N-{4-[(3S)-1-cyano-3-hydroxycyclopentyl]phenyl}-2-[(pyridin-4-ylmethyl)amino]pyridine-3-carboxamide hydrochloride

• ChemBase ID: 170131
• Molecular Formular: C24H24ClN5O2
• Molecular Mass: 449.93266
• Monoisotopic Mass: 449.16185271
• SMILES: c1c(ccc(c1)NC(=O)c1cccnc1NCc1ccncc1)C1(CC[C@@H](C1)O)C#N.Cl
• Canonical SMILES: N#CC1(CC[C@@H](C1)O)c1ccc(cc1)NC(=O)c1cccnc1NCc1ccncc1.Cl
• InChI: InChI=1S/C24H23N5O2.ClH/c25-16-24(10-7-20(30)14-24)18-3-5-19(6-4-18)29-23(31)21-2-1-11-27-22(21)28-15-17-8-12-26-13-9-17;/h1-6,8-9,11-13,20,30H,7,10,14-15H2,(H,27,28)(H,29,31);1H/t20-,24?;/m0./s1
• InChIKey: MKYYCCAFGYUXJH-BAHZNLOQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-[(3S)-1-cyano-3-hydroxycyclopentyl]phenyl}-2-[(pyridin-4-ylmethyl)amino]pyridine-3-carboxamide hydrochloride
• IUPAC Traditional name: N-{4-[(3S)-1-cyano-3-hydroxycyclopentyl]phenyl}-2-[(pyridin-4-ylmethyl)amino]pyridine-3-carboxamide hydrochloride
• Synonyms: rel-N-[4-[(1R,3S)-1-Cyano-3-hydroxycyclopentyl]phenyl]-2-[(4-pyridinylmethyl)amino]-3-pyridinecarboxamide Hydrochloride; trans-3-Hydroxy-apatinib Hydrochloride; rac trans-3-Hydroxy Apatinib Hydrochloride

Database IDs

• PubChem SID: 164226041
• PubChem CID: 71748820

CALCULATED PROPERTIES

• Acid pKa: 11.698761
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.6336548
• LogD (pH = 7.4): 2.9007492
• Log P: 2.9048853
• Molar Refractivity: 120.8293 cm^3
• Polarizability: 44.491985 Å^3
• Polar Surface Area: 110.93 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H802105

trans-3-Hydroxy Apatinib is 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)