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	N-pteroyl-L-glutamic acid N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid Pteroyl-L-glutamic acid Vitamin B9 PGA Fols?ure Folic acid ácido fólico Pteroylglutamic acid Vitamin M Acidum folicum Folate Folate sodium Vitamin Bc PteGlu Pteroyl-L-glutamate Folacin Pteroyl-L-monoglutamic acid Acide folique
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Away Formula Cavan X AxiFol Ply Vi Sol Chewable Tab Se-Plete DHA Folic Acid 1 mg Swiss One Multi Vit & Chel Min Tab FUSION Sprinkles Folic Acid Tab 0.4mg USP Vp-heme Ob Folika-V WesNatal DHA Complete Children's Chewable Multiple Vitamins - Tab Liqui B Complex Plus PureFe OB Plus B-complex 100 Dexivite FolaPrime Multi Vitamines - Liq Gestamine Comprimes Tl-hem 150 Folic Acid 0.4mg B-100 Complex Tablets Keylosa Multiple Vitamins With Iron B-100 Vitamin Supplement Folcaps Care One Prenatryl Ultimate Tab Cavan Alpha Folditam Vita-Rx Diabetic Vitamin AzesChew iFerex 150 Forte B-50 Complex Tricon Iron Aspartate Glycinate and Polysaccharide Complex, Ascorbic Calcium, Vitamin B12, Folic Acid, Calcium Threonate and Succinic Acid Folic Acid Tab 5mg Natelle One MYNEPHROCAPS DIALYSIS/STRESS Vitamin Supplement Q.T. #4 Vitamin and Mineral Dietary Supplement Sodium Polysulthionate and Folic Acid Vit B Complex Ctr Childrens Chewable Multiple Vitamins Stress Tab With Iron and Vitamin E Palm Springs Multvit and Min Tab Prenatal Vitamins and Minerals Tablets Nutra Boost Virt Vite GT Rocky Mountain Multiple Vit and Min Mega Tab Vitamin B Compound W C Tab 500mg Virt-Nate DHA Vitaplex Hi Potency Stress B Tension With C Multivitamin & Multimineral Stressmates Iron Polysaccharides Folic Acid DHA MultiVitamin with Fluoride Chewable Multivitamins Plus Iron Active FE P.R.O. Complex Quflora Gummies Children's Chewable Multivitamins and Minerals Tandem DHA Nitro Vites - Tab PR Natal 400 ec Femitab Tab CitraNatal Bloom CitraNatal B-Calm Derma-force TRONVite Timed Release B-complex 100 Folvik-D Super Pantoplex B6, B12 & Folic Acid One-A-day Advance Men's ProFola Triveen-PRx RNF NuFera Vitrexyl plus Iron Vp-CH-pnv Maxum Multi-vite Nicaprin Dialyvite C.R.D.-force Chromagen Multi Tabs Vp-ggr-B6 V-Natal Revit Plus Cap PreFol-DHA Folbic Multivitamins and Multiminerals Formula Regular Tablet Ocuvel TL-Fluorivite TL-Select DHA Folinex FolaMax Formula Int Materna-tab Zavara PNV Tabs 20-1 FE C Tab Plus VP CH Ultra VitaXyme Lexazin PNV Prenatal Vitamin Plus Vitamin A Hylazinc Focalgin CA HemeNatal OB Virt-Vite Plus Viva CT Prenatal Balanced B-100 B-complex Vitamins Tab Children's Chewable Multiple Vitamins With Iron Tablets (chewable Tablets) BiferaRx Ferrex 28 TL-Icon Children's Vitamins W Iron Chewable Fib-C Melts Enrich Core Pack - Children Vitamin and Mineral Supplement Daily Energy Brand B-complex Iron, Vit & Min Supp Children's Chewable Vit and Min Tab Nestabs ONE Stress B Complex With C, E & Iron Folic Acid Macuzin Chewable Multiple Vitamins Plus Extra C One-A-day Advance Fem - Tablets Multiple Vitamins Prenatal Formula Tab VP-Iron-C Plus Multivitamin & Minerals (iron Free) Essential Vitamins and Minerals PreNexa premier Vitalife - Capsule T.R.I. 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Multipack II Multi-11 Taliment Folika-T NEONATAL Complete Folvite CitraNatal Assure Liqui B Complex Multi Vitamin & Minerals Rogenic Mvc 9 Plus 3 Inj Novo-folacid 5mg Virt-Advance Virt-Vite Forte RE FAC-x Hypo Vites Tab Vita-worth B-complex Tablets Multi Vitamin and Mineral vitamin Thrivite Rx PNV-Omega Strovite One Caplets Stress Formula Multi-B Comp + 500mg Vit C Cap FeRiva Multi #2 Ultra Hr Folic Acid Ctr Srt 800mcg Bugs Bunny Chew Multi Vit Plus Iron Animal Shapes w/Iron Chewtabs Multi Enfants Tab C-B Complex Lorid Prenate Pixie Folitin-Z Isotonix Advanced B-complex Vitamins With Potassium and Magnesium Multi-actin Super Stress Mega B Plus 1000mg Vit C Tab Sun-rype Vitaburst Vitamin B Compound Tab Multiple Vitamins With Iron Tablets Stress Forte Plus Lipotropic Factors Genicin Vita-S KeyFolic Swiss Total One Super Kids Chewable Multivitamin Multimineral (chewable Tablets) Formula L.G.I. TriStart FREE VP CH Plus Multivitamin Flintstones Multiple Vitamins Tab Folic Acid Tab 1mg Multi-12 Pediatric Nutri-Tab OB Oveeza Folic D3 Children's Chewable Multi Vit W Iron Multivitamines Et Mineraux Reguliers / Regular Multivitamins and Minerals Virt-Tabs Wellness Formula M.V.I. Adult CitraNatal Rx Folite Tricare Prenatal DHA One Zoo Chews Focalgin DSS PureVit DualFe Plus Ferrex 150 Forte Multicaps Ferrex 150 Forte Plus Vasculine Stress Formula C. Vit-min Formula Restora Rx Feminex 300 Tab Florravite Vitranol B Complex 50+ Caplet Extra Once A Day Corvite 150 Maxi 10 Tab Orifer F Super Vita-vim With Beta-carotene - Tab FolaGent DHA Prefera OB plus DHA L.C. Supplement Vitazyme Formula Cp Cap Falessa Formula U - Tab Childrens Chew Multi Vitamin Tab For Kids Only Chewable Multivitamins - Tab Dalivit Formula Inf Cda-21 Vitamins With Non-medicinal Probiotic Complex Niferex Folivane-OB Century Complete Right Choice A.M. Multi Formula - Caplet Supravite Stress Avec Vit E Cuivre Et Zinc WesNate DHA CitraNatal Bloom DHA Totalvit Plus Time Release B 100 Compound - Tablet Neutral C + Coenzyme Q10 Plus Vitamins & Minerals Nu-folic Corvita 150 Ferotrin Ziphex Dayavite Children's Chewable Multi Vitamins Avon Nutrivance Vitamin E Plus Bugs Bunny and Friends Multiple Vitamins Prenavite Forte Tablets Pro His Mint Integra Plus Stress B Complex With C, E and Iron Tab Dotremin Hemocyte F Iron Folate Plus Multi-vitamins With Minerals Mycelized Childrens Multi-vitamin Liq Animi-3 with Vitamin D Prenaissance Ez-flex B-complex 50 Myferon 150 Forte Noxifol-D Folivane-PRx DHA Puralor Recal D PR Natal 400 CitraNatal 90 DHA Carbassist Tablets Isotonix Multitech Vitamin Mineral Supplemen Folivane-F Zatean-Pn Plus Dexatran Venexa FE Trinaz New Chapter's D'adamo 4 Your Type Multiple for Type O Bseltzer Fortamines 10 Capsules B-plex Magnum-75 Vitamin and Mineral Supplement Corvite Free Thrivite 19 Essential B Tablets Women's Change Formula Prenate Elite Total Living Concepts Formula One - Tab TriphroCaps Acti-folic + Dibencozide Caplets Pnv-dha Vigo Multivitamins Drops/lozenge Bev B-150 Tri-Zel Centratex Multi-vitamins PNV Tabs 29-1 Acide Folique 5 Tab Multiple Vitamins Plus Iron - Tab Multivitamins and Minerals Tablets TL-Fol 500 Vitamin B12-folic Acid Timed Release Vita-vim Srt Omniquin Natalvirt Ca Tricare Prenatal Vitrexate Select-OB Plus DHA Prenatal Supplement Plus DHA Vitaphil DHA Multiple Vitamins & Minerals Tablets Fem - Protect Folcaps Omega-3 DermacinRx FoliPlus D Nutrilite Double X B Stress C + Iron & Vite Kanga-kid Multi-vitamin & Mineral PNV-First Provida OB Imubolic Natural Source Spectrum With Beta Carotene RenaPlex-D Vita Balance 2000 UltimateCare ONE NF One A Day Multiple Vit W Minerals PaxLyte Nicotinamide Zcf Vitamin B Complex Tab 24 Multivitamins + Minerals Animi-3 Folic Acid-b12 Tab Nexa Plus Prenavite Forte Nicomide Stress Formula Tab Zalvit Doctor's Choice Brand for Men Multra With Iron Vege Swiss One Multivitamin W Chel Mins Tab Folic Acid Inj 5mg/ml USP Liqui Vita Zolate Fortamines-10 Comprimes Childrens Chewable Multiple Vitamins Tab Classic Swiss One 10 Multivitamin and Mineral Tab Cardiotek-RX Se-Natal One Men's Biomultiple Vitamin and Mineral Supplement Bacmin Multi Plex I - Tab One A Day Advance Adults 50+ Multi-Vitamin VirtPrex Vita-B Senior Multi One CitraNatal DHA Timed Release B Complex 100 Srt Abavite Concept OB Revit Multi-vitamins and Minerals Tricare Prenatal DHA One Rx Multivitamin Chewable Multivitamins Prena1 Women's Formula Kanga-V Multivitamins & Minerals Flintstones Multiple Vitamins Plus Iron Foltrexyl
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