13-L-Hydroperoxylinoleic acid (BioDeep_00000003299)

 

Secondary id: BioDeep_00001868772

human metabolite Endogenous blood metabolite


代谢物信息卡片


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

化学式: C18H32O4 (312.23)
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 Homo sapiens(plant) 13.19%

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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 ALOX5, APP, BMAL1, CAT, CYP2E1, DCTN4, HPGDS, MTOR, PNPLA2, PRKAA2, SREBF1
Peripheral membrane protein 3 ALOX5, CYP2E1, MTOR
Endoplasmic reticulum membrane 6 CYP2E1, HMGCR, MTOR, PNPLA2, SREBF1, STAR
Nucleus 7 APP, BMAL1, DCTN4, GABPA, MTOR, PRKAA2, SREBF1
autophagosome 1 MAP1LC3A
cytosol 11 ALOX5, APP, CAT, DCTN4, GPT, HPGDS, MAP1LC3A, MTOR, PNPLA2, PRKAA2, SREBF1
dendrite 3 APP, MTOR, PRKAA2
phagocytic vesicle 1 MTOR
centrosome 1 DCTN4
nucleoplasm 9 ALOX5, BMAL1, GABPA, GLDC, HPGDS, MTOR, PNPLA2, PRKAA2, SREBF1
Cell membrane 4 APP, PNPLA2, STAR, TNF
Lipid-anchor 1 MAP1LC3A
Cytoplasmic side 1 MTOR
Cell projection, growth cone 1 APP
Multi-pass membrane protein 3 HMGCR, PNPLA2, SREBF1
Golgi apparatus membrane 2 MTOR, SREBF1
Synapse 1 APP
cell cortex 1 DCTN4
cell surface 2 APP, TNF
ciliary rootlet 1 APP
dendritic shaft 1 APP
glutamatergic synapse 1 MAP1LC3A
Golgi apparatus 2 APP, PRKAA2
Golgi membrane 2 MTOR, SREBF1
growth cone 1 APP
lysosomal membrane 1 MTOR
mitochondrial inner membrane 2 APP, CYP2E1
neuromuscular junction 1 APP
neuronal cell body 2 PRKAA2, TNF
smooth endoplasmic reticulum 1 APP
synaptic vesicle 1 APP
Cytoplasm, cytosol 1 ALOX5
Lysosome 1 MTOR
endosome 1 APP
plasma membrane 5 APP, GLDC, PNPLA2, STAR, TNF
presynaptic active zone 1 APP
Membrane 6 APP, CAT, HMGCR, MTOR, PNPLA2, PRKAA2
axon 2 APP, PRKAA2
extracellular exosome 3 APP, CAT, GPT
Lysosome membrane 1 MTOR
endoplasmic reticulum 3 APP, HMGCR, SREBF1
extracellular space 4 ALOX5, APP, CCL2, TNF
perinuclear region of cytoplasm 2 ALOX5, APP
mitochondrion 3 CAT, GLDC, STAR
protein-containing complex 2 CAT, SREBF1
intracellular membrane-bounded organelle 5 BMAL1, CAT, CYP2E1, HPGDS, MAP1LC3A
Microsome membrane 2 CYP2E1, MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 2 APP, STAR
Secreted 2 APP, CCL2
extracellular region 5 ALOX5, APP, CAT, CCL2, TNF
Mitochondrion outer membrane 1 MTOR
mitochondrial outer membrane 1 MTOR
mitochondrial matrix 3 CAT, GLDC, STAR
transcription regulator complex 1 BMAL1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 DCTN4
Nucleus membrane 1 ALOX5
nuclear membrane 1 ALOX5
external side of plasma membrane 1 TNF
dendritic spine 1 APP
perikaryon 1 APP
cytoplasmic vesicle 1 APP
Early endosome 1 APP
Membrane, clathrin-coated pit 1 APP
apical part of cell 1 APP
cell-cell junction 1 APP
clathrin-coated pit 1 APP
COPII-coated ER to Golgi transport vesicle 1 APP
Golgi-associated vesicle 1 APP
recycling endosome 2 APP, TNF
spindle midzone 1 APP
Single-pass type II membrane protein 1 TNF
vesicle 1 APP
Cytoplasm, perinuclear region 1 ALOX5
Mitochondrion inner membrane 1 CYP2E1
Membrane raft 2 APP, TNF
Cytoplasm, cytoskeleton 2 DCTN4, MAP1LC3A
focal adhesion 2 CAT, DCTN4
microtubule 1 MAP1LC3A
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 2 CAT, HMGCR
Nucleus, PML body 2 BMAL1, MTOR
PML body 2 BMAL1, MTOR
mitochondrial intermembrane space 1 STAR
nuclear speck 1 PRKAA2
Cytoplasm, myofibril, sarcomere 1 DCTN4
Late endosome 1 MAP1LC3A
sarcomere 1 DCTN4
receptor complex 1 APP
chromatin 3 BMAL1, GABPA, SREBF1
Cytoplasmic vesicle, autophagosome membrane 1 MAP1LC3A
autophagosome membrane 1 MAP1LC3A
phagocytic cup 1 TNF
spindle pole 1 DCTN4
Cytoplasm, cell cortex 1 DCTN4
organelle membrane 1 MAP1LC3A
nuclear envelope 3 ALOX5, MTOR, SREBF1
Nucleus envelope 1 ALOX5
Endomembrane system 2 MAP1LC3A, MTOR
endosome lumen 1 APP
Lipid droplet 1 PNPLA2
aryl hydrocarbon receptor complex 1 BMAL1
Cytoplasmic vesicle membrane 1 SREBF1
cytoplasmic stress granule 1 PRKAA2
Peroxisome membrane 1 HMGCR
stress fiber 1 DCTN4
trans-Golgi network membrane 1 APP
ficolin-1-rich granule lumen 2 ALOX5, CAT
secretory granule lumen 2 ALOX5, CAT
Golgi lumen 1 APP
endoplasmic reticulum lumen 2 APP, PNPLA2
nuclear matrix 1 ALOX5
platelet alpha granule lumen 1 APP
chromatoid body 1 BMAL1
CLOCK-BMAL transcription complex 1 BMAL1
dynactin complex 1 DCTN4
kinetochore 1 DCTN4
cytoplasmic dynein complex 1 DCTN4
ER to Golgi transport vesicle membrane 1 SREBF1
Nucleus matrix 1 ALOX5
nuclear envelope lumen 2 ALOX5, APP
Cytoplasm, cytoskeleton, stress fiber 1 DCTN4
nucleotide-activated protein kinase complex 1 PRKAA2
Cytoplasmic vesicle, phagosome 1 MTOR
Cytoplasmic vesicle, COPII-coated vesicle membrane 1 SREBF1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
Autolysosome 1 MAP1LC3A
catalase complex 1 CAT
[C83]: Endoplasmic reticulum 1 APP
[C99]: Early endosome 1 APP
[Soluble APP-beta]: Secreted 1 APP
[Amyloid-beta protein 40]: Cell surface 1 APP
[Amyloid-beta protein 42]: Cell surface 1 APP
[Gamma-secretase C-terminal fragment 59]: Nucleus 1 APP
Nucleus intermembrane space 1 ALOX5
glycine cleavage complex 1 GLDC
[Sterol regulatory element-binding protein 1]: Endoplasmic reticulum membrane 1 SREBF1
[Processed sterol regulatory element-binding protein 1]: Nucleus 1 SREBF1
[Isoform SREBP-1aDelta]: Nucleus 1 SREBF1
[Isoform SREBP-1cDelta]: Nucleus 1 SREBF1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

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  • Dillon Hershelman, Kirsten M Kahler, Morgan J Price, Iris Lu, Yuhan Fu, Patricia A Plumeri, Fred Karaisz, Natasha F Bassett, Peter M Findeis, Charles H Clapp. Oxygenation reactions catalyzed by the F557V mutant of soybean lipoxygenase-1: Evidence for two orientations of substrate binding. Archives of biochemistry and biophysics. 2019 10; 674(?):108082. doi: 10.1016/j.abb.2019.108082. [PMID: 31473191]
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  • Jing Lu, Baochen Fang, Yixuan Huang, Siyu Tao, Bo Sun, Shuang Guan, Yingli Jin. Epigallocatechin-3-gallate protects against 1,3-dichloro-2-propanol-induced lipid accumulation in C57BL/6J mice. Life sciences. 2018 Sep; 209(?):324-331. doi: 10.1016/j.lfs.2018.08.007. [PMID: 30092300]
  • Yana Y Toporkova, Svetlana S Gorina, Elena K Bessolitsyna, Elena O Smirnova, Valeria S Fatykhova, Fredi Brühlmann, Tatiana M Ilyina, Lucia S Mukhtarova, Alexander N Grechkin. Double function hydroperoxide lyases/epoxyalcohol synthases (CYP74C) of higher plants: identification and conversion into allene oxide synthases by site-directed mutagenesis. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2018 Apr; 1863(4):369-378. doi: 10.1016/j.bbalip.2018.01.002. [PMID: 29325723]
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  • Svetlana S Gorina, Yana Y Toporkova, Lucia S Mukhtarova, Elena O Smirnova, Ivan R Chechetkin, Bulat I Khairutdinov, Yuri V Gogolev, Alexander N Grechkin. Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Molecular cloning and identification of divinyl ether synthases CYP74M1 and CYP74M3. Biochimica et biophysica acta. 2016 Apr; 1861(4):301-9. doi: 10.1016/j.bbalip.2016.01.001. [PMID: 26776054]
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