Details of Metabolite (Meta)

General Information of Metabolite (ID: MT047)
  Meta Name
Iso-butyrate
  Unify Name
Isobutyric acid
  Synonym    Click to Show/Hide the Detailed Synonyms of This Metabolite
2,2-Dimethylacetic acid;2-METHYL-propionIC ACID;2-Methylpropanoate;2-Methylpropanoic acid;2-Methylpropionsaeure;alpha-Isobutyric acid;alpha-Methylpropanoic acid;alpha-Methylpropionic acid;Dimethylacetic acid;iso-Butyric acid;iso-C3H7COOH;Isobutanoate;Isobutanoic acid;Isobuttersaeure;Isobutyrate;Isopropylformic acid;2,2-Dimethylacetate;2-METHYL-propionate;a-Isobutyrate;a-Isobutyric acid;alpha-Isobutyrate;Alpha-isobutyrate;Alpha-isobutyric acid;a-Methylpropanoate;a-Methylpropanoic acid;alpha-Methylpropanoate;Alpha-methylpropanoate;Alpha-methylpropanoic acid;a-Methylpropionate;a-Methylpropionic acid;alpha-Methylpropionate;Alpha-methylpropionate;Alpha-methylpropionic acid;Dimethylacetate;iso-Butyrate;Isopropylformate;2-Methylpropionate;2-Methylpropionic acid;I-butyrate;I-butyric acid;Ammonium isobutyrate;Isobutyric acid, ammonium salt;Isobutyric acid, sodium salt;2-Methpropanoic acid;Isobutyric acid, hemiammoniate;Sodium isobutyrate;Isobutyric acid, calcium salt;Isobutyric acid, nickel salt;Isobutyric acid, potassium salt;Isobutyric acid, sodium salt, 11C-labeled;Isobutyric acid, sodium salt, 14C-labeled;
  Molecule Type
Short-chain fatty acids (SCFAs)
  Formula
C4H7O2
  Inchi Key
KQNPFQTWMSNSAP-UHFFFAOYSA-N
  Description    Click to Show/Hide the Detailed Description of This Metabolite
Human Metabolome Database (HMDB): Isobutyric acid is a carboxylic or short chain fatty acid with characteristic sweat-like smell. Small amount of isobutyrate is generated via microbial (gut) metabolism. Small amounts may also be found in certain foods or fermented beverages. There is anosmia (genetic inability to smell) for the odor of isobutyric acid with a frequency of about 2.5%. (OMIM 207000). Isobutyric acid is slightly soluble in water but much more soluble in ethanol, ether and organic solvents. Isobutyric acid can affect people if breathed in and may be absorbed through the skin. Contact can irritate and burn the skin and eyes. Breathing Isobutyric acid can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath.
  External Links   HMDB ID   HMDB0001873
  VMH ID   isobut
  KEGG ID   C02632
  Metlin ID   106

The epigenetic modification information of this metabolite
Modification Type Molecule EM Info Cell/Tissue Type Modified sites Condition REF
Histone Methylation EZH2 EM Info BCBL1 cells . Periodontitis [1]
Histone Isobutyrylation H3 EM Info 293T cells lysine 14 . [2], [3]
Histone Isobutyrylation H3 EM Info 293T cells lysine 23 . [4], [5]
Histone Isobutyrylation H4 EM Info 293T cells lysine . [6], [5]
Histone Methylation SUV39H1 EM Info BCBL1 cells . Periodontitis [1]

The microbes that produce this metabolite
      Fusobacterium nucleatum
         Detailed Information MIC Info click to show the detail information of this Microbiota [1]
         Description
Fusobacteria nucleatum is a species of gram-negative, anaerobic bacteria from the genus Fusobacteria.
      Eubacterium
         Detailed Information MIC Info click to show the detail information of this Microbiota [3], [7]
         Description
Eubacteria is a genus of gram-positive bacteria in the family Eubacteriaceae. These bacteria are characterised by a rigid cell wall. They may either be motile or nonmotile. If motile, they have a flagellum. A typical flagellum consists of a basal body, filament, and hook. The long filament is the organ which helps eubacteria move.
      Roseburia
         Detailed Information MIC Info click to show the detail information of this Microbiota [8], [3]
         Description
Roseburia is a genus of butyrate-producing, gram-positive anaerobic bacteria that inhabit the human colon.
      Anaerostipes hadrus
         Detailed Information MIC Info click to show the detail information of this Microbiota [3]
         Description
Anaerostipes hadrus is a gram-positive bacteria from the genus of Anaerostipes which has been isolated from human faeces.
      Faecalibacterium
         Detailed Information MIC Info click to show the detail information of this Microbiota [2], [3]
         Description
Faecalibacteria is a genus of bacteria. Its sole known species, Faecalibacteria prausnitzii is gram-positive, mesophilic, rod-shaped, anaerobic and is one of the most abundant and important commensal bacteria of the human gut microbiota. These bacteria produce butyrate and other short-chain fatty acids through the fermentation of dietary fiber.
      Coprococcus catus
         Detailed Information MIC Info click to show the detail information of this Microbiota [3], [9]
         Description
Coprococcus catus is a species of anaerobic cocci which are part of the human faecal microbiota.
      Porphyromonas gingivalis
         Detailed Information MIC Info click to show the detail information of this Microbiota [10]
         Description
Porphyromonas gingivalis belongs to the phylum Bacteroidetes and is a nonmotile, gram-negative, rod-shaped, anaerobic, pathogenic bacteria. It forms black colonies on blood agar.
      Lactobacillus
         Detailed Information MIC Info click to show the detail information of this Microbiota [8], [3]
         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 Short-chain fatty acids from periodontal pathogens suppress histone deacetylases, EZH2, and SUV39H1 to promote Kaposi's sarcoma-associated herpesvirus replication. J Virol. 2014 Apr;88(8):4466-79. doi: 10.1128/JVI.03326-13. Epub 2014 Feb 5.
2 Human gut bacteria as potent class I histone deacetylase inhibitors in vitro through production of butyric acid and valeric acid. PLoS One. 2018 Jul 27;13(7):e0201073. doi: 10.1371/journal.pone.0201073. eCollection 2018.
3 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.
4 Commensal microbe-derived butyrate induces the differentiation of colonic regulatory T cells. Nature. 2013 Dec 19;504(7480):446-50. doi: 10.1038/nature12721. Epub 2013 Nov 13.
5 Blood Pressure Abnormalities Associated with Gut Microbiota-Derived Short Chain Fatty Acids in Children with Congenital Anomalies of the Kidney and Urinary Tract J Clin Med. 2019 Jul 24;8(8):1090. doi: 10.3390/jcm8081090.
6 Crosstalk between the microbiome and epigenome: messages from bugs. J Biochem. 2018 Feb 1;163(2):105-112. doi: 10.1093/jb/mvx080.
7 c-Abl kinase regulates neutrophil extracellular trap formation, inflammation, and tissue damage in severe acute pancreatitis. J Leukoc Biol. 2019 Aug;106(2):455-466. doi: 10.1002/JLB.3A0618-222RR. Epub 2019 Mar 12.
8 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.
9 Identification of lysine isobutyrylation as a new histone modification mark. Nucleic Acids Res. 2021 Jan 11;49(1):177-189. doi: 10.1093/nar/gkaa1176.
10 Epigenetic Modifications of Histones in Periodontal Disease. J Dent Res. 2016 Feb;95(2):215-22. doi: 10.1177/0022034515611876. Epub 2015 Oct 23.

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