Details of Metabolite (Meta)

General Information of Metabolite (ID: MT072)
Meta Name	Docosahexaenoic acid
Unify Name	Docosahexaenoic acid
Synonym	Click to Show/Hide the Detailed Synonyms of This Metabolite (4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid;22:6(N-3);22:6-4, 7,10,13,16,19;4,7,10,13,16,19-Docosahexaenoic acid;all-cis-4,7,10,13,16,19-Docosahexaenoic acid;all-cis-DHA;Cervonic acid;DHA;Doconexent;DOCOSA-4,7,10,13,16,19-hexaenoIC ACID;Docosahexaenoate;4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoic acid;(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid;(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoate;4,7,10,13,16,19-Docosahexaenoate;all-cis-4,7,10,13,16,19-Docosahexaenoate;Cervonate;DOCOSA-4,7,10,13,16,19-hexaenoate;4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoate;(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoate;all-Z-Docosahexaenoate;all-Z-Docosahexaenoic acid;cis-4,7,10,13,16,19-Docosahexanoate;cis-4,7,10,13,16,19-Docosahexanoic acid;Doconexento;Doconexentum;Doxonexent;Acids, docosahexaenoic;Acids, docosahexenoic;Docosahexaenoic acid, 4,7,10,13,16,19-(all-Z-isomer);Docosahexaenoic acid (all-Z isomer);Docosahexaenoic acid, 4,7,10,13,16,19-isomer;Efalex;(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid;(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexenoic acid;(all-Z)-4,7,10,13,16,19-Docosahexaenoic acid;4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-Docosahexaenoic acid;Docosahexaenoic acid;FA(22:6(4Z,7Z,10Z,13Z,16Z,19Z));FA(22:6n3);delta4,7,10,13,16,19-Docosahexaenoic acid;delta4,7,10,13,16,19-Docosahexaenoic acid
Molecule Type	Polyunsaturated fatty acid (PUFAs)
Formula	C22H31O2
Inchi Key	MBMBGCFOFBJSGT-KXRQTMKUSA-M
Description	Click to Show/Hide the Detailed Description of This Metabolite Human Metabolome Database (HMDB): Docosahexaenoic acid (DHA) is an omega-3 essential fatty acid. Chemically, DHA is a carboxylic acid with a 22-carbon chain and six cis double bonds with the first double bond is located at the third carbon from the omega end. DHA is most often found in fish oil. It is a major fatty acid in sperm and brain phospholipids, especially in the retina. Dietary DHA can reduce the level of blood triglycerides in humans, which may reduce the risk of heart disease (wikipedia). Docosahexaenoic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
External Links	HMDB ID	HMDB0002183
	VMH ID	crvnc
	KEGG ID	C06429
	Metlin ID	3457

The epigenetic modification information of this metabolite
Modification Type	Molecule	EM Info	Cell/Tissue Type	Modified sites	Condition	REF
DNA Methylation	ACER2	EM Info	Jurkat T cells	chr9:19408000	.	[1], [2]
DNA Methylation	ANKRD28	EM Info	Jurkat T cells	chr3:15838030	.	[1], [2]
DNA Methylation	ARHGAP21	EM Info	Jurkat T cells	chr10:24995583	.	[1], [2]
DNA Methylation	ASAP2	EM Info	Jurkat T cells	chr2:9381833	.	[1], [2]
DNA Methylation	ATXN10	EM Info	Jurkat T cells	chr22:46067508	.	[1], [2]
DNA Methylation	BCL2L11	EM Info	Jurkat T cells	chr2:111877753	.	[1], [2]
DNA Methylation	BMP3	EM Info	Jurkat T cells	chr4:81960704	.	[1], [2]
DNA Methylation	BNC2	EM Info	Jurkat T cells	chr9:16726627	.	[1], [2]
DNA Methylation	C18orf63	EM Info	Jurkat T cells	chr18:72021321	.	[1], [2]
DNA Methylation	CACNA1C	EM Info	Jurkat T cells	chr12:2198113	.	[1], [2]
DNA Methylation	CDHR3	EM Info	Jurkat T cells	chr7:105655497	.	[1], [2]
DNA Methylation	CDKN2A	EM Info	Jurkat T cells	chr9:21986062	.	[1], [2]
DNA Methylation	CHODL	EM Info	Jurkat T cells	chr21:19616644	.	[1], [2]
DNA Methylation	CLNK	EM Info	Jurkat T cells	chr4:10531768	.	[1], [2]
DNA Methylation	DMRTA1	EM Info	Jurkat T cells	chr9:22446830	.	[1], [2]
DNA Methylation	EMX2OS	EM Info	Jurkat T cells	chr10:119292371	.	[1], [2]
DNA Methylation	FGF13	EM Info	Jurkat T cells	chrX:137794264	.	[1], [2]
DNA Methylation	GDF7	EM Info	Jurkat T cells	chr2:20866414	.	[1], [2]
DNA Methylation	GLT25D2	EM Info	Jurkat T cells	chr1:183995878	.	[1], [2]
DNA Methylation	HEATR4	EM Info	Jurkat T cells	chr14:74003851	.	[1], [2]
DNA Methylation	HSPBAP1	EM Info	Jurkat T cells	chr3:122510658	.	[1], [2]
DNA Methylation	INTS8	EM Info	Jurkat T cells	chr8:95888145	.	[1], [2]
DNA Methylation	KCNMB2	EM Info	Jurkat T cells	chr3:178275369	.	[1], [2]
DNA Methylation	KIF13B	EM Info	Jurkat T cells	chr8:29020165	.	[1], [2]
DNA Methylation	LOC101927476	EM Info	Jurkat T cells	chrX:40141241	.	[1], [2]
DNA Methylation	MAGEE1	EM Info	Jurkat T cells	chrX:75648802	.	[1], [2]
DNA Methylation	MAP3K13	EM Info	Jurkat T cells	chr3:185046594	.	[1], [2]
DNA Methylation	MEP1A	EM Info	Jurkat T cells	chr6:46760919	.	[1], [2]
DNA Methylation	MIR137HG	EM Info	Jurkat T cells	chr1:98500398	.	[1], [2]
DNA Methylation	MORC2	EM Info	Jurkat T cells	chr22:31344805	.	[1], [2]
DNA Methylation	MSH6	EM Info	Jurkat T cells	chr2:48011201	.	[1], [2]
DNA Methylation	MSX2	EM Info	Jurkat T cells	chr5:174150712	.	[1], [2]
DNA Methylation	MYO6	EM Info	Jurkat T cells	chr6:76553236	.	[1], [2]
DNA Methylation	NC	EM Info	Jurkat T cells	chr10:48952010	.	[1], [2]
DNA Methylation	NC	EM Info	Jurkat T cells	chr17:40834511	.	[1], [2]
DNA Methylation	NCRNA00171	EM Info	Jurkat T cells	chr6:30016420	.	[1], [2]
DNA Methylation	PHF20L1	EM Info	Jurkat T cells	chr8:133788834	.	[1], [2]
DNA Methylation	PRDM6	EM Info	Jurkat T cells	chr5:122452418	.	[1], [2]
DNA Methylation	PTCH1	EM Info	Jurkat T cells	chr9:98265802	.	[1], [2]
DNA Methylation	PXDNL	EM Info	Jurkat T cells	chr8:52589863	.	[1], [2]
DNA Methylation	RASSF8	EM Info	Jurkat T cells	chr12:26112480	.	[1], [2]
DNA Methylation	RBMS2	EM Info	Jurkat T cells	chr12:56966920	.	[1], [2]
DNA Methylation	RGS1	EM Info	Jurkat T cells	chr1:192544252	.	[1], [2]
DNA Methylation	SCN7A	EM Info	Jurkat T cells	chr2:167344458	.	[1], [2]
DNA Methylation	SYN1	EM Info	Jurkat T cells	chrX:47468321	.	[1], [2]
DNA Methylation	SYNPR	EM Info	Jurkat T cells	chr3:63428587	.	[1], [2]
DNA Methylation	THRSP	EM Info	Jurkat T cells	chr11:77773924	.	[1], [2]
DNA Methylation	TMEM117	EM Info	Jurkat T cells	chr12:44292779	.	[1], [2]
DNA Methylation	TNIK	EM Info	Jurkat T cells	chr3:171102373	.	[1], [2]
DNA Methylation	TRAF3IP1	EM Info	Jurkat T cells	chr2:239241869	.	[1], [2]
DNA Methylation	TRIM26	EM Info	Jurkat T cells	chr6:30165652	.	[1], [2]
DNA Methylation	XIRP2	EM Info	Jurkat T cells	chr2:168043663	.	[1], [2]
Histone Trimethylation	H3	EM Info	Breast cancer cells	lysine 27	Breast cancer	[3], [4]

The microbes that produce this metabolite
Roseburia
Detailed Information	MIC Info click to show the detail information of this Microbiota	[5], [1]
Description	Roseburia is a genus of butyrate-producing, gram-positive anaerobic bacteria that inhabit the human colon.
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.
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.
Klebsiella
Detailed Information	MIC Info click to show the detail information of this Microbiota	[1], [2]
Description	Klebsiella is a genus of gram-negative, oxidase-negative, rod-shaped bacteria from the family Enterobacteriaceae
Enterobacter
Detailed Information	MIC Info click to show the detail information of this Microbiota	[1], [2]
Description	Enterobacter is a genus of common gram-negative, facultatively anaerobic, rod-shaped, non-spore-forming bacteria of the family Enterobacteriaceae. It is the type genus of the order Enterobacterales.
Citrobacter
Detailed Information	MIC Info click to show the detail information of this Microbiota	[1], [2]
Description	Citrobacter is a genus of gram-negative coliform bacteria in the family Enterobacteriaceae. The species C. amalonaticus, C. koseri, and C. freundii can use citrate as a sole carbon source. Citrobacter species are differentiated by their ability to convert tryptophan to indole, ferment lactose, and use malonate.
Lactobacillus
Detailed Information	MIC Info click to show the detail information of this Microbiota	[5], [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.
Schizochytrium sp. S31
Detailed Information	MIC Info click to show the detail information of this Microbiota	[3], [4]
Description	Schizochytrium sp. S31 belongs to the order Thraustochytriale and is a spherical unicellular microorganism.

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	Impact of dietary gut microbial metabolites on the epigenome. Philos Trans R Soc Lond B Biol Sci. 2018 Jun 5;373(1748):20170359. doi: 10.1098/rstb.2017.0359.
4	Production of High-Value Polyunsaturated Fatty Acids Using Microbial Cultures. Methods Mol Biol. 2019;1995:229-248. doi: 10.1007/978-1-4939-9484-7_15.
5	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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