(2R)-2-({4-[(3S)-6-[(2R,4S,5R)-2,4-diamino-6-oxo-1,3-diazinan-5-yl]-1,1,1-trifluoro-2,2-dihydroxyhexan-3-yl]phenyl}formamido)pentanedioic acid

• ChemBase ID: 3213
• Molecular Formular: C22H30F3N5O8
• Molecular Mass: 549.4975096
• Monoisotopic Mass: 549.20464761
• SMILES: N[C@@H]1N[C@H](N)[C@@H](CCC[C@@H](c2ccc(cc2)C(=O)N[C@H](CCC(=O)O)C(=O)O)C(O)(O)C(F)(F)F)C(=O)N1
• Canonical SMILES: N[C@@H]1N[C@H](N)[C@H](C(=O)N1)CCC[C@H](C(C(F)(F)F)(O)O)c1ccc(cc1)C(=O)N[C@@H](C(=O)O)CCC(=O)O
• InChI: InChI=1S/C22H30F3N5O8/c23-22(24,25)21(37,38)13(3-1-2-12-16(26)29-20(27)30-18(12)34)10-4-6-11(7-5-10)17(33)28-14(19(35)36)8-9-15(31)32/h4-7,12-14,16,20,29,37-38H,1-3,8-9,26-27H2,(H,28,33)(H,30,34)(H,31,32)(H,35,36)/t12-,13+,14-,16+,20-/m1/s1
• InChIKey: KOLDLUFBEMUZIM-WUAYEBGVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-({4-[(3S)-6-[(2R,4S,5R)-2,4-diamino-6-oxo-1,3-diazinan-5-yl]-1,1,1-trifluoro-2,2-dihydroxyhexan-3-yl]phenyl}formamido)pentanedioic acid
• IUPAC Traditional name: @10-CF3C(OH)2-ddacthf
• Synonyms: Hydrolyzed Form of 10-trifluoroacetyl-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid; 10-CF3C(OH)2-DDACTHF

Database IDs

• PubChem SID: 160966656; 46505325
• PubChem CID: 46936711

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.8423786
• H Acceptors: 11
• H Donor: 9
• LogD (pH = 5.5): -4.099282
• LogD (pH = 7.4): -5.8346095
• Log P: -3.7524304
• Molar Refractivity: 122.564 cm^3
• Polarizability: 47.729424 Å^3
• Polar Surface Area: 237.33 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.33
• LOG S: -2.72
• Solubility (Water): 1.04e+00 g/l

DETAILS

DrugBank - DB03546

Drug information: experimental