13-L-Hydroperoxylinoleic acid (BioDeep_00000003299)

 

Secondary id: BioDeep_00001868772

human metabolite Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


(9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid

化学式: C18H32O4 (312.2300472)
中文名称: 13-氢过氧-9Z，11E-十八碳二烯酸
谱图信息: 最多检出来源 Viridiplantae(plant) 0.07%

分子结构信息

SMILES: C(CCCCCC/C=C\C=C\[C@H](CCCCC)OO)C(=O)O
InChI: InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/b9-7?,15-12+

描述信息

(9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate, also known as 13s-hydroperoxy-9z,11e-octadecadienoic acid or 13(S)-hpode, belongs to lineolic acids and derivatives class of compounds. Those are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate is considered to be an octadecanoid lipid molecule (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate can be synthesized from octadeca-9,11-dienoic acid (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate can also be synthesized into pinellic acid and 13(S)-HPODE methyl ester (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate can be found in a number of food items such as lingonberry, lemon thyme, watermelon, and agave, which makes (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate a potential biomarker for the consumption of these food products (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate can be found primarily in blood.
13-L-Hydroperoxylinoleic acid (13(S)-HPODE) is one of the primary products of the major polyunsaturated fatty acids (linoleic acid and arachidonic acid) from the 15-lipoxygenase pathway (EC 1.13.11.31). 13(S)-HPODE is a rather unstable metabolite and is rapidly metabolized to more stable secondary products such as diverse forms of hydroxy fatty acids (via reduction of the hydroperoxy group), alkoxy radicals (via homolytic cleavage of the peroxy group), forms of dihydro(pero)xy fatty acids (via lipoxygenase-catalysed double and triple oxygenation), or epoxy leukotrienes (via a hydrogen abstraction from a doubly allylic methylene group and a homolytic cleavage of the hydroperoxy group) (PMID: 9082450).
D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

同义名列表

28 个代谢物同义名

(9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid; 13-Hydroperoxy-9,11-octadecadienoic acid, (Z,e)-isomer; (9Z,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid; (13S,9Z,11E)-13-Hydroperoxy-9,11-octadecadienoic acid; 13-L-Hydroperoxy-9-cis,11-trans-octadecadienoic acid; 13-L-Hydroperoxy-cis-9,trans-11-octadecadienoic acid; (9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoate; (13S,9Z,11E)-13-Hydroperoxy-9,11-octadecadienoate; (9Z,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoate; 13-L-Hydroperoxy-cis-9,trans-11-octadecadienoate; 13-L-Hydroperoxy-9-cis,11-trans-octadecadienoate; 13(S)-Hydroperoxy-9Z,11E-octadecadienoic acid; 13S-hydroperoxy-9Z,11E-octadecadienoic acid; 13(S)-Hydroperoxy-9Z,11E-octadecadienoate; 13-hydroperoxyoctadeca-9,11-dienoic acid; 13-Hydroperoxy-9,11-octadecadienoic acid; 13S-Hydroperoxy-9Z,11E-octadecadienoate; 13-Hydroperoxyoctadecadienoic acid; Linoleic acid 13(S)-hydroperoxide; 13(S)-Hydroperoxylinoleic acid; 13-L-Hydroperoxylinoleic acid; 13-L-Hydroperoxylinoleate; 13(S)-HPODE; 13-HpODE; 13-HPOD; Hpode; (9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid; 13-Hydroperoxy-9Z,11E-octadecadienoic acid



数据库引用编号

30 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

305 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(304)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

7 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

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  • Barbara Soldo, Matilda Šprung, Gloria Mušac, Maja Pavela-Vrančić, Ivica Ljubenkov. Evaluation of Olive Fruit Lipoxygenase Extraction Protocols on 9- and 13-Z,E-HPODE Formation. Molecules (Basel, Switzerland). 2016 Apr; 21(4):506. doi: 10.3390/molecules21040506. [PMID: 27104512]
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  • Valerie E Ryman, Nandakumar Packiriswamy, Lorraine M Sordillo. Apoptosis of Endothelial Cells by 13-HPODE Contributes to Impairment of Endothelial Barrier Integrity. Mediators of inflammation. 2016; 2016(?):9867138. doi: 10.1155/2016/9867138. [PMID: 27818578]
  • Ryo Takahashi, Takaaki Goto, Tomoyuki Oe, Seon Hwa Lee. Angiotensin II modification by decomposition products of linoleic acid-derived lipid hydroperoxide. Chemico-biological interactions. 2015 Sep; 239(?):87-99. doi: 10.1016/j.cbi.2015.06.029. [PMID: 26111765]
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  • Chun-Hua Huang, Fu-Rong Ren, Guo-Qiang Shan, Hao Qin, Li Mao, Ben-Zhan Zhu. Molecular mechanism of metal-independent decomposition of organic hydroperoxides by halogenated quinoid carcinogens and the potential biological implications. Chemical research in toxicology. 2015 May; 28(5):831-7. doi: 10.1021/tx500486z. [PMID: 25789984]
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  • Kiyotaka Nakagawa, Shunji Kato, Teruo Miyazawa. Determination of Phosphatidylcholine Hydroperoxide (PCOOH) as a Marker of Membrane Lipid Peroxidation. Journal of nutritional science and vitaminology. 2015; 61 Suppl(?):S78-80. doi: 10.3177/jnsv.61.s78. [PMID: 26598897]
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