(2S)-4-[(5-aminopentyl)carbamoyl]-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]butanoic acid

• ChemBase ID: 160387
• Molecular Formular: C25H34N10O4
• Molecular Mass: 538.60206
• Monoisotopic Mass: 538.27644962
• SMILES: n1c(nc2c(c1N)nc(cn2)CN(c1ccc(cc1)C(=O)N[C@@H](CCC(=O)NCCCCCN)C(=O)O)C)N
• Canonical SMILES: NCCCCCNC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)N(Cc1cnc2c(n1)c(N)nc(n2)N)C
• InChI: InChI=1S/C25H34N10O4/c1-35(14-16-13-30-22-20(31-16)21(27)33-25(28)34-22)17-7-5-15(6-8-17)23(37)32-18(24(38)39)9-10-19(36)29-12-4-2-3-11-26/h5-8,13,18H,2-4,9-12,14,26H2,1H3,(H,29,36)(H,32,37)(H,38,39)(H4,27,28,30,33,34)/t18-/m0/s1
• InChIKey: DYRNPWYHGNQALD-SFHVURJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-[(5-aminopentyl)carbamoyl]-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]butanoic acid
• IUPAC Traditional name: (2S)-4-[(5-aminopentyl)carbamoyl]-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]butanoic acid
• Synonyms: N-(5-Aminopentyl)-N2-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamine; MTX-DAP; N-(5-Aminopentyl) Methotrexate Amide

Database IDs

• CAS Number: 136672-64-5
• PubChem SID: 162254522
• PubChem CID: 10174893

CALCULATED PROPERTIES

• Acid pKa: 3.3122365
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -2.625423
• LogD (pH = 7.4): -2.62374
• Log P: -2.6233983
• Molar Refractivity: 147.9905 cm^3
• Polarizability: 54.860966 Å^3
• Polar Surface Area: 228.36 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A619600

The 5-aminopentyl amide derivative of the folic acid antagonist Methotrexate (M260675) used in the study of membrane-associated folate transporters from L1210 cells.

REFERENCES

• Fan, J. et al.: J. Biol. Chem., 266, 14862 (1991)