(2S)-2-({4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]phenyl}formamido)pentanedioic acid

• ChemBase ID: 176853
• Molecular Formular: C23H23N7O5
• Molecular Mass: 477.47262
• Monoisotopic Mass: 477.17606687
• SMILES: n1c(nc2c(c1N)nc(cn2)CC(c1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O)CC#C)N
• Canonical SMILES: C#CCC(c1ccc(cc1)C(=O)N[C@H](C(=O)O)CCC(=O)O)Cc1cnc2c(n1)c(N)nc(n2)N
• InChI: InChI=1S/C23H23N7O5/c1-2-3-14(10-15-11-26-20-18(27-15)19(24)29-23(25)30-20)12-4-6-13(7-5-12)21(33)28-16(22(34)35)8-9-17(31)32/h1,4-7,11,14,16H,3,8-10H2,(H,28,33)(H,31,32)(H,34,35)(H4,24,25,26,29,30)/t14?,16-/m0/s1
• InChIKey: OGSBUKJUDHAQEA-WMCAAGNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-({4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]phenyl}formamido)pentanedioic acid
• IUPAC Traditional name: pralatrexate
• Synonyms: N-[4-[1-[(2,4-Diamino-6-pteridinyl)methyl]-3-butyn-1-yl]benzoyl]-L-glutamic Acid; N-[4-[1-[(2,4-Diamino-6-pteridinyl)methyl]-3-butynyl]benzoyl]-L-glutamic Acid; 10-Propargyl-10-deazaaminopterin; Folotyn; PDX; Pralatrexate; Pralatrexate(Folotyn)

Database IDs

• CAS Number: 146464-95-1
• PubChem SID: 164232763
• PubChem CID: 148121

CALCULATED PROPERTIES

• Acid pKa: 3.2835035
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -2.7740548
• LogD (pH = 7.4): -5.7050033
• Log P: 0.61516607
• Molar Refractivity: 126.8184 cm^3
• Polarizability: 46.611214 Å^3
• Polar Surface Area: 207.3 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Target: DHFR

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - P700500

An antifolate with high affinity for the reduced folate carrier-type 1, produces marked complete and durable remissions in a diversity of chemotherapy refractory cases of T-cell lymphoma.

REFERENCES

• Krug, L.M. et al.: Clin. Cancer Res., 6, 3493 (2000)
• O'Connor, O.A. et al.: Br. J. Haematol., 139, 425 (2000)
• O'Connor, O.A. et al.: J. Clin. Oncol., 29, 1182 (2000)