9,12,13-TriHOME (BioDeep_00000004047)

 

Secondary id: BioDeep_00000035645

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoic acid

化学式: C18H34O5 (330.2406)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(blood) 6.79%

分子结构信息

SMILES: C(CCCCCCC[C@H](O)/C=C/[C@H](O)[C@@H](O)CCCCC)(=O)O
InChI: InChI=1S/C18H34O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16+,17-/m0/s1

描述信息

9,12,13-TriHOME is a trihydroxyoctadecenoic acid metabolite of linoleic acid, one of the major fatty acids found in lipids. Vascular tissue converts various polyunsaturated fatty acids to monohydroxy and trihydroxy metabolites derived from hydroperoxides which may be involved in regulating prostaglandin synthesis. The absolute amounts of 9,12,13-TriHOME varies considerably from one species to another. There are several possible mechanisms for the formation of esterified oxygenated polyunsaturated fatty acids: oxygenated and then incorporated into lipids, not well incorporated into either vascular endothelial or smooth muscle cells, or could accumulated in lipids either due to autoxidation in vivo or to the action of an enzyme similar to Iipoxygenase. (PMID: 3997883, 6414520) [HMDB]
9,12,13-TriHOME is a trihydroxyoctadecenoic acid metabolite of linoleic acid, one of the major fatty acids found in lipids. Vascular tissue converts various polyunsaturated fatty acids to monohydroxy and trihydroxy metabolites derived from hydroperoxides which may be involved in regulating prostaglandin synthesis. The absolute amounts of 9,12,13-TriHOME varies considerably from one species to another. There are several possible mechanisms for the formation of esterified oxygenated polyunsaturated fatty acids: oxygenated and then incorporated into lipids, not well incorporated into either vascular endothelial or smooth muscle cells, or could accumulated in lipids either due to autoxidation in vivo or to the action of an enzyme similar to Iipoxygenase. (PMID: 3997883, 6414520).
Pinellic acid is a trihydroxyoctadecenoic acid with hydroxy groups at positions C-9, -12, and 13, and an E (cis) double bond at position 10. It has a role as an adjuvant and an anti-inflammatory agent. It is functionally related to a 13(S)-HPODE.
Pinellic acid is a natural product found in Pinellia ternata, Bupleurum falcatum, and other organisms with data available.
A trihydroxyoctadecenoic acid with hydroxy groups at positions C-9, -12, and 13, and an E (cis) double bond at position 10.

同义名列表

17 个代谢物同义名

(10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoic acid; (9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid; (9s,12s,13s)-e-9,12,13-trihydroxy-10-octadecaenoic acid; (10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoate; (E,9S,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid; 9(S),12(S),13(S)-Trihydroxy-10(E)-octadecenoic acid; 9(S),12(S),13(S)-Trihydroxy-10(E)-octadecenoate; 9S,12S,13S-trihydroxy-10E-octadecenoic acid; 9,12,13-Trihydroxyoctadec-10-enoic acid; 9S,12S,13S-trihydroxy-10E-octadecenoate; MDIUMSLCYIJBQC-MVFSOIOZSA-N; 9(S),12(S),13(S)-TriHOME; Dihydrofulgidic acid; 9,12,13-TriHOME; Pinellic acid; FA 18:1;O3; 9,12,13-Todea



数据库引用编号

22 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

6 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

  • Mikio Doi, Naoki Morita, Tsugumi Okuzawa, Satoru Ohgiya, Daisaku Okamoto, Kenichi Sato, Yukiya Ito, Hideyuki Matsuura, Yasuyuki Hashidoko. Pinellic Acid Isolated from Quercetin-rich Onions has a Peroxisome Proliferator-Activated Receptor-Alpha/Gamma (PPAR-α/γ) Transactivation Activity. Planta medica. 2022 May; 88(6):440-446. doi: 10.1055/a-1345-9471. [PMID: 35038752]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Rukaiyya Sirajuddin Khan, Mahibalan Senthi, Poorna Chandra Rao, Ameer Basha, Mallika Alvala, Dinesh Tummuri, Hironori Masubuti, Yoshinori Fujimoto, Ahil Sajeli Begum. Cytotoxic constituents of Abutilon indicum leaves against U87MG human glioblastoma cells. Natural product research. 2015; 29(11):1069-73. doi: 10.1080/14786419.2014.976643. [PMID: 25422029]
  • Hyun Gyu Choi, Yu Mi Park, Yue Lu, Hyeun Wook Chang, Minkyun Na, Seung Ho Lee. Inhibition of prostaglandin D₂ production by trihydroxy fatty acids isolated from Ulmus davidiana var. japonica. Phytotherapy research : PTR. 2013 Sep; 27(9):1376-80. doi: 10.1002/ptr.4882. [PMID: 23147809]
  • Jian-Hua Zhu, Wei Wen, Yan-Shan Hu, Yu Tang, Rong-Min Yu. Hydroxyl octadecenoic acids biosynthesized by crown galls of Panax quinquefolium induced by artermisinic acid. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2012 Jun; 35(6):869-72. doi: ". [PMID: 23236817]
  • Jing Li, Pei-Ji Zhao, Chang-Le Ma, Ying Zeng. A chitosan induced 9-lipoxygenase in Adelostemma gracillimum seedlings. International journal of molecular sciences. 2012; 13(1):540-551. doi: 10.3390/ijms13010540. [PMID: 22312270]
  • Saskia Floerl, Andrzej Majcherczyk, Mareike Possienke, Kirstin Feussner, Hella Tappe, Christiane Gatz, Ivo Feussner, Ursula Kües, Andrea Polle. Verticillium longisporum infection affects the leaf apoplastic proteome, metabolome, and cell wall properties in Arabidopsis thaliana. PloS one. 2012; 7(2):e31435. doi: 10.1371/journal.pone.0031435. [PMID: 22363647]
  • Mats Hamberg, Ulrika Olsson. Efficient and specific conversion of 9-lipoxygenase hydroperoxides in the beetroot. Formation of pinellic acid. Lipids. 2011 Sep; 46(9):873-8. doi: 10.1007/s11745-011-3592-7. [PMID: 21744276]
  • Boglárka Csupor-Löffler, Zsuzsanna Hajdú, István Zupkó, Judit Molnár, Peter Forgo, Andrea Vasas, Zoltán Kele, Judit Hohmann. Antiproliferative constituents of the roots of Conyza canadensis. Planta medica. 2011 Jul; 77(11):1183-8. doi: 10.1055/s-0030-1270714. [PMID: 21294076]
  • Dale R Walters, Tracy Cowley, Hans Weber. Rapid accumulation of trihydroxy oxylipins and resistance to the bean rust pathogen Uromyces fabae following wounding in Vicia faba. Annals of botany. 2006 May; 97(5):779-84. doi: 10.1093/aob/mcl034. [PMID: 16492683]
  • Hideto Kimura, Kazushige Yokota. Characterization of metabolic pathway of linoleic acid 9-hydroperoxide in cytosolic fraction of potato tubers and identification of reaction products. Applied biochemistry and biotechnology. 2004 Jul; 118(1-3):115-32. doi: 10.1385/abab:118:1-3:115. [PMID: 15304744]
  • G Siegel, J Wilke. The accumulation of immunoglobulins in the human tonsil. Acta biologica et medica Germanica. 1976; 35(7):1031-3. doi: NULL. [PMID: 65082]