General Information of Metabolite (ID: MT069)
  Meta Name
Folate (B9)
  Unify Name
Folic acid
  Synonym    Click to Show/Hide the Detailed Synonyms of This Metabolite
Folate;Folsaeure;N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid;N-Pteroyl-L-glutamic acid;PGA;PteGlu;Pteroyl-L-glutamic acid;Pteroyl-L-monoglutamic acid;Pteroylglutamic acid;Vitamin BC;Vitamin m;N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamate;N-Pteroyl-L-glutamate;Pteroyl-L-glutamate;Pteroyl-L-monoglutamate;Pteroylglutamate;Acifolic;Cytofol;Dosfolat b activ;Folacid;Folacin;Folbal;Folcidin;Foldine;Folettes;Foliamin;Folicet;Folipac;Folsan;Folsaure;Folsav;Folvite;Incafolic;Liver lactobacillus casei factor;Millafol;N-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid;N-[4-[[(2-amino-3,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-glutamic acid;Pteroylmonoglutamic acid;Vitamin be;Folic acid, (DL)-isomer;Folic acid, sodium salt;Folic acid, (D)-isomer;Folic acid, monosodium salt;Folic acid, potassium salt;b9, Vitamin;Folic acid, calcium salt (1:1);Folic acid, monopotassium salt;Vitamin b9;
  Molecule Type
Vitamins
  Formula
C19H18N7O6
  Inchi Key
OVBPIULPVIDEAO-LBPRGKRZSA-M
  Description    Click to Show/Hide the Detailed Description of This Metabolite
Human Metabolome Database (HMDB): 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.
  External Links   HMDB ID   HMDB0000121
  VMH ID   fol
  KEGG ID   C00504
  Metlin ID   246

The epigenetic modification information of this metabolite
Modification Type Molecule EM Info Cell/Tissue Type Modified sites Condition REF
DNA Methylation Ccl3 EM Info Hippocampal cells Promoter . [1], [2]
DNA Methylation MGMT EM Info Serum CpG site . [1], [2]
DNA Methylation MLH1 EM Info Serum CpG site . [1], [2]
DNA Methylation p16 EM Info Serum CpG site . [1], [2]
Histone Methylation H3K27 EM Info . Hes1 promoter . [3], [4]
Histone Methylation H3K27 EM Info . Neurog2 promoter . [1], [2]
Histone Deacetylation Sirtuin 4 EM Info . . . [1]
miRNA miR-10A EM Info . . . [1], [2]
miRNA miR-149-5p EM Info QGY-7703 cells . Normal [1], [5]
miRNA miR-149-5p EM Info HL-7702 cells . Normal [1], [2]
miRNA miR-149-5p EM Info QGY-7703 cells . Cancerous [1], [2]
miRNA miR-22-3p EM Info HL-7702 cells . Normal [1], [2]
miRNA miR-22-3p EM Info QGY-7703 cells . Normal [6], [1]
miRNA miR-22-3p EM Info QGY-7703 cells . Cancerous [7], [8]

The microbes that produce this metabolite
      Escherichia coli
         Detailed Information MIC Info click to show the detail information of this Microbiota [1]
         Description
Escherichia coli, also known as E. coli, is a gram-negative, facultative anaerobic, rod-shaped, coliform bacteria of the genus Escherichia.
      Bacteroidetes
         Detailed Information MIC Info click to show the detail information of this Microbiota [6], [1]
         Description
The phylum "Bacteroidetes" is composed of three large classes of gram-negative, nonsporeforming, anaerobic or aerobic, and rod-shaped bacteria that are widely distributed in the environment, including in soil, sediments, and sea water, as well as in the guts and on the skin of animals.
      Bifidobacterium
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Bifidobacteria is a genus of gram-positive, nonmotile, often branched anaerobic bacteria. They are ubiquitous inhabitants of the gastrointestinal tract, vagina and mouth of mammals, including humans.
      Bacillus subtilis
         Detailed Information MIC Info click to show the detail information of this Microbiota [1]
         Description
Bacillus subtilis, known also as the hay bacillus or grass bacillus, is a gram-positive, catalase-positive bacteria, found in soil and the gastrointestinal tract of ruminants and humans.
      Fusobacteria
         Detailed Information MIC Info click to show the detail information of this Microbiota [1]
         Description
Fusobacteria are obligately anaerobic non-sporeforming gram-negative bacilli.
      Proteobacteria
         Detailed Information MIC Info click to show the detail information of this Microbiota [1]
         Description
Proteobacteria is a major phylum of gram-negative bacteria. It includes a wide variety of pathogenic genera, such as Escherichia, Salmonella, Vibrio, Helicobacter, Yersinia, Legionellales, and many others.
      Actinobacteria
         Detailed Information MIC Info click to show the detail information of this Microbiota [1]
         Description
Actinobacteria are ubiquitous gram-positive bacteria with high guanine and cytosine contents in DNA, having a characteristic filamentous morphology.
      Lactococcus lactis
         Detailed Information MIC Info click to show the detail information of this Microbiota [7], [8]
         Description
Lactococcus lactis is a facultative anaerobic, gram-positive non-sporulating and non-motile bacteria.
      Lactobacillus gasseri
         Detailed Information MIC Info click to show the detail information of this Microbiota [9], [8]
         Description
Lactobacillus gasseriis an anaerobic, gram-positive bacteria that falls into the category of lactic acid bacteria.
      Lactobacillus reuteri
         Detailed Information MIC Info click to show the detail information of this Microbiota [9], [10]
         Description
Lactobacillus reuteri is a facultative anaerobic, gram-positive bacteria that naturally inhabits the gut of mammals and birds.
      Lactobacillus reuteri 6475
         Detailed Information MIC Info click to show the detail information of this Microbiota [6], [1]
         Description
Lactobacillus reuteri is a lactic acid bacteria found in a variety of natural environments, including the gastrointestinal tract of humans and other animals. It does not appear to be pathogenic and may have health effects.
      Lactobacillus
         Detailed Information MIC Info click to show the detail information of this Microbiota [11], [1]
         Description
Lactobacillus is a genus of gram-positive, facultative anaerobic or microaerophilic, rod-shaped, non-spore-forming bacteria. They are a major part of the lactic acid bacteria group. In humans, they constitute a significant component of the microbiota at a number of body sites, such as the digestive system, urinary system, and genital system.

References
1 Gut Microbiota as Important Mediator Between Diet and DNA Methylation and Histone Modifications in the Host. Nutrients. 2020 Feb 25;12(3):597. doi: 10.3390/nu12030597.
2 Arachidonic and oleic acid exert distinct effects on the DNA methylome. Epigenetics. 2016 May 3;11(5):321-34. doi: 10.1080/15592294.2016.1161873. Epub 2016 Apr 18.
3 Two-carbon folate cycle of commensal Lactobacillus reuteri 6475 gives rise to immunomodulatory ethionine, a source for histone ethylation. FASEB J. 2019 Mar;33(3):3536-3548. doi: 10.1096/fj.201801848R. Epub 2018 Nov 19.
4 Methionine-dependent histone methylation at developmentally important gene loci in mouse preimplantation embryos. J Nutr Biochem. 2015 Dec;26(12):1664-9. doi: 10.1016/j.jnutbio.2015.08.009. Epub 2015 Aug 20.
5 Effect of phenolic acids of microbial origin on production of reactive oxygen species in mitochondria and neutrophils J Biomed Sci. 2012 Oct 12;19(1):89. doi: 10.1186/1423-0127-19-89.
6 Response of MiRNA-22-3p and MiRNA-149-5p to Folate Deficiency and the Differential Regulation of MTHFR Expression in Normal and Cancerous Human Hepatocytes. PLoS One. 2017 Jan 3;12(1):e0168049. doi: 10.1371/journal.pone.0168049. eCollection 2017.
7 Associations of dietary methyl donor intake with MLH1 promoter hypermethylation and related molecular phenotypes in sporadic colorectal cancer. Carcinogenesis. 2008 Sep;29(9):1765-73. doi: 10.1093/carcin/bgn074. Epub 2008 Mar 13.
8 Biosynthesis of Vitamins by Probiotic Bacteria.
9 Dietary metabolites derived from gut microbiota: critical modulators of epigenetic changes in mammals. Nutr Rev. 2017 May 1;75(5):374-389. doi: 10.1093/nutrit/nux001.
10 Metabolic engineering of lactic acid bacteria for the production of industrially important compounds Comput Struct Biotechnol J. 2012 Oct 29;3:e201210003. doi: 10.5936/csbj.201210003. eCollection 2012.
11 Valerian and valeric acid inhibit growth of breast cancer cells possibly by mediating epigenetic modifications. Sci Rep. 2021 Jan 28;11(1):2519. doi: 10.1038/s41598-021-81620-x.

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