Hexadecenal (BioDeep_00000002512)
Main id: BioDeep_00000629938
human metabolite Endogenous
代谢物信息卡片
2-(15,15,16,16,16-D5)-Hexadecenal
化学式: C16H30O (238.2297)
中文名称: 2-十六烯醛
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCCCCCCCCCC=CC=O
InChI: InChI=1S/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h14-16H,2-13H2,1H3/b15-14+
描述信息
Among the 19 human ALDHs, ALDH3A2 is the only known ALDH that catalyzes the oxidation of long-chain fatty aldehydes including C16 aldehydes (hexadecanal and trans-2-hexadecenal) generated through sphingolipid metabolism. (PMID: 23721920) We recently identified that two products within the sphingolipid pathway, sphingosine-1-PO4 and hexadecenal, directly regulate BAK and BAX activation, respectively. (PMID: 23750296) Sphingosine-1-phosphate lyase (SPL) is the only known enzyme that irreversibly cleaves sphingosine-1-phosphate (S1P) into phosphoethanolamine and (2E)-hexadecenal during the final step of sphingolipid catabolism. (PMID: 22444536) Sphingosine 1-phosphate, a bioactive signaling molecule with diverse cellular functions, is irreversibly degraded by the endoplasmic reticulum enzyme sphingosine 1-phosphate lyase, generating trans-2-hexadecenal and phosphoethanolamine. We recently demonstrated that trans-2-hexadecenal causes cytoskeletal reorganization, detachment, and apoptosis in multiple cell types via a JNK-dependent pathway. (PMID: 22727907)
同义名列表
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:17585
- KEGG: C06123
- PubChem: 5280541
- PubChem: 145684
- HMDB: HMDB0060482
- Metlin: METLIN36630
- CAS: 22644-96-8
- CAS: 27104-14-9
- CAS: 3163-37-9
- PMhub: MS000003068
- PubChem: 8380
- LipidMAPS: LMFA06000089
- 3DMET: B00906
- NIKKAJI: J346.316H
- RefMet: Hexadecenal
分类词条
相关代谢途径
BioCyc(0)
PlantCyc(0)
代谢反应
67 个相关的代谢反应过程信息。
Reactome(60)
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Metabolism of lipids:
H+ + LTHSOL + Oxygen + TPNH ⟶ 7-dehydroCHOL + H2O + TPN - Sphingolipid metabolism:
3-ketosphinganine + H+ + TPNH ⟶ SPA + TPN - Sphingolipid de novo biosynthesis:
3-ketosphinganine + H+ + TPNH ⟶ SPA + TPN - 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 - Sphingolipid metabolism:
H2O + dehydroepiandrosterone sulfate ⟶ DHEA + SO4(2-) - 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 - Sphingolipid metabolism:
3-ketosphinganine + H+ + TPNH ⟶ SPA + TPN - 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 - Sphingolipid metabolism:
H2O + dehydroepiandrosterone sulfate ⟶ DHEA + SO4(2-) - 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 - Sphingolipid metabolism:
H2O + dehydroepiandrosterone sulfate ⟶ DHEA + SO4(2-) - Metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Metabolism of lipids:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Sphingolipid metabolism:
3-ketosphinganine + H+ + TPNH ⟶ SPA + TPN - 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 - Sphingolipid metabolism:
3-ketosphinganine + H+ + TPNH ⟶ SPA + TPN - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Sphingolipid metabolism:
H2O + dehydroepiandrosterone sulfate ⟶ DHEA + SO4(2-) - 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 - Sphingolipid metabolism:
H2O + dehydroepiandrosterone sulfate ⟶ DHEA + SO4(2-) - 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 - Sphingolipid metabolism:
H2O + dehydroepiandrosterone sulfate ⟶ DHEA + SO4(2-) - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Metabolism of lipids:
H+ + LTHSOL + Oxygen + TPNH ⟶ 7-dehydroCHOL + H2O + TPN - Sphingolipid metabolism:
3-ketosphinganine + H+ + TPNH ⟶ SPA + TPN - Sphingolipid de novo biosynthesis:
3-ketosphinganine + H+ + TPNH ⟶ SPA + TPN - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Sphingolipid metabolism:
H2O + dehydroepiandrosterone sulfate ⟶ DHEA + SO4(2-) - Metabolism:
CAR + propionyl CoA ⟶ CoA-SH + Propionylcarnitine - Metabolism of lipids:
CAR + propionyl CoA ⟶ CoA-SH + Propionylcarnitine - Sphingolipid metabolism:
3-ketosphinganine + H+ + TPNH ⟶ SPA + TPN - Metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Metabolism of lipids:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Sphingolipid metabolism:
H2O + dehydroepiandrosterone sulfate ⟶ DHEA + SO4(2-) - 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 - Sphingolipid metabolism:
H2O + dehydroepiandrosterone sulfate ⟶ DHEA + SO4(2-) - Sphingolipid de novo biosynthesis:
3-ketosphinganine + H+ + TPNH ⟶ SPA + TPN - Sphingolipid catabolism:
H2O + HD2NAL + NAD ⟶ H+ + NADH + PALM - Sphingolipid catabolism:
H2O + Plant-Ceramides-II ⟶ RCOO- + phytosphingosine - Sphingolipid catabolism:
H2O + HD2NAL + NAD ⟶ H+ + NADH + PALM - Sphingolipid catabolism:
H2O + Plant-Ceramides-II ⟶ RCOO- + phytosphingosine - Sphingolipid catabolism:
H2O + Plant-Ceramides-II ⟶ RCOO- + phytosphingosine - Sphingolipid catabolism:
H2O + Plant-Ceramides-II ⟶ RCOO- + phytosphingosine - Sphingolipid catabolism:
H2O + HD2NAL + NAD ⟶ H+ + NADH + PALM - Sphingolipid catabolism:
H2O + Plant-Ceramides-II ⟶ RCOO- + phytosphingosine - Sphingolipid catabolism:
H2O + Plant-Ceramides-II ⟶ RCOO- + phytosphingosine - Sphingolipid catabolism:
H2O + Plant-Ceramides-II ⟶ RCOO- + phytosphingosine - Sphingolipid catabolism:
H2O + Plant-Ceramides-II ⟶ RCOO- + phytosphingosine - Sphingolipid catabolism:
H2O + Plant-Ceramides-II ⟶ RCOO- + phytosphingosine
BioCyc(6)
- sphingosine and sphingosine-1-phosphate metabolism:
sphingosine 1-phosphate ⟶ (2E)-hexadecenal + O-phosphoethanolamine - sphingosine and sphingosine-1-phosphate metabolism:
NADP+ + palmitaldehyde ⟶ (2E)-hexadecenal + H+ + NADPH - sphingosine and sphingosine-1-phosphate metabolism:
NADP+ + palmitaldehyde ⟶ (2E)-hexadecenal + H+ + NADPH - sphingosine and sphingosine-1-phosphate metabolism:
ATP + sphingosine ⟶ ADP + H+ + sphingosine-1-phosphate - sphingosine and sphingosine-1-phosphate metabolism:
ATP + sphingosine ⟶ ADP + H+ + sphingosine-1-phosphate - sphingosine and sphingosine-1-phosphate metabolism:
ATP + sphingosine ⟶ ADP + H+ + sphingosine-1-phosphate
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
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。
文献列表
- Kyong-Oh Shin, Maftuna Shamshiddinova, Jung-No Lee, Kwang-Sik Lee, Yong-Moon Lee. A Bioassay Using a Pentadecanal Derivative to Measure S1P Lyase Activity.
International journal of molecular sciences.
2021 Feb; 22(3):. doi:
10.3390/ijms22031438. [PMID: 33535437] - Daniel T Cohen, Thomas E Wales, Matthew W McHenry, John R Engen, Loren D Walensky. Site-Dependent Cysteine Lipidation Potentiates the Activation of Proapoptotic BAX.
Cell reports.
2020 03; 30(10):3229-3239.e6. doi:
10.1016/j.celrep.2020.02.057. [PMID: 32160532] - Gopala Krishna Jarugumilli, Jong-Ryoul Choi, PuiYee Chan, Meilan Yu, Yang Sun, Baoen Chen, Jixiao Niu, Michael DeRan, Baohui Zheng, Raphael Zoeller, Cheng Lin, Xu Wu. Chemical Probe to Identify the Cellular Targets of the Reactive Lipid Metabolite 2- trans-Hexadecenal.
ACS chemical biology.
2018 05; 13(5):1130-1136. doi:
10.1021/acschembio.7b01063. [PMID: 29608264] - Fabian Schumacher, Corinna Neuber, Hannah Finke, Kai Nieschalke, Jessica Baesler, Erich Gulbins, Burkhard Kleuser. The sphingosine 1-phosphate breakdown product, (2E)-hexadecenal, forms protein adducts and glutathione conjugates in vitro.
Journal of lipid research.
2017 08; 58(8):1648-1660. doi:
10.1194/jlr.m076562. [PMID: 28588048] - Max T Bourdillon, Benjamin A Ford, Ashley T Knulty, Colleen N Gray, Miao Zhang, David Ford, Ryan D McCulla. Oxidation of Plasmalogen, Low-Density Lipoprotein and RAW 264.7 Cells by Photoactivatable Atomic Oxygen Precursors.
Photochemistry and photobiology.
2014 Mar; 90(2):386-93. doi:
10.1111/php.12201. [PMID: 27096146] - Anja Lüth, Corinna Neuber, Burkhard Kleuser. Novel methods for the quantification of (2E)-hexadecenal by liquid chromatography with detection by either ESI QTOF tandem mass spectrometry or fluorescence measurement.
Analytica chimica acta.
2012 Apr; 722(?):70-9. doi:
10.1016/j.aca.2012.01.063. [PMID: 22444536] - Jerry E Chipuk, Gavin P McStay, Archana Bharti, Tomomi Kuwana, Christopher J Clarke, Leah J Siskind, Lina M Obeid, Douglas R Green. Sphingolipid metabolism cooperates with BAK and BAX to promote the mitochondrial pathway of apoptosis.
Cell.
2012 Mar; 148(5):988-1000. doi:
10.1016/j.cell.2012.01.038. [PMID: 22385963] - Samy Selim, Manjula Sunkara, Abdelghaffar K Salous, Steve W Leung, Evgeny V Berdyshev, Alison Bailey, Charles L Campbell, Richard Charnigo, Andrew J Morris, Susan S Smyth. Plasma levels of sphingosine 1-phosphate are strongly correlated with haematocrit, but variably restored by red blood cell transfusions.
Clinical science (London, England : 1979).
2011 Dec; 121(12):565-72. doi:
10.1042/cs20110236. [PMID: 21749329] - N Hagen, M Hans, D Hartmann, D Swandulla, G van Echten-Deckert. Sphingosine-1-phosphate links glycosphingolipid metabolism to neurodegeneration via a calpain-mediated mechanism.
Cell death and differentiation.
2011 Aug; 18(8):1356-65. doi:
10.1038/cdd.2011.7. [PMID: 21331079] - William B Rizzo. The role of fatty aldehyde dehydrogenase in epidermal structure and function.
Dermato-endocrinology.
2011 Apr; 3(2):91-9. doi:
10.4161/derm.3.2.14619. [PMID: 21695018] - Evgeny V Berdyshev, Irina Gorshkova, Peter Usatyuk, Satish Kalari, Yutong Zhao, Nigel J Pyne, Susan Pyne, Roger A Sabbadini, Joe G N Garcia, Viswanathan Natarajan. Intracellular S1P generation is essential for S1P-induced motility of human lung endothelial cells: role of sphingosine kinase 1 and S1P lyase.
PloS one.
2011 Jan; 6(1):e16571. doi:
10.1371/journal.pone.0016571. [PMID: 21304987] - Andrea Huwiler, Florence Bourquin, Nataliya Kotelevets, Oleksandr Pastukhov, Guido Capitani, Markus G Grütter, Uwe Zangemeister-Wittke. A prokaryotic S1P lyase degrades extracellular S1P in vitro and in vivo: implication for treating hyperproliferative disorders.
PloS one.
2011; 6(8):e22436. doi:
10.1371/journal.pone.0022436. [PMID: 21829623] - Kacee Sims, Christopher A Haynes, Samuel Kelly, Jeremy C Allegood, Elaine Wang, Amin Momin, Martina Leipelt, Donna Reichart, Christopher K Glass, M Cameron Sullards, Alfred H Merrill. Kdo2-lipid A, a TLR4-specific agonist, induces de novo sphingolipid biosynthesis in RAW264.7 macrophages, which is essential for induction of autophagy.
The Journal of biological chemistry.
2010 Dec; 285(49):38568-79. doi:
10.1074/jbc.m110.170621. [PMID: 20876532] - Mariana Bertea, Markus F Rütti, Alaa Othman, Jaqueline Marti-Jaun, Martin Hersberger, Arnold von Eckardstein, Thorsten Hornemann. Deoxysphingoid bases as plasma markers in diabetes mellitus.
Lipids in health and disease.
2010 Aug; 9(?):84. doi:
10.1186/1476-511x-9-84. [PMID: 20712864] - Sarah T Pruett, Anatoliy Bushnev, Kerri Hagedorn, Madhura Adiga, Christopher A Haynes, M Cameron Sullards, Dennis C Liotta, Alfred H Merrill. Biodiversity of sphingoid bases ('sphingosines') and related amino alcohols.
Journal of lipid research.
2008 Aug; 49(8):1621-39. doi:
10.1194/jlr.r800012-jlr200. [PMID: 18499644] - Padmavathi Bandhuvula, Henrik Fyrst, Julie D Saba. A rapid fluorescence assay for sphingosine-1-phosphate lyase enzyme activity.
Journal of lipid research.
2007 Dec; 48(12):2769-78. doi:
10.1194/jlr.d700010-jlr200. [PMID: 17872591] - Viral V Brahmbhatt, Fong-Fu Hsu, Jeff L-F Kao, Erin C Frank, David A Ford. Novel carbonyl and nitrile products from reactive chlorinating species attack of lysosphingolipid.
Chemistry and physics of lipids.
2007 Feb; 145(2):72-84. doi:
10.1016/j.chemphyslip.2006.10.006. [PMID: 17126823] - Mika Ikeda, Akio Kihara, Yuki Kariya, Yong-Moon Lee, Yasuyuki Igarashi. Sphingolipid-to-glycerophospholipid conversion in SPL-null cells implies the existence of an alternative isozyme.
Biochemical and biophysical research communications.
2005 Apr; 329(2):474-9. doi:
10.1016/j.bbrc.2005.02.014. [PMID: 15737611] - . .
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