636
• LogD (pH = 7.4): -1.6982456
• Log P: -0.21917419
• Molar Refractivity: 153.11 cm^3
• Polarizability: 58.092827 Å^3
• Polar Surface Area: 207.15 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H802110

cis-3-Hydroxy Apatinib 3-O-β-D-Glucuronide is a glucuronide conjugate of cis-3-Hydroxy Apatinib and a metabolite of the antiangiogenic agent and selective VEGFR2 inhibitor Apatinib (A726150).

REFERENCES

• Ding, J, et al.: J. Chrom B Anal. Technol. Biomed. Life Sci., 895, 108 (2012)