Ascofuranone (BioDeep_00000238067)

   

Chemicals and Drugs


代谢物信息卡片


Ascofuranone

化学式: C23H29ClO5 (420.17034140000004)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(c(c(c(c(c1O)Cl)C)C=O)O)C/C=C(/CC/C=C(/[C@@H]1OC(C(=O)C1)(C)C)\C)\C
InChI: InChI=1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1

描述信息

A dihydroxybenzaldehyde that is 2,4-dihydroxybenzaldehyde which is substituted by a (2E,6E)-7-[(2S)-5,5-dimethyl-4-oxotetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl group at position 3, chlorine at position 5, and a methyl group at position 6. A meroterpenoid produced by the soil fungus, Acremonium sclerotigenum. It is a promising drug candidate against the tropical disease, African trypanosomiasis.
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents

同义名列表

1 个代谢物同义名

Ascofuranone



数据库引用编号

8 个数据库交叉引用编号

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代谢反应

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  • 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。

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文献列表

  • Xiaomeng Hao, Shasha Li, Jun Ni, Guiyang Wang, Fang Li, Qin Li, Shuzhen Chen, Jicheng Shu, Maoluo Gan. Acremopeptaibols A-F, 16-Residue Peptaibols from the Sponge-Derived Acremonium sp. IMB18-086 Cultivated with Heat-Killed Pseudomonas aeruginosa. Journal of natural products. 2021 11; 84(11):2990-3000. doi: 10.1021/acs.jnatprod.1c00834. [PMID: 34781681]
  • Godwin U Ebiloma, Teresa Díaz Ayuga, Emmanuel O Balogun, Lucía Abad Gil, Anne Donachie, Marcel Kaiser, Tomás Herraiz, Daniel K Inaoka, Tomoo Shiba, Shigeharu Harada, Kiyoshi Kita, Harry P de Koning, Christophe Dardonville. Inhibition of trypanosome alternative oxidase without its N-terminal mitochondrial targeting signal (ΔMTS-TAO) by cationic and non-cationic 4-hydroxybenzoate and 4-alkoxybenzaldehyde derivatives active against T. brucei and T. congolense. European journal of medicinal chemistry. 2018 Apr; 150(?):385-402. doi: 10.1016/j.ejmech.2018.02.075. [PMID: 29544150]
  • Ryan A West, Oran G O'Doherty, Trevor Askwith, John Atack, Paul Beswick, Jamie Laverick, Michael Paradowski, Lewis E Pennicott, Srinivasa P S Rao, Gareth Williams, Simon E Ward. African trypanosomiasis: Synthesis & SAR enabling novel drug discovery of ubiquinol mimics for trypanosome alternative oxidase. European journal of medicinal chemistry. 2017 Dec; 141(?):676-689. doi: 10.1016/j.ejmech.2017.09.067. [PMID: 29107420]
  • Young-Chae Chang, Hyun-Ji Cho. Ascofuranone stimulates expression of adiponectin and peroxisome proliferator activated receptor through the modulation of mitogen activated protein kinase family members in 3T3-L1, murine pre-adipocyte cell line. Biochemical and biophysical research communications. 2012 Jun; 422(3):423-8. doi: 10.1016/j.bbrc.2012.05.008. [PMID: 22580003]
  • Kosuke Nakamura, Sunao Fujioka, Shinya Fukumoto, Noboru Inoue, Kimitoshi Sakamoto, Haruyuki Hirata, Yasutoshi Kido, Yoshisada Yabu, Takashi Suzuki, Yoh-ichi Watanabe, Hiroyuki Saimoto, Hiroshi Akiyama, Kiyoshi Kita. Trypanosome alternative oxidase, a potential therapeutic target for sleeping sickness, is conserved among Trypanosoma brucei subspecies. Parasitology international. 2010 Dec; 59(4):560-4. doi: 10.1016/j.parint.2010.07.006. [PMID: 20688188]
  • Vincenzo Cardinale, Domenico Alvaro. Ascofuranone: a possible therapeutic tool for autosomal dominant polycystic kidney disease?. Molecular cancer therapeutics. 2010 Nov; 9(11):3100; author reply 3101. doi: 10.1158/1535-7163.mct-10-0741. [PMID: 20978157]
  • Seung-Lark Hwang, Hyeun-Wook Chang, In-Kyu Lee, Byung-Keun Yang, Junji Magae, Young-Chae Chang. Ascofuranone prevents ER stress-induced insulin resistance via activation of AMP-activated protein kinase in L6 myotube cells. Biochemical and biophysical research communications. 2010 Jun; 396(4):967-72. doi: 10.1016/j.bbrc.2010.05.034. [PMID: 20460103]
  • Yasutoshi Kido, Kimitoshi Sakamoto, Kosuke Nakamura, Michiyo Harada, Takashi Suzuki, Yoshisada Yabu, Hiroyuki Saimoto, Fumiyuki Yamakura, Daijiro Ohmori, Anthony Moore, Shigeharu Harada, Kiyoshi Kita. Purification and kinetic characterization of recombinant alternative oxidase from Trypanosoma brucei brucei. Biochimica et biophysica acta. 2010 Apr; 1797(4):443-50. doi: 10.1016/j.bbabio.2009.12.021. [PMID: 20056101]
  • Jeong-Han Kang, Hyun-Ji Cho, In-Seon Lee, Moonkyu Kim, In-Kyu Lee, Young-Chae Chang. Comparative proteome analysis of TGF-beta1-induced fibrosis processes in normal rat kidney interstitial fibroblast cells in response to ascofuranone. Proteomics. 2009 Oct; 9(19):4445-56. doi: 10.1002/pmic.200800941. [PMID: 19688726]
  • Hyun-Ji Cho, Jeong-Han Kang, Teoan Kim, Kwang-Kyun Park, Cheorl-Ho Kim, In-Seon Lee, Kwan-Sik Min, Junji Magae, Hiroo Nakajima, Young-Seuk Bae, Young-Chae Chang. Suppression of PAI-1 expression through inhibition of the EGFR-mediated signaling cascade in rat kidney fibroblast by ascofuranone. Journal of cellular biochemistry. 2009 May; 107(2):335-44. doi: 10.1002/jcb.22130. [PMID: 19306296]
  • Akiko Tsuda, William H Witola, Kazuhiko Ohashi, Misao Onuma. Expression of alternative oxidase inhibits programmed cell death-like phenomenon in bloodstream form of Trypanosoma brucei rhodesiense. Parasitology international. 2005 Dec; 54(4):243-51. doi: 10.1016/j.parint.2005.06.007. [PMID: 16115792]
  • Takashi Suzuki, Coh-ichi Nihei, Yoshisada Yabu, Tetsuo Hashimoto, Mitsuko Suzuki, Ayako Yoshida, Kazuo Nagai, Tomoyoshi Hosokawa, Nobuko Minagawa, Shuichi Suzuki, Kiyoshi Kita, Nobuo Ohta. Molecular cloning and characterization of Trypanosoma vivax alternative oxidase (AOX) gene, a target of the trypanocide ascofuranone. Parasitology international. 2004 Sep; 53(3):235-45. doi: 10.1016/j.parint.2004.02.001. [PMID: 15468531]
  • Yoshihisa Fukai, Coichi Nihei, Keisuke Kawai, Yoshisada Yabu, Takasi Suzuki, Nobuo Ohta, Nobuko Minagawa, Kazuo Nagai, Kiyoshi Kita. Overproduction of highly active trypanosome alternative oxidase in Escherichia coli heme-deficient mutant. Parasitology international. 2003 Sep; 52(3):237-41. doi: 10.1016/s1383-5769(03)00007-2. [PMID: 14550479]
  • Coichi Nihei, Yoshihisa Fukai, Keisuke Kawai, Arihiro Osanai, Yoshisada Yabu, Takashi Suzuki, Nobuo Ohta, Nobuko Minagawa, Kazuo Nagai, Kiyoshi Kita. Purification of active recombinant trypanosome alternative oxidase. FEBS letters. 2003 Mar; 538(1-3):35-40. doi: 10.1016/s0014-5793(03)00120-0. [PMID: 12633849]
  • Coichi Nihei, Yoshihisa Fukai, Kiyoshi Kita. Trypanosome alternative oxidase as a target of chemotherapy. Biochimica et biophysica acta. 2002 Jul; 1587(2-3):234-9. doi: 10.1016/s0925-4439(02)00086-8. [PMID: 12084465]
  • Y Fukai, H Amino, H Hirawake, Y Yabu, N Ohta, N Minagawa, S Sakajo, A Yoshimoto, K Nagai, S Takamiya, S Kojima, K Kita. Functional expression of the ascofuranone-sensitive Trypanosoma brucei brucei alternative oxidase in the cytoplasmic membrane of Escherichia coli. Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology. 1999 Oct; 124(2):141-8. doi: 10.1016/s0742-8413(99)00040-7. [PMID: 10622429]
  • A S Trenin. [Hypolipidemic action of ascofuranone in hepatoblastoma G2 cell culture]. Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic]. 1999; 44(9):7-9. doi: ". [PMID: 10511901]
  • N Minagawa, Y Yabu, K Kita, K Nagai, N Ohta, K Meguro, S Sakajo, A Yoshimoto. An antibiotic, ascofuranone, specifically inhibits respiration and in vitro growth of long slender bloodstream forms of Trypanosoma brucei brucei. Molecular and biochemical parasitology. 1997 Feb; 84(2):271-80. doi: 10.1016/s0166-6851(96)02797-1. [PMID: 9084049]
  • N Minagawa, Y Yabu, K Kita, K Nagai, N Ohta, K Meguro, S Sakajo, A Yoshimoto. An antibiotic, ascofuranone, specifically inhibits respiration and in vitro growth of long slender bloodstream forms of Trypanosoma brucei brucei. Molecular and biochemical parasitology. 1996 Oct; 81(2):127-36. doi: 10.1016/0166-6851(96)02665-5. [PMID: 8898329]
  • J Magae, K Nagai, S Suzuki, M Yamasaki, K Ando, G Tamura. Macrophage-specific effect on lipid metabolism by an antibiotic, ascofuranone. The Journal of antibiotics. 1987 Feb; 40(2):202-8. doi: 10.7164/antibiotics.40.202. [PMID: 3570969]
  • J Magae, T Hosokawa, Y Matsuda, M Hotta, J Hayasaki, K Nagai, K Ando, M Yamasaki, G Tamura. Suppression of hypertriglyceridemia of Ehrlich carcinoma-bearing mice by an antibiotic, ascofuranone. Cancer research. 1987 Jan; 47(1):96-9. doi: NULL. [PMID: 3791222]
  • J Magae, M Hotta, K Nagai, S Suzuki, K Ando, M Yamasaki, G Tamura. Activation of natural cytotoxic activity and concomitant reduction of triglyceride content of murine spleen, treated with an antitumor antibiotic, ascofuranone. The Journal of antibiotics. 1986 May; 39(5):676-81. doi: 10.7164/antibiotics.39.676. [PMID: 3733517]
  • T Hosokawa, T Okutomi, M Sawada, K Ando, G Tamura. Unusual concentration of urine and prevention of polydipsia by fungal prenylphenols in DOCA hypertensive rats. European journal of pharmacology. 1981 Feb; 69(4):429-38. doi: 10.1016/0014-2999(81)90446-5. [PMID: 7018911]