Eicosanoyl-CoA (BioCAD00000010493)

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Metabolite Card

Formula: C41H74N7O17P3S (1061.4075)
SMILES: CCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

Synonyms [en]

Eicosanoyl-CoA; icosanoyl-CoA; Arachidoyl-CoA; Eicosyl-coenzyme A; Arachidinoyl-CoA; Arachidyl CoA

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Eicosanoyl-CoA. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000010493). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Eicosanoyl-CoA is an intermediate metabolite in the synthesis of phosphatidic acid, a substrate of lysophosphatidic acid acyltransferase with high specificity as an acyl donor. Cells and membranes of mammalian cells synthesize their glycerophospholipids and triglycerides to maintain the cellular integrity and to provide energy for cellular functions. The phospholipids are synthesized de novo in cells through an evolutionary conserved process involving serial acylations of glycerol-3-phosphate. Several isoforms of the enzyme 1-acylglycerol-3-phosphate-O-acyltransferase (EC 2.3.1.51, AGPAT) acylate lysophosphatidic acid at the sn-2 position to produce phosphatidic acid. Bile acid-CoA:amino acid N-acyltransferase (EC 2.3.1.65, BACAT) catalyzes the conjugation of bile acids to glycine and taurine for excretion into bile and can utilize Eicosanoyl-CoA as an acyl donor as well; this may play important roles in protection against toxicity by accumulation of unconjugated bile acids and non-esterified very long-chain fatty acids. (PMID: 17535882, 12810727).

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 15895-27-9
  • PubChem: 3081439
  • ChEBI: ChEBI:15527
  • HMDB: HMDB0004258
  • HMDB: HMDB04258
  • LipidMaps: LMFA07050006
  • LipidMaps: LMFA07050329
  • KEGG: C02041
  • NCBI MeSH: arachidoyl-coenzyme A
  • RefMet: RM0160070
  • Metlin: METLIN_36638
  • Coconut NaturalProduct: CNP0345985.1
  • Coconut NaturalProduct: CNP0345985.2
  • Coconut NaturalProduct: CNP0345985.3

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02224 stearoyl-CoA:malonyl-CoA C-acyltransferase (decarboxylating, oxoacyl- and enoyl-reducing)
KEGG:R08175 3.1.2.2 icosanoyl-CoA hydrolase
KEGG:R10926 1.14.19.10 icosanoyl-CoA,ferrocytochrome b5:oxygen oxidoreductase (5,6 cis-dehydrogenating)
KEGG:R11450 2.3.1.111 eicosanoyl-CoA:methylmalonyl-CoA C-acyltransferase (mycocerosate-forming)
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
BioCyc:MOUSE_PWY-5885 wax esters biosynthesis II
BioCyc:THAPS_PWY-5885 wax esters biosynthesis II
BioCyc:PCHR_PWY-5885 wax esters biosynthesis II
WikiPathways:WP4725 Sphingolipid metabolism overview
WikiPathways:WP4690 Sphingolipid metabolism (integrated pathway)
WikiPathways:WP4724 Omega-9 fatty acid synthesis
WikiPathways:WP5179 Biosynthesis and turnover of 1-deoxy-sphingoid bases
WikiPathways:WP4344 Sphingolipid metabolism overview
WikiPathways:WP4351 Omega-9 fatty acid synthesis
WikiPathways:WP4726 Sphingolipid metabolism: integrated pathway
View All Pathways