Human Metabolome Database Version 3.5

Showing metabocard for Folic acid (HMDB00121)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:55 -0700
HMDB ID HMDB00121
Secondary Accession Numbers None
Metabolite Identification
Common Name Folic acid
Description Folic acid is a member of the vitamin B family that stimulates the hematopoietic system. It is present in the liver and kidney and is found in mushrooms, spinach, yeast, green leaves, and grasses (poaceae). Folic acid, being biochemically inactive, is converted to tetrahydrofolic acid and methyltetrahydrofolate by dihydrofolate reductase. These folic acid congeners are transported across cells by receptor-mediated endocytosis where they are needed to maintain normal erythropoiesis, synthesize purine and thymidylate nucleic acids, interconvert amino acids, methylated tRNA, and generate and use formate. Folic acid is used in the treatment and prevention of folate deficiencies and megaloblastic anemia.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Acifolic
  2. Cytofol
  3. Dosfolat B activ
  4. Folacid
  5. Folacin
  6. Folate
  7. Folbal
  8. Folcidin
  9. Foldine
  10. Folettes
  11. Foliamin
  12. Folic acid
  13. Folicet
  14. Folipac
  15. Folsan
  16. Folsaure
  17. Folsav
  18. Folvite
  19. Incafolic
  20. Liver Lactobacillus casei factor
  21. Millafol
  22. N-(4-{[(2-Amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid
  23. N-Pteroyl-L-glutamic acid
  24. N-[(4-{[(2-Amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid
  25. N-[4-[[(2-Amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid
  26. PGA
  27. PteGlu
  28. Pteroyl-L-glutamate
  29. Pteroyl-L-glutamic acid
  30. Pteroyl-L-monoglutamate
  31. Pteroyl-L-monoglutamic acid
  32. Pteroylglutamate
  33. Pteroylglutamic acid
  34. Pteroylmonoglutamic acid
  35. Vitamin Bc
  36. Vitamin Be
  37. Vitamin M
Chemical Formula C19H19N7O6
Average Molecular Weight 441.3975
Monoisotopic Molecular Weight 441.139681375
IUPAC Name (2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Traditional IUPAC Name folic acid
CAS Registry Number 59-30-3
SMILES NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=CN=C2N1
InChI Identifier 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
InChI Key OVBPIULPVIDEAO-LBPRGKRZSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Pteridines and Derivatives
Sub Class Pterins and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • N-acylamino acid(ChEBI)
  • Water-soluble vitamins(KEGG)
  • folate(ChEBI)
Substituents
  • Alpha Amino Acid Or Derivative
  • Aminobenzamide
  • Aminopyrimidine
  • Benzamide
  • Benzoyl
  • Carboxamide Group
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Hippurate
  • N Acyl Alpha Amino Acid
  • N Substituted Alpha Amino Acid
  • Polyamine
  • Pteroic Acid Derivative
  • Pyrazine
  • Pyrimidine
  • Pyrimidone
  • Secondary Carboxylic Acid Amide
Direct Parent Folic Acid Derivatives
Ontology
Status Detected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Component of Cyanoamino acid metabolism
  • Component of Folate biosynthesis
  • Component of Glycine, serine and threonine metabolism
  • Component of Glyoxylate and dicarboxylate metabolism
  • Component of Methane metabolism
  • Component of Pyrimidine metabolism
  • DNA component
  • Enzyme co-factor
  • Essential vitamins
Application Not Available
Cellular locations
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 250 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.0016 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.076 g/L ALOGPS
LogP -0.04 ALOGPS
LogP -0.68 ChemAxon
LogS -3.76 ALOGPS
pKa (strongest acidic) 3.37 ChemAxon
pKa (strongest basic) 2.09 ChemAxon
Hydrogen Acceptor Count 12 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 208.99 A2 ChemAxon
Rotatable Bond Count 9 ChemAxon
Refractivity 111.01 ChemAxon
Polarizability 42.06 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Erythrocyte
  • Kidney
  • Liver
  • Brain
Pathways
Name SMPDB Link KEGG Link
Pterine Biosynthesis SMP00005 map00790 Link_out
Folate Metabolism SMP00053 map00670 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.021 (0.017-0.025) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.039 (0.01 - 0.14) uM Newborn (0-30 days old) Not Specified Normal
  • Geigy Scient...
Blood Detected and Quantified
0.011 (0.004 - 0.028) uM Children (1-13 year old) Not Specified Normal
  • Geigy Scient...
Blood Detected and Quantified
0.009 (0.0024 - 0.024) uM Adult (>18 years old) Not Specified Normal
  • Geigy Scient...
Blood Detected and Quantified
0.077 (0.071 - 0.083) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.02 (0.011- 0.036) uM Adult (>18 years old) Both Normal
  • Wu AHB. Tiet...
Blood Detected and Quantified
0.009 (0.0026-0.026) uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
0.023 (0.002-0.045) uM Children (1-13 year old) Both Normal
Cellular Cytoplasm Detected and Quantified
0.735 +/- 0.202 uM Newborn (0-30 days old) Not Specified Normal
  • Geigy Scient...
Cellular Cytoplasm Detected and Quantified
0.453 +/- 0.131 uM Adult (>18 years old) Not Specified Normal
  • Geigy Scient...
Cellular Cytoplasm Detected and Quantified
> 0.35 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0078 +/- 0.0011 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.053 +/- 0.024 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
0.006 +/- 0.0005 uM Elderly (>65 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0202 +/- 0.00567 uM Adult (>18 years old) Female Normal
Urine Detected and Quantified
0.00065 (0.000092-0.0013) umol/mmol creatinine Adult (>18 years old) Female Normal
  • Geigy Scient...
Urine Detected and Quantified
0.0014 (0.000013-0.0026) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
< 0.01 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.023 (0.019-0.028) uM Adult (>18 years old) Both Comment Rheumatoid arthritis
Blood Detected and Quantified 0.023 (0.020-0.026) uM Adult (>18 years old) Both Comment Rheumatoid arthritis
Blood Detected and Quantified 0.003 (0.0 - 0.007) uM Adult (>18 years old) Both Folate deficiency
  • Wu AHB. Tiet...
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0203 +/- 0.0017 uM Adult (>18 years old) Not Specified Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0209 +/- 0.00703 uM Adult (>18 years old) Not Specified fibromyalgia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.008 +/- 0.0011 uM Elderly (>65 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0056 +/- 0.005 uM Adult (>18 years old) Both Alzheimer's disease
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  • Selley ML, Close DR, Stern SE: The effect of increased concentrations of homocysteine on the concentration of (E)-4-hydroxy-2-nonenal in the plasma and cerebrospinal fluid of patients with Alzheimer's disease. Neurobiol Aging. 2002 May-Jun;23(3):383-8. Pubmed: 11959400 Link_out
      Folate deficiency
        • Wu AHB. Tietz clinical guide to laboratory tests. 4th ed. St. Louis: Saunders/Elsevier. 2006.
          Rheumatoid arthritis
          • Chiang EP, Smith DE, Selhub J, Dallal G, Wang YC, Roubenoff R: Inflammation causes tissue-specific depletion of vitamin B6. Arthritis Res Ther. 2005;7(6):R1254-62. Epub 2005 Sep 13. Pubmed: 16277678 Link_out
              Associated OMIM IDs
              DrugBank ID DB00158 Link_out
              DrugBank Metabolite ID Not Available
              Phenol Explorer Compound ID Not Available
              Phenol Explorer Metabolite ID Not Available
              FoodDB ID FDB014504
              KNApSAcK ID C00001539 Link_out
              Chemspider ID 5815 Link_out
              KEGG Compound ID C00504 Link_out
              BioCyc ID FOLATE Link_out
              BiGG ID 35180 Link_out
              Wikipedia Link Folic acid Link_out
              NuGOwiki Link HMDB00121 Link_out
              Metagene Link HMDB00121 Link_out
              METLIN ID 246 Link_out
              PubChem Compound 6037 Link_out
              PDB ID FOL Link_out
              ChEBI ID 27470 Link_out
              References
              Synthesis Reference Piper, James R.; McCaleb, George S.; Montgomery, John A. Synthesis of 10-propargylfolic acid from 2-amino-6-(bromomethyl)-4(1H)-pteridinone. Journal of Heterocyclic Chemistry (1987), 24(1), 279-82.
              Material Safety Data Sheet (MSDS) Download (PDF)
              General References
              1. Kopczynska E, Ziolkowski M, Jendryczka-Mackiewicz E, Odrowaz-Sypniewska G, Opozda K, Tyrakowski T: [The concentrations of homocysteine, folic acid and vitamin B12 in alcohol dependent male patients] Psychiatr Pol. 2004 Sep-Oct;38(5):947-56. Pubmed: 15523939 Link_out
              2. Gregory JF 3rd, Williamson J, Liao JF, Bailey LB, Toth JP: Kinetic model of folate metabolism in nonpregnant women consuming [2H2]folic acid: isotopic labeling of urinary folate and the catabolite para-acetamidobenzoylglutamate indicates slow, intake-dependent, turnover of folate pools. J Nutr. 1998 Nov;128(11):1896-906. Pubmed: 9808640 Link_out
              3. Lin Y, Dueker SR, Follett JR, Fadel JG, Arjomand A, Schneider PD, Miller JW, Green R, Buchholz BA, Vogel JS, Phair RD, Clifford AJ: Quantitation of in vivo human folate metabolism. Am J Clin Nutr. 2004 Sep;80(3):680-91. Pubmed: 15321809 Link_out
              4. Rodriguez Flores J, Penalvo GC, Mansilla AE, Gomez MJ: Capillary electrophoretic determination of methotrexate, leucovorin and folic acid in human urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 May 5;819(1):141-7. Pubmed: 15797531 Link_out
              5. Selley ML, Close DR, Stern SE: The effect of increased concentrations of homocysteine on the concentration of (E)-4-hydroxy-2-nonenal in the plasma and cerebrospinal fluid of patients with Alzheimer's disease. Neurobiol Aging. 2002 May-Jun;23(3):383-8. Pubmed: 11959400 Link_out
              6. Litwin M, Abuauba M, Wawer ZT, Grenda R, Kuryl T, Pietraszek E: [Sulphur amino acids, vitamin B12 and folic acid in children with chronic renal failure] Pol Merkur Lekarski. 2000 Apr;8(46):268-9. Pubmed: 10897644 Link_out
              7. Gregory JF 3rd, Williamson J, Bailey LB, Toth JP: Urinary excretion of [2H4]folate by nonpregnant women following a single oral dose of [2H4]folic acid is a functional index of folate nutritional status. J Nutr. 1998 Nov;128(11):1907-12. Pubmed: 9808641 Link_out
              8. Dietrich M, Brown CJ, Block G: The effect of folate fortification of cereal-grain products on blood folate status, dietary folate intake, and dietary folate sources among adult non-supplement users in the United States. J Am Coll Nutr. 2005 Aug;24(4):266-74. Pubmed: 16093404 Link_out
              9. Pufulete M, Al-Ghnaniem R, Khushal A, Appleby P, Harris N, Gout S, Emery PW, Sanders TA: Effect of folic acid supplementation on genomic DNA methylation in patients with colorectal adenoma. Gut. 2005 May;54(5):648-53. Pubmed: 15831910 Link_out
              10. Clifford AJ, Arjomand A, Dueker SR, Schneider PD, Buchholz BA, Vogel JS: The dynamics of folic acid metabolism in an adult given a small tracer dose of 14C-folic acid. Adv Exp Med Biol. 1998;445:239-51. Pubmed: 9781393 Link_out
              11. Olthof MR, Bots ML, Katan MB, Verhoef P: Effect of folic Acid and betaine supplementation on flow-mediated dilation: a randomized, controlled study in healthy volunteers. PLoS Clin Trials. 2006 Jun;1(2):e10. Epub 2006 Jun 9. Pubmed: 16871332 Link_out
              12. Stern LL, Bagley PJ, Rosenberg IH, Selhub J: Conversion of 5-formyltetrahydrofolic acid to 5-methyltetrahydrofolic acid is unimpaired in folate-adequate persons homozygous for the C677T mutation in the methylenetetrahydrofolate reductase gene. J Nutr. 2000 Sep;130(9):2238-42. Pubmed: 10958818 Link_out
              13. Stuerenburg HJ, Ganzer S, Arlt S, Muller-Thomsen T: The influence of smoking on plasma folate and lipoproteins in Alzheimer disease, mild cognitive impairment and depression. Neuro Endocrinol Lett. 2005 Jun;26(3):261-3. Pubmed: 15990733 Link_out
              14. Cahill E, McPartlin J, Gibney MJ: The effects of fasting and refeeding healthy volunteers on serum folate levels. Int J Vitam Nutr Res. 1998;68(2):142-5. Pubmed: 9565830 Link_out
              15. Raiten DJ, Fisher KD: Assessment of folate methodology used in the Third National Health and Nutrition Examination Survey (NHANES III, 1988-1994). J Nutr. 1995 May;125(5):1371S-1398S. Pubmed: 7738698 Link_out
              16. Zittoun J: [Anemias due to disorder of folate, vitamin B12 and transcobalamin metabolism]. Rev Prat. 1993 Jun 1;43(11):1358-63. Pubmed: 8235383 Link_out
              17. Kamen B: Folate and antifolate pharmacology. Semin Oncol. 1997 Oct;24(5 Suppl 18):S18-30-S18-39. Pubmed: 9420019 Link_out
              18. Fenech M, Aitken C, Rinaldi J: Folate, vitamin B12, homocysteine status and DNA damage in young Australian adults. Carcinogenesis. 1998 Jul;19(7):1163-71. Pubmed: 9683174 Link_out
              19. Alaimo K, McDowell MA, Briefel RR, Bischof AM, Caughman CR, Loria CM, Johnson CL: Dietary intake of vitamins, minerals, and fiber of persons ages 2 months and over in the United States: Third National Health and Nutrition Examination Survey, Phase 1, 1988-91. Adv Data. 1994 Nov 14;(258):1-28. Pubmed: 10138938 Link_out

              Enzymes
              Name: Methylenetetrahydrofolate reductase
              Reactions: Not Available
              Gene Name: MTHFR
              Uniprot ID: P42898 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Glycine N-methyltransferase
              Reactions: Not Available
              Gene Name: GNMT
              Uniprot ID: Q14749 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Formimidoyltransferase-cyclodeaminase
              Reactions: Not Available
              Gene Name: FTCD
              Uniprot ID: O95954 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Dihydrofolate reductase
              Reactions:
              Tetrahydrofolic acid + NAD unknown Folic acid + NADH + Hydrogen Ion details
              Tetrahydrofolic acid + NADP unknown Folic acid + NADPH + Hydrogen Ion details
              Dihydrofolic acid + NAD unknown Folic acid + NADH + Hydrogen Ion details
              Dihydrofolic acid + NADP unknown Folic acid + NADPH + Hydrogen Ion details
              Gene Name: DHFR
              Uniprot ID: P00374 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: 5-formyltetrahydrofolate cyclo-ligase
              Reactions: Not Available
              Gene Name: MTHFS
              Uniprot ID: P49914 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cytochrome P450 2E1
              Reactions: Not Available
              Gene Name: CYP2E1
              Uniprot ID: P05181 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Folate receptor alpha
              Reactions: Not Available
              Gene Name: FOLR1
              Uniprot ID: P15328 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Folate transporter 1
              Reactions: Not Available
              Gene Name: SLC19A1
              Uniprot ID: P41440 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Thiamine transporter 1
              Reactions: Not Available
              Gene Name: SLC19A2
              Uniprot ID: O60779 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Folate receptor gamma
              Reactions: Not Available
              Gene Name: FOLR3
              Uniprot ID: P41439 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Gamma-glutamyl hydrolase
              Reactions: Not Available
              Gene Name: GGH
              Uniprot ID: Q92820 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Dihydrofolate reductase
              Reactions: Not Available
              Gene Name: DYR
              Uniprot ID: B0YJ76 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Folate receptor beta
              Reactions: Not Available
              Gene Name: FOLR2
              Uniprot ID: P14207 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Folate transporter-like protein C2orf83
              Reactions: Not Available
              Gene Name: C2orf83
              Uniprot ID: Q53S99 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Probable folate receptor delta
              Reactions: Not Available
              Gene Name: FOLR4
              Uniprot ID: A6ND01 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Dihydrofolate reductase, mitochondrial
              Reactions:
              Tetrahydrofolic acid + NAD unknown Folic acid + NADH + Hydrogen Ion details
              Tetrahydrofolic acid + NADP unknown Folic acid + NADPH + Hydrogen Ion details
              Dihydrofolic acid + NAD unknown Folic acid + NADH + Hydrogen Ion details
              Dihydrofolic acid + NADP unknown Folic acid + NADPH + Hydrogen Ion details
              Gene Name: DHFRL1
              Uniprot ID: Q86XF0 Link_out
              Protein Sequence: FASTA
              Transporters
              Name: Canalicular multispecific organic anion transporter 2
              Reactions: Not Available
              Gene Name: ABCC3
              Uniprot ID: O15438 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: ATP-binding cassette sub-family G member 2
              Reactions: Not Available
              Gene Name: ABCG2
              Uniprot ID: Q9UNQ0 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Proton-coupled folate transporter
              Reactions: Not Available
              Gene Name: SLC46A1
              Uniprot ID: Q96NT5 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Multidrug resistance-associated protein 4
              Reactions: Not Available
              Gene Name: ABCC4
              Uniprot ID: O15439 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Solute carrier family 22 member 6
              Reactions: Not Available
              Gene Name: SLC22A6
              Uniprot ID: Q4U2R8 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: ATP-binding cassette sub-family C member 11
              Reactions: Not Available
              Gene Name: ABCC11
              Uniprot ID: Q96J66 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Mitochondrial folate transporter/carrier
              Reactions: Not Available
              Gene Name: SLC25A32
              Uniprot ID: Q9H2D1 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA