FOL

FOLIC ACID

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

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Chemical Details
Formal Charge	0
Atom Count	51
Chiral Atom Count	1
Bond Count	53
Aromatic Bond Count	17

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Chemical Component Summary
Name	FOLIC ACID
Systematic Name (OpenEye OEToolkits)	(2S)-2-[[4-[(2-amino-4-oxo-1H-pteridin-6-yl)methylamino]phenyl]carbonylamino]pentanedioic acid
Formula	C₁₉ H₁₉ N₇ O₆
Molecular Weight	441.397
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)C(NC(=O)c1ccc(cc1)NCc2nc3c(nc2)NC(=NC3=O)N)CCC(=O)O
SMILES	CACTVS	3.341	NC1=NC(=O)c2nc(CNc3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O)cnc2N1
SMILES	OpenEye OEToolkits	1.5.0	c1cc(ccc1C(=O)NC(CCC(=O)O)C(=O)O)NCc2cnc3c(n2)C(=O)N=C(N3)N
Canonical SMILES	CACTVS	3.341	NC1=NC(=O)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2N1
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCc2cnc3c(n2)C(=O)N=C(N3)N
InChI	InChI	1.03	InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1
InChIKey	InChI	1.03	OVBPIULPVIDEAO-LBPRGKRZSA-N

Drug Info: DrugBank

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

DrugBank ID	DB00158 ?
Name	Folic acid
Groups	nutraceutical vet_approved approved
Description	Folic acid, also known as folate or Vitamin B9, is a member of the B vitamin family and an essential cofactor for enzymes involved in DNA and RNA synthesis. More specifically, folic acid is required by the body for the synthesis of purines, pyrimidines, and methionine before incorporation into DNA or protein. Folic acid is particularly important during phases of rapid cell division, such as infancy, pregnancy, and erythropoiesis, and plays a protective factor in the development of cancer. As humans are unable to synthesize folic acid endogenously, diet and supplementation is necessary to prevent deficiencies. For example, folic acid is present in green vegetables, beans, avocado, and some fruits.[L5744] In order to function within the body, folic acid must first be reduced by the enzyme dihydrofolate reductase (DHFR) into the cofactors dihydrofolate (DHF) and tetrahydrofolate (THF). This important pathway, which is required for de novo synthesis of nucleic acids and amino acids, is disrupted by anti-metabolite therapies such as [DB00563] as they function as DHFR inhibitors to prevent DNA synthesis in rapidly dividing cells, and therefore prevent the formation of DHF and THF. When used in high doses such as for cancer therapy, or in low doses such as for Rheumatoid Arthritis or psoriasis, [DB00563] impedes the body's ability to create folic acid. This results in a deficiency of coenzymes and a resultant buildup of toxic substances that are responsible for numerous adverse side effects. As a result, supplementation with 1-5mg of folic acid is recommended to prevent deficiency and a number of side effects associated with MTX therapy including mouth ulcers and gastrointestinal irritation. [DB00650] (also known as folinic acid) supplementation is typically used for high-dose MTX regimens for the treatment of cancer. Levoleucovorin and leucovorin are analogs of tetrahydrofolate (THF) and are able to bypass DHFR reduction to act as a cellular replacement for the co-factor THF. There are also several antiepileptic drugs (AEDs) that are associated with reduced serum and red blood cell folate, including [DB00564] (CBZ), [DB00252] (PHT), or barbiturates.[A37004] Folic acid is therefore often provided as supplementation to individuals using these medications, particularly to women of child-bearing age. Inadequate folate levels can result in a number of health concerns including cardiovascular disease, megaloblastic anemias, cognitive deficiencies, and neural tube defects (NTDs). Folic acid is typically supplemented during pregnancy to prevent the development of NTDs and in individuals with alcoholism to prevent the development of neurological disorders, for example.
Synonyms	Pteroylglutamic acid Acidum folicum N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid ácido fólico Pteroyl-L-monoglutamic acid Pteroyl-L-glutamic acid Vitamin Bc N-pteroyl-L-glutamic acid Folic acid Vitamin B9 Folacin Vitamin M Acide folique Fols?ure Folate Pteroyl-L-glutamate PteGlu Folate sodium PGA
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Complex PreNatal 19 Taron BC Childrens Chewable Tab Chromagen Nicazyme Chewable Multivitamins Plus Iron Vitafol Ultra SetonET Card-floe II Tab Virt Nate Folixapure Multivitamin DuetDHA Balanced Folika-V Natal PNV Multi-11 Stress Formula Multi-B Comp + 500mg Vit C Cap Virt-Vite Plus Avon Vitadvance Multi-kids Complete Daily Balance Tab Corvite 150 Lipo-B-C Tab Macuvex Children's Chewable Multivitamins With Minerals Prenatal and Post Partum Supplement Childrens Chew Multi Vitamin Tab Multipack II Vitafol Fe Plus TM-Vite RX Materna B Stress C + Iron & Vite B Complex 25mg Vitamin Supplement Men's Multi Master Formula Multiple Vitamins - Tablet Quflora Pediatric Maintain Multiple Vitamin & Minerals Integra Plus Dothelle DHA Children's Chewable Multi Vitamins Fem - Protect Twin Opti Pwr TriAdvance Paire OB Plus DHA Prenaissance Plus Multivitamins and Multiminerals Formula Regular Tablet Tricare Prenatal Compleat Vitamin B Compound W Vit C 250mg Tab RenaPlex-D Relnate DHA Vitafol Plus Isotonix Vitamin B-folic Acid-mineral Supple Vitazyme Twin G.F. 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B-plex Src Ferotrin Folic Acid Tab 25mg Stress B-complex Plus Iron With Vitamins C&e Swiss One Multivitamin and Mineral Caplet Stresstabs + Zinc-copper TL-Select DHA Balanced B-50 Complex Right Choice A.M. Multi Formula - Caplet Super Multi Formula Ch. Les. Swiss One Children's Chewable Multivitamins and Minerals Multiple Vitamins Docosavit Hsn Formula MYNEPHROCAPS DIALYSIS/STRESS Vitamin Supplement ProFola Ciferex Multivitamins and Minerals for Men Adult Infuvite Multiple Vitamins PM Caps Multi-vitamin Dietary Supplement One-A-day Advance Men's Venexa FE Vitamin B6 & B12 With Folic Acid FolaGent DHA Vitafol OB Caplet M.V.I. Pediatric Mega 13 Multivitamin Formula Chewable Adult Multivitamins With Minerals Children's Chewable Tab Folvite-FE Multiple Vitamins Plus Iron Tab Neutral C + Coenzyme Q10 Plus Vitamins & Minerals PRENATE Restore Virt Vite GT Body Rox Multivitamines Pour Enfants (chewable Tablets) Vitafol-OB Plus DHA Prenatal Supplement Plus DHA B-plex Central-vite 18 Essential One Daily Vitamin and Mineral Dietary Supplement Tianshi Vital Powder I Chewable Children's Complete Multivitamins With Essential Minerals Timed Release Vita-vim Srt V-Natal Complexe B-75 Foliflex TL-Fol 500 CitraNatal Essence FUSION Sprinkles Nicadan ZX Trinatal Ultra Calcium PNV Folvik-D Advanced B & T Formula For Kids Only Chewable Multivitamins Prenate Mini PNV Prenatal Vitamin Re Kar C Plus Folic Acid 800mcg Tab Folic Acid 0.4 Mg Tablet Prefera OB plus DHA Super B Compound W 500mg Vit C Multiple Vitamins & Minerals Tablets Kimchi Vitamin chewable multivitamin Active OB Multivitamine Neonatal Plus Vitamin Preplus Nicadan Folbic Iron, Vit & Min Supp B Complex 50 Vitamin Cap Sodium polysulthionate and folic acid Reliv So Sense Daily Vitamin Supplement Flinstones Multiple Plus Iron K.L. Vitamin-mineral Reebok Hylazinc Vitrexyl plus Iron Zatean-Pn Plus Complete Mega B Tandem - F Corvita Cifrazol Folic Acid 0.8mg Iron Folate-F Bev 29 Tab Folivane-Plus with Ascorbic Acid Precursors Multi Plex I - Tab Multi Vitamines - Liq Nutra Boost Stress B Capsules With Vitamin C Vege 1 Daily Tab Foltamin Virt-Care One PNV-Select Childrens Chewable Multiple Vitamins Tab B 50 Capsules Se-Natal Fizz Multivitamins for Kids W C Loz Animal Shapes Fusion Plus For Men Neonatal19 PreferaOB One Se-Plete DHA Multinate DHA Dalivit CitraNatal Harmony PNV-Omega Innersource Tab Virt-Nate Chewable Multiple Vitamins Plus Extra C Nestabs ONE Balanced B-50 B-complex Vitamins Tab Complexe B Compose 75 Macuzin One Daily VITES FE C Tab Plus Folic D3 For Kids Only Chewable Multivit. Plus Iron Multicaps MVC-Fluoride Children's Chewable Vit and Min Tab Super Kids Chewable Multivitamin Multimineral (chewable Tablets) Vp-zel Dotremin PNV Prenatal Vitamin Plus Vitamin A Cholecal DF OB Complete Petite Kanga-kid Multi-vitamin & Mineral B-Serene Rx Phytovim Cap Only One - Tablet Chewable Multiple Vit Plus Iron for Children Niron Komplete Methaver Pregvit Folic 4 Omnivex TL-Folate PreferaOB ONE B-100 Vitamin Supplement Ultimate Tab Vitafol One Reno Caps vitaMedMD Rx Plus FaBB Vitaplex Se-Care Chewable Vitogen B Stress C Vit E Zinc & Cop Hi Potency B52 B Complex Tab Multitam Active FE Formula Hh PROTECT IRON Liquid Folic Acid (1mg Tablet) Time Release B 100 Compound - Tablet Liqui B Complex AxiFol Prenatryl Virt-Vite Forte Balanced B-complex Vit + Vit C&e Tab Nu-folic Floriva Natalvirt FLT FeRiva 21 7 Usana Megavitamin Tablets - Tab Nioxin Recharging Complex Bal-Care DHA Essential Homosismin WesTab Plus Prenate Elite Focalgin DSS Nexa Plus Prenaissance Diaplex
Indication	Folic acid is indicated for the treatment of folic acid deficiency, megaloblastic anemia, and in anemias of nutritional origins, pregnancy, infancy, or childhood.
Categories	Antianemic Preparations Autacoids BCRP/ABCG2 Substrates Biological Factors Diagnostic Agents Diet, Food, and Nutrition Dietary Supplements Drugs that are Mainly Renally Excreted Folic Acid and Derivatives Food Growth Substances Hematinics Hematologic Agents Heterocyclic Compounds, Fused-Ring Micronutrients OAT1/SLC22A6 inhibitors Pteridines Pterins Supplements Vitamin B Complex Vitamin B12 and Folic Acid Vitamins
ATC-Code	B03AE02 B03AD04 V04CX02 B03AD01 B03BB51 B03AD03 B03BB01 B03AE01 B03AD05 B03AD02
CAS number	59-30-3

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
Proton-coupled folate transporter	MEGSASPPEKPRARPAAAVLCRGPVEPLVFLANFALVLQGPLTTQYLWHR...	unknown	modulator
Reduced folate transporter	MVPSSPAVEKQVPVEPGPDPELRSWRHLVCYLCFYGFMAQIRPGESFITP...	unknown	modulator
Folate receptor gamma	MDMAWQMMQLLLLALVTAAGSAQPRSARARTDLLNVCMNAKHHKTQPSPE...	unknown	binder
Folate receptor beta	MVWKWMPLLLLLVCVATMCSAQDRTDLLNVCMDAKHHKTKPGPEDKLHDQ...	unknown	binder
Folate receptor alpha	MAQRMTTQLLLLLVWVAVVGEAQTRIAWARTELLNVCMNAKHHKEKPGPE...	unknown
Gamma-glutamyl hydrolase	MASPGCLLCVLGLLLCGAASLELSRPHGDTAKKPIIGILMQKCRNKVMKN...	unknown	substrate
Methylenetetrahydrofolate reductase (NADPH)	MVNEARGNSSLNPCLEGSASSGSESSKDSSRCSTPGLDPERHERLREKMR...	unknown	substrate
Dihydrofolate reductase	MVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL...	unknown	substrate
ATP-binding cassette sub-family C member 11	MTRKRTYWVPNSSGGLVNRGIDIGDDMVSGLIYKTYTLQDGPWSQQERNP...	unknown	substrate
ATP-binding cassette sub-family C member 3	MDALCGSGELGSKFWDSNLSVHTENPDLTPCFQNSLLAWVPCIYLWVALP...	unknown	substrate
Solute carrier family 22 member 6	MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...	unknown	inhibitor
ATP-binding cassette sub-family C member 4	MLPVYQEVKPNPLQDANLCSRVFFWWLNPLFKIGHKRRLEEDDMYSVLPE...	unknown	inhibitor
Broad substrate specificity ATP-binding cassette transporter ABCG2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate
Proton-coupled folate transporter	MEGSASPPEKPRARPAAAVLCRGPVEPLVFLANFALVLQGPLTTQYLWHR...	unknown	substrate
Solute carrier family 25 member 32	MTGQGQSASGSSAWSTVFRHVRYENLIAGVSGGVLSNLALHPLDLVKIRF...	unknown	substrate
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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