C2F

5-METHYL-5,6,7,8-TETRAHYDROFOLIC ACID



Chemical Component Summary

Name5-METHYL-5,6,7,8-TETRAHYDROFOLIC ACID
Identifiers(2S)-2-[[4-[[(5R,6S)-2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl]methylamino]phenyl]carbonylamino]pentanedioic acid
FormulaC20 H25 N7 O6
Molecular Weight459.456
TypeNON-POLYMER
Isomeric SMILESC[N@@]1[C@H](CNC2=C1C(=O)NC(=N2)N)CNc3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
InChIInChI=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
InChIKeyZNOVTXRBGFNYRX-STQMWFEESA-N

Chemical Details

Formal Charge0
Atom Count58
Chiral Atom Count2
Bond Count60
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB11256 
NameLevomefolic acid
Groups
  • approved
  • investigational
DescriptionLevomefolic acid (INN) is the metabolite of folic acid (Vitamin B9) and it is a predominant active form of folate found in foods and in the blood circulation, accounting for 98% of folates in human plasma [A19276]. It is transported across the membranes including the blood-brain barrier into various tissues where it plays an essential role in the DNA synthesis, cysteine cycle and regulation of homocysteine, where it methylates homocysteine and forms methionine and tetrahydrofolate (THF). Levomefolate is approved as a food additive and is designated a GRAS (generally regarded as safe) compound [L773]. It is available commercially as a crystalline form of the calcium salt (Metafolin(R)), which has the stability required for use as a supplement [A19276]. Supplementation of levomefolic acid is desired over folic acid due to reduced potential for masking vitamin B12 deficiency symptoms.
Synonyms
  • Levomefolate
  • 5-methyl-(6S)-tetrahydrofolic acid
  • LMSR
  • N-[4-[[[(6S)-2-Amino-3,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-L-glutamic acid
  • L-methylfolate
Brand Names
  • Levomefolate Calcium, Cyanocobalamin and Pyridoxine Hydrochloride
  • Virt-Pn
  • ProFola
  • Quflora Pediatric
  • PNV Tabs 20-1
IndicationFor the treatment and prevention of folate deficiency and for use as an antidote against folic acid antagonists. Contained in oral contraceptives to reduce the risk of neural tube defects arising from folic acid deficiency for pregnant women who conceived during use or shortly after the discontinuation of the product. Being studied for use as a treatment for cardiovascular diseases [A19273] and adjunct therapy for patients undergoing antidepressant pharmacotherapy [A19271, A19272].
Categories
  • Amino Acids
  • Amino Acids, Acidic
  • Amino Acids, Dicarboxylic
  • Amino Acids, Peptides, and Proteins
  • Coenzymes
CAS number31690-09-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Methionine synthaseMSPALQDLSQPEGLKKTLRDEINAILQKRIMVLDGGMGTMIQREKLNEEH...unknownsubstrate,cofactor
Proton-coupled folate transporterMEGSASPPEKPRARPAAAVLCRGPVEPLVFLANFALVLQGPLTTQYLWHR...unknownsubstrate
Folate transporter 1MVPSSPAVEKQVPVEPGPDPELRSWRHLVCYLCFYGFMAQIRPGESFITP...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 135398561, 444412, 5287865
ChEMBL CHEMBL1231574
ChEBI CHEBI:136009, CHEBI:15641