(2R)-2-{[4-({[(6R)-2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid

• ChemBase ID: 3967
• Molecular Formular: C20H25N7O6
• Molecular Mass: 459.4558
• Monoisotopic Mass: 459.18663156
• SMILES: CN1[C@H](CNc2ccc(cc2)C(=O)N[C@H](CCC(=O)O)C(=O)O)CNc2c1c(=O)[nH]c(N)n2
• Canonical SMILES: OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)NC[C@@H]1CNc2c(N1C)c(=O)[nH]c(n2)N
• InChI: InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12-,13-/m1/s1
• InChIKey: ZNOVTXRBGFNYRX-CHWSQXEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[4-({[(6R)-2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
• IUPAC Traditional name: (2R)-2-{[4-({[(6R)-2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
• Synonyms: 5-Methyl-5,6,7,8-Tetrahydrofolic Acid

Database IDs

• PubChem SID: 46505979; 160967402
• PubChem CID: 46936961

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.2189753
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -4.9213276
• LogD (pH = 7.4): -7.6960106
• Log P: -2.8438423
• Molar Refractivity: 126.8813 cm^3
• Polarizability: 43.15752 Å^3
• Polar Surface Area: 198.48 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.26
• LOG S: -3.12
• Solubility (Water): 3.46e-01 g/l

DETAILS

DrugBank - DB04375

Drug information: experimental