DUB OM HTO (BioDeep_00000000894)

 

Secondary id: BioDeep_00000861806

PANOMIX_OTCML-2023


代谢物信息卡片


(Z)-9-octadecenoic acid, methyl ester;methyl (Z)-9-octadecenoate;methyl cis-9-octadecenoate;methyl-cis-oleate

化学式: C19H36O2 (296.2715)
中文名称: 油酸甲酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 81.41%

分子结构信息

SMILES: C(=C/CCCCCCCC)/CCCCCCCC(OC)=O
InChI: InChI=1S/C19H36O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h10-11H,3-9,12-18H2,1-2H3/b11-10-

描述信息

Oleic acid methyl ester is a clear to amber liquid. Insoluble in water. (NTP, 1992)
Methyl oleate is a fatty acid methyl ester resulting from the formal condensation of the carboxy group of oleic acid with methanol. It is functionally related to an oleic acid.
Methyl oleate is a natural product found in Anchietea pyrifolia, Lepidium meyenii, and other organisms with data available.
Methyl oleate is a fatty acid methyl ester (FAME). Methyl oleate substantially improves the antioxidation ability but markedly impaired the antiwear capacity of zinc dialkyldithiophosphate (ZDDP)[1].
Methyl oleate is a fatty acid methyl ester (FAME). Methyl oleate substantially improves the antioxidation ability but markedly impaired the antiwear capacity of zinc dialkyldithiophosphate (ZDDP)[1].

同义名列表

64 个代谢物同义名

(Z)-9-octadecenoic acid, methyl ester;methyl (Z)-9-octadecenoate;methyl cis-9-octadecenoate;methyl-cis-oleate; Methyl Oleate, Pharmaceutical Secondary Standard; Certified Reference Material; 9-Octadecenoic acid (9Z)-, methyl ester, sulfurized, copper-treated; 9-Octadecenoic acid (Z)-, methyl ester, sulfurized, copper-treated; Methyl oleate, United States Pharmacopeia (USP) Reference Standard; 9-octadecenoic acid, methyl ester, (9E)-; 9-Octadecenoic acid (9Z)-, methyl ester; cis-9-Octyldecenoic acid, methyl ester; 9-OCTADECENOIC ACID(CIS), METHYL ESTER; 9-Octadecenoic acid (Z)-, methyl ester; Octadecenoic acid methyl ester, 9-(Z)-; cis-9-Octadecenoic acid, methyl ester; (Z)-9-Octadecenoic acid, methyl ester; 9-octadecenoic acid, methyl ester (Z); 1B317D43-CBCA-4348-B5B9-4687B6A3C698; cis-9-octadecenoic acid methyl ester; Methyl oleate, technical grade, 70\\%; (Z)-9-Octadecenoic acid methyl ester; Methyl oleate, analytical standard; Oleic acid, methyl ester, cis-; OLEIC ACID METHYL ESTER (CIS); Methyl (9Z)-9-octadecenoate #; Methyl 9-octadecenoate, cis-; Methyl (9Z)-octadec-9-enoate; methyl (Z)-octadec-9-enoate; cis-Methyl oleic acid ester; Methyl 9-(Z)-octadecenoate; Methyl (Z)-9-octadecenoate; Methyl cis-9-octadecenoate; (Z)-9-Methyl octadecenoate; methyl oleate, (E)-isomer; Methyl Oleate, 99per cent; Methyl oleate, tech grade; Oleic acid, methyl ester; Methyl Z-9-octadecenoate; oleic acid methyl ester; Emery, oleic acid ester; Oleic acid-methyl ester; METHYL OLEATE (USP-RS); METHYL OLEATE [USP-RS]; Methyl 9-octadecenoate; METHYL OLEATE [INCI]; METHYL OLEATE [HSDB]; Methyl oleate, 99\\%; Methyl (Z)-9-oleate; methyl-cis-oleate; AEC METHYL OLEATE; Edenor Me 90/95V; Oleic acid, cis-; methyl elaidate; methyl oleoate; Exceparl M-OL; WLN: 9U8VO1-C; Methyl oleate; Edenor MeTiO5; methyl oleat; methyloleate; Tox21_200225; DUB OM HTO; AI3-00651; SFE 19:1; C19H36O2; methyl octadec-9-enoate; Oleic acid methyl ester



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

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)

27 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 9 ARHGAP45, BCLAF1, CASP3, CEL, GAPDH, ITPRID2, PLA2G12A, PRPF19, THRSP
Nucleus 7 BCLAF1, CASP3, GAPDH, MMP2, MYOZ1, PRPF19, THRSP
cytosol 9 ARHGAP45, CASP3, CBL, GAPDH, ITPRID2, LIPE, MAT1A, THRSP, TNNI3
nucleoplasm 7 ANO1, ATP2B1, BCLAF1, CASP3, ITPRID2, PRPF19, THRSP
Cell membrane 3 ANO1, ATP2B1, LIPE
ruffle membrane 1 ARHGAP45
Multi-pass membrane protein 2 ANO1, ATP2B1
Synapse 1 ATP2B1
glutamatergic synapse 2 ATP2B1, CASP3
Golgi apparatus 2 ATRN, CBL
growth cone 1 CBL
neuronal cell body 1 CASP3
presynaptic membrane 1 ATP2B1
Cytoplasm, cytosol 2 GAPDH, LIPE
Presynapse 1 ANO1
plasma membrane 8 ANO1, ARHGAP45, ATP2B1, ATRN, CBL, GAPDH, ITPRID2, MMP2
synaptic vesicle membrane 1 ATP2B1
Membrane 6 ANO1, ARHGAP45, ATP2B1, GAPDH, LIPE, PRPF19
apical plasma membrane 1 ANO1
basolateral plasma membrane 1 ATP2B1
caveola 1 LIPE
extracellular exosome 5 ANO1, ATP2B1, ATRN, CEL, GAPDH
extracellular space 4 ATRN, CEL, LIPC, MMP2
perinuclear region of cytoplasm 2 CBL, GAPDH
mitochondrion 1 MMP2
intracellular membrane-bounded organelle 2 ATP2B1, GAPDH
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 ATRN
Secreted 3 CEL, LIPC, PLA2G12A
extracellular region 5 ARHGAP45, CEL, LIPC, MMP2, PLA2G12A
[Isoform 2]: Secreted 1 ATRN
Cell projection, cilium 1 CBL
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
nuclear membrane 1 GAPDH
high-density lipoprotein particle 1 LIPC
actin cytoskeleton 2 MYOZ1, MYOZ3
Z disc 2 MYOZ1, MYOZ3
microtubule cytoskeleton 1 GAPDH
vesicle 1 GAPDH
Apical cell membrane 1 ANO1
Cell projection, ruffle membrane 1 ARHGAP45
Cytoplasm, perinuclear region 1 GAPDH
Membrane raft 1 CBL
Cytoplasm, cytoskeleton 1 GAPDH
Cytoplasm, cytoskeleton, spindle 1 PRPF19
focal adhesion 1 CBL
spindle 1 PRPF19
flotillin complex 1 CBL
extracellular matrix 1 MMP2
collagen-containing extracellular matrix 1 MMP2
lateral plasma membrane 1 ATP2B1
nuclear speck 2 BCLAF1, PRPF19
sarcomere 2 MMP2, TNNI3
cilium 1 CBL
mediator complex 1 BCLAF1
cell projection 2 ANO1, ATP2B1
cytoskeleton 1 GAPDH
Basolateral cell membrane 1 ATP2B1
spliceosomal complex 1 PRPF19
site of double-strand break 1 PRPF19
[Isoform 3]: Secreted 1 ATRN
Lipid droplet 3 GAPDH, LIPE, PRPF19
Membrane, caveola 1 LIPE
chloride channel complex 1 ANO1
Nucleus, nucleoplasm 2 BCLAF1, PRPF19
Nucleus speckle 1 BCLAF1
Presynaptic cell membrane 1 ATP2B1
pseudopodium 1 MYOZ1
Cytoplasm, myofibril, sarcomere, Z line 1 MYOZ3
secretory granule lumen 1 ARHGAP45
endoplasmic reticulum lumen 1 LIPC
[Isoform 1]: Secreted, extracellular space, extracellular matrix 1 MMP2
azurophil granule lumen 1 ARHGAP45
immunological synapse 1 ATP2B1
ribonucleoprotein complex 1 GAPDH
exon-exon junction complex 1 BCLAF1
U2-type catalytic step 1 spliceosome 1 PRPF19
death-inducing signaling complex 1 CASP3
[Isoform 1]: Cell membrane 1 ATRN
catalytic step 2 spliceosome 1 PRPF19
Prp19 complex 1 PRPF19
U2-type catalytic step 2 spliceosome 1 PRPF19
GAIT complex 1 GAPDH
cardiac myofibril 1 TNNI3
troponin complex 1 TNNI3
photoreceptor ribbon synapse 1 ATP2B1
cardiac Troponin complex 1 TNNI3
methionine adenosyltransferase complex 1 MAT1A


文献列表

  • Marta Martinez-Garcia, Wouter Van Hecke, Hilde Peeters, Dries Gabriels, Pieter Van der Weeën, Winnie Dejonghe, Yamini Satyawali. Methyl oleate for plant protection products formulations: Enzymatic synthesis, reaction kinetics and application testing. Journal of biotechnology. 2024 Jan; 379(?):78-86. doi: 10.1016/j.jbiotec.2023.12.004. [PMID: 38072327]
  • María Molina-Gutiérrez, Leonor Rodríguez-Sánchez, Carmen Doñoro, M Jesús Martínez, Alicia Prieto. Sustainable and Green Synthesis of Stanol Esters from Oil Wastes. Journal of agricultural and food chemistry. 2021 Jan; 69(1):286-293. doi: 10.1021/acs.jafc.0c06581. [PMID: 33375783]
  • Julien Peyrton, Clémence Chambaretaud, Luc Avérous. New Insight on the Study of the Kinetic of Biobased Polyurethanes Synthesis Based on Oleo-Chemistry. Molecules (Basel, Switzerland). 2019 Nov; 24(23):. doi: 10.3390/molecules24234332. [PMID: 31783536]
  • Juan Carlos de Haro, Daniel López-Pedrajas, Ángel Pérez, Juan Francisco Rodríguez, Manuel Carmona. Synthesis of rigid polyurethane foams from phosphorylated biopolyols. Environmental science and pollution research international. 2019 Feb; 26(4):3174-3183. doi: 10.1007/s11356-017-9765-z. [PMID: 28822032]
  • Todd Clark Brelje, Nicholas V Bhagroo, Laurence E Stout, Robert L Sorenson. Prolactin and oleic acid synergistically stimulate β-cell proliferation and growth in rat islets. Islets. 2017 07; 9(4):e1330234. doi: 10.1080/19382014.2017.1330234. [PMID: 28686504]
  • Hosni Sassi, Frank Delvigne, Tambi Kar, Jean-Marc Nicaud, Anne-Marie Crutz-Le Coq, Sebastien Steels, Patrick Fickers. Deciphering how LIP2 and POX2 promoters can optimally regulate recombinant protein production in the yeast Yarrowia lipolytica. Microbial cell factories. 2016 Sep; 15(1):159. doi: 10.1186/s12934-016-0558-8. [PMID: 27651221]
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  • Sara Santos, José Graça. Stereochemistry of C18 monounsaturated cork suberin acids determined by spectroscopic techniques including (1) H-NMR multiplet analysis of olefinic protons. Phytochemical analysis : PCA. 2014 May; 25(3):192-200. doi: 10.1002/pca.2491. [PMID: 24307616]
  • A B Seres, E Ducza, M Báthori, A Hunyadi, Z Béni, M Dékány, J Hajagos-Tóth, J Verli, Róbert Gáspár. Androgenic effect of honeybee drone milk in castrated rats: roles of methyl palmitate and methyl oleate. Journal of ethnopharmacology. 2014 Apr; 153(2):446-53. doi: 10.1016/j.jep.2014.02.050. [PMID: 24607508]
  • Arturo Morales, Susana Marmesat, M Carmen Dobarganes, Gloria Márquez-Ruiz, Joaquín Velasco. Evaporative light scattering detector in normal-phase high-performance liquid chromatography determination of FAME oxidation products. Journal of chromatography. A. 2012 Sep; 1254(?):62-70. doi: 10.1016/j.chroma.2012.07.028. [PMID: 22840820]
  • Chenxing Sun, Yuan-Yuan Zhao, Jonathan M Curtis. A study of the ozonolysis of model lipids by electrospray ionization mass spectrometry. Rapid communications in mass spectrometry : RCM. 2012 Apr; 26(8):921-30. doi: 10.1002/rcm.6183. [PMID: 22396028]
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  • Jumat Salimon, Nadia Salih, Bashar Mudhaffar Abdullah. Improvement of physicochemical characteristics of monoepoxide linoleic acid ring opening for biolubricant base oil. Journal of biomedicine & biotechnology. 2011; 2011(?):196565. doi: 10.1155/2011/196565. [PMID: 22131799]
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  • Kevin Huvaere, Daniel R Cardoso, Paula Homem-de-Mello, Signe Westermann, Leif H Skibsted. Light-induced oxidation of unsaturated lipids as sensitized by flavins. The journal of physical chemistry. B. 2010 Apr; 114(16):5583-93. doi: 10.1021/jp9121744. [PMID: 20377218]
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  • Sabreen F Fostok, Rima A Ezzeddine, Fadia R Homaidan, Jamal A Al-Saghir, Ralph G Salloum, Najat A Saliba, Rabih S Talhouk. Interleukin-6 and Cyclooxygenase-2 downregulation by fatty-acid fractions of Ranunculus constantinopolitanus. BMC complementary and alternative medicine. 2009 Nov; 9(?):44. doi: 10.1186/1472-6882-9-44. [PMID: 19917107]
  • Catherine M Klapperich, Cassandra L Noack, Jessica D Kaufman, Lin Zhu, Laetitia Bonnaillie, Richard P Wool. A novel biocompatible adhesive incorporating plant-derived monomers. Journal of biomedical materials research. Part A. 2009 Nov; 91(2):378-84. doi: 10.1002/jbm.a.32250. [PMID: 18980208]
  • Atanu Biswas, Brajendra K Sharma, Kenneth M Doll, Sevim Z Erhan, Julious L Willett, H N Cheng. Synthesis of an amine-oleate derivative using an ionic liquid catalyst. Journal of agricultural and food chemistry. 2009 Sep; 57(18):8136-41. doi: 10.1021/jf901401s. [PMID: 19719124]
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  • Satoshi Yoshida, Qin-Zeng Zhang, Shu Sakuyama, Satoshi Matsushima. Metabolism of fatty acids and lipid hydroperoxides in human body monitoring with Fourier transform Infrared Spectroscopy. Lipids in health and disease. 2009 Jul; 8(?):28. doi: 10.1186/1476-511x-8-28. [PMID: 19627618]
  • Lei Guo, Guo Qing Li. Olfactory perception of oviposition-deterring fatty acids and their methyl esters by the Asian corn borer, Ostrinia furnacalis. Journal of insect science (Online). 2009; 9(?):1-9. doi: 10.1673/031.009.6701. [PMID: 20053122]
  • Bassie B Marvey. Extrudate versus powder silica alumina as support for Re₂O₇ catalyst in the metathesis of seed oil-derivatives - a comparison. International journal of molecular sciences. 2009 Jan; 10(1):213-220. doi: 10.3390/ijms10010213. [PMID: 19333442]
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  • Marie Zarevúcka, Zdeněk Wimmer. Plant products for pharmacology: application of enzymes in their transformations. International journal of molecular sciences. 2008 Dec; 9(12):2447-2473. doi: 10.3390/ijms9122447. [PMID: 19330086]
  • Mariusz Kepczyński, Kinga Nawalany, Marta Kumorek, Agnieszka Kobierska, Barbara Jachimska, Maria Nowakowska. Which physical and structural factors of liposome carriers control their drug-loading efficiency?. Chemistry and physics of lipids. 2008 Sep; 155(1):7-15. doi: 10.1016/j.chemphyslip.2008.05.174. [PMID: 18590712]
  • Atanu Biswas, Brajendra K Sharma, J L Willett, Atanu Advaryu, S Z Erhan, H N Cheng. Azide derivatives of soybean oil and fatty esters. Journal of agricultural and food chemistry. 2008 Jul; 56(14):5611-6. doi: 10.1021/jf800123t. [PMID: 18558698]
  • Jyunichi Kawata, Munekazu Kameda, Mitsuo Miyazawa. Cyclooxygenase-2 inhibitory effects and composition of the volatile oil from the dried roots of Lithospermum erythrorhizon. Journal of natural medicines. 2008 Apr; 62(2):239-43. doi: 10.1007/s11418-007-0221-0. [PMID: 18404332]
  • Guoguang Liu, Xiaohua Kong, Hayley Wan, Suresh Narine. Production of 9-hydroxynonanoic Acid from methyl oleate and conversion into lactone monomers for the synthesis of biodegradable polylactones. Biomacromolecules. 2008 Mar; 9(3):949-53. doi: 10.1021/bm7012235. [PMID: 18271512]
  • James D Vasta, Bernard Fried, Joseph Sherma. High performance thin layer chromatographic analysis of neutral lipids in the urine of BALB/c mice infected with Echinostoma caproni. Parasitology research. 2008 Mar; 102(4):625-9. doi: 10.1007/s00436-007-0798-y. [PMID: 18040717]
  • G Márquez-Ruiz, F Holgado, M C García-Martínez, M C Dobarganes. A direct and fast method to monitor lipid oxidation progress in model fatty acid methyl esters by high-performance size-exclusion chromatography. Journal of chromatography. A. 2007 Sep; 1165(1-2):122-7. doi: 10.1016/j.chroma.2007.08.001. [PMID: 17706232]
  • Muhammad Ishtiaq Ch, Yang F Wen, YiYu Cheng. Gas chromatographic/mass spectrometric analysis of the essential oil of Houttuynia cordata Thunb by using on-column methylation with tetramethylammonium acetate. Journal of AOAC International. 2007 Jan; 90(1):60-7. doi: . [PMID: 17373437]
  • Ivan Tubert-Brohman, Orlando Acevedo, William L Jorgensen. Elucidation of hydrolysis mechanisms for fatty acid amide hydrolase and its Lys142Ala variant via QM/MM simulations. Journal of the American Chemical Society. 2006 Dec; 128(51):16904-13. doi: 10.1021/ja065863s. [PMID: 17177441]
  • V A Men'shov, L N Shishkina. [Effect of hydrophobicity of yeast cell envelope on the rate of autooxidation of methyloleate]. Biofizika. 2006 May; 51(3):491-8. doi: ". [PMID: 16808349]
  • L N Shishkina, N V Khrustova. [The kinetic characteristics of lipids of animal tissues in autooxidation reactions]. Biofizika. 2006 Mar; 51(2):340-6. doi: ". [PMID: 16637343]
  • Xiao Yi Li, Leif A Eriksson. Photoreaction of skin-sensitizing trimethyl psoralen with lipid membrane models. Photochemistry and photobiology. 2005 Sep; 81(5):1153-60. doi: 10.1562/2005-03-21-ra-467. [PMID: 15882092]
  • Katrin Sinderhauf, Wolfgang Schwack. Photodegradation of phosmet in wool wax models and on sheep wool: determination of wool wax bound phosmet by means of isotope ratio mass spectrometry. Journal of agricultural and food chemistry. 2005 Jun; 53(12):4873-9. doi: 10.1021/jf047834b. [PMID: 15941329]
  • Jacqueline Destain, Patrick Fickers, Frédéric Weekers, Benoît Moreau, Philippe Thonart. Utilization of methyloleate in production of microbial lipase. Applied biochemistry and biotechnology. 2005; 121-124(?):269-77. doi: 10.1385/abab:121:1-3:0269. [PMID: 15917605]
  • Katrin Sinderhauf, Wolfgang Schwack. Photodegradation chemistry of the insecticide phosmet in lipid models and in the presence of wool wax, employing a 15N-labeled compound. Journal of agricultural and food chemistry. 2004 Dec; 52(26):8046-52. doi: 10.1021/jf048537+. [PMID: 15612794]
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