Myristoleate (14:1n5) (BioDeep_00000000627)

 

Secondary id: BioDeep_00000229652

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


Myristoleic acid, >=99\\% (capillary GC)

化学式: C14H26O2 (226.1932696)
中文名称: 肉豆蔻油酸, 肉豆蔻酸, 肉豆蔻烯酸
谱图信息: 最多检出来源 Homo sapiens(blood) 3.46%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Myristoleate (14:1n5). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/myristoleate_(14:1n5) (retrieved 2024-09-18) (BioDeep RN: BioDeep_00000000627). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(/C=C\CCCC)CCCCCCC(=O)O
InChI: InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5+

描述信息

Myristoleic acid, also known as 9-tetradecenoate or myristoleate, 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. Myristoleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Myristoleic acid exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, myristoleic acid is found in the highest concentration within a few different foods, such as milk (cow), butter, and margarine-like spreads, and in a lower concentration in creams, meat bouillons, and chocolates. Myristoleic acid has also been detected, but not quantified in, several different foods, such as anchovies, loganberries, sunflowers, yellow zucchinis, and dates. This could make myristoleic acid a potential biomarker for the consumption of these foods. Myristoleic acid is a monounsaturated fatty acid that represents approximately 0.3-0.7\\\\% of the total fatty acid composition of adipose tissue triacylglycerol in humans (PMID: 10393134). It has been suggested that its effective cytotoxic (i.e. cell death inducer) activity could be used for the treatment of prostate cancer (PMID: 11304730).
Myristoleic acid is a tetradecenoic acid in which the double bond is at the 9-10 position and has Z configuration. Myristoleic acid has been isolated from Serenoa repens and has cytotoxic and apoptosis-inducing effects. It has a role as an apoptosis inducer, a plant metabolite and an EC 3.1.1.1 (carboxylesterase) inhibitor. It is a tetradecenoic acid and a long-chain fatty acid. It is a conjugate acid of a myristoleate.
Myristoleic acid is a natural product found in Gladiolus italicus, Erucaria microcarpa, and other organisms with data available.
Myristoleic acid is a metabolite found in or produced by Saccharomyces cerevisiae.
A tetradecenoic acid in which the double bond is at the 9-10 position and has Z configuration. Myristoleic acid has been isolated from Serenoa repens and has cytotoxic and apoptosis-inducing effects.
Occurs in natural fats, e.g. Cottonseed oil
KEIO_ID M044
Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells[1].
Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells[1].

同义名列表

47 个代谢物同义名

Myristoleic acid, >=99\\% (capillary GC); Myristoleic acid, analytical standard; cis-Delta(9)-tetradecenoic acid; CIS-.DELTA.9-TETRADECENOIC ACID; cis-delta9-Tetradecenoic acid; cis-Delta(9)-tetradecenoate; 9-Tetradecenoic acid, (9Z)-; cis-Δ(9)-tetradecenoic acid; 9-Tetradecenoic acid, (Z)-; Tetradecenoic acid (cis-9); (9Z)-tetradec-9-enoic acid; cis-Δ9-Tetradecenoic acid; (9Z)-9-Tetradecenoic acid; cis-tetradec-9-enoic acid; (Z)-Tetradec-9-enoic acid; (z)-9-tetradecenoic acid; cis-9-tetradecenoic acid; 9-cis-Tetradecenoic acid; (9Z)-Tetradecenoic acid; cis-Δ(9)-tetradecenoate; Z-tetradec-9-enoic acid; 9(Z)-Tetradecenoic acid; (Z)-9-Tetradecenoicacid; (9Z)-Tetradec-9-enoate; Myristoleic acid, 99\\%; Z-9-Tetradecenoic acid; (Z)-Tetradec-9-enoate; cis-Tetradec-9-enoate; 9Z-tetradecenoic acid; cis-9-tetradecenoate; 9-tetradecenoic acid; (9Z)-tetradecenoate; 9Z-tetradecenoate; Myristolenic acid; Oleomyristic acid; 9-tetradecenoate; Myristoleic acid; UNII-RF23WGD123; FA(14:1(9Z)); Myristoleate; RF23WGD123; FA(14:1n5); 14:1(N-5); C14:1n-5; FA 14:1; tetradec-9-enoic acid; Myristoleic acid



数据库引用编号

28 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)

100 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

  • Alexander Y Starikov, Roman A Sidorov, Kirill S Mironov, Dmitry A Los. The Specificities of Lysophosphatidic Acid Acyltransferase and Fatty Acid Desaturase Determine the High Content of Myristic and Myristoleic Acids in Cyanobacterium sp. IPPAS B-1200. International journal of molecular sciences. 2024 Jan; 25(2):. doi: 10.3390/ijms25020774. [PMID: 38255848]
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  • Jun-Oh Kwon, Won Jong Jin, Bongjun Kim, Hong-Hee Kim, Zang Hee Lee. Myristoleic acid inhibits osteoclast formation and bone resorption by suppressing the RANKL activation of Src and Pyk2. European journal of pharmacology. 2015 Dec; 768(?):189-98. doi: 10.1016/j.ejphar.2015.10.053. [PMID: 26528796]
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