(2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

• ChemBase ID: 128056
• Molecular Formular: C20H25N7O6
• Molecular Mass: 459.4558
• Monoisotopic Mass: 459.18663156
• SMILES: O=C(O)[C@H](NC(=O)c1ccc(cc1)NCC1N(c2c([nH]c(nc2=O)N)NC1)C)CCC(=O)O
• Canonical SMILES: OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)NCC1CNc2c(N1C)c(=O)nc([nH]2)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-ZGTCLIOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: levomefolic acid
• Synonyms: 5-methyltetrahydrofolic acid (5-Me-THFA, 5-Me-H₄FA); anion: 5-methyltetrahydrofolate (5-Me-THF, 5-Me-H₄F); L-methylfolate; Metafolin; Extrafolate-S; Levomefolic acid

Database IDs

• CAS Number: 134-35-0
• PubChem SID: 162222372
• PubChem CID: 444412; 439234
• ATC CODE: B03BB51
• Chemspider ID: 388371
• KEGG ID: D09353
• MeSH Name: 5-methyltetrahydrofolate
• Unique Ingredient Identifier: 8S95DH25XC
• Wikipedia Title: Levomefolic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.4979396
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -5.439699
• LogD (pH = 7.4): -8.076839
• Log P: -2.428055
• Molar Refractivity: 126.6813 cm^3
• Polarizability: 43.15752 Å^3
• Polar Surface Area: 198.48 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: oral, transdermal, subcutaneous
• Legal Status: medical food (US)
• Pregnancy Category: N