Linoleoyl-CoA (BioDeep_00000004832)

Main id: BioDeep_00000630247

 

human metabolite Endogenous


代谢物信息卡片


{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

化学式: C39H66N7O17P3S (1029.3449)
中文名称: 亚麻酰基辅酵素 a
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@H](n2cnc3c(N)ncnc23)O1)O)OP(=O)(O)O)O
InChI: InChI=1S/C39H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8-,12-11-/t28-,32-,33-,34+,38-/m1/s1

描述信息

Linoleoyl-CoA is the acyl-CoA of linoleic acid found in the human body. It binds to and results in decreased activity of glutathione S-transferase1. It has been proposed that inhibition of mitochondrial adenine nucleotide translocator by long-chain acyl-CoA underlies the mechanism associating obesity and type 2 diabetes. Unsaturated fatty acids play an important role in the prevention of human diseases such as diabetes, obesity, cancer, and neurodegeneration. Their oxidation in vivo by acyl-CoA dehydrogenases (ACADs) catalyze the first step of each cycle of mitochondrial fatty acid beta-oxidation. ACAD-9 had maximal activity with long-chain unsaturated acyl-CoAs as substrates (PMID: 17184976, 16020546).

同义名列表

15 个代谢物同义名

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid; S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (9Z,12Z)-octadeca-9,12-dienethioate; S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl](9Z,12Z)-octadeca-9,12-dienethioate; (9Z,12Z)-Octadecadienoyl-coenzyme A; Linoleoyl-coenzyme A, (Z,Z)-isomer; (Z,Z)-9,12-Octadecadienoyl-CoA; (9Z,12Z)-Octadecadienoyl-CoA; 6Z,9Z-octadecadienoyl-CoA; Linoleoyl-coenzyme A; Linoleoyl coenzyme A; Linoleic coenzyme A; Linoleyl-coenzyme A; CoA(18:2(9Z,12Z)); Linoleoyl-CoA; Linoleyl-CoA



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(6)

BioCyc(0)

PlantCyc(0)

代谢反应

80 个相关的代谢反应过程信息。

Reactome(77)

BioCyc(0)

WikiPathways(3)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

2 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 4 ALB, CAT, G6PD, LYPLA2
Peripheral membrane protein 1 G6PD
Endosome membrane 1 MRC1
Endoplasmic reticulum membrane 8 DGAT1, FADS2, HSP90B1, LPCAT3, LPCAT4, MBOAT7, SCD, SLC33A1
Nucleus 2 ALB, HSP90B1
cytosol 6 ALB, CAT, FXN, G6PD, HSP90B1, LYPLA2
centrosome 1 ALB
nucleoplasm 1 LYPLA2
Cell membrane 3 IL6R, MRC1, TNF
Multi-pass membrane protein 7 DGAT1, FADS2, LPCAT3, LPCAT4, MBOAT7, SCD, SLC33A1
cell surface 2 MRC1, TNF
Golgi apparatus 1 ALB
Golgi membrane 2 INS, SLC33A1
neuronal cell body 1 TNF
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 G6PD
plasma membrane 6 DGAT1, FADS2, IL6R, MRC1, SLC33A1, TNF
Membrane 11 CAT, DGAT1, FADS2, G6PD, HSP90B1, IL6R, LPCAT3, LPCAT4, MBOAT7, SCD, SLC33A1
apical plasma membrane 1 IL6R
extracellular exosome 6 ALB, CAT, CPN2, G6PD, HSP90B1, LYPLA2
endoplasmic reticulum 6 ALB, HSP90B1, LPCAT3, LPCAT4, MBOAT7, SCD
extracellular space 7 ALB, CPN2, CXCL10, IL4, IL6R, INS, TNF
perinuclear region of cytoplasm 1 HSP90B1
mitochondrion 2 CAT, FXN
protein-containing complex 3 ALB, CAT, HSP90B1
intracellular membrane-bounded organelle 2 CAT, G6PD
Single-pass type I membrane protein 2 IL6R, MRC1
Secreted 4 ALB, CXCL10, IL4, INS
extracellular region 9 ALB, CAT, CPN2, CXCL10, HSP90B1, IL4, IL6R, INS, TNF
cytoplasmic side of plasma membrane 1 G6PD
[Isoform 2]: Secreted 1 IL6R
mitochondrial matrix 2 CAT, FXN
anchoring junction 1 ALB
centriolar satellite 1 G6PD
external side of plasma membrane 3 CXCL10, IL6R, TNF
nucleolus 1 SCD
midbody 1 HSP90B1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 1 TNF
focal adhesion 2 CAT, HSP90B1
extracellular matrix 1 CPN2
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 HSP90B1
receptor complex 1 IL6R
ciliary basal body 1 ALB
phagocytic cup 1 TNF
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 2 ALB, CPN2
endosome lumen 1 INS
mitochondria-associated endoplasmic reticulum membrane contact site 1 MBOAT7
specific granule membrane 1 DGAT1
Melanosome 1 HSP90B1
sperm plasma membrane 1 HSP90B1
Golgi stack 1 LYPLA2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 ALB, HSP90B1, INS
platelet alpha granule lumen 1 ALB
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
iron-sulfur cluster assembly complex 1 FXN
mitochondrial 1 FXN
Sarcoplasmic reticulum lumen 1 HSP90B1
[Isoform 1]: Cell membrane 1 IL6R
endocytic vesicle lumen 1 HSP90B1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6R
endoplasmic reticulum chaperone complex 1 HSP90B1
[Soluble interleukin-6 receptor subunit alpha]: Secreted 1 IL6R
ciliary neurotrophic factor receptor complex 1 IL6R
ciliary transition fiber 1 ALB
[Frataxin mature form]: Mitochondrion 1 FXN
[Extramitochondrial frataxin]: Cytoplasm, cytosol 1 FXN
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Kenshi Watanabe, Makoto Ohno, Masahiro Taguchi, Seiji Kawamoto, Kazuhisa Ono, Tsunehiro Aki. Identification of amino acid residues that determine the substrate specificity of mammalian membrane-bound front-end fatty acid desaturases. Journal of lipid research. 2016 Jan; 57(1):89-99. doi: 10.1194/jlr.m064121. [PMID: 26590171]
  • Mauricio A Retamal, Flavio Evangelista-Martínez, Carmen G León-Paravic, Guillermo A Altenberg, Luis Reuss. Biphasic effect of linoleic acid on connexin 46 hemichannels. Pflugers Archiv : European journal of physiology. 2011 Jun; 461(6):635-43. doi: 10.1007/s00424-011-0936-3. [PMID: 21360038]
  • Wei Gao, Hong-Ye Li, Shi Xiao, Mee-Len Chye. Protein interactors of acyl-CoA-binding protein ACBP2 mediate cadmium tolerance in Arabidopsis. Plant signaling & behavior. 2010 Aug; 5(8):1025-7. doi: 10.4161/psb.5.8.12294. [PMID: 20657176]
  • A L Thompson, G J Cooney. Acyl-CoA inhibition of hexokinase in rat and human skeletal muscle is a potential mechanism of lipid-induced insulin resistance. Diabetes. 2000 Nov; 49(11):1761-5. doi: 10.2337/diabetes.49.11.1761. [PMID: 11078441]
  • G Griffiths, A K Stobart, S Stymne. Delta 6- and delta 12-desaturase activities and phosphatidic acid formation in microsomal preparations from the developing cotyledons of common borage (Borago officinalis). The Biochemical journal. 1988 Jun; 252(3):641-7. doi: 10.1042/bj2520641. [PMID: 3421914]
  • T Kawasaki, F Snyder. Synthesis of a novel acetylated neutral lipid related to platelet-activating factor by acyl-CoA:1-O-alkyl-2-acetyl-sn-glycerol acyltransferase in HL-60 cells. The Journal of biological chemistry. 1988 Feb; 263(6):2593-6. doi: . [PMID: 3422635]
  • S Stymne, A K Stobart. Biosynthesis of gamma-linolenic acid in cotyledons and microsomal preparations of the developing seeds of common borage (Borago officinalis). The Biochemical journal. 1986 Dec; 240(2):385-93. doi: 10.1042/bj2400385. [PMID: 3028375]
  • O Colard, M Breton, R Infante, G Bereziat, J Polonovski. 1-Acyl-lysolecithin acyltransferase and synthesis of biliary lecithins in rat liver. Biochimie. 1984 Mar; 66(3):215-21. doi: 10.1016/0300-9084(84)90065-8. [PMID: 6743697]
  • P B Smith, R C Reitz, D Kelley. Acyl-CoA synthase and acyltransferase activity in developing skeletal muscle membranes. Biochimica et biophysica acta. 1982 Oct; 713(1):128-35. doi: 10.1016/0005-2760(82)90175-8. [PMID: 7138893]
  • M Mahfouz, S Johnson, R T Holman. Inhibition of desaturation of palmitic, linoleic and eicosa-8,11,14-trienoic acids in vitro by isomeric cis-octadecenoic acids. Biochimica et biophysica acta. 1981 Jan; 663(1):58-68. doi: 10.1016/0005-2760(81)90194-6. [PMID: 7213772]
  • T Okayasu. [Purification and characterization of Linoleoyl-CoA desaturase from rat liver microsomes (author's transl)]. [Hokkaido igaku zasshi] The Hokkaido journal of medical science. 1981 Jan; 56(1):43-54. doi: . [PMID: 7262818]
  • B Schreiber, W Homann, M Mlynek, P Mellin. Ureteral replacement with a new prosthesis. Transactions - American Society for Artificial Internal Organs. 1979; 25(?):61-5. doi: 10.1097/00002480-197902500-00012. [PMID: 160647]
  • O V Popov, R R Smiller. [State of glucocorticoid activity in patients with different histologic variants of Hodgkin's disease]. Problemy gematologii i perelivaniia krovi. 1977 Jan; 22(1):11-5. doi: NULL. [PMID: 834733]
  • . . . . doi: . [PMID: 18781350]