2,2-Dimethyl-N-(2,4,6-trimethoxyphenyl)dodecanamide (BioDeep_00000177472)

   

human metabolite blood metabolite


代谢物信息卡片


2,2-Dimethyl-N-(2,4,6-trimethoxyphenyl)dodecanamide

化学式: C23H39NO4 (393.28789340000003)
中文名称: 2,2-二甲基-N-(2,4,6-三甲氧基苯基)月桂酰胺
谱图信息: 最多检出来源 Homo sapiens(blood) 18.11%

分子结构信息

SMILES: CCCCCCCCCCC(C)(C)C(=O)NC1=C(C=C(C=C1OC)OC)OC
InChI: InChI=1S/C23H39NO4/c1-7-8-9-10-11-12-13-14-15-23(2,3)22(25)24-21-19(27-5)16-18(26-4)17-20(21)28-6/h16-17H,7-15H2,1-6H3,(H,24,25)

描述信息

D004791 - Enzyme Inhibitors
PD 128042 (CI 976) is a potent, orally active, and selective inhibitor of ACAT (acyl coenzyme A:cholesterol acyltransferase) with an IC50s of 73 nM. PD 128042 is also a potent LPAT (lysophospholipid acyltransferase) inhibitor. PD 128042 inhibits Golgi-associated LPAT activity (IC50=15 μM). PD 128042 inhibits multiple membrane trafficking steps, including ones found in the endocytic and secretory pathway[1][2][3].

同义名列表

3 个代谢物同义名

2,2-Dimethyl-N-(2,4,6-trimethoxyphenyl)dodecanamide; PD 128042; CI 976



数据库引用编号

7 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)

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

  • Jiahui Dong, Hui Pang, Lingyan Zhao. [Hyperuricemia among Mongolian adults and the related factors in Inner Mongolia Autonomous Region from 2018 to 2020]. Wei sheng yan jiu = Journal of hygiene research. 2022 Nov; 51(6):940-946. doi: 10.19813/j.cnki.weishengyanjiu.2022.06.014. [PMID: 36539870]
  • Kimiyuki Shibuya, Katsumi Kawamine, Toru Miura, Chiyoka Ozaki, Toshiyuki Edano, Ken Mizuno, Yasunobu Yoshinaka, Yoshihiko Tsunenari. Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors. Bioorganic & medicinal chemistry. 2018 08; 26(14):4001-4013. doi: 10.1016/j.bmc.2018.06.024. [PMID: 29945757]
  • Takashi Baba, Akitsugu Yamamoto, Mitsuo Tagaya, Katsuko Tani. A lysophospholipid acyltransferase antagonist, CI-976, creates novel membrane tubules marked by intracellular phospholipase A1 KIAA0725p. Molecular and cellular biochemistry. 2013 Apr; 376(1-2):151-61. doi: 10.1007/s11010-013-1563-4. [PMID: 23378048]
  • Bishuang Cai, Steve Caplan, Naava Naslavsky. cPLA2α and EHD1 interact and regulate the vesiculation of cholesterol-rich, GPI-anchored, protein-containing endosomes. Molecular biology of the cell. 2012 May; 23(10):1874-88. doi: 10.1091/mbc.e11-10-0881. [PMID: 22456504]
  • Yunjeong Kim, David George, Allan M Prior, Keshar Prasain, Shuanghong Hao, Duy D Le, Duy H Hua, Kyeong-Ok Chang. Novel triacsin C analogs as potential antivirals against rotavirus infections. European journal of medicinal chemistry. 2012 Apr; 50(?):311-8. doi: 10.1016/j.ejmech.2012.02.010. [PMID: 22365411]
  • John A Schmidt, William J Brown. Lysophosphatidic acid acyltransferase 3 regulates Golgi complex structure and function. The Journal of cell biology. 2009 Jul; 186(2):211-8. doi: 10.1083/jcb.200904147. [PMID: 19635840]
  • Dawn L Geiser, Meng-Chieh Shen, Jonathan J Mayo, Joy J Winzerling. Iron loaded ferritin secretion and inhibition by CI-976 in Aedes aegypti larval cells. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2009 Apr; 152(4):352-63. doi: 10.1016/j.cbpb.2009.01.002. [PMID: 19168145]
  • Y Matsui, K Horiuchi, K Yamamoto, K Kanai. Pharmacological properties of R-755, a novel acyl-CoA:cholesterol acyltransferase inhibitor, in cholesterol-fed rats, hamsters and rabbits. Japanese journal of pharmacology. 2001 Apr; 85(4):423-33. doi: 10.1254/jjp.85.423. [PMID: 11388647]
  • A Tanaka, T Terasawa, H Hagihara, Y Sakuma, N Ishibe, M Sawada, H Takasugi, H Tanaka. Inhibitors of acyl-CoA:cholesterol O-acyltransferase (ACAT). Part 1: identification and structure-activity relationships of a novel series of substituted N-alkyl-N-biphenylylmethyl-N'-arylureas. Bioorganic & medicinal chemistry. 1998 Jan; 6(1):15-30. doi: 10.1016/s0968-0896(97)10009-8. [PMID: 9502102]
  • M Yasuhara, K Saito, H Kubota, H Ohmizu, T Suzuki. Inhibitory effect of a new ureidophenol derivative T-2591 on LDL oxidation and ACAT activity. Biological & pharmaceutical bulletin. 1997 Oct; 20(10):1056-60. doi: 10.1248/bpb.20.1056. [PMID: 9353564]
  • M W Sinz, A E Black, S M Bjorge, A Holmes, B K Trivedi, T F Woolf. In vitro and in vivo disposition of 2,2-dimethyl-N-(2,4,6-trimethoxyphenyl)dodecanamide (CI-976). Identification of a novel five-carbon cleavage metabolite in rats. Drug metabolism and disposition: the biological fate of chemicals. 1997 Jan; 25(1):123-30. doi: NULL. [PMID: 9010639]
  • S Murakami, Y Ohta, Y Asami, I Yamagishi, Y Toda, M Sato, K Tomisawa. The hypolipidemic action of the ACAT inhibitor HL-004 in hamsters fed normal chow. General pharmacology. 1996 Dec; 27(8):1383-6. doi: 10.1016/s0306-3623(96)00070-5. [PMID: 9304411]
  • A D White, C F Purchase, J A Picard, M K Anderson, S B Mueller, T M Bocan, R F Bousley, K L Hamelehle, B R Krause, P Lee, R L Stanfield, J F Reindel. Heterocyclic amides: inhibitors of acyl-CoA:cholesterol O-acyl transferase with hypocholesterolemic activity in several species and antiatherosclerotic activity in the rabbit. Journal of medicinal chemistry. 1996 Sep; 39(20):3908-19. doi: 10.1021/jm9604033. [PMID: 8831757]
  • P M O'Brien, D R Sliskovic, J A Picard, H T Lee, C F Purchase, B D Roth, A D White, M Anderson, S B Mueller, T Bocan, R Bousley, K L Hamelehle, R Homan, P Lee, B R Krause, J F Reindel, R L Stanfield, D Turluck. Inhibitors of acyl-CoA:cholesterol O-acyltransferase. synthesis and pharmacological activity of (+/-)-2-dodecyl-alpha-phenyl-N-(2,4,6-trimethoxyphenyl)-2H-tetrazole-5- acetamide and structurally related tetrazole amide derivatives. Journal of medicinal chemistry. 1996 Jun; 39(12):2354-66. doi: 10.1021/jm960170f. [PMID: 8691430]
  • K Kataoka, T Shiota, T Takeyasu, T Minoshima, K Watanabe, H Tanaka, T Mochizuki, K Taneda, M Ota, H Tanabe, H Yamaguchi. Potent inhibitors of acyl-CoA:cholesterol acyltransferase. 2. Structure-activity relationships of novel N-(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)amides. Journal of medicinal chemistry. 1996 Mar; 39(6):1262-70. doi: 10.1021/jm950828+. [PMID: 8632433]
  • Y Sakuma, H Hagihara, K Ohne, A Nagayoshi, S Mutoh, Y Ito, Y Notsu, M Okuhara. Plasma cholesterol reducing effect of FR129169, a novel acyl-CoA:cholesterol acyltransferase inhibitor, in the rat. Japanese journal of pharmacology. 1996 Jan; 70(1):35-41. doi: 10.1254/jjp.70.35. [PMID: 8822087]
  • R A Harte, S J Yeaman, B Jackson, K E Suckling. Effect of membrane environment on inhibition of acyl-CoA:cholesterol acyltransferase by a range of synthetic inhibitors. Biochimica et biophysica acta. 1995 Oct; 1258(3):241-50. doi: 10.1016/0005-2760(95)00113-q. [PMID: 7548193]
  • K Kataoka, T Shiota, T Takeyasu, T Mochizuki, K Taneda, M Ota, H Tanabe, H Yamaguchi. Potent inhibitors of acyl-CoA:cholesterol acyltransferase. Structure-activity relationships of novel N-(4-oxochroman-8-yl)amides. Journal of medicinal chemistry. 1995 Aug; 38(16):3174-86. doi: 10.1021/jm00016a021. [PMID: 7636880]
  • R E Burrier, A A Smith, D G McGregor, L M Hoos, D L Zilli, H R Davis. The effect of acyl CoA: cholesterol acyltransferase inhibition on the uptake, esterification and secretion of cholesterol by the hamster small intestine. The Journal of pharmacology and experimental therapeutics. 1995 Jan; 272(1):156-63. doi: NULL. [PMID: 7815329]
  • T P Carr, R L Hamilton, L L Rudel. ACAT inhibitors decrease secretion of cholesteryl esters and apolipoprotein B by perfused livers of African green monkeys. Journal of lipid research. 1995 Jan; 36(1):25-36. doi: 10.1016/s0022-2275(20)39751-0. [PMID: 7706945]
  • P M O'Brien, D R Sliskovic, C J Blankley, B D Roth, M W Wilson, K L Hamelehle, B R Krause, R L Stanfield. Inhibitors of acyl-CoA:cholesterol O-acyl transferase (ACAT) as hypocholesterolemic agents. 8. Incorporation of amide or amine functionalities into a series of disubstituted ureas and carbamates. Effects on ACAT inhibition in vitro and efficacy in vivo. Journal of medicinal chemistry. 1994 Jun; 37(12):1810-22. doi: 10.1021/jm00038a010. [PMID: 8021920]
  • H Tanaka, I Ohtsuka, M Kogushi, T Kimura, T Fujimori, T Saeki, K Hayashi, H Kobayashi, T Yamada, H Hiyoshi. Effect of the acyl-CoA:cholesterol acyltransferase inhibitor, E5324, on experimental atherosclerosis in rabbits. Atherosclerosis. 1994 Jun; 107(2):187-201. doi: 10.1016/0021-9150(94)90020-5. [PMID: 7980693]
  • B R Krause, M E Pape, K Kieft, B Auerbach, C L Bisgaier, R Homan, R S Newton. ACAT inhibition decreases LDL cholesterol in rabbits fed a cholesterol-free diet. Marked changes in LDL cholesterol without changes in LDL receptor mRNA abundance. Arteriosclerosis and thrombosis : a journal of vascular biology. 1994 Apr; 14(4):598-604. doi: 10.1161/01.atv.14.4.598. [PMID: 8148358]
  • Y Y Shum, A Black, T Chang. Determination of 2,2-dimethyl-N-(2,4,6-trimethoxyphenyl) dodecanamide, CI-976, in rat plasma by reversed-phase high-performance liquid chromatography. Journal of chromatography. B, Biomedical applications. 1994 Mar; 653(2):205-9. doi: 10.1016/0378-4347(93)e0424-o. [PMID: 8205247]
  • T F Woolf, A Black, Y Y Shum, W McNally, H Lee, T Chang. Biodisposition studies with the acyl-coenzyme A: cholesterol acyltransferase inhibitor 2,2-dimethyl-N-(2,4,6-trimethoxyphenyl)dodecanamide, CI-976. Drug metabolism and disposition: the biological fate of chemicals. 1993 Nov; 21(6):1112-8. doi: . [PMID: 7905392]
  • C E Augelli-Szafran, C J Blankley, B D Roth, B K Trivedi, R F Bousley, A D Essenburg, K L Hamelehle, B R Krause, R L Stanfield. Inhibitors of acyl-CoA:cholesterol acyltransferase. 5. Identification and structure-activity relationships of novel beta-ketoamides as hypocholesterolemic agents. Journal of medicinal chemistry. 1993 Oct; 36(20):2943-9. doi: 10.1021/jm00072a014. [PMID: 8411011]
  • D J Hauss, P J Martin, S C Mehta, G W Radebaugh. Determination of 2,2-dimethyl-N-(2,4,6-trimethoxyphenyl)-dodecanamide, a lipid regulator, in rat plasma and mesenteric lymph by reversed-phase high-performance liquid chromatography. Journal of chromatography. 1993 Apr; 613(2):336-9. doi: 10.1016/0378-4347(93)80151-s. [PMID: 8491822]
  • T M Bocan, S B Mueller, P D Uhlendorf, E Q Brown, M J Mazur, A E Black. Inhibition of acyl-CoA cholesterol O-acyltransferase reduces the cholesteryl ester enrichment of atherosclerotic lesions in the Yucatan micropig. Atherosclerosis. 1993 Mar; 99(2):175-86. doi: 10.1016/0021-9150(93)90020-u. [PMID: 8503946]
  • B R Krause, M Anderson, C L Bisgaier, T Bocan, R Bousley, P DeHart, A Essenburg, K Hamelehle, R Homan, K Kieft. In vivo evidence that the lipid-regulating activity of the ACAT inhibitor CI-976 in rats is due to inhibition of both intestinal and liver ACAT. Journal of lipid research. 1993 Feb; 34(2):279-94. doi: . [PMID: 8429262]
  • B R Krause, R F Bousley, K A Kieft, R L Stanfield. Effect of the ACAT inhibitor CI-976 on plasma cholesterol concentrations and distribution in hamsters fed zero- and low-cholesterol diets. Clinical biochemistry. 1992 Oct; 25(5):371-7. doi: 10.1016/0009-9120(92)80020-h. [PMID: 1490301]
  • B D Roth, C J Blankley, M L Hoefle, A Holmes, W H Roark, B K Trivedi, A D Essenburg, K A Kieft, B R Krause, R L Stanfield. Inhibitors of acyl-CoA:cholesterol acyltransferase. 1. Identification and structure-activity relationships of a novel series of fatty acid anilide hypocholesterolemic agents. Journal of medicinal chemistry. 1992 May; 35(9):1609-17. doi: 10.1021/jm00087a016. [PMID: 1578488]
  • T M Bocan, S B Mueller, P D Uhlendorf, R S Newton, B R Krause. Comparison of CI-976, an ACAT inhibitor, and selected lipid-lowering agents for antiatherosclerotic activity in iliac-femoral and thoracic aortic lesions. A biochemical, morphological, and morphometric evaluation. Arteriosclerosis and thrombosis : a journal of vascular biology. 1991 Nov; 11(6):1830-43. doi: 10.1161/01.atv.11.6.1830. [PMID: 1931885]