C2F

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

Created:	1999-07-08
Last modified:	2011-06-04

Find Related PDB Entry
24 entries where C2F is found as a standalone ligand4 entries where C2F is covalently linked to polymer or other heterogen groups

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	58
Chiral Atom Count	2
Bond Count	60
Aromatic Bond Count	12

Toggle Hydrogen Toggle Labels

Chemical Component Summary
Name	5-METHYL-5,6,7,8-TETRAHYDROFOLIC ACID
Systematic Name (OpenEye OEToolkits)	(2S)-2-[[4-[[(5R,6S)-2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl]methylamino]phenyl]carbonylamino]pentanedioic acid
Formula	C₂₀ H₂₅ N₇ O₆
Molecular Weight	459.456
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)C(NC(=O)c1ccc(cc1)NCC2N(C=3C(=O)NC(=NC=3NC2)N)C)CCC(=O)O
SMILES	CACTVS	3.341	CN1[CH](CNc2ccc(cc2)C(=O)N[CH](CCC(O)=O)C(O)=O)CNC3=C1C(=O)NC(=N3)N
SMILES	OpenEye OEToolkits	1.5.0	CN1C(CNC2=C1C(=O)NC(=N2)N)CNc3ccc(cc3)C(=O)NC(CCC(=O)O)C(=O)O
Canonical SMILES	CACTVS	3.341	CN1[C@@H](CNc2ccc(cc2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNC3=C1C(=O)NC(=N3)N
Canonical SMILES	OpenEye OEToolkits	1.5.0	C[N@@]1[C@H](CNC2=C1C(=O)NC(=N2)N)CNc3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
InChI	InChI	1.03	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	InChI	1.03	ZNOVTXRBGFNYRX-STQMWFEESA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

DrugBank ID	DB11256
Name	Levomefolic acid
Groups	investigational approved
Description	Levomefolic 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	(6S)-5-methyltetrahydrofolate 5-methyl-(6S)-tetrahydrofolic acid L-methylfolate Levomefolate (6S)-5-Methyltetrahydrofolic acid L-5-MTHF L-5-methyltetrahydrofolate (6S)-5-MTHF LMSR Levomefolate glucosamine Levomefolate magnesium Levomefolic acid Levomefolate calcium N-[4-[[[(6S)-2-Amino-3,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-L-glutamic acid
Brand Names	Levomefolate Calcium and Schizochytrium DHA NuFera PaxLyte TL-Folate Puralor Virt-PN DHA Livita Adults OBTREX DHA Combo Pack Davimet with Iron Vitafol Ultra Poly-Vi-Flor with Iron Tricare Prenatal Quick Dissolve Floriva L-Methylfolate Calcium Quflora Pediatric Drops Obstetrix EC Virt-Pn PNV Tabs 20-1 Poly-Vi-Flor Tricare Prenatal 2-part Daily Prenatal Vitamin System Zatean-Pn Plus Levomefolate Calcium-Pyridoxal Phosphate-Mecobalamin Natal PNV Levomefolate Calcium and Algal PramLyte Levomefolate Calcium, Acetylcysteine, Mecobalamin and Algal L-Methyl PNV DHA Zatean-Pn Medi-10 Safyral Prenate Elite L-Methyl-MC L-Methyl MC Multitol-M Multi-Vit-Flor Levomefolate Calcium Acetylcysteine Mecobalamin Algal Prenate Essential Virt-PN L-Methyl MC NAC Obstetrix ONE Virt-Pn DHA Levomefolate Calcium Pyridoxal-5 Phosphate Mecobalamin Algal Drospirenone, Ethinyl Estradiol and Levomefolate Calcium and Levomefolate Calcium Tri-Vi-Flor Zatean-Pn DHA WesCap-PN DHA LorMate Prenate Mini Select-OB Plus DHA Prenatal Supplement Plus DHA Rajani L-Methyl-B6-B12 Tricare Prenatal DHA One With Folate Floriva Plus Levomefolate Calcium, Cyanocobalamin and Pyridoxine Hydrochloride Drospirenone/Ethinyl Estradiol/Levomefolate Calcium and Levomefolate Calcium Davimet with Fluoride EnBrace HR Prenate Pixie Denovo BumP DHA Livita Children Maxaron Forte Tendera-OB TriStart DHA Multivitamin with Fluoride Florravite Drospirenone/ethinyl estradiol/levomefolate calcium and levomefolate calcium Enl Quflora FE Select OB Levomefolate Calcium Acetylcysteine and Mecobalamin Algal Beyaz Niferex MaxFe Levomefolate Calcium, Pyridoxal 5-phosphate, Methylcobalamin and Schizochytrium DHA Oil PreGenna Sodium polysulthionate, 5-methyltetrahydrofolate Prenatol-M Davimet-M Sulfzix Yaz Plus Folene Folixate Vitafol Fe Plus Vitafol Nano Obstetrix DHA Combo Pack EnLyte FolaMax FolaPrime Inflamex Finazol L-Methyl-MC-NAC ProFola Rulavite DHA Quflora Pediatric WestGel DHA Yasmin Plus Biopar delta-FORTE WellFola Chromagen Quflora FE Pediatric Drops Virt-PN Plus Menatrol Poly-VI-flor Tydemy KeyFolic Hemax Obtrex One FloraFol Hematron-AF
Indication	For 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 Enzymes and Coenzymes Folate Analog Folic Acid and Derivatives Heterocyclic Compounds, Fused-Ring Pteridines Pterins Vitamin B Complex Vitamins
CAS number	31690-09-2

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

Name	Target Sequence	Pharmacological Action	Actions
Methionine synthase	MSPALQDLSQPEGLKKTLRDEINAILQKRIMVLDGGMGTMIQREKLNEEH...	unknown	substrate,cofactor
Proton-coupled folate transporter	MEGSASPPEKPRARPAAAVLCRGPVEPLVFLANFALVLQGPLTTQYLWHR...	unknown	substrate
Reduced folate transporter	MVPSSPAVEKQVPVEPGPDPELRSWRHLVCYLCFYGFMAQIRPGESFITP...	unknown	substrate

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