CE(20:4(5Z,8Z,11Z,14Z)) (BioDeep_00000023991)
Secondary id: BioDeep_00000598559, BioDeep_00000912165, BioDeep_00001104135, BioDeep_00001872010
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite
代谢物信息卡片
化学式: C47H76O2 (672.5844996)
中文名称:
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 7.79%
分子结构信息
SMILES: CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
InChI: InChI=1S/C47H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h11-12,14-15,17-18,20-21,28,37-38,40-44H,7-10,13,16,19,22-27,29-36H2,1-6H3/b12-11-,15-14-,18-17-,21-20-/t38-,40+,41+,42-,43+,44+,46+,47-/m1/s1
描述信息
CE(20:4(5Z,8Z,11Z,14Z)) 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.
Cholesteryl arachidonate is an endogenous metabolite.
同义名列表
32 个代谢物同义名
(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate; (2R,5S,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid; (2R,5S,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid; Cholest-5-en-3-ol (3beta)- 5,8,11,14-eicosatetraenoic acid; Cholest-5-en-3-ol (3beta)- 5,8,11,14-eicosatetraenoate; Cholesterol 1-(5Z,8Z,11Z,14Z-eicosatetraenoic acid); Cholesteryl 1-(5Z,8Z,11Z,14Z-eicosatetraenoic acid); Cholesteryl arachidonate, (3beta)-(all Z)-isomer; Cholesteryl 1-(5Z,8Z,11Z,14Z-eicosatetraenoate); Cholesterol 1-(5Z,8Z,11Z,14Z-eicosatetraenoate); 1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-cholesterol; Cholesteryl arachidonate eicosatetraenoate; 20:4(5Z,8Z,11Z,14Z) Cholesterol ester; (5Z,8Z,11Z,14Z-Eicosatetraenoic acid; (5Z,8Z,11Z,14Z-Eicosatetraenoate); (5Z,8Z,11Z,14Z-Eicosatetraenoate; Cholesterol 1-arachidonoic acid; Cholesteryl 1-arachidonoic acid; Cholesteryl arachidonic acid; Cholesterol ester(20:4/0:0); Cholesterol 1-arachidonoate; Cholesteryl 1-arachidonoate; 1-Arachidonoyl-cholesterol; Cholesterol arachidonate; Cholesteryl arachidonate; CE(20:4(5Z,8Z,11Z,14Z)); Cholesterol ester(20:4); 20:4 Cholesterol ester; Cholest-5-en-3beta-yl; CE(20:4/0:0); DB-053615; CE(20:4)
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:82751
- PubChem: 3632206
- PubChem: 6479222
- HMDB: HMDB0006726
- foodb: FDB112234
- chemspider: 4980154
- CAS: 604-34-2
- PMhub: MS000123719
- medchemexpress: HY-113369
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)
1 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
- Shanshan Zhong, Luxiao Li, Xia Shen, Qiujing Li, Wenxin Xu, Xiaoping Wang, Yongzhen Tao, Huiyong Yin. An update on lipid oxidation and inflammation in cardiovascular diseases.
Free radical biology & medicine.
2019 11; 144(?):266-278. doi:
10.1016/j.freeradbiomed.2019.03.036
. [PMID: 30946962] - 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] - Thai Q Do, Safiehkhatoon Moshkani, Patricia Castillo, Suda Anunta, Adelina Pogosyan, Annie Cheung, Beth Marbois, Kym F Faull, William Ernst, Su Ming Chiang, Gary Fujii, Catherine F Clarke, Krishna Foster, Edith Porter. Lipids including cholesteryl linoleate and cholesteryl arachidonate contribute to the inherent antibacterial activity of human nasal fluid.
Journal of immunology (Baltimore, Md. : 1950).
2008 Sep; 181(6):4177-87. doi:
10.4049/jimmunol.181.6.4177
. [PMID: 18768875] - Richard Harkewicz, Karsten Hartvigsen, Felicidad Almazan, Edward A Dennis, Joseph L Witztum, Yury I Miller. Cholesteryl ester hydroperoxides are biologically active components of minimally oxidized low density lipoprotein.
The Journal of biological chemistry.
2008 Apr; 283(16):10241-51. doi:
10.1074/jbc.m709006200
. [PMID: 18263582] - Huiyong Yin, Jason D Morrow, Ned A Porter. Identification of a novel class of endoperoxides from arachidonate autoxidation.
The Journal of biological chemistry.
2004 Jan; 279(5):3766-76. doi:
10.1074/jbc.m307137200
. [PMID: 14594817] - Huiyong Yin, Christine M Havrilla, Jason D Morrow, Ned A Porter. Formation of isoprostane bicyclic endoperoxides from the autoxidation of cholesteryl arachidonate.
Journal of the American Chemical Society.
2002 Jul; 124(26):7745-54. doi:
10.1021/ja0201092
. [PMID: 12083928] - V Schlotte, A Sevanian, P Hochstein, K U Weithmann. Effect of uric acid and chemical analogues on oxidation of human low density lipoprotein in vitro.
Free radical biology & medicine.
1998 Nov; 25(7):839-47. doi:
10.1016/s0891-5849(98)00160-9
. [PMID: 9823550] - 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]
- J V Hunt, K L Carpenter, M A Bottoms, N P Carter, C E Marchant, M J Mitchinson. Flow cytometric measurement of ceroid accumulation in macrophages.
Atherosclerosis.
1993 Jan; 98(2):229-39. doi:
10.1016/0021-9150(93)90132-e
. [PMID: 8457262] - N Araki, S Horiuchi, A T Rahim, K Takata, Y Morino. Microquantification of cholesterol and cholesteryl esters in rat peritoneal macrophages by reverse-phase high-performance liquid chromatography.
Analytical biochemistry.
1990 Mar; 185(2):339-45. doi:
10.1016/0003-2697(90)90305-s
. [PMID: 2339790] - Y Yamamoto, E Niki. Presence of cholesteryl ester hydroperoxide in human blood plasma.
Biochemical and biophysical research communications.
1989 Dec; 165(3):988-93. doi:
10.1016/0006-291x(89)92700-9
. [PMID: 2610703] - R Y Ball, K L Carpenter, M J Mitchinson. Ceroid accumulation by murine peritoneal macrophages exposed to artificial lipoproteins: ultrastructural observations.
British journal of experimental pathology.
1988 Feb; 69(1):43-56. doi:
. [PMID: 3348959]
- N P Odushko, N F Muliar. [Serum cholesterol ester level in patients with ischemic heart disease and liver disease].
Kardiologiia.
1984 Oct; 24(10):90-3. doi:
NULL
. [PMID: 6521191] - D A Wiebe, J T Bernert. Influence of incomplete cholesteryl ester hydrolysis on enzymic measurements of cholesterol.
Clinical chemistry.
1984 Mar; 30(3):352-6. doi:
10.1093/clinchem/30.3.352
. [PMID: 6697478] - J M Smaby, H L Brockman. Novel surface phase containing cholesteryl esters. 2. Nonequivalence of cholesteryl arachidonate and those with 18-carbon, cis-unsaturated acyl groups.
Biochemistry.
1981 Feb; 20(4):724-30. doi:
10.1021/bi00507a009
. [PMID: 7213606]