C2F

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

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

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