2-({6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl}methyl)-4-fluorobenzonitrile; trifluoroacetic acid

• ChemBase ID: 160438
• Molecular Formular: C20H21F4N5O4
• Molecular Mass: 471.4054528
• Monoisotopic Mass: 471.15296706
• SMILES: C1CN(C[C@@H](C1)N)c1cc(=O)n(c(=O)n1Cc1cc(ccc1C#N)F)C.C(F)(F)(F)C(=O)O
• Canonical SMILES: OC(=O)C(F)(F)F.N#Cc1ccc(cc1Cn1c(cc(=O)n(c1=O)C)N1CCC[C@H](C1)N)F
• InChI: InChI=1S/C18H20FN5O2.C2HF3O2/c1-22-17(25)8-16(23-6-2-3-15(21)11-23)24(18(22)26)10-13-7-14(19)5-4-12(13)9-20;3-2(4,5)1(6)7/h4-5,7-8,15H,2-3,6,10-11,21H2,1H3;(H,6,7)/t15-;/m1./s1
• InChIKey: RPRCIXKRLHWPJO-XFULWGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl}methyl)-4-fluorobenzonitrile; trifluoroacetic acid
• IUPAC Traditional name: 2-({6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl}methyl)-4-fluorobenzonitrile; trifluoroacetic acid
• Synonyms: 2-[[6-[(3R)-3-Amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-4-fluorobenzonitrile Trifluoroacetate

Database IDs

• CAS Number: 928201-45-0
• PubChem SID: 162254573
• PubChem CID: 49871605

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.6874496
• LogD (pH = 7.4): -0.7264871
• Log P: 1.2983421
• Molar Refractivity: 104.4796 cm^3
• Polarizability: 35.515724 Å^3
• Polar Surface Area: 93.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A627960

2-[[6-[(3R)-3-Amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-4-fluorobenzonitrile trifluoroacetate is a potent, selective, and noncovalent inhibitor of dipeptidyl peptidase IV (DPP-4). This inhibitor provides sustained reduc

REFERENCES

• Augeri, D., et al.: J. Med. Chem., 48, 5025 (2005)
• Drucker, D., et al.: Lancet, 368, 1696 (2005)
• Cvetkovic, R., et al.: Drugs, 67, 935 (2005)