Arachidonyl-CoA (BioDeep_00000004884)

 

Secondary id: BioDeep_00000630274, BioDeep_00001868981

human metabolite Endogenous


代谢物信息卡片


{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-{[2-({2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

化学式: C41H66N7O17P3S (1053.3449)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 45.83%

分子结构信息

SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=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/C41H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h8-9,11-12,14-15,17-18,28-30,34-36,40,51-52H,4-7,10,13,16,19-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/b9-8-,12-11-,15-14-,18-17-/t30-,34-,35-,36+,40-/m1/s1

描述信息

Arachidonyl-CoA is an intermediate in Biosynthesis of unsaturated fatty acids. Arachidonyl-CoA is produced from 8,11,14-Eicosatrienoyl-CoA via the enzyme fatty acid desaturase 1 (EC 1.14.19.-). It is then converted to Arachidonic acid via the enzymepalmitoyl-CoA hydrolase (EC 3.1.2.2).

同义名列表

11 个代谢物同义名

{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-{[2-({2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid; [(2R,3R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3R)-3-hydroxy-3-{[2-({2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxyphosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid; S-[2-[3-[[(2R)-4-[[[(2R,3R,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] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenethioate; (5Z,8Z,11Z,14Z)-Icosatetraenoyl-coenzyme A; (5Z,8Z,11Z,14Z)-Icosatetraenoyl-CoA; Arachidonoyl-coenzyme A; Arachidonyl-coenzyme A; Arachidonoyl-CoA; Arachidonyl-CoA; S-[2-[3-[[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](5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenethioate; Arachidonyl-CoA



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

2977 个相关的代谢反应过程信息。

Reactome(36)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(2939)

PharmGKB(0)

1 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 8 ACSL4, ALB, COASY, KAT5, PLA2G12A, PTGS2, RBFOX3, SH3GL2
Peripheral membrane protein 3 AP1S2, PTGS2, SH3GL2
Endoplasmic reticulum membrane 4 ACSL4, LPCAT3, MBOAT7, PTGS2
Nucleus 5 ALB, KAT5, PLCZ1, PPARA, RBFOX3
cytosol 7 ACOX1, ALB, AP1S2, KAT5, PLCZ1, PRKCQ, SH3GL2
centrosome 1 ALB
nucleoplasm 3 KAT5, PLCZ1, PPARA
Cell membrane 1 ACSL4
Cytoplasmic side 1 AP1S2
Multi-pass membrane protein 2 LPCAT3, MBOAT7
glutamatergic synapse 1 SH3GL2
Golgi apparatus 2 ALB, AP1S2
Golgi membrane 3 AP1S2, INS, SH3GL2
lysosomal membrane 1 AP1S2
Presynapse 1 SH3GL2
plasma membrane 5 ACSL4, F2, KNG1, PRKCQ, SH3GL2
Membrane 6 ACOX1, ACSL4, LCAT, LPCAT3, MBOAT7, SH3GL2
caveola 1 PTGS2
extracellular exosome 7 ACSL4, ALB, COASY, CPN2, F2, KNG1, LCAT
endoplasmic reticulum 5 ACSL4, ALB, LPCAT3, MBOAT7, PTGS2
extracellular space 6 ALB, CPN2, F2, INS, KNG1, LCAT
perinuclear region of cytoplasm 3 KAT5, PLCZ1, SH3GL2
mitochondrion 2 ACSL4, COASY
protein-containing complex 2 ALB, PTGS2
intracellular membrane-bounded organelle 2 AP1S2, KAT5
Microsome membrane 2 ACSL4, PTGS2
pronucleus 1 PLCZ1
Secreted 5 ALB, F2, INS, LCAT, PLA2G12A
extracellular region 7 ALB, CPN2, F2, INS, KNG1, LCAT, PLA2G12A
Mitochondrion outer membrane 1 ACSL4
mitochondrial outer membrane 2 ACSL4, COASY
Mitochondrion matrix 1 COASY
mitochondrial matrix 1 COASY
anchoring junction 1 ALB
transcription regulator complex 1 KAT5
centriolar satellite 1 PRKCQ
high-density lipoprotein particle 1 LCAT
perikaryon 1 RBFOX3
nucleolus 2 KAT5, PLCZ1
Early endosome 2 AP1S2, SH3GL2
Membrane, clathrin-coated pit 1 AP1S2
clathrin-coated pit 1 AP1S2
Cytoplasm, perinuclear region 2 KAT5, PLCZ1
extracellular matrix 1 CPN2
Peroxisome 1 ACOX1
peroxisomal matrix 1 ACOX1
peroxisomal membrane 2 ACOX1, ACSL4
collagen-containing extracellular matrix 2 F2, KNG1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
ciliary basal body 1 ALB
chromatin 2 KAT5, PPARA
cell projection 1 SH3GL2
Chromosome 1 KAT5
centriole 1 ALB
Secreted, extracellular space 1 KNG1
Nucleus, nucleolus 1 KAT5
spindle pole 1 ALB
blood microparticle 4 ALB, CPN2, F2, KNG1
NuA4 histone acetyltransferase complex 1 KAT5
site of double-strand break 1 KAT5
Cytoplasm, cytoskeleton, spindle pole 1 KAT5
Endomembrane system 1 AP1S2
endosome lumen 1 INS
Lipid droplet 1 ACSL4
Chromosome, centromere, kinetochore 1 KAT5
mitochondria-associated endoplasmic reticulum membrane contact site 2 ACSL4, MBOAT7
Cytoplasmic vesicle membrane 1 AP1S2
Peroxisome membrane 1 ACSL4
trans-Golgi network membrane 1 AP1S2
secretory granule lumen 1 INS
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 5 ALB, F2, INS, KNG1, PTGS2
platelet alpha granule lumen 2 ALB, KNG1
kinetochore 1 KAT5
mitotic spindle pole 1 KAT5
transport vesicle 1 INS
Single-pass type III membrane protein 1 ACSL4
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
clathrin-coated endocytic vesicle membrane 1 SH3GL2
histone acetyltransferase complex 1 KAT5
nucleosome 1 KAT5
Swr1 complex 1 KAT5
AP-type membrane coat adaptor complex 1 AP1S2
membrane coat 1 AP1S2
AP-1 adaptor complex 1 AP1S2
sperm head 1 PLCZ1
ciliary transition fiber 1 ALB
piccolo histone acetyltransferase complex 1 KAT5


文献列表

  • Bin Dong, Chin Fung Kelvin Kan, Amar B Singh, Jingwen Liu. High-fructose diet downregulates long-chain acyl-CoA synthetase 3 expression in liver of hamsters via impairing LXR/RXR signaling pathway. Journal of lipid research. 2013 May; 54(5):1241-54. doi: 10.1194/jlr.m032599. [PMID: 23427282]
  • Jeffrey M McCue, William J Driscoll, Gregory P Mueller. In vitro synthesis of arachidonoyl amino acids by cytochrome c. Prostaglandins & other lipid mediators. 2009 Nov; 90(1-2):42-8. doi: 10.1016/j.prostaglandins.2009.08.001. [PMID: 19683594]
  • Satoru Sakuma, Kumiko Usa, Yohko Fujimoto. The regulation of formation of prostaglandins and arachidonoyl-CoA from arachidonic acid in rabbit kidney medulla microsomes by linoleic acid hydroperoxide. Prostaglandins & other lipid mediators. 2006 May; 79(3-4):271-7. doi: 10.1016/j.prostaglandins.2006.02.005. [PMID: 16647640]
  • Ka-Chun Leung, Hong-Ye Li, Shi Xiao, Muk-Hei Tse, Mee-Len Chye. Arabidopsis ACBP3 is an extracellularly targeted acyl-CoA-binding protein. Planta. 2006 Apr; 223(5):871-81. doi: 10.1007/s00425-005-0139-2. [PMID: 16231156]
  • Rebeca Pérez, Xavier Matabosch, Amadeu Llebaria, María A Balboa, Jesús Balsinde. Blockade of arachidonic acid incorporation into phospholipids induces apoptosis in U937 promonocytic cells. Journal of lipid research. 2006 Mar; 47(3):484-91. doi: 10.1194/jlr.m500397-jlr200. [PMID: 16326977]
  • Yohko Fujimoto, Kumiko Usa, Satoru Sakuma. Effects of endocrine disruptors on the formation of prostaglandin and arachidonoyl-CoA formed from arachidonic acid in rabbit kidney medulla microsomes. Prostaglandins, leukotrienes, and essential fatty acids. 2005 Dec; 73(6):447-52. doi: 10.1016/j.plefa.2005.08.002. [PMID: 16181777]
  • D P Lee, A S Deonarine, M Kienetz, Q Zhu, M Skrzypczak, M Chan, P C Choy. A novel pathway for lipid biosynthesis: the direct acylation of glycerol. Journal of lipid research. 2001 Dec; 42(12):1979-86. doi: . [PMID: 11734570]
  • K Murakami, T Ide, T Nakazawa, T Okazaki, T Mochizuki, T Kadowaki. Fatty-acyl-CoA thioesters inhibit recruitment of steroid receptor co-activator 1 to alpha and gamma isoforms of peroxisome-proliferator-activated receptors by competing with agonists. The Biochemical journal. 2001 Jan; 353(Pt 2):231-8. doi: 10.1042/0264-6021:3530231. [PMID: 11139385]
  • S Sakuma, Y Fujimoto, Y Katoh, A Kitao, T Fujita. The regulation of prostaglandin and arachidonoyl-CoA formation from arachidonic acid in rabbit kidney medulla microsomes by palmitoyl-CoA. Life sciences. 2000 Feb; 66(12):1147-53. doi: 10.1016/s0024-3205(00)00418-5. [PMID: 10737365]
  • S Sakuma, Y Fujimoto, T Sawada, K Saeki, M Akimoto, T Fujita. Existence of acyl-CoA hydrolase-mediated pathway supplying arachidonic acid for prostaglandin synthesis in microsomes from rabbit kidney medulla. Prostaglandins & other lipid mediators. 1999 May; 57(2-3):63-72. doi: 10.1016/s0090-6980(98)00072-0. [PMID: 10410378]
  • E Grange, O Rabin, J Bell, M C Chang. Manoalide, a phospholipase A2 inhibitor, inhibits arachidonate incorporation and turnover in brain phospholipids of the awake rat. Neurochemical research. 1998 Oct; 23(10):1251-7. doi: 10.1023/a:1020788031720. [PMID: 9804280]
  • R P Strosznajder. Acute hypoxia modulates arachidonic acid metabolism in cat carotid bodies. Role of dopamine. Acta neurobiologiae experimentalis. 1996; 56(2):535-43. doi: 10.55782/ane-1996-1157. [PMID: 8768303]
  • M Goppelt-Struebe, I Winter. Effects of hexadecylphosphocholine on fatty acid metabolism: relation to cytotoxicity. Cancer chemotherapy and pharmacology. 1995; 35(6):519-26. doi: 10.1007/bf00686838. [PMID: 7882461]
  • K Washizaki, Q R Smith, S I Rapoport, A D Purdon. Brain arachidonic acid incorporation and precursor pool specific activity during intravenous infusion of unesterified [3H]arachidonate in the anesthetized rat. Journal of neurochemistry. 1994 Aug; 63(2):727-36. doi: 10.1046/j.1471-4159.1994.63020727.x. [PMID: 8035197]
  • S Sakuma, Y Fujimoto, K Doi, S Nagamatsu, H Nishida, T Fujita. Existence of an enzymatic pathway furnishing arachidonic acid for prostaglandin synthesis from arachidonoyl CoA in rabbit kidney medulla. Biochemical and biophysical research communications. 1994 Jul; 202(2):1054-9. doi: 10.1006/bbrc.1994.2035. [PMID: 8048918]
  • A Cantafora, C C Yan, Y Sun, R Masella. Effects of taurine on microsomal enzyme activities involved in liver lipid metabolism of Wistar rats. Advances in experimental medicine and biology. 1994; 359(?):99-110. doi: 10.1007/978-1-4899-1471-2_11. [PMID: 7887294]
  • S Sakuma, Y Fujimoto, M Okumura, H Nishida, I Yamamoto, T Fujita. The effects of arachidonic acid and its CoA ester on the catabolism of prostaglandin E2 in rabbit kidney cortex. Biochemistry international. 1992 Jul; 27(2):291-9. doi: . [PMID: 1323964]
  • K K Vaswani, R W Ledeen. Purified rat brain myelin contains measurable acyl-CoA:lysophospholipid acyltransferase(s) but little, if any, glycerol-3-phosphate acyltransferase. Journal of neurochemistry. 1989 Jan; 52(1):69-74. doi: 10.1111/j.1471-4159.1989.tb10899.x. [PMID: 2908893]
  • N Morisaki, T Kanzaki, Y Saito, S Yoshida. Fatty acid specificity of acyl-CoA synthetase in rat glomeruli. Biochimica et biophysica acta. 1986 Feb; 875(2):311-5. doi: 10.1016/0005-2760(86)90181-5. [PMID: 3942768]
  • T S Reddy, N G Bazan. Synthesis of arachidonoyl coenzyme A and docosahexaenoyl coenzyme A in synaptic plasma membranes of cerebrum and microsomes of cerebrum, cerebellum, and brain stem of rat brain. Journal of neuroscience research. 1985; 13(3):381-90. doi: 10.1002/jnr.490130305. [PMID: 3989882]
  • W B Weglicki, J H Kramer, F F Kennett, T E Knauer, K Owens. Perturbations of sarcolemmal and microsomal enzymes by amphiphilic lipids and drugs. Advances in myocardiology. 1985; 6(?):127-36. doi: . [PMID: 2986257]
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