Vernolic acid (BioDeep_00000629436)

Main id: BioDeep_00000003295

 

PANOMIX_OTCML-2023


代谢物信息卡片


(9Z)-(12S,13R)-12,13-Epoxyoctadecenoic acid

化学式: C18H32O3 (296.2351)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(CCCCCCC/C=C\C[C@@H]1O[C@@H]1CCCCC)(=O)O
InChI: InChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-

描述信息

A monounsaturated epoxy fatty acid composed of cis-9-octadecenoic acid having a 12,13-epoxy group.

同义名列表

6 个代谢物同义名

Vernolic acid; (9Z)-(12S,13R)-12,13-Epoxyoctadecenoic acid; 12S,13R-epoxy-9Z-octadecenoic acid; 12S,13R-EpOME; FA 18:2;O; Vernolic acid



数据库引用编号

11 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

12 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 4 ARHGAP45, CYP2C9, RAC1, SCP2
Peripheral membrane protein 1 CYP1B1
Endoplasmic reticulum membrane 6 CYP1B1, CYP2C9, DGAT1, DGAT2, RAC1, SCD
Nucleus 3 CA9, RAC1, SCP2
cytosol 7 ARHGAP45, DGAT2, EPHX2, LIPE, MB, RAC1, SCP2
dendrite 1 RAC1
trans-Golgi network 1 RAC1
nucleoplasm 1 SCP2
Cell membrane 4 CA9, LIPE, RAC1, SERINC3
Lipid-anchor 1 RAC1
Cytoplasmic side 1 RAC1
lamellipodium 1 RAC1
ruffle membrane 2 ARHGAP45, RAC1
Multi-pass membrane protein 4 DGAT1, DGAT2, SCD, SERINC3
Golgi apparatus membrane 1 SERINC3
Synapse 1 RAC1
cell cortex 1 RAC1
glutamatergic synapse 1 RAC1
Golgi membrane 1 SERINC3
postsynapse 1 RAC1
Cytoplasm, cytosol 1 LIPE
plasma membrane 6 ARHGAP45, CA9, CYP2C9, DGAT1, RAC1, SERINC3
Membrane 10 ARHGAP45, CA9, CYP1B1, DGAT1, DGAT2, LIPE, RAC1, SCD, SCP2, SERINC3
basolateral plasma membrane 1 CA9
caveola 1 LIPE
extracellular exosome 3 EPHX2, MB, RAC1
endoplasmic reticulum 3 DGAT2, SCD, SCP2
perinuclear region of cytoplasm 2 DGAT2, SERINC3
mitochondrion 4 CYP1B1, DGAT2, GLS2, SCP2
protein-containing complex 1 SCP2
intracellular membrane-bounded organelle 3 CYP1B1, CYP2C9, DGAT2
Microsome membrane 2 CYP1B1, CYP2C9
Single-pass type I membrane protein 1 CA9
Secreted 1 RAC1
extracellular region 2 ARHGAP45, RAC1
mitochondrial matrix 1 GLS2
dendritic spine 1 RAC1
cytoplasmic vesicle 1 RAC1
nucleolus 2 CA9, SCD
sarcoplasm 1 MB
Cell projection, lamellipodium 1 RAC1
Cell projection, ruffle membrane 1 ARHGAP45
Cytoplasm, perinuclear region 2 DGAT2, SERINC3
focal adhesion 1 RAC1
perinuclear endoplasmic reticulum membrane 1 DGAT2
Peroxisome 2 EPHX2, SCP2
peroxisomal matrix 2 EPHX2, SCP2
Chromosome 1 SCP2
cytoskeleton 1 RAC1
cytoplasmic ribonucleoprotein granule 1 RAC1
Nucleus, nucleolus 1 CA9
condensed chromosome, centromeric region 1 SCP2
Cell projection, microvillus membrane 1 CA9
microvillus membrane 1 CA9
Recycling endosome membrane 1 RAC1
Lipid droplet 2 DGAT2, LIPE
Membrane, caveola 1 LIPE
lateral element 1 SCP2
Cell projection, dendrite 1 RAC1
specific granule membrane 1 DGAT1
Melanosome 1 RAC1
secretory granule lumen 1 ARHGAP45
secretory granule membrane 1 RAC1
azurophil granule lumen 1 ARHGAP45
ficolin-1-rich granule membrane 1 RAC1
synaptonemal complex 1 SCP2
Cytoplasm, sarcoplasm 1 MB
NADPH oxidase complex 1 RAC1
[Isoform SCP2]: Peroxisome 1 SCP2
[Isoform SCPx]: Peroxisome 1 SCP2


文献列表

  • Mohammad Vatanparast, Shabbir Ahmed, Dong-Hee Lee, Sung Hee Hwang, Bruce Hammock, Yonggyun Kim. EpOMEs act as immune suppressors in a lepidopteran insect, Spodoptera exigua. Scientific reports. 2020 11; 10(1):20183. doi: 10.1038/s41598-020-77325-2. [PMID: 33214688]
  • Isabelle Billault, Alicia Le Du, Minale Ouethrani, Zeinab Serhan, Philippe Lesot, Richard J Robins. Probing substrate-product relationships by natural abundance deuterium 2D NMR spectroscopy in liquid-crystalline solvents: epoxidation of linoleate to vernoleate by two different plant enzymes. Analytical and bioanalytical chemistry. 2012 Mar; 402(9):2985-98. doi: 10.1007/s00216-012-5748-6. [PMID: 22349323]
  • Tanya Hutter, Charles Linder, Eliahu Heldman, Sarina Grinberg. Interfacial and self-assembly properties of bolaamphiphilic compounds derived from a multifunctional oil. Journal of colloid and interface science. 2012 Jan; 365(1):53-62. doi: 10.1016/j.jcis.2011.08.057. [PMID: 21963206]
  • Runzhi Li, Keshun Yu, Tomoko Hatanaka, David F Hildebrand. Vernonia DGATs increase accumulation of epoxy fatty acids in oil. Plant biotechnology journal. 2010 Feb; 8(2):184-95. doi: 10.1111/j.1467-7652.2009.00476.x. [PMID: 20078841]
  • Yonghua Li, Fred Beisson. The biosynthesis of cutin and suberin as an alternative source of enzymes for the production of bio-based chemicals and materials. Biochimie. 2009 Jun; 91(6):685-91. doi: 10.1016/j.biochi.2009.03.016. [PMID: 19344744]
  • Keshun Yu, Runzhi Li, Tomoko Hatanaka, David Hildebrand. Cloning and functional analysis of two type 1 diacylglycerol acyltransferases from Vernonia galamensis. Phytochemistry. 2008 Mar; 69(5):1119-27. doi: 10.1016/j.phytochem.2007.11.015. [PMID: 18179805]
  • Keshun Yu, Charles T McCracken, Runzhi Li, David F Hildebrand. Diacylglycerol acyltransferases from Vernonia and Stokesia prefer substrates with vernolic acid. Lipids. 2006 Jun; 41(6):557-66. doi: 10.1007/s11745-006-5005-x. [PMID: 16981434]
  • Enea Rezzonico, Laurence Moire, Syndie Delessert, Yves Poirier. Level of accumulation of epoxy fatty acid in Arabidopsis thaliana expressing a linoleic acid delta12-epoxygenase is influenced by the availability of the substrate linoleic acid. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 2004 Sep; 109(5):1077-82. doi: 10.1007/s00122-004-1721-x. [PMID: 15221145]
  • N Tsevegsuren, K Aitzetmuller, K Vosmann. Geranium sanguineum (Geraniaceae) seed oil: a new source of petroselinic and vernolic acid. Lipids. 2004 Jun; 39(6):571-6. doi: 10.1007/s11745-004-1265-8. [PMID: 15554157]
  • Laurence Moire, Enea Rezzonico, Simon Goepfert, Yves Poirier. Impact of unusual fatty acid synthesis on futile cycling through beta-oxidation and on gene expression in transgenic plants. Plant physiology. 2004 Jan; 134(1):432-42. doi: 10.1104/pp.103.032938. [PMID: 14671017]
  • Johan Edqvist, Isabelle Farbos. Characterization of germination-specific lipid transfer proteins from Euphorbia lagascae. Planta. 2002 May; 215(1):41-50. doi: 10.1007/s00425-001-0717-x. [PMID: 12012240]
  • Edgar B Cahoon, Kevin G Ripp, Sarah E Hall, Brian McGonigle. Transgenic production of epoxy fatty acids by expression of a cytochrome P450 enzyme from Euphorbia lagascae seed. Plant physiology. 2002 Feb; 128(2):615-24. doi: 10.1104/pp.010768. [PMID: 11842164]
  • L Liu, E G Hammond, B J Nikolau. In vivo studies of the biosynthesis of vernolic acid in the seed of Vernonia galamensis. Lipids. 1998 Dec; 33(12):1217-21. doi: 10.1007/s11745-998-0326-3. [PMID: 9930408]
  • M Lee, M Lenman, A Banaś, M Bafor, S Singh, M Schweizer, R Nilsson, C Liljenberg, A Dahlqvist, P O Gummeson, S Sjödahl, A Green, S Stymne. Identification of non-heme diiron proteins that catalyze triple bond and epoxy group formation. Science (New York, N.Y.). 1998 May; 280(5365):915-8. doi: 10.1126/science.280.5365.915. [PMID: 9572738]
  • I Ncube, T Gitlesen, P Adlercreutz, J S Read, B Mattiasson. Fatty acid selectivity of a lipase purified from Vernonia galamensis seed. Biochimica et biophysica acta. 1995 Jul; 1257(2):149-56. doi: 10.1016/0005-2760(95)00067-m. [PMID: 7619855]
  • G Eggink, P de Waard, G N Huijberts. Formation of novel poly(hydroxyalkanoates) from long-chain fatty acids. Canadian journal of microbiology. 1995; 41 Suppl 1(?):14-21. doi: 10.1139/m95-163. [PMID: 7606658]
  • M Bafor, M A Smith, L Jonsson, K Stobart, S Stymne. Biosynthesis of vernoleate (cis-12-epoxyoctadeca-cis-9-enoate) in microsomal preparations from developing endosperm of Euphorbia lagascae. Archives of biochemistry and biophysics. 1993 May; 303(1):145-51. doi: 10.1006/abbi.1993.1265. [PMID: 8489257]
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