THH

N-[4-({[(6S)-2-AMINO-4-HYDROXY-5-METHYL-5,6,7,8-TETRAHYDROPTERIDIN-6-YL]METHYL}AMINO)BENZOYL]-L-GLUTAMIC ACID

Created:	2004-11-16
Last modified:	2020-06-05

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13 entries where THH is found as a standalone ligand

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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	N-[4-({[(6S)-2-AMINO-4-HYDROXY-5-METHYL-5,6,7,8-TETRAHYDROPTERIDIN-6-YL]METHYL}AMINO)BENZOYL]-L-GLUTAMIC ACID
Synonyms	5-METHYLTETRAHYDROFOLATE
Systematic Name (OpenEye OEToolkits)	(2S)-2-[[4-[[(6S)-2-amino-4-hydroxy-5-methyl-7,8-dihydro-6H-pteridin-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(c3c(nc(nc3NC2)N)O)C)CCC(=O)O
SMILES	CACTVS	3.341	CN1[CH](CNc2ccc(cc2)C(=O)N[CH](CCC(O)=O)C(O)=O)CNc3nc(N)nc(O)c13
SMILES	OpenEye OEToolkits	1.5.0	CN1c2c(nc(nc2O)N)NCC1CNc3ccc(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)CNc3nc(N)nc(O)c13
Canonical SMILES	OpenEye OEToolkits	1.5.0	CN1c2c(nc(nc2O)N)NC[C@@H]1CNc3ccc(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	L-methylfolate 5-methyl-(6S)-tetrahydrofolic acid Levomefolate (6S)-5-methyltetrahydrofolate Levomefolate glucosamine Levomefolate magnesium L-5-methyltetrahydrofolate (6S)-5-Methyltetrahydrofolic acid Levomefolate calcium (6S)-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 L-5-MTHF LMSR Levomefolic acid
Brand Names	Drospirenone, Ethinyl Estradiol and Levomefolate Calcium and Levomefolate Calcium Yasmin Plus Vitafol Ultra Denovo PaxLyte Prenate Elite Levomefolate Calcium Pyridoxal-5 Phosphate Mecobalamin Algal Levomefolate Calcium-Pyridoxal Phosphate-Mecobalamin Levomefolate Calcium, Acetylcysteine, Mecobalamin and Algal Quflora Pediatric Tricare Prenatal 2-part Daily Prenatal Vitamin System L-Methyl MC Poly-Vi-Flor with Iron Virt-PN DHA Rajani Prenate Essential Tendera-OB KeyFolic Poly-VI-flor L-Methyl MC NAC Levomefolate Calcium Acetylcysteine and Mecobalamin Algal NuFera FolaMax WestGel DHA TriStart DHA Vitafol Fe Plus BumP DHA Zatean-Pn DHA Chromagen Maxaron Forte Natal PNV Levomefolate Calcium Acetylcysteine Mecobalamin Algal Floriva Hemax Obstetrix EC FloraFol Multi-Vit-Flor L-Methyl PNV DHA L-Methyl-MC-NAC Quflora FE Pediatric Drops Medi-10 Folene EnBrace HR Livita Adults Hematron-AF Obstetrix ONE MaxFe FolaPrime Florravite PramLyte Levomefolate Calcium, Cyanocobalamin and Pyridoxine Hydrochloride Davimet with Fluoride Menatrol Drospirenone/ethinyl estradiol/levomefolate calcium and levomefolate calcium TL-Folate Levomefolate Calcium, Pyridoxal 5-phosphate, Methylcobalamin and Schizochytrium DHA Oil Prenate Pixie LorMate PNV Tabs 20-1 Select OB Poly-Vi-Flor Virt-Pn WellFola Beyaz Zatean-Pn Plus Safyral Virt-Pn DHA Sodium polysulthionate, 5-methyltetrahydrofolate Folixate L-Methyl-B6-B12 Quflora Pediatric Drops Multitol-M Davimet with Iron WesCap-PN DHA Biopar delta-FORTE Quflora FE L-Methylfolate Calcium Floriva Plus Inflamex Multivitamin with Fluoride Virt-PN Plus Sulfzix Prenatol-M Rulavite DHA Tydemy OBTREX DHA Combo Pack Tricare Prenatal DHA One With Folate Davimet-M Tri-Vi-Flor Drospirenone/Ethinyl Estradiol/Levomefolate Calcium and Levomefolate Calcium Enl L-Methyl-MC Obstetrix DHA Combo Pack PreGenna Zatean-Pn Virt-PN Vitafol Nano Levomefolate Calcium and Schizochytrium DHA Livita Children Yaz Plus Select-OB Plus DHA Prenatal Supplement Plus DHA Tricare Prenatal Quick Dissolve ProFola Prenate Mini Niferex EnLyte Finazol Puralor Obtrex One Levomefolate Calcium and Algal
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