cis-Vaccenic acid (BioDeep_00000169696)

human metabolite PANOMIX_OTCML-2023

代谢物信息卡片

(11Z)-octadec-11-enoic acid

化学式: C18H34O2 (282.2558664)
中文名称: 反式-11-十八烯酸, 11-顺－十八碳烯酸
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 7.69%

分子结构信息

SMILES: C(CCCCCCC(=O)O)CC/C=C\CCCCCC
InChI: InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7-

描述信息

cis-11-Octadecenoic acid, also known as (Z)-octadec-11-enoic acid or asclepic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. cis-11-Octadecenoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Occurs in small proportions in ruminant fats (e.g., butter) via biohydrogenation of dietary polyene acids. Vaccenic acid is found in many foods, some of which are almond, romaine lettuce, butter, and pak choy.
trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.
trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.

同义名列表

24 个代谢物同义名

(11Z)-octadec-11-enoic acid; cis-Octadec-11-enoic acid; (Z)-Octadec-11-enoic acid; (Z)-11-Octadecenoic acid; cis-11-Octadecanoic acid; cis-11-octadecenoic acid; (11Z)-Octadecenoic acid; (Z)-Octadec-11-enoate; cis-Octadec-11-enoate; 11Z-octadecenoic acid; cis-11-Octadecenoate; 11-Octadecenoic acid; (Z)-11-Octadecenoate; (11Z)-Octadecenoate; Vaccenic acid, cis-; trans-Vaccenic acid; 11Z-Octadecenoate; cis-vaccenic acid; 11-Octadecenoate; cis-Vaccenate; Asclepic acid; VACCENIC ACID; Vaccenate; Asclepate

数据库引用编号

17 个数据库交叉引用编号

ChEBI: CHEBI:50464
KEGG: C21944
PubChem: 5282761
HMDB: HMDB0240219
DrugBank: DB04801
ChEMBL: CHEMBL1236642
KNApSAcK: C00000347
foodb: FDB002952
chemspider: 4445888
CAS: 506-17-2
CAS: 693-72-1
PubChem: 376218977
LipidMAPS: LMFA01030076
PDB-CCD: 4IF
PDB-CCD: VCA
RefMet: cis-Vaccenic acid
medchemexpress: HY-113427

分类词条

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)

19 个相关的物种来源信息

2893770 - Acioa longipendula: 10.1007/BF02663764
79798 - Agaricus blazei: 10.1248/YAKUSHI1947.114.5_342
40674 - Animals: -
2708713 - Anisophyllea laurina: 10.1007/BF00580077
48545 - Asclepias syriaca: 10.1139/V60-116
80265 - Elaeis oleifera: 10.1007/BF02535295
193516 - Hippophae rhamnoides: 10.1021/JF001059S
9606 - Homo sapiens: -
9606 - Homo sapiens: 10.1007/S11306-015-0840-5
51240 - Juglans regia: 10.1021/JF030451D
882062 - Leptolyngbya tenuis:
13824 - Lygodium japonicum: 10.1248/BPB.25.622
29780 - Mangifera indica: 10.1016/S0031-9422(03)00466-7
392747 - Paullinia cupana: 10.1007/S11745-003-1126-5
126344 - Phormidium tenue: 10.1248/CPB.38.812
88728 - Pinus koraiensis: 10.1016/J.CHROMA.2011.05.064
3347 - Pinus radiata: 10.1016/0031-9422(82)83099-9
46147 - Portulaca oleracea: 10.1111/JPHP.12315
66668 - Sterculia tragacantha: 10.1007/BF02542627

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

Pritipadma Panda, Priyanka Dash, Goutam Ghosh. Chemometric profile, antioxidant and tyrosinase inhibitory activity of Camel's foot creeper leaves (Bauhinia vahlii). Natural product research. 2018 Mar; 32(5):596-599. doi: 10.1080/14786419.2017.1326487. [PMID: 28508671]
Shamima Akter, Kayo Kurotani, Masao Sato, Takuya Hayashi, Keisuke Kuwahara, Yumi Matsushita, Tohru Nakagawa, Maki Konishi, Toru Honda, Shuichiro Yamamoto, Takeshi Hayashi, Mitsuhiko Noda, Tetsuya Mizoue. High Serum Phospholipid Dihomo-γ-Linoleic Acid Concentration and Low Δ5-Desaturase Activity Are Associated with Increased Risk of Type 2 Diabetes among Japanese Adults in the Hitachi Health Study. The Journal of nutrition. 2017 08; 147(8):1558-1566. doi: 10.3945/jn.117.248997. [PMID: 28637686]
Karina Gutiérrez-García, Adriana Neira-González, Rosa Martha Pérez-Gutiérrez, Giovana Granados-Ramírez, Ramon Zarraga, Kazimierz Wrobel, Francisco Barona-Gómez, Luis B Flores-Cotera. Phylogenomics of 2,4-Diacetylphloroglucinol-Producing Pseudomonas and Novel Antiglycation Endophytes from Piper auritum. Journal of natural products. 2017 07; 80(7):1955-1963. doi: 10.1021/acs.jnatprod.6b00823. [PMID: 28704049]
Dimitrios Tsikas. Letter to the Editor regarding 'Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans'. Analytical and bioanalytical chemistry. 2017 03; 409(9):2495. doi: 10.1007/s00216-017-0229-6. [PMID: 28168548]
Waldemar Röhrig, Reiner Waibel, Christopher Perlwitz, Monika Pischetsrieder, Tobias Hoch. Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans. Analytical and bioanalytical chemistry. 2016 Sep; 408(22):6141-51. doi: 10.1007/s00216-016-9720-8. [PMID: 27334716]
Damien Sorigué, Bertrand Légeret, Stéphan Cuiné, Pablo Morales, Boris Mirabella, Geneviève Guédeney, Yonghua Li-Beisson, Reinhard Jetter, Gilles Peltier, Fred Beisson. Microalgae Synthesize Hydrocarbons from Long-Chain Fatty Acids via a Light-Dependent Pathway. Plant physiology. 2016 08; 171(4):2393-405. doi: 10.1104/pp.16.00462. [PMID: 27288359]
W Krusong, S Kerdpiboon, A Jindaprasert, S Yaiyen, S Pornpukdeewatana, S Tantratian. Influence of calcium chloride in the high temperature acetification by strain Acetobacter aceti WK for vinegar. Journal of applied microbiology. 2015 Nov; 119(5):1291-300. doi: 10.1111/jam.12930. [PMID: 26268669]
Peter Sec, Martina Garaiova, Peter Gajdos, Milan Certik, Peter Griac, Ivan Hapala, Roman Holic. Baker's Yeast Deficient in Storage Lipid Synthesis Uses cis-Vaccenic Acid to Reduce Unsaturated Fatty Acid Toxicity. Lipids. 2015 Jul; 50(7):621-30. doi: 10.1007/s11745-015-4022-z. [PMID: 25908426]
Chris R Kerth, Amanda L Harbison, Stephen B Smith, Rhonda K Miller. Consumer sensory evaluation, fatty acid composition, and shelf-life of ground beef with subcutaneous fat trimmings from different carcass locations. Meat science. 2015 Jun; 104(?):30-6. doi: 10.1016/j.meatsci.2015.01.014. [PMID: 25688688]
Luc Djoussé, Chisa Matsumoto, Naomi Q Hanson, Natalie L Weir, Michael Y Tsai, J Michael Gaziano. Plasma cis-vaccenic acid and risk of heart failure with antecedent coronary heart disease in male physicians. Clinical nutrition (Edinburgh, Scotland). 2014 Jun; 33(3):478-82. doi: 10.1016/j.clnu.2013.07.001. [PMID: 23880347]
Jihane Gasmi, J Thomas Sanderson. Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: a mechanistic and 3-D structure-activity study. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Jun; 20(8-9):734-42. doi: 10.1016/j.phymed.2013.01.012. [PMID: 23453308]
Shizuyo Tanaka, Chiho Kojiguchi, Tohru Yamazaki, Atsushi Mitsumoto, Daisuke Kobayashi, Naomi Kudo, Yoichi Kawashima. Altered fatty acid profile in the liver and serum of stroke-prone spontaneously hypertensive rats: reduced proportion of cis-vaccenic acid. Journal of oleo science. 2013; 62(11):933-48. doi: 10.5650/jos.62.933. [PMID: 24200942]
Luc Djoussé, Nirupa R Matthan, Alice H Lichtenstein, John M Gaziano. Red blood cell membrane concentration of cis-palmitoleic and cis-vaccenic acids and risk of coronary heart disease. The American journal of cardiology. 2012 Aug; 110(4):539-44. doi: 10.1016/j.amjcard.2012.04.027. [PMID: 22579341]
Robert Block, Lisa Kakinami, Scott Liebman, Gregory C Shearer, Holly Kramer, Michael Tsai. Cis-vaccenic acid and the Framingham risk score predict chronic kidney disease: the multi-ethnic study of atherosclerosis (MESA). Prostaglandins, leukotrienes, and essential fatty acids. 2012 Apr; 86(4-5):175-82. doi: 10.1016/j.plefa.2012.02.009. [PMID: 22417701]
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