Compound: Levomefolic acid
SMILES: O=c1nc([nH]c2c1N([C@H](CN2)CNc3ccc(C(=O)N[C@H](C(=O)O)CCC(=O)O)cc3)C)N
InChIKey: ZNOVTXRBGFNYRX-STQMWFEESA-N
Synonyms: Levomefolic acid, 31690-09-2, Levomefolinic acid, LMSR, L-methylfolate, Nutrifolin, L-5-MTHF, Acido levomefolico, 5-methyl-(6s)-tetrahydrofolic acid, Acide levomefolique, 8S95DH25XC, (2S)-2-[[4-[[(6S)-2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid, DTXSID00185583, L-methyl folate, (2S)-2-[[4-[[(6S)-2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid, acidum levomefolicum, (2S)-2-((4-(((6S)-2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino)benzoyl)amino)pentanedioic acid, (2S)-2-((4-(((6S)-2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methylamino)benzoyl)amino)pentanedioic acid, L-methyltetrahydrofolate, RefChem:799024, DTXCID40108074, 5-methyltetrahydrofolate, (L-Glu)-(S)-, N-(4-((((6S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzoyl)-L-glutamate, 5-mthf, Deplin, LEVOMEFOLATE, Levomefolicacid, (S)-2-(4-((((S)-2-Amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzamido)pentanedioic acid, 5-Methyltetrahydrofolate, L-5-Methyltetrahydrofolate, (6S)-5-methyltetrahydrofolate, 5- methyltetrahydrofolate, MFCD00870135, [(6S)-5-methyl-5,6,7,8-tetrahydropteroyl]glutamate, N-(5-methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid, Metafolin (TN), (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, N-[4-({[(6S)-2-AMINO-4-HYDROXY-5-METHYL-5,6,7,8-TETRAHYDROPTERIDIN-6-YL]METHYL}AMINO)BENZOYL]-L-GLUTAMIC ACID, (S)-N-[4-[[(2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid, N-[4-[[[(6S)-2-Amino-3,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-L-glutamic acid, THH, L-5-Methyltetrahydrofolic acid, Levomefolic acid [USAN], Levomefolinic acid [USAN], UNII-8S95DH25XC, (6s)-5-methyltetrahydrofolic acid, (S)-2-[4-[[[(S)-2-Amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl]amino]benzamido]pentanedioic Acid, N-(4-((((6S)-2-Amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzoyl)-L-glutamic acid, N-[4-({[(6S)-2-Amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid, LEVOMEFOLATE [VANDF], SCHEMBL79586, Levomefolic acid (USAN/INN), Levomefolic acid [USAN:INN], L-METHYLFOLATE [VANDF], LEVOMEFOLIC ACID [INN], CHEMBL1231574, SCHEMBL12704423, SCHEMBL14462652, SCHEMBL30051011, SCHEMBL31090431, (6S)-5-MTHF, CHEBI:136009, LEVOMEFOLIC ACID [WHO-DD], ZNOVTXRBGFNYRX-STQMWFEESA-N, BDBM50391007, EBC-27152, MSK000416, s6909, AKOS016008744, AKOS025402272, AC-7460, AS-0793, DB11256, FL24884, NCGC00378841-01, NCGC00485934-01, HY-14781, L-Glutamic acid, N-(4-(((2-amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-, (S)-, SY420414, L0335, NS00014759, (6s)-5-methyl-5,6,7,8-tetrahydrofolic acid, C00440, D09353, (6S)-5-METHYLTETRAHYDROFOLATE [WHO-DD], EN300-19768229, Q192553, BRD-K28580965-238-01-3, BRD-K28580965-238-02-1, Levomefolic acid 100 microg/mL in Acetonitrile:Water, (2S)-2-[[4-[[(6S)-2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl]methylamino]benzoyl]amino]pentanedioicacid, (2S)-2-{[4-({[(6S)-2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid, L-GLUTAMIC ACID, N-(4-((((6S)-2-AMINO-3,4,5,6,7,8-HEXAHYDRO-5-METHYL-4-OXO-6- PTERIDINYL)METHYL)AMINO)BENZOYL)-, L-Glutamic acid, N-[4-[[(2-amino-3,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-, N-(4-((((6S)-2-AMINO-5-METHYL-4-OXO-1,4,5,6,7,8-HEXAHYDROPTERIDIN-6- YL)METHYL)AMINO)BENZOYL)-L-GLUTAMIC ACID, N-{[4-({[(6S)-2-amino-4-hydroxy-5-methyl-5,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]carbonyl}-L-glutamic acid, N-{[4-({[(6S)-2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]carbonyl}-L-glutamic acid
Theoretical properties:
molecular_formula: C20H25N7O6
molecular_weight: 459.5 g/mol
exact_mass: 459.18663154 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 9
heavy_atom_count: 33
topological_polar_surface_area: 198 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: Approximately 0.3 mg/ml
Descriptions:
{"pubchem": "5-methyltetrahydrofolic acid is a tetrahydrofolic acid that is 5,6,7,8-tetrahydrofolic acid substituted by a methyl group at position 5. It has a role as a human metabolite. It is functionally related to a 5,6,7,8-tetrahydrofolic acid. It is a conjugate acid of a 5-methyltetrahydrofolate(2-).", "chebi": "A 5-methyltetrahydrofolic acid that has 6<i>S</i>-configuration.", "chembl": "LEVOMEFOLIC ACID is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Levomefolic acid (INN, also known as L-5-MTHF, L-methylfolate and L-5-methyltetrahydrofolate and (6S)-5-methyltetrahydrofolate, and (6S)-5-MTHF) is the primary biologically active form of folate used at the cellular level for DNA reproduction, the cysteine cycle and the regulation of homocysteine. It is also the form found in circulation and transported across membranes into tissues and across the blood\u2013brain barrier. In the cell, L-methylfolate is used in the methylation of homocysteine to form methionine and tetrahydrofolate (THF). THF is the immediate acceptor of one carbon unit for the synthesis of thymidine-DNA, purines (RNA and DNA) and methionine. The un-methylated form, folic acid (vitamin B9), is a synthetic form of folate, and must undergo enzymatic reduction by dihydrofolate reductase (DHFR) to become biologically active. Systematic reviews suggest that adjunctive L-methylfolate modestly improves symptoms in major depressive disorder.\nIt is synthesized in the absorptive cells of the small intestine from polyglutamylated dietary folate. It is a methylated derivative of tetrahydrofolate. Levomefolic acid is generated by methylenetetrahydrofolate reductase (MTHFR) from 5,10-methylenetetrahydrofolate (MTHF) and used to recycle homocysteine back to methionine by methionine synthase (MS).\nL-methylfolate is water-soluble and primarily excreted via the kidneys. In a study of 21 subjects with coronary artery disease, peak plasma levels were reached in one to three hours following oral or parenteral administration. Peak concentrations were found to be more than seven times higher than folic acid (129 ng/ml vs. 14.1 ng/ml).\nPatients at risk for vitamin B12 deficiency should consult with their medical provider prior to taking L-Methylfolate. The interrelationship between these two vitamins (L-Methylfolate and B12) is best explained by the methyl trap hypothesis.\n\n"}