FOL

FOLIC ACID

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

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Chemical Details

Formal Charge0
Atom Count51
Chiral Atom Count1
Bond Count53
Aromatic Bond Count17
2D diagram of FOL
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Chemical Component Summary

NameFOLIC ACID
Systematic Name (OpenEye OEToolkits)(2S)-2-[[4-[(2-amino-4-oxo-1H-pteridin-6-yl)methylamino]phenyl]carbonylamino]pentanedioic acid
FormulaC19 H19 N7 O6
Molecular Weight441.397
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(O)C(NC(=O)c1ccc(cc1)NCc2nc3c(nc2)NC(=NC3=O)N)CCC(=O)O
SMILESCACTVS3.341NC1=NC(=O)c2nc(CNc3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O)cnc2N1
SMILESOpenEye OEToolkits1.5.0c1cc(ccc1C(=O)NC(CCC(=O)O)C(=O)O)NCc2cnc3c(n2)C(=O)N=C(N3)N
Canonical SMILESCACTVS3.341 NC1=NC(=O)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2N1
Canonical SMILESOpenEye OEToolkits1.5.0 c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCc2cnc3c(n2)C(=O)N=C(N3)N
InChIInChI1.03 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
InChIKeyInChI1.03 OVBPIULPVIDEAO-LBPRGKRZSA-N

Drug Info: DrugBank

DrugBank IDDB00158 
NameFolic acid
Groups
  • approved
  • vet_approved
  • nutraceutical
DescriptionFolic 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-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid
  • Folsäure
  • Folacin
  • Acide folique
  • Vitamin B9
Brand Names
  • Prenatal Vitamins Plus
  • G.A.S. Complex
  • Foltrate
  • MultiVitamin with Fluoride
  • Super Pantoplex
IndicationFolic 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
ATC-Code
  • B03AE02
  • B03AD04
  • V04CX02
  • B03AD01
  • B03BB51
CAS number59-30-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Folate receptor gammaMAWQMMQLLLLALVTAAGSAQPRSARARTDLLNVCMNAKHHKTQPSPEDE...unknownbinder
Folate receptor betaMVWKWMPLLLLLVCVATMCSAQDRTDLLNVCMDAKHHKTKPGPEDKLHDQ...unknownbinder
Folate receptor alphaMAQRMTTQLLLLLVWVAVVGEAQTRIAWARTELLNVCMNAKHHKEKPGPE...unknown
Gamma-glutamyl hydrolaseMASPGCLLCVLGLLLCGAASLELSRPHGDTAKKPIIGILMQKCRNKVMKN...unknownsubstrate
Methylenetetrahydrofolate reductaseMVNEARGNSSLNPCLEGSASSGSESSKDSSRCSTPGLDPERHERLREKMR...unknownsubstrate
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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

Related Resource References

Resource NameReference
PubChem 135398658, 6037, 5280354
ChEMBL CHEMBL1622
ChEBI CHEBI:27470