Details of Metabolite (Meta)

General Information of Metabolite (ID: MT029)
  Meta Name
Phenylbutyrate
  Unify Name
3-Phenylbutyric acid
  Synonym    Click to Show/Hide the Detailed Synonyms of This Metabolite
3-Phenylbutyrate;3-Phenylbutiric acid;3-Phenylbutirate;(RS)-3-Phenylbutanoate;(RS)-3-Phenylbutanoic acid;3-Phenylbutanoate
  Molecule Type
Amino acid (AAs)
  Formula
C10H12O2
  Inchi Key
ZZEWMYILWXCRHZ-UHFFFAOYSA-N
  Description    Click to Show/Hide the Detailed Description of This Metabolite
3-Phenylbutyric acid, also known as 3-phenylbutyrate or (RS)-3-phenylbutanoate, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 3-Phenylbutyric acid is a weakly acidic compound (based on its pKa). Adverse effects Nearly 1/4 women may experience an adverse effect of amenorrhea or menstrual dysfunction. Sodium phenylbutyrate can act as a chemical chaperone, stabilising the mutant CFTR in the endoplasmic reticulum and allowing it to reach the cell surface. A 5g tablet or powder of sodium phenylbutyrate taken by mouth can be detected in the blood within 15 minutes, and reaches peak concentration in the bloodstream within an hour. As of July 2011 they plan on testing phenylbutyrate for the treatment of Parkinson's disease in humans.
  External Links   HMDB ID   HMDB0001955
  Metlin ID   6399

The epigenetic modification information of this metabolite
Modification Type Molecule EM Info Cell/Tissue Type Modified sites Condition REF
Histone Acetylation H3 EM Info D283-MED cells . . [1], [2]
Histone Acetylation H3 EM Info DAOY cells . . [1], [3]
Histone Acetylation H4 EM Info D283-MED cells . . [4], [5]
Histone Deacetylation HDAC EM Info . . . [1], [2]

The microbes that produce this metabolite
      Bacteroides
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [3]
         Description
Bacteroides is a genus of gram-negative, obligate anaerobic bacteria.
      Eubacterium limosum
         Detailed Information MIC Info click to show the detail information of this Microbiota [4], [5]
         Description
Eubacteria limosum is the type species of the genus Eubacteria. Cells stain gram-positive, are nonmotile, and occur often with swollen ends. The anaerobic type strain grows autotrophically using H 2 + CO 2 or CO as carbon and energy source.
      Clostridium
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Clostridium is a genus of gram-positive, anaerobic bacteria from the family Bacillaceae.
      Eggerthella lenta
         Detailed Information MIC Info click to show the detail information of this Microbiota [6], [7]
         Description
Eggerthella lenta is a species of aerobic, gram-negative, rod shaped bacteria in the phylum Actinobacteria. E. lenta is a commensal organism of the gastrointestinal tract and is rarely associated with infections.

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 Phenylbutyrate and phenylacetate induce differentiation and inhibit proliferation of human medulloblastoma cells. Clin Cancer Res. 2004 Feb 1;10(3):1150-9. doi: 10.1158/1078-0432.ccr-0747-3.
4 Butyrate greatly enhances derivation of human induced pluripotent stem cells by promoting epigenetic remodeling and the expression of pluripotency-associated genes. Stem Cells. 2010 Apr;28(4):713-20. doi: 10.1002/stem.402.
5 Eubacterium limosum ameliorates experimental colitis and metabolite of microbe attenuates colonic inflammatory action with increase of mucosal integrity World J Gastroenterol. 2006 Feb 21;12(7):1071-7. doi: 10.3748/wjg.v12.i7.1071.
6 Acetate functions as an epigenetic metabolite to promote lipid synthesis under hypoxia. Nat Commun. 2016 Jun 30;7:11960. doi: 10.1038/ncomms11960.
7 Bile acid oxidation by Eggerthella lenta strains C592 and DSM 2243(T) Gut Microbes. 2018 Nov 2;9(6):523-539. doi: 10.1080/19490976.2018.1458180. Epub 2018 May 24.

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