C2F

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

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

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25 entries where C2F is found as a standalone ligand4 entries where C2F is covalently linked to polymer or other heterogen groups

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

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