(2S)-2-hydroxybutanedioic acid; 1-N'-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}-1-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

• ChemBase ID: 163523
• Molecular Formular: C32H30FN3O10
• Molecular Mass: 635.5931032
• Monoisotopic Mass: 635.1915224
• SMILES: C1(CC1)(C(=O)Nc1ccc(cc1)Oc1ccnc2c1cc(c(c2)OC)OC)C(=O)Nc1ccc(cc1)F.C(=O)(O)C[C@@H](C(=O)O)O
• Canonical SMILES: OC(=O)C[C@@H](C(=O)O)O.COc1cc2nccc(c2cc1OC)Oc1ccc(cc1)NC(=O)C1(CC1)C(=O)Nc1ccc(cc1)F
• InChI: InChI=1S/C28H24FN3O5.C4H6O5/c1-35-24-15-21-22(16-25(24)36-2)30-14-11-23(21)37-20-9-7-19(8-10-20)32-27(34)28(12-13-28)26(33)31-18-5-3-17(29)4-6-18;5-2(4(8)9)1-3(6)7/h3-11,14-16H,12-13H2,1-2H3,(H,31,33)(H,32,34);2,5H,1H2,(H,6,7)(H,8,9)/t;2-/m.0/s1
• InChIKey: HFCFMRYTXDINDK-WNQIDUERSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-hydroxybutanedioic acid; 1-N'-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}-1-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide; (2S)-2-hydroxybutanedioic acid; N'1-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}-N1-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide
• IUPAC Traditional name: (-)-malic acid; cabozantinib
• Synonyms: N-[4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl]-N'-(4-fluorophenyl)-1,1-cyclopropanedicarboxamide (2S)-2-Hydroxybutanedioic Acid; Cabozantinib S-Malate; XL 184; Cabozantinib L-Malate Salt; Cabozantinib malate

Database IDs

• CAS Number: 1140909-48-3
• PubChem SID: 162257658
• PubChem CID: 25102846

CALCULATED PROPERTIES

• Acid pKa: 13.461886
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 4.162173
• LogD (pH = 7.4): 4.645291
• Log P: 4.6580625
• Molar Refractivity: 136.1206 cm^3
• Polarizability: 52.4303 Å^3
• Polar Surface Area: 98.78 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 166-169°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Target: VEGFR

Product Information

• Salt Data: Malate

DETAILS

Toronto Research Chemicals - C051500

Cabozantinib is a small molecule C-Met modulator. Cabozantinib acts as a potent multitargeted VEGFR2, Met, FLT3, Tie2, Kit and Ret inhibitor with IC50 of 0.035, 1.8, 14.4, 14.3 and 4.6 nM for VEGFR2, Met, FLT3, Tie2 and Kit, respectively. Cabozantinib sho

REFERENCES

• Wells, S., et al.: J. Clin. Oncol., 28, 767 (1999)
• Camp, R., et al.: Cancer, 86, 2259 (1999)
• Morello, S., et al.: J. Cell Physiol., 189, 285 (1999)
• Zhang, Y., et al.: Oncogene, 21, 217 (1999)