Nafenopin (BioDeep_00000858754)
Main id: BioDeep_00000008630
代谢物信息卡片
Nafenopin
化学式: C20H22O3 (310.1569)
中文名称: 萘酚平
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C)(C(=O)O)OC1=CC=C(C=C1)C2CCCC3=CC=CC=C23
InChI: InChI=1S/C20H22O3/c1-20(2,19(21)22)23-16-12-10-15(11-13-16)18-9-5-7-14-6-3-4-8-17(14)18/h3-4,6,8,10-13,18H,5,7,9H2,1-2H3,(H,21,22)
描述信息
C78276 - Agent Affecting Digestive System or Metabolism > C29711 - Anti-diabetic Agent > C154291 - Peroxisome Proliferator-Activated Receptor Agonist
C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent > C98150 - Fibrate Antilipidemic Agent
D009676 - Noxae > D002273 - Carcinogens > D020025 - Peroxisome Proliferators
D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents
D009676 - Noxae > D000963 - Antimetabolites
Same as: D05102
同义名列表
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:77649
- ChEBI: CHEBI:7449
- KEGG: C11371
- KEGGdrug: D05102
- PubChem: 19592
- ChEMBL: CHEMBL1909070
- MeSH: Nafenopin
- CAS: 3771-19-5
- PubChem: 13545
- NIKKAJI: J8.248A
- KNApSAcK: 7449
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)
0 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
- Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology.
2019 11; 96(5):629-640. doi:
10.1124/mol.119.115964. [PMID: 31515284] - David A Rudnick, Nicholas O Davidson. Functional Relationships between Lipid Metabolism and Liver Regeneration.
International journal of hepatology.
2012; 2012(?):549241. doi:
10.1155/2012/549241. [PMID: 22319652] - Tsuyoshi Kurokawa, Yoshiharu Shimomura, Gustavo Bajotto, Katsuhiro Kotake, Takashi Arikawa, Nobuhiro Ito, Akira Yasuda, Hiroshi Nagata, Toshiaki Nonami, Kazuo Masuko. Peroxisome proliferator-activated receptor α (PPARα) mRNA expression in human hepatocellular carcinoma tissue and non-cancerous liver tissue.
World journal of surgical oncology.
2011 Dec; 9(?):167. doi:
10.1186/1477-7819-9-167. [PMID: 22168458] - Lena Burri, Bodil Bjørndal, Hege Wergedahl, Kjetil Berge, Pavol Bohov, Asbjørn Svardal, Rolf K Berge. Tetradecylthioacetic acid increases hepatic mitochondrial β-oxidation and alters fatty acid composition in a mouse model of chronic inflammation.
Lipids.
2011 Aug; 46(8):679-89. doi:
10.1007/s11745-011-3536-2. [PMID: 21479675] - Ivan V Shirinsky, Valery S Shirinsky. Targeting Nuclear Hormone Receptors: PPARα Agonists as Potential Disease-Modifying Drugs for Rheumatoid Arthritis.
International journal of rheumatology.
2011; 2011(?):937843. doi:
10.1155/2011/937843. [PMID: 21760804] - Sean R Pyper, Navin Viswakarma, Songtao Yu, Janardan K Reddy. PPARalpha: energy combustion, hypolipidemia, inflammation and cancer.
Nuclear receptor signaling.
2010 Apr; 8(?):e002. doi:
10.1621/nrs.08002. [PMID: 20414453] - Sean R Pyper, Navin Viswakarma, Yuzhi Jia, Yi-Jun Zhu, Joseph D Fondell, Janardan K Reddy. PRIC295, a Nuclear Receptor Coactivator, Identified from PPARα-Interacting Cofactor Complex.
PPAR research.
2010; 2010(?):. doi:
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PPAR research.
2010; 2010(?):. doi:
10.1155/2010/542359. [PMID: 20847941] - Hanna Amelina, Susana Cristobal. Proteomic study on gender differences in aging kidney of mice.
Proteome science.
2009 Apr; 7(?):16. doi:
10.1186/1477-5956-7-16. [PMID: 19358702] - Keisuke Tachibana, Daisuke Yamasaki, Kenji Ishimoto, Takefumi Doi. The Role of PPARs in Cancer.
PPAR research.
2008; 2008(?):102737. doi:
10.1155/2008/102737. [PMID: 18584037] - Sebastian Luci, Beatrice Giemsa, Gerd Hause, Holger Kluge, Klaus Eder. Clofibrate treatment in pigs: effects on parameters critical with respect to peroxisome proliferator-induced hepatocarcinogenesis in rodents.
BMC pharmacology.
2007 Apr; 7(?):6. doi:
10.1186/1471-2210-7-6. [PMID: 17437637] - Jonathan M Shipley, Christopher H Hurst, Sue S Tanaka, Fred L DeRoos, John L Butenhoff, Andrew M Seacat, David J Waxman. trans-activation of PPARalpha and induction of PPARalpha target genes by perfluorooctane-based chemicals.
Toxicological sciences : an official journal of the Society of Toxicology.
2004 Jul; 80(1):151-60. doi:
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Archives of toxicology.
2003 Mar; 77(3):150-9. doi:
10.1007/s00204-002-0422-y. [PMID: 12632255] - B Kalderon, V Sheena, S Shachrur, R Hertz, J Bar-Tana. Modulation by nutrients and drugs of liver acyl-CoAs analyzed by mass spectrometry.
Journal of lipid research.
2002 Jul; 43(7):1125-32. doi:
10.1194/jlr.m200060-jlr200. [PMID: 12091497] - W Parzefall, W Berger, E Kainzbauer, O Teufelhofer, R Schulte-Hermann, R G Thurman. Peroxisome proliferators do not increase DNA synthesis in purified rat hepatocytes.
Carcinogenesis.
2001 Mar; 22(3):519-23. doi:
10.1093/carcin/22.3.519. [PMID: 11238195] - B C Sallustio, S Nunthasomboon, C J Drogemuller, K M Knights. In vitro covalent binding of nafenopin-CoA to human liver proteins.
Toxicology and applied pharmacology.
2000 Mar; 163(2):176-82. doi:
10.1006/taap.1999.8868. [PMID: 10698675] - D W Singleton, X D Lei, S J Webb, R A Prough, T E Geoghegan. Cytochrome P-450 mRNAs are modulated by dehydroepiandrosterone, nafenopin, and triiodothyronine.
Drug metabolism and disposition: the biological fate of chemicals.
1999 Feb; 27(2):193-200. doi:
. [PMID: 9929502] - S C Hasmall, N H James, A R Soames, R A Roberts. The peroxisome proliferator nafenopin does not suppress hepatocyte apoptosis in guinea-pig liver in vivo nor in human hepatocytes in vitro.
Archives of toxicology.
1998 Dec; 72(12):777-83. doi:
10.1007/s002040050573. [PMID: 9950074] - C N Palmer, E Axen, V Hughes, C R Wolf. The repressor protein, Bm3R1, mediates an adaptive response to toxic fatty acids in Bacillus megaterium.
The Journal of biological chemistry.
1998 Jul; 273(29):18109-16. doi:
10.1074/jbc.273.29.18109. [PMID: 9660768] - W W Huber, B Grasl-Kraupp, H Stekel, C Gschwentner, H Lang, R Schulte-Hermann. Inhibition instead of enhancement of lipid peroxidation by pretreatment with the carcinogenic peroxisome proliferator nafenopin in rat liver exposed to a high single dose of corn oil.
Archives of toxicology.
1997; 71(9):575-81. doi:
10.1007/s002040050429. [PMID: 9285040] - H K Bojes, R G Thurman. Potent peroxisome proliferators inhibit beta-oxidation in the isolated perfused rat liver.
Toxicology and applied pharmacology.
1996 Oct; 140(2):322-7. doi:
10.1006/taap.1996.0227. [PMID: 8887448] - S J Webb, G H Xiao, T E Geoghegan, R A Prough. Regulation of CYP4A expression in rat by dehydroepiandrosterone and thyroid hormone.
Molecular pharmacology.
1996 Feb; 49(2):276-87. doi:
. [PMID: 8632760] - P Garberg, M Thullberg. Decreased glutathione peroxidase activity in mice in response to nafenopin is caused by changes in selenium metabolism.
Chemico-biological interactions.
1996 Jan; 99(1-3):165-77. doi:
10.1016/0009-2797(95)03667-9. [PMID: 8620565] - H K Bojes, R G Thurman. Peroxisome proliferators activate Kupffer cells in vivo.
Cancer research.
1996 Jan; 56(1):1-4. doi:
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Journal of biochemical toxicology.
1995 Apr; 10(2):87-94. doi:
10.1002/jbt.2570100205. [PMID: 7562957] - G Jedlitschky, I Leier, M Böhme, U Buchholz, J Bar-Tana, D Keppler. Hepatobiliary elimination of the peroxisome proliferator nafenopin by conjugation and subsequent ATP-dependent transport across the canalicular membrane.
Biochemical pharmacology.
1994 Sep; 48(6):1113-20. doi:
10.1016/0006-2952(94)90147-3. [PMID: 7945404] - K E Tomaszewski, R L Melnick. In vitro evidence for involvement of CoA thioesters in peroxisome proliferation and hypolipidaemia.
Biochimica et biophysica acta.
1994 Jan; 1220(2):118-24. doi:
10.1016/0167-4889(94)90126-0. [PMID: 7906145] - A C Bayly, N J French, C Dive, R A Roberts. Non-genotoxic hepatocarcinogenesis in vitro: the FaO hepatoma line responds to peroxisome proliferators and retains the ability to undergo apoptosis.
Journal of cell science.
1993 Feb; 104 ( Pt 2)(?):307-15. doi:
10.1242/jcs.104.2.307. [PMID: 8389374] - E Persohn, H Thomas, F Waechter. Immunoelectron microscopic localization of cytochrome P-450 isoenzyme CYP4A1 in liver, ileum and kidney of nafenopin treated male rats.
Cell biology international.
1993 Jan; 17(1):99-103. doi:
10.1006/cbir.1993.1010. [PMID: 8495232] - G M Ledda-Columbano, P Coni, M Curto, L Giacomini, G Faa, S Oliverio, M Piacentini, A Columbano. Induction of two different modes of cell death, apoptosis and necrosis, in rat liver after a single dose of thioacetamide.
The American journal of pathology.
1991 Nov; 139(5):1099-109. doi:
NULL. [PMID: 1683163] - M S Rao, J K Reddy. An overview of peroxisome proliferator-induced hepatocarcinogenesis.
Environmental health perspectives.
1991 Jun; 93(?):205-9. doi:
10.1289/ehp.9193205. [PMID: 1685443] - W Huber, B Kraupp-Grasl, H Esterbauer, R Schulte-Hermann. Role of oxidative stress in age dependent hepatocarcinogenesis by the peroxisome proliferator nafenopin in the rat.
Cancer research.
1991 Apr; 51(7):1789-92. doi:
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The American journal of physiology.
1991 Feb; 260(2 Pt 2):R278-83. doi:
10.1152/ajpregu.1991.260.2.r278. [PMID: 1996714] - K E Tomaszewski, S W Heindel, W L Jenkins, R L Melnick. Induction of peroxisomal acyl CoA oxidase activity and lipid peroxidation in primary rat hepatocyte cultures.
Toxicology.
1990 Dec; 65(1-2):49-60. doi:
10.1016/0300-483x(90)90078-u. [PMID: 2274969] - A G Smith, J E Francis, D G Walters, B G Lake. Protection against iron-induced uroporphyria in C57BL/10ScSn mice by the peroxisome proliferator nafenopin.
Biochemical pharmacology.
1990 Dec; 40(11):2564-8. doi:
10.1016/0006-2952(90)90102-q. [PMID: 2268375] - A M Stoddart, W G Levine. Azoreduction of dimethylaminoazobenzene (DAB) in primary cultures of rat hepatocytes. Effect of hypolipidemic agents.
Drug metabolism and disposition: the biological fate of chemicals.
1990 Jan; 18(1):36-41. doi:
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Toxicology letters.
1989 Feb; 45(2-3):221-9. doi:
10.1016/0378-4274(89)90013-1. [PMID: 2919403] - M Germer, P Bentley, W Stäubli, F Wächter. [Immunohistochemical localization of epoxide hydrolases in various organs of untreated and with nafenopin treated DBA/2 mice].
Acta histochemica. Supplementband.
1989; 37(?):199-201. doi:
NULL. [PMID: 2505313] - F Waechter, P Bentley, F Bieri, S Muakkassah-Kelly, W Stäubli, M Villermain. Organ distribution of epoxide hydrolases in cytosolic and microsomal fractions of normal and nafenopin-treated male DBA/2 mice.
Biochemical pharmacology.
1988 Oct; 37(20):3897-903. doi:
10.1016/0006-2952(88)90071-8. [PMID: 3190736] - E G Butler, P J England, G M Williams. Effect of peroxisome proliferating hypolipidemic agents on serum activity levels of arylesterase and cholinesterase in rats and mice.
Research communications in chemical pathology and pharmacology.
1988 Apr; 60(1):125-8. doi:
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Endocrinology.
1988 Mar; 122(3):1087-93. doi:
10.1210/endo-122-3-1087. [PMID: 3342745] - M N Milton, C R Elcombe, G E Kass, G G Gibson. Lack of evidence for a hepatic peroxisome proliferator receptor and an explanation for the binding of hypolipidaemic drugs to liver homogenates.
Biochemical pharmacology.
1988 Mar; 37(5):793-8. doi:
10.1016/0006-2952(88)90163-3. [PMID: 3345197] - J Seifert, H Mostecká. Effect of nafenopin and clofibrate on uptake and utilization of labeled thymidine for DNA synthesis in rat liver and kidney.
Carcinogenesis.
1988 Jan; 9(1):3-8. doi:
10.1093/carcin/9.1.3. [PMID: 2446797] - F Bieri, W Stäubli, S Kelly, F Waechter, P Bentley. Assessment of peroxisome proliferation and liver growth-stimulating potential by nondirectly genotoxic compounds in cultured hepatocytes.
Molecular toxicology.
1987 198; 1(4):439-44. doi:
NULL. [PMID: 3151502] - W Bursch, B Düsterberg, R Schulte-Hermann. Growth, regression and cell death in rat liver as related to tissue levels of the hepatomitogen cyproterone acetate.
Archives of toxicology.
1986 Dec; 59(4):221-7. doi:
10.1007/bf00290542. [PMID: 2435263] - K E Tomaszewski, D K Agarwal, R L Melnick. In vitro steady-state levels of hydrogen peroxide after exposure of male F344 rats and female B6C3F1 mice to hepatic peroxisome proliferators.
Carcinogenesis.
1986 Nov; 7(11):1871-6. doi:
10.1093/carcin/7.11.1871. [PMID: 3769136] - C Robba, G Mazzocchi, G Gottardo, G G Nussdorfer. Effects of the hypolipidemic drug nafenopin on the zona glomerulosa of the rat adrenal cortex: morphological counterparts of functional alterations.
Anatomischer Anzeiger.
1986; 161(1):35-41. doi:
. [PMID: 3010777] - O D Wiestler, I Schmerold, B Fringes, B Volk, P Kleihues. Nafenopin-induced rat liver peroxisome proliferation reduces DNA methylation by N-nitrosodimethylamine in vivo.
Carcinogenesis.
1985 Sep; 6(9):1309-13. doi:
10.1093/carcin/6.9.1309. [PMID: 4028330] - N D Lalwani, W E Fahl, J K Reddy. Detection of a nafenopin-binding protein in rat liver cytosol associated with the induction of peroxisome proliferation by hypolipidemic compounds.
Biochemical and biophysical research communications.
1983 Oct; 116(2):388-93. doi:
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Archives of biochemistry and biophysics.
1983 Apr; 222(1):123-32. doi:
10.1016/0003-9861(83)90509-x. [PMID: 6838215] - G Mazzocchi, C Robba, P Rebuffat, A S Belloni, G G Nussdorfer. Effects of the hypolipidemic drug nafenopin on the zona fasciculata of the rat adrenal cortex: a correlated biochemical and stereological study.
The Anatomical record.
1982 Nov; 204(3):245-54. doi:
10.1002/ar.1092040309. [PMID: 7158828] - D Charpentier, B Tuchweber. Increased hepatotoxicity of carbon tetrachloride by the hypolipidemic drug nafenopin in rats.
Research communications in chemical pathology and pharmacology.
1982 Jun; 36(3):449-61. doi:
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Annals of the New York Academy of Sciences.
1982; 386(?):138-52. doi:
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International journal of obesity.
1980; 4(1):1-10. doi:
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The Journal of biological chemistry.
1979 Jun; 254(12):4957-9. doi:
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Xenobiotica; the fate of foreign compounds in biological systems.
1979 Apr; 9(4):247-52. doi:
10.3109/00498257909038727. [PMID: 483860] - K Bjondahl. A study on cerium-induced liver injury in rats after pretreatment with spironolactone, phenobarbital, pregnenolone-16 alpha-carbonitrile and nafenopin.
Arzneimittel-Forschung.
1978; 28(5):817-9. doi:
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Laboratory investigation; a journal of technical methods and pathology.
1977 Nov; 37(5):479-86. doi:
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Virchows Archiv. B, Cell pathology.
1977 Oct; 25(2):161-9. doi:
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The Journal of pharmacology and experimental therapeutics.
1977 Jul; 202(1):8-21. doi:
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Medical biology.
1976 Dec; 54(6):454-60. doi:
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Archives internationales de pharmacodynamie et de therapie.
1976 Aug; 222(2):309-21. doi:
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The Journal of pharmacology and experimental therapeutics.
1976 Feb; 196(2):486-92. doi:
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Investigative ophthalmology.
1975 Nov; 14(11):866-72. doi:
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Il Farmaco; edizione scientifica.
1975 Oct; 30(10):847-58. doi:
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Biochemistry.
1975 Jun; 14(12):2749-54. doi:
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Drug metabolism and disposition: the biological fate of chemicals.
1975 May; 3(3):220-5. doi:
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Naunyn-Schmiedeberg's archives of pharmacology.
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Advances in experimental medicine and biology.
1975; 63(?):349-57. doi:
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Naunyn-Schmiedeberg's archives of pharmacology.
1975; 290(2-3):221-34. doi:
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Atherosclerosis.
1974 Sep; 20(2):141-53. doi:
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The Journal of cell biology.
1974 May; 61(2):344-58. doi:
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Biochemical pharmacology.
1974 Feb; 23(3):685-96. doi:
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Advances in experimental medicine and biology.
1973; 38(?):171-98. doi:
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Lipids.
1972 Oct; 7(10):644-52. doi:
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Advances in experimental medicine and biology.
1972; 26(0):113-33. doi:
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Atherosclerosis.
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