Oleoyl-CoA (BioDeep_00000004437)
Secondary id: BioDeep_00000605035, BioDeep_00000630242
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)-octadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
化学式: C39H68N7O17P3S (1031.3605)
中文名称:
谱图信息:
最多检出来源 Mus musculus(lipidsearch) 41.33%
分子结构信息
SMILES: CCCCCCCC/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/C39H68N7O17P3S/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/h11-12,26-28,32-34,38,49-50H,4-10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/t28-,32-,33-,34?,38-/m1/s1
描述信息
Oleoyl-CoA is a substrate for Acyl-CoA desaturase and Protein FAM34A. [HMDB]. Oleoyl-CoA is found in many foods, some of which are cardoon, fruits, hyssop, and rice.
Oleoyl-CoA is a substrate for Acyl-CoA desaturase and Protein FAM34A.
同义名列表
20 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)-octadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid; S-[(9Z)-Octadec-9-enoyl]-coenzyme A; (9Z)-Octadec-9-enoyl-coenzyme A; Coenzyme A cis-9-octadecenoate; cis-9-Octadecenoyl-coenzyme A; S-[(9Z)-Octadec-9-enoyl]-CoA; 9-Octadecenoyl-coenzyme A; (9Z)-Octadec-9-enoyl-CoA; cis-9-Octadecenoyl-CoA; (9Z)-Octadecenoyl-CoA; 9-Octadecenoyl-CoA; S-Oleoylcoenzyme A; Coenzyme A oleate; Oleoyl-coenzyme A; Oleoyl coenzyme A; Oleyl coenzyme A; Oleyl-coenzyme A; S-Oleoyl-CoA; oleoyl-CoA; Oleyl-CoA
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:15534
- KEGG: C00510
- PubChem: 5497111
- PubChem: 966
- HMDB: HMDB0001322
- MetaCyc: OLEOYL-COA
- foodb: FDB022554
- chemspider: 4593689
- CAS: 1716-06-9
- PMhub: MS000016887
- PubChem: 3793
- LipidMAPS: LMFA07050356
- PDB-CCD: 3VV
- 3DMET: B04691
- NIKKAJI: J203.108F
- RefMet: Oleoyl-CoA
分类词条
相关代谢途径
BioCyc(0)
PlantCyc(0)
代谢反应
70 个相关的代谢反应过程信息。
Reactome(68)
- Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Metabolism of lipids:
H+ + LTHSOL + Oxygen + TPNH ⟶ 7-dehydroCHOL + H2O + TPN - Fatty acid metabolism:
Ac-CoA + H2O ⟶ CH3COO- + CoA-SH - Fatty acyl-CoA biosynthesis:
ATP + CoA-SH + VLCFA ⟶ AMP + PPi + VLCFA-CoA - Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA - Metabolism of lipids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA - Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acyl-CoA biosynthesis:
Mal-CoA + PALM-CoA ⟶ 3OOD-CoA + CoA-SH + carbon dioxide - Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Metabolism of lipids:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Fatty acid metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Metabolism of lipids:
3-oxopristanoyl-CoA + CoA-SH ⟶ 4,8,12-trimethyltridecanoyl-CoA + propionyl CoA - Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acid metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Metabolism of lipids:
H2O + lysoPC ⟶ GPCho + LCFA(-) - Fatty acid metabolism:
12S-HpETE + GSH ⟶ 12S-HETE + GSSG + H2O - Fatty acyl-CoA biosynthesis:
Mal-CoA + PALM-CoA ⟶ 3OOD-CoA + CoA-SH + carbon dioxide - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Metabolism:
CAR + propionyl CoA ⟶ CoA-SH + Propionylcarnitine - Metabolism of lipids:
CAR + propionyl CoA ⟶ CoA-SH + Propionylcarnitine - Fatty acid metabolism:
CAR + propionyl CoA ⟶ CoA-SH + Propionylcarnitine - Fatty acyl-CoA biosynthesis:
ATP + Ac-CoA + HCO3- ⟶ ADP + Mal-CoA + Pi - Metabolism:
GAA + SAM ⟶ CRET + H+ + SAH - Metabolism of lipids:
ACA + H+ + NADH ⟶ NAD + bHBA - Fatty acid metabolism:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Metabolism of lipids:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Fatty acid metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Fatty acyl-CoA biosynthesis:
ATP + CIT + CoA-SH ⟶ ADP + Ac-CoA + OA + Pi - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Fatty acyl-CoA biosynthesis:
ATP + CoA + VLCFA ⟶ AMP + PPi + VLCFA-CoA - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
BioCyc(0)
WikiPathways(2)
- Mitochondrial beta oxidation:
5Z,8Z-tetradecadienoyl-CoA ⟶ 2E,5Z,8Z-tetradecatrienoyl-CoA - Omega-9 fatty acid synthesis:
CoA(18:1(9Z)) ⟶ Oleic acid
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
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
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。
文献列表
- Lucas M O'Neill, Chang-An Guo, Fang Ding, Yar Xin Phang, Zhaojin Liu, Sohel Shamsuzzaman, James M Ntambi. Stearoyl-CoA Desaturase-2 in Murine Development, Metabolism, and Disease.
International journal of molecular sciences.
2020 Nov; 21(22):. doi:
10.3390/ijms21228619. [PMID: 33207603] - Romy R Schmidt, Martin Fulda, Melanie V Paul, Max Anders, Frederic Plum, Daniel A Weits, Monika Kosmacz, Tony R Larson, Ian A Graham, Gerrit T S Beemster, Francesco Licausi, Peter Geigenberger, Jos H Schippers, Joost T van Dongen. Low-oxygen response is triggered by an ATP-dependent shift in oleoyl-CoA in Arabidopsis.
Proceedings of the National Academy of Sciences of the United States of America.
2018 12; 115(51):E12101-E12110. doi:
10.1073/pnas.1809429115. [PMID: 30509981] - Rashmi Panigrahi, Tsutomu Matsui, Andrew H Song, Kristian Mark P Caldo, Howard S Young, Randall J Weselake, M Joanne Lemieux. Intrinsic disorder in the regulatory N-terminal domain of diacylglycerol acyltransferase 1 from Brassica napus.
Scientific reports.
2018 11; 8(1):16665. doi:
10.1038/s41598-018-34339-1. [PMID: 30420764] - Kristian Mark P Caldo, Wei Shen, Yang Xu, Linda Hanley-Bowdoin, Guanqun Chen, Randall J Weselake, M Joanne Lemieux. Diacylglycerol acyltransferase 1 is activated by phosphatidate and inhibited by SnRK1-catalyzed phosphorylation.
The Plant journal : for cell and molecular biology.
2018 10; 96(2):287-299. doi:
10.1111/tpj.14029. [PMID: 30003607] - Jessica Seeßle, Gerhard Liebisch, Gerd Schmitz, Wolfgang Stremmel, Walee Chamulitrat. Palmitate activation by fatty acid transport protein 4 as a model system for hepatocellular apoptosis and steatosis.
Biochimica et biophysica acta.
2015 May; 1851(5):549-65. doi:
10.1016/j.bbalip.2015.01.004. [PMID: 25603556] - Jee-Hee Seo, Mun-Ock Kim, Ah-Reum Han, Eun-Bin Kwon, Myung Ji Kang, Sungchan Cho, Dong-Oh Moon, Jung-Ran Noh, Chul-Ho Lee, Young-Soo Kim, Hyun-Sun Lee. Oleanane-type triterpenoids of Aceriphyllum rossii and their diacylglycerol acyltransferase-inhibitory activity.
Planta medica.
2015 Feb; 81(3):228-34. doi:
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Molecular nutrition & food research.
2014 Apr; 58(4):760-7. doi:
10.1002/mnfr.201300304. [PMID: 24142580] - José María Arroyo-Caro, Tarik Chileh, Diego López Alonso, Federico García-Maroto. Molecular characterization of a lysophosphatidylcholine acyltransferase gene belonging to the MBOAT family in Ricinus communis L.
Lipids.
2013 Jul; 48(7):663-74. doi:
10.1007/s11745-013-3797-z. [PMID: 23700249] - 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:
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2010 Sep; 1801(9):1082-9. doi:
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2010 Aug; 24(8):2795-803. doi:
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Plant signaling & behavior.
2009 Nov; 4(11):1063-5. doi:
10.4161/psb.4.11.9718. [PMID: 20009557] - Shi Xiao, Qin-Fang Chen, Mee-Len Chye. Light-regulated Arabidopsis ACBP4 and ACBP5 encode cytosolic acyl-CoA-binding proteins that bind phosphatidylcholine and oleoyl-CoA ester.
Plant physiology and biochemistry : PPB.
2009 Oct; 47(10):926-33. doi:
10.1016/j.plaphy.2009.06.007. [PMID: 19589686] - Caryl J Antalis, Tyler Arnold, Bonggi Lee, Kimberley K Buhman, Rafat A Siddiqui. Docosahexaenoic acid is a substrate for ACAT1 and inhibits cholesteryl ester formation from oleic acid in MCF-10A cells.
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2009 Feb; 80(2-3):165-71. doi:
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American journal of physiology. Endocrinology and metabolism.
2008 Sep; 295(3):E678-85. doi:
10.1152/ajpendo.90287.2008. [PMID: 18593850] - Gregory P Mueller, William J Driscoll. In vitro synthesis of oleoylglycine by cytochrome c points to a novel pathway for the production of lipid signaling molecules.
The Journal of biological chemistry.
2007 Aug; 282(31):22364-9. doi:
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The Journal of physiology.
2006 Sep; 575(Pt 2):433-42. doi:
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European journal of pharmacology.
2006 Jul; 540(1-3):121-30. doi:
10.1016/j.ejphar.2006.04.022. [PMID: 16730694] - Markus Rapedius, Malle Soom, Ekaterina Shumilina, Dirk Schulze, Roland Schönherr, Cornelia Kirsch, Florian Lang, Stephen J Tucker, Thomas Baukrowitz. Long chain CoA esters as competitive antagonists of phosphatidylinositol 4,5-bisphosphate activation in Kir channels.
The Journal of biological chemistry.
2005 Sep; 280(35):30760-7. doi:
10.1074/jbc.m503503200. [PMID: 15980413] - Ka-Chun Leung, Hong-Ye Li, Girish Mishra, Mee-Len Chye. ACBP4 and ACBP5, novel Arabidopsis acyl-CoA-binding proteins with kelch motifs that bind oleoyl-CoA.
Plant molecular biology.
2004 May; 55(2):297-309. doi:
10.1007/s11103-004-0642-z. [PMID: 15604682] - Tibor Rohács, Coeli M B Lopes, Taihao Jin, Pavan P Ramdya, Zoltán Molnár, Diomedes E Logothetis. Specificity of activation by phosphoinositides determines lipid regulation of Kir channels.
Proceedings of the National Academy of Sciences of the United States of America.
2003 Jan; 100(2):745-50. doi:
10.1073/pnas.0236364100. [PMID: 12525701] - M Miyazaki, H J Kim, W C Man, J M Ntambi. Oleoyl-CoA is the major de novo product of stearoyl-CoA desaturase 1 gene isoform and substrate for the biosynthesis of the Harderian gland 1-alkyl-2,3-diacylglycerol.
The Journal of biological chemistry.
2001 Oct; 276(42):39455-61. doi:
10.1074/jbc.m106442200. [PMID: 11500518] - 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] - M L Chye, H Y Li, M H Yung. Single amino acid substitutions at the acyl-CoA-binding domain interrupt 14[C]palmitoyl-CoA binding of ACBP2, an Arabidopsis acyl-CoA-binding protein with ankyrin repeats.
Plant molecular biology.
2000 Dec; 44(6):711-21. doi:
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Biochemical Society transactions.
2000 Dec; 28(6):972-4. doi:
10.1042/bst0280972. [PMID: 11171276] - 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:
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FEBS letters.
2000 Sep; 481(2):189-92. doi:
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Molecular and cellular biochemistry.
2000 Feb; 205(1-2):83-90. doi:
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Biochimica et biophysica acta.
1999 Aug; 1439(3):371-83. doi:
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Plant molecular biology.
1998 Nov; 38(5):827-38. doi:
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Biochimica et biophysica acta.
1998 Jul; 1393(1):128-36. doi:
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Journal of lipid research.
1998 May; 39(5):1118-26. doi:
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The Journal of biological chemistry.
1998 May; 273(18):11049-55. doi:
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Biochimica et biophysica acta.
1997 Jun; 1346(2):163-72. doi:
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Archives of biochemistry and biophysics.
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