(2S)-2-[(4-{[(2,7-dimethyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl](prop-2-yn-1-yl)amino}-2-fluorophenyl)formamido]-4-(1H-1,2,3,4-tetrazol-5-yl)butanoic acid

• ChemBase ID: 176828
• Molecular Formular: C26H25FN8O4
• Molecular Mass: 532.5263032
• Monoisotopic Mass: 532.19827954
• SMILES: c12c(c(=O)nc([nH]1)C)cc(c(c2)C)CN(c1ccc(c(c1)F)C(=O)N[C@@H](CCc1[nH]nnn1)C(=O)O)CC#C
• Canonical SMILES: C#CCN(c1ccc(c(c1)F)C(=O)N[C@H](C(=O)O)CCc1nnn[nH]1)Cc1cc2c(=O)nc([nH]c2cc1C)C
• InChI: InChI=1S/C26H25FN8O4/c1-4-9-35(13-16-11-19-22(10-14(16)2)28-15(3)29-25(19)37)17-5-6-18(20(27)12-17)24(36)30-21(26(38)39)7-8-23-31-33-34-32-23/h1,5-6,10-12,21H,7-9,13H2,2-3H3,(H,30,36)(H,38,39)(H,28,29,37)(H,31,32,33,34)/t21-/m0/s1
• InChIKey: IEJSCSAMMLUINT-NRFANRHFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{[(2,7-dimethyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl](prop-2-yn-1-yl)amino}-2-fluorophenyl)formamido]-4-(1H-1,2,3,4-tetrazol-5-yl)butanoic acid
• IUPAC Traditional name: plevitrexedumplevitrexed
• Synonyms: (αS)-α-[[4-[[(1,4-Dihydro-2,7-dimethyl-4-oxo-6-quinazolinyl)methyl]-2-propynylamino]-2-fluorobenzoyl]amino]-1H-tetrazole-5-butanoic Acid; BGC 9331; NSC 696259; ZD 9331; Vamidex; Plevitrexed

Database IDs

• CAS Number: 153537-73-6
• PubChem SID: 164232738
• PubChem CID: 213022

CALCULATED PROPERTIES

• Acid pKa: 3.1285524
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -0.95870906
• LogD (pH = 7.4): -2.7073512
• Log P: 2.3511338
• Molar Refractivity: 144.2951 cm^3
• Polarizability: 51.001663 Å^3
• Polar Surface Area: 165.56 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P625000

A novel non-polyglutamated thymidylate synthase inhibitor, in adult patients with solid tumors.

REFERENCES

• Sirotnak, F., et al.: Cancer Res., 45, 3992 (1985)
• Touroutoglou, N., et al.: Clin. Cancer Res., 2, 227 (1985)
• Twelves, C., et al.: Clin. Cancer Res., 5, 1696 (1985)
• Goh, B., et al.: J. Clin. Oncol., 19, 1476 (1985)