Cholesteryl ester hydroperoxide (BioDeep_00000173662)
human metabolite blood metabolite
代谢物信息卡片
3-hydroperoxy-10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene
化学式: C27H46O2 (402.34976159999997)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OO)C)C
InChI: InChI=1S/C27H46O2/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(29-28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3
数据库引用编号
分类词条
相关代谢途径
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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)
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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
- Iku Sazaki, Toshihiro Sakurai, Arisa Yamahata, Sumire Mogi, Nao Inoue, Koutaro Ishida, Ami Kikkai, Hana Takeshita, Akiko Sakurai, Yuji Takahashi, Hitoshi Chiba, Shu-Ping Hui. Oxidized Low-Density Lipoproteins Trigger Hepatocellular Oxidative Stress with the Formation of Cholesteryl Ester Hydroperoxide-Enriched Lipid Droplets.
International journal of molecular sciences.
2023 Feb; 24(5):. doi:
10.3390/ijms24054281. [PMID: 36901709] - Shuyuan Guo, Jianhong Lu, Yujuan Zhuo, Mengqing Xiao, Xinli Xue, Shanshan Zhong, Xia Shen, Chunzhao Yin, Luxiao Li, Qun Chen, Mingjiang Zhu, Buxing Chen, Mingming Zhao, Lemin Zheng, Yongzhen Tao, Huiyong Yin. Endogenous cholesterol ester hydroperoxides modulate cholesterol levels and inhibit cholesterol uptake in hepatocytes and macrophages.
Redox biology.
2019 02; 21(?):101069. doi:
10.1016/j.redox.2018.101069. [PMID: 30576926] - Weiyu Chen, Ghassan J Maghzal, Anita Ayer, Cacang Suarna, Louise L Dunn, Roland Stocker. Absence of the biliverdin reductase-a gene is associated with increased endogenous oxidative stress.
Free radical biology & medicine.
2018 02; 115(?):156-165. doi:
10.1016/j.freeradbiomed.2017.11.020. [PMID: 29195835] - Enkhtsetseg Sukhbold, Shogo Sekimoto, Emiko Watanabe, Akane Yamazaki, Lifeng Yang, Mikako Takasugi, Koji Yamada, Ryota Hosomi, Kenji Fukunaga, Hirofumi Arai. Effects of oolonghomobisflavan A on oxidation of low-density lipoprotein.
Bioscience, biotechnology, and biochemistry.
2017 Aug; 81(8):1569-1575. doi:
10.1080/09168451.2017.1314758. [PMID: 28463548] - Rojeet Shrestha, Shu-Ping Hui, Toshihiro Sakurai, Akiko Yagi, Yuji Takahashi, Seiji Takeda, Shigeki Jin, Hirotoshi Fuda, Hitoshi Chiba. Identification of molecular species of cholesteryl ester hydroperoxides in very low-density and intermediate-density lipoproteins.
Annals of clinical biochemistry.
2014 Nov; 51(Pt 6):662-71. doi:
10.1177/0004563213516093. [PMID: 24353240] - Jin Young Kim, Jeong-Yong Cho, Young Kyu Ma, Yu Geon Lee, Jae-Hak Moon. Nonallergenic urushiol derivatives inhibit the oxidation of unilamellar vesicles and of rat plasma induced by various radical generators.
Free radical biology & medicine.
2014 Jun; 71(?):379-389. doi:
10.1016/j.freeradbiomed.2014.03.041. [PMID: 24721153] - Jeong-Yong Cho, Chan Mi Kim, Hyoung Jae Lee, Sang-Hyun Lee, Jeong-An Cho, Wol-Soo Kim, Keun-Hyung Park, Jae-Hak Moon. Caffeoyl triterpenes from pear (Pyrus pyrifolia Nakai) fruit peels and their antioxidative activities against oxidation of rat blood plasma.
Journal of agricultural and food chemistry.
2013 May; 61(19):4563-9. doi:
10.1021/jf400524b. [PMID: 23611412] - Hyoung Jae Lee, Jeong-Yong Cho, Jae-Hak Moon. Comparison of the inhibitory effect against copper ion-induced oxidation in rat plasma after oral administration of salvianolic acid B and its decocted solutions.
Journal of medicinal food.
2013 Mar; 16(3):239-45. doi:
10.1089/jmf.2012.2456. [PMID: 23477623] - Shu-Ping Hui, Toshihiro Sakurai, Futaba Ohkawa, Hiroaki Furumaki, Shigeki Jin, Hirotoshi Fuda, Seiji Takeda, Takao Kurosawa, Hitoshi Chiba. Detection and characterization of cholesteryl ester hydroperoxides in oxidized LDL and oxidized HDL by use of an Orbitrap mass spectrometer.
Analytical and bioanalytical chemistry.
2012 Jul; 404(1):101-12. doi:
10.1007/s00216-012-6118-0. [PMID: 22710566] - 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] - Yoshichika Kawai, Mariko Miyoshi, Jae-Hak Moon, Junji Terao. Detection of cholesteryl ester hydroperoxide isomers using gas chromatography-mass spectrometry combined with thin-layer chromatography blotting.
Analytical biochemistry.
2007 Jan; 360(1):130-7. doi:
10.1016/j.ab.2006.09.028. [PMID: 17097596] - G Ferretti, T Bacchetti, F Principi, F Di Ludovico, B Viti, V A Angeleri, M Danni, L Provinciali. Increased levels of lipid hydroperoxides in plasma of patients with multiple sclerosis: a relationship with paraoxonase activity.
Multiple sclerosis (Houndmills, Basingstoke, England).
2005 Dec; 11(6):677-82. doi:
10.1191/1352458505ms1240oa. [PMID: 16320727] - Chiemi Kamada, Edson L da Silva, Mayumi Ohnishi-Kameyama, Jae-Hak Moon, Junji Terao. Attenuation of lipid peroxidation and hyperlipidemia by quercetin glucoside in the aorta of high cholesterol-fed rabbit.
Free radical research.
2005 Feb; 39(2):185-94. doi:
10.1080/10715760400019638. [PMID: 15763966] - Ryo Yamauchi, Peter Southwell-Keely, Cacang Suarna, Sangeeta Ray, Mark Raftery, Osamu Cynshi, Roland Stocker. Characterization of the oxidation products of BO-653 formed during peroxyl radical-mediated oxidation of human plasma.
Free radical biology & medicine.
2005 Jan; 38(1):32-40. doi:
10.1016/j.freeradbiomed.2004.09.018. [PMID: 15589369] - Takao Kamezaki, Kiyoyuki Yanaka, Sohji Nagase, Keishi Fujita, Noriyuki Kato, Tadao Nose. Increased levels of lipid peroxides as predictive of symptomatic vasospasm and poor outcome after aneurysmal subarachnoid hemorrhage.
Journal of neurosurgery.
2002 Dec; 97(6):1302-5. doi:
10.3171/jns.2002.97.6.1302. [PMID: 12507127] - Y Yamamoto. Role of active oxygen species and antioxidants in photoaging.
Journal of dermatological science.
2001 Aug; 27 Suppl 1(?):S1-4. doi:
10.1016/s0923-1811(01)00120-7. [PMID: 11514118] - A Baoutina, R T Dean, W Jessup. Antioxidant properties of macrophages toward low-density lipoprotein.
Trends in cardiovascular medicine.
2001 Jan; 11(1):1-7. doi:
10.1016/s1050-1738(01)00075-5. [PMID: 11413045] - E L da Silva, D S Abdalla, J Terao. Inhibitory effect of flavonoids on low-density lipoprotein peroxidation catalyzed by mammalian 15-lipoxygenase.
IUBMB life.
2000 Apr; 49(4):289-95. doi:
10.1080/15216540050033159. [PMID: 10995031] - A Baoutina, R T Dean, W Jessup. Macrophages can decrease the level of cholesteryl ester hydroperoxides in low density lipoprotein.
The Journal of biological chemistry.
2000 Jan; 275(3):1635-44. doi:
10.1074/jbc.275.3.1635. [PMID: 10636856] - Y Yamamoto, R Mashima. Presence of regio-isomeric cholesteryl linoleate hydroperoxides and hydroxides in plasma from healthy humans as evidence of free radical-mediated lipid peroxidation in vivo.
Redox report : communications in free radical research.
2000; 5(2-3):162-3. doi:
10.1179/135100000101535582. [PMID: 10939304] - N Yamamoto, J H Moon, T Tsushida, A Nagao, J Terao. Inhibitory effect of quercetin metabolites and their related derivatives on copper ion-induced lipid peroxidation in human low-density lipoprotein.
Archives of biochemistry and biophysics.
1999 Dec; 372(2):347-54. doi:
10.1006/abbi.1999.1516. [PMID: 10600174] - H Arai, S Kashiwagi, Y Nagasaka, K Uchida, Y Hoshii, K Nakamura. Oxidative modification of apolipoprotein E in human very-low-density lipoprotein and its inhibition by glycosaminoglycans.
Archives of biochemistry and biophysics.
1999 Jul; 367(1):1-8. doi:
10.1006/abbi.1999.1222. [PMID: 10375392] - L Chancharme, P Thérond, F Nigon, S Lepage, M Couturier, M J Chapman. Cholesteryl ester hydroperoxide lability is a key feature of the oxidative susceptibility of small, dense LDL.
Arteriosclerosis, thrombosis, and vascular biology.
1999 Mar; 19(3):810-20. doi:
10.1161/01.atv.19.3.810. [PMID: 10073990] - G T Shwaery, H Mowri, J F Keaney, B Frei. Preparation of lipid hydroperoxide-free low-density lipoproteins.
Methods in enzymology.
1999; 300(?):17-23. doi:
10.1016/s0076-6879(99)00108-1. [PMID: 9919504] - M C Polidori, B Frei, A Cherubini, G Nelles, G Rordorf, J F Keaney, L Schwamm, P Mecocci, W J Koroshetz, M F Beal. Increased plasma levels of lipid hydroperoxides in patients with ischemic stroke.
Free radical biology & medicine.
1998 Sep; 25(4-5):561-7. doi:
10.1016/s0891-5849(98)00085-9. [PMID: 9741593] - E L da Silva, M K Piskula, N Yamamoto, J H Moon, J Terao. Quercetin metabolites inhibit copper ion-induced lipid peroxidation in rat plasma.
FEBS letters.
1998 Jul; 430(3):405-8. doi:
10.1016/s0014-5793(98)00709-1. [PMID: 9688581] - O Vieira, J Laranjinha, V Madeira, L Almeida. Cholesteryl ester hydroperoxide formation in myoglobin-catalyzed low density lipoprotein oxidation: concerted antioxidant activity of caffeic and p-coumaric acids with ascorbate.
Biochemical pharmacology.
1998 Feb; 55(3):333-40. doi:
10.1016/s0006-2952(97)00470-x. [PMID: 9484800] - T M Berger, M C Polidori, A Dabbagh, P J Evans, B Halliwell, J D Morrow, L J Roberts, B Frei. Antioxidant activity of vitamin C in iron-overloaded human plasma.
The Journal of biological chemistry.
1997 Jun; 272(25):15656-60. doi:
10.1074/jbc.272.25.15656. [PMID: 9188455] - M Yasuda, S Narita. Simultaneous determination of phospholipid hydroperoxides and cholesteryl ester hydroperoxides in human plasma by high-performance liquid chromatography with chemiluminescence detection.
Journal of chromatography. B, Biomedical sciences and applications.
1997 May; 693(1):211-7. doi:
10.1016/s0378-4347(97)00034-0. [PMID: 9200537] - M C Polidori, B Frei, G Rordorf, C S Ogilvy, W J Koroshetz, M F Beal. Increased levels of plasma cholesteryl ester hydroperoxides in patients with subarachnoid hemorrhage.
Free radical biology & medicine.
1997; 23(5):762-7. doi:
10.1016/s0891-5849(97)00053-1. [PMID: 9296453] - N Noguchi, E Niki. Inhibition of plasma cholesterol ester hydroperoxide and phosphatidylcholine hydroperoxide formation as measures of antioxidant status.
Methods in enzymology.
1997; 282(?):271-8. doi:
10.1016/s0076-6879(97)82114-3. [PMID: 9330295] - Y Yamamoto. Chemiluminescence-based high-performance liquid chromatography assay of lipid hydroperoxides.
Methods in enzymology.
1994; 233(?):319-24. doi:
10.1016/s0076-6879(94)33036-0. [PMID: 8015466] - N Noguchi, N Gotoh, E Niki. Dynamics of the oxidation of low density lipoprotein induced by free radicals.
Biochimica et biophysica acta.
1993 Jul; 1168(3):348-57. doi:
10.1016/0005-2760(93)90192-c. [PMID: 8323975] - Y Yamamoto, Y Nagata, E Niki, K Watanabe, S Yoshimura. Plasma glutathione peroxidase reduces phosphatidylcholine hydroperoxide.
Biochemical and biophysical research communications.
1993 May; 193(1):133-8. doi:
10.1006/bbrc.1993.1600. [PMID: 8503899]