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

• ChemBase ID: 4335
• 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)nc(N)[nH]2
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NC[C@H]1CNc2c(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-/m0/s1
• InChIKey: ZNOVTXRBGFNYRX-STQMWFEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[4-({[(6S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
• IUPAC Traditional name: 5-methyltetrahydrofolate
• Synonyms: N-[4-[[[(6S)-2-Amino-3,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-L-glutamic Acid; (6S)-5-Methyltetrahydrofolic Acid; 5-Methyl-(6S)-tetrahydrofolic Acid; LMSR; l-N5; Methyl-L-tetrahydrofolic Acid; Levomefolic Acid(See also L375720); [(6S)-5-methyl-5,6,7,8-tetrahydropteroyl]glutamate; N-(5-methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid; 5-methyltetrahydrofolate

Database IDs

• CAS Number: 134-35-0; 31690-09-2
• PubChem SID: 46505172; 160967767
• PubChem CID: 444412

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.419046
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -5.4424167
• LogD (pH = 7.4): -8.077267
• Log P: -2.288805
• 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

ALOGPS 2.1

• Log P: -0.58
• LOG S: -3.14
• Solubility (Water): 3.32e-01 g/l

PROPERTIES

Physical Property

• Solubility: Aqueous Base
• Apperance: Off-White Solid
• Melting Point: 221-224°C (dec.)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

DrugBank - DB04789

• Drug Groups: experimental
• Description: 5-Methyltetrahydrofolate is a methylated derivate of tetrahydrofolate. It is generated by methylenetetrahydrofolate reductase from 5,10-methylenetetrahydrofolate and used to recycle homocysteine back to methionine by 5-methyltetrahydrofolate-homocysteine methyltransferases (also called methionine synthases).
• External Links: Wikipedia

Toronto Research Chemicals - L375730

A natural, active form of folic acid used at the cellular level for DNA reproduction, the cysteine cycle and the regulation of homocysteine among other functions. It is a coenzymated form of folic acid and a more bioavailable alternative in dietary supple

REFERENCES

• Willems, F. et al.: Br. J. Pharmacol., 145, 823 (2004)
• Prinz-Langhebohi, R.: et al., Br. J. Pharmacol., 158, 2014 (2004)
• Wright, A. et al.: Brit, J. Nutrit., 103, 724 (2010)