CE(14:0) (BioDeep_00000025428)
Secondary id: BioDeep_00001874435
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite
代谢物信息卡片
化学式: C41H72O2 (596.5532012)
中文名称: 豆蔻酸胆固醇酯
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 3.66%
分子结构信息
SMILES: CCCCCCCCCCCCCC(=O)OC1CCC2(C)C(=CCC3C2CCC2(C)C(C(C)CCCC(C)C)CCC32)C1
InChI: InChI=1S/C41H72O2/c1-7-8-9-10-11-12-13-14-15-16-17-21-39(42)43-34-26-28-40(5)33(30-34)22-23-35-37-25-24-36(32(4)20-18-19-31(2)3)41(37,6)29-27-38(35)40/h22,31-32,34-38H,7-21,23-30H2,1-6H3/t32-,34+,35+,36-,37+,38+,40+,41-/m1/s1
描述信息
CE(14:0) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. [HMDB]
CE(14:0) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells.
Cholesterol myristate is a natural steroid present in traditional Chinese medicine. Cholesterol myristate binds to several ion channels such as the nicotinic acetylcholine receptor, GABAA receptor, and the inward-rectifier potassium ion channel.
同义名列表
28 个代谢物同义名
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl tetradecanoate; Cholest-5-en-3-ol (3beta)-tetradecanoic acid; Cholest-5-en-3-ol (3beta)-, tetradecanoate; Cholest-5-en-3-ol (3beta)-tetradecanoate; Cholest-5-en-3beta-yl tetradecanoic acid; cholest-5-en-3beta-yl tetradecanoate; Cholesterol 1-tetradecanoic acid; cholesteryl 1-tetradecanoic acid; Cholest-5-en-3beta-yl myristate; Cholesteryl tetradecanoic acid; Cholesterol 1-tetradecanoate; cholesterol 1-myristoic acid; cholesteryl 1-myristoic acid; cholesteryl 1-tetradecanoate; Cholesterol ester(14:0/0:0); 1-tetradecanoyl-cholesterol; Cholesteryl tetradecanoate; cholesteryl 1-myristoate; cholesterol 1-myristoate; Cholestryl myristic acid; 1-Myristoyl-cholesterol; Cholesterol ester(14:0); 14:0 Cholesterol ester; Cholesteryl myristate; Cholesterol myristate; Cholestryl myristate; CE(14:0/0:0); CE(14:0)
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:84304
- PubChem: 313252
- PubChem: 99486
- HMDB: HMDB0006725
- foodb: FDB024041
- chemspider: 89882
- CAS: 1989-52-2
- PMhub: MS000186936
- medchemexpress: HY-N2338
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(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PharmGKB(0)
3 个相关的物种来源信息
- 10212 - Bugula neritina: 10.1007/S10600-010-9625-2
- 9606 - Homo sapiens: -
- 161594 - Trachyrhamphus serratus: 10.1007/S10600-011-9966-5
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
- Yanbo Yang, Takashi Kuwano, William R Lagor, Carolyn J Albert, Siobhan Brenton, Daniel J Rader, David A Ford, Robert J Brown. Lipidomic analyses of female mice lacking hepatic lipase and endothelial lipase indicate selective modulation of plasma lipid species.
Lipids.
2014 Jun; 49(6):505-15. doi:
10.1007/s11745-014-3907-6
. [PMID: 24777581] - Eva Kupetz, Lutz Preu, Conrad Kunick, Heike Bunjes. Parenteral formulation of an antileishmanial drug candidate--tackling poor solubility, chemical instability, and polymorphism.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.
2013 Nov; 85(3 Pt A):511-20. doi:
10.1016/j.ejpb.2013.02.001
. [PMID: 23454203] - Ting-Ting Wang, Wei Chen, He-Ping Zeng, Dong-Feng Chen. Chemical components in extracts from Plastrum testudinis with proliferation-promoting effects on rat mesenchymal stem cells.
Chemical biology & drug design.
2012 Jun; 79(6):1049-55. doi:
10.1111/j.1747-0285.2012.01361.x
. [PMID: 22339978] - Friederike Mengersen, Heike Bunjes. PEGylation of supercooled smectic cholesteryl myristate nanoparticles.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.
2012 Jun; 81(2):409-17. doi:
10.1016/j.ejpb.2012.03.011
. [PMID: 22487056] - Silvia Petersen, Frank Steiniger, Dagmar Fischer, Alfred Fahr, Heike Bunjes. The physical state of lipid nanoparticles influences their effect on in vitro cell viability.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.
2011 Sep; 79(1):150-61. doi:
10.1016/j.ejpb.2011.03.022
. [PMID: 21458564] - Dong-Feng Chen, Jia-hui Cao, Yang Liu, Yiling Wu, Shao-Hui Du, Hui Li, Jian-Hong Zhou, Yi-Wei Li, He-Ping Zeng, Zi-Chun Hua. BMP-Id pathway targeted by cholesterol myristate suppresses the apoptosis of PC12 cells.
Brain research.
2011 Jan; 1367(?):33-42. doi:
10.1016/j.brainres.2010.10.025
. [PMID: 20970407] - Dong-Feng Chen, Hai-Ling Zhang, Shao-Hui Du, Hui Li, Jian-Hong Zhou, Yi-Wei Li, He-Ping Zeng, Zi-Chun Hua. Cholesterol myristate suppresses the apoptosis of mesenchymal stem cells via upregulation of inhibitor of differentiation.
Steroids.
2010 Dec; 75(13-14):1119-26. doi:
10.1016/j.steroids.2010.07.009
. [PMID: 20674581] - Dong-Feng Chen, Ling-Jie Meng, Shao-Hui Du, Hai-Ling Zhang, Hui Li, Jian-Hong Zhou, Yi-Wei Li, He-Ping Zeng, Zi-Chun Hua. (+)-Cholesten-3-one induces differentiation of neural stem cells into dopaminergic neurons through BMP signaling.
Neuroscience research.
2010 Nov; 68(3):176-84. doi:
10.1016/j.neures.2010.07.2043
. [PMID: 20708045] - Dong-Feng Chen, Shao-Hui Du, Hai-Ling Zhang, Hui Li, Jian-Hong Zhou, Yi-Wei Li, Xiang-Hua Yi, Qiu-Ke Hou, Jing Wu, He-Ping Zeng, Zi-Chun Hua. Autocrine BMP4 signaling involves effect of cholesterol myristate on proliferation of mesenchymal stem cells.
Steroids.
2009 Nov; 74(13-14):1066-72. doi:
10.1016/j.steroids.2009.08.008
. [PMID: 19723531] - Stefanie Y Nishimura, Giovanni Mata Magana, Howard A Ketelson, Gerald G Fuller. Effect of lysozyme adsorption on the interfacial rheology of DPPC and cholesteryl myristate films.
Langmuir : the ACS journal of surfaces and colloids.
2008 Oct; 24(20):11728-33. doi:
10.1021/la8016485
. [PMID: 18783258] - J Kuntsche, H Bunjes. Influence of preparation conditions and heat treatment on the properties of supercooled smectic cholesteryl myristate nanoparticles.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.
2007 Nov; 67(3):612-20. doi:
10.1016/j.ejpb.2007.04.019
. [PMID: 17574399] - B Cheng, J Kowal. Analysis of adrenal cholesteryl esters by reversed phase high performance liquid chromatography.
Journal of lipid research.
1994 Jun; 35(6):1115-21. doi:
. [PMID: 8077850]
- W Guo, J A Hamilton. Molecular organization and motions of cholesteryl esters in crystalline and liquid crystalline phases: a 13C and 1H magic angle spinning NMR study.
Biochemistry.
1993 Sep; 32(35):9038-52. doi:
10.1021/bi00086a009
. [PMID: 8369277] - D L Dorset. Thermotropic mesomorphism of cholesteryl myristate. An electron diffraction study.
Journal of lipid research.
1985 Sep; 26(9):1142-50. doi:
10.1016/s0022-2275(20)34288-7
. [PMID: 4067434] - R P Wilson, P L Fowlkes. Activity of glutamine synthetase in channel catfish tissues determined by an improved tissue assay method.
Comparative biochemistry and physiology. B, Comparative biochemistry.
1976; 54(3):365-8. doi:
10.1016/0305-0491(76)90258-3
. [PMID: 6197]