Mitoflaxone (BioDeep_00000180982)

   

human metabolite blood metabolite


代谢物信息卡片


2-(4-oxo-2-phenyl-4H-chromen-8-yl)acetic acid

化学式: C17H12O4 (280.0736)
中文名称: 米托拉酮
谱图信息: 最多检出来源 Homo sapiens(blood) 77.27%

分子结构信息

SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=CC=CC(=C3O2)CC(=O)O
InChI: InChI=1S/C17H12O4/c18-14-10-15(11-5-2-1-3-6-11)21-17-12(9-16(19)20)7-4-8-13(14)17/h1-8,10H,9H2,(H,19,20)

描述信息

C26170 - Protective Agent > C275 - Antioxidant > C306 - Bioflavonoid
D000970 - Antineoplastic Agents
D007155 - Immunologic Factors

同义名列表

6 个代谢物同义名

2-(4-oxo-2-phenyl-4H-chromen-8-yl)acetic acid; 2-(4-oxo-2-Phenyl-4H-chromen-8-yl)acetate; (4-oxo-2-phenylchromen-8-yl)acetic acid; Flavone-8-acetic acid; Flavone acetic acid; mitoflaxone



数据库引用编号

5 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。

亚细胞结构定位 关联基因列表


文献列表

  • Toyoaki Hida, Motohiro Tamiya, Makoto Nishio, Nobuyuki Yamamoto, Tomonori Hirashima, Takeshi Horai, Hiromi Tanii, Michael M Shi, Ken Kobayashi, Yoshitsugu Horio. Phase I study of intravenous ASA404 (vadimezan) administered in combination with paclitaxel and carboplatin in Japanese patients with non-small cell lung cancer. Cancer science. 2011 Apr; 102(4):845-51. doi: 10.1111/j.1349-7006.2010.01839.x. [PMID: 21205086]
  • M J McKeage, J Von Pawel, M Reck, M B Jameson, M A Rosenthal, R Sullivan, D Gibbs, P N Mainwaring, M Serke, J-J Lafitte, C Chouaid, L Freitag, E Quoix. Randomised phase II study of ASA404 combined with carboplatin and paclitaxel in previously untreated advanced non-small cell lung cancer. British journal of cancer. 2008 Dec; 99(12):2006-12. doi: 10.1038/sj.bjc.6604808. [PMID: 19078952]
  • Peter Kovacic. Fundamental, electron transfer mechanism by pyrylium-type ions for the anticancer drugs 5,6-dimethylxanthenone-4-acetic acid (DMXAA) and flavone-8-acetic acid (FAA). Current medicinal chemistry. Anti-cancer agents. 2005 Sep; 5(5):501-6. doi: 10.2174/1568011054866919. [PMID: 16178775]
  • L Zhao, L-M Ching, P Kestell, B C Baguley. The antitumour activity of 5,6-dimethylxanthenone-4-acetic acid (DMXAA) in TNF receptor-1 knockout mice. British journal of cancer. 2002 Aug; 87(4):465-70. doi: 10.1038/sj.bjc.6600479. [PMID: 12177785]
  • Shufeng Zhou, Philip Kestell, Bruce C Baguley, James W Paxton. 5,6-dimethylxanthenone-4-acetic acid (DMXAA): a new biological response modifier for cancer therapy. Investigational new drugs. 2002 Aug; 20(3):281-95. doi: 10.1023/a:1016215015530. [PMID: 12201491]
  • J S Mruk, M W Webster, M Heras, J M Reid, D E Grill, J H Chesebro. Flavone-8-acetic acid (Flavonoid) profoundly reduces platelet-dependent thrombosis and vasoconstriction after deep arterial injury In vivo. Circulation. 2000 Jan; 101(3):324-8. doi: 10.1161/01.cir.101.3.324. [PMID: 10645930]
  • B C Baguley, L Zhuang, P Kestell. Increased plasma serotonin following treatment with flavone-8-acetic acid, 5,6-dimethylxanthenone-4-acetic acid, vinblastine, and colchicine: relation to vascular effects. Oncology research. 1997; 9(2):55-60. doi: NULL. [PMID: 9167186]
  • M E Watts, S Arnold, D J Chaplin. Changes in coagulation and permeability properties of human endothelial cells in vitro induced by TNF-alpha or 5,6 MeXAA. The British journal of cancer. Supplement. 1996 Jul; 27(?):S164-7. doi: NULL. [PMID: 8763872]
  • S A Hill, L E Sampson, D J Chaplin. Anti-vascular approaches to solid tumour therapy: evaluation of vinblastine and flavone acetic acid. International journal of cancer. 1995 Sep; 63(1):119-23. doi: 10.1002/ijc.2910630121. [PMID: 7558438]
  • J L Franco, P Ghosh, R H Wiltrout, C R Carter, A H Zea, N Momozaki, A C Ochoa, D L Longo, T J Sayers, K L Komschlies. Partial degradation of T-cell signal transduction molecules by contaminating granulocytes during protein extraction of splenic T cells from tumor-bearing mice. Cancer research. 1995 Sep; 55(17):3840-6. doi: NULL. [PMID: 7641202]
  • L K Webster, A G Ellis, P Kestell, G W Rewcastle. Metabolism and elimination of 5,6-dimethylxanthenone-4-acetic acid in the isolated perfused rat liver. Drug metabolism and disposition: the biological fate of chemicals. 1995 Mar; 23(3):363-8. doi: NULL. [PMID: 7628302]
  • M de Forni, G G Chabot, J P Armand, A Gouyette, M Klink-Alak, G Recondo. Phase I and pharmacology study of flavone acetic acid administered two or three times weekly without alkalinization. Cancer chemotherapy and pharmacology. 1995; 35(3):219-24. doi: 10.1007/bf00686551. [PMID: 7805180]
  • E Veszelovsky, N H Holford, L L Thomsen, R G Knowles, B C Baguley. Plasma nitrate clearance in mice: modeling of the systemic production of nitrate following the induction of nitric oxide synthesis. Cancer chemotherapy and pharmacology. 1995; 36(2):155-9. doi: 10.1007/bf00689201. [PMID: 7539338]
  • P Ghosh, A Sica, H A Young, J Ye, J L Franco, R H Wiltrout, D L Longo, N R Rice, K L Komschlies. Alterations in NF kappa B/Rel family proteins in splenic T-cells from tumor-bearing mice and reversal following therapy. Cancer research. 1994 Jun; 54(11):2969-72. doi: NULL. [PMID: 8187083]
  • M V Relling, R R Evans, S Groom, W R Crom, C B Pratt. Saturable elimination and saturable protein binding account for flavone acetic acid pharmacokinetics. Journal of pharmacokinetics and biopharmaceutics. 1993 Dec; 21(6):639-51. doi: 10.1007/bf01113499. [PMID: 8138891]
  • C Haworth, S M O'Reilly, E Chu, G J Rustin, M Feldmann. Flavone acetic acid (FAA) with recombinant interleukin-2 (rIL-2) in advanced malignant melanoma. III: Cytokine studies. British journal of cancer. 1993 Jun; 67(6):1346-50. doi: 10.1038/bjc.1993.249. [PMID: 8512819]
  • M R Stratford, G J Rustin, M F Dennis, R R Watfa, N Howells, S M O'Reilly. Flavone acetic acid (FAA) with recombinant interleukin-2 (rIL-2) in advanced malignant melanoma. IV: Pharmacokinetics and toxicity of flavone acetic acid and its metabolites. British journal of cancer. 1993 Jun; 67(6):1351-5. doi: 10.1038/bjc.1993.250. [PMID: 8512820]
  • S M O'Reilly, G J Rustin, K Farmer, M Burke, S Hill, J Denekamp. Flavone acetic acid (FAA) with recombinant interleukin-2 (rIL-2) in advanced malignant melanoma: I. Clinical and vascular studies. British journal of cancer. 1993 Jun; 67(6):1342-5. doi: 10.1038/bjc.1993.248. [PMID: 8512818]
  • E Veszelovszky, L L Thomsen, Z Li, B C Baguley. Flavone acetic acid and 5,6-dimethylxanthenone-4-acetic acid: relationship between plasma nitrate elevation and the induction of tumour necrosis. European journal of cancer (Oxford, England : 1990). 1993; 29A(3):404-8. doi: 10.1016/0959-8049(93)90396-w. [PMID: 8398341]
  • G G Chabot, D Branellec, A Sassi, J P Armand, A Gouyette, S Chouaib. Tumour necrosis factor-alpha plasma levels after flavone acetic acid administration in man and mouse. European journal of cancer (Oxford, England : 1990). 1993; 29A(5):729-33. doi: 10.1016/s0959-8049(05)80355-7. [PMID: 8471332]
  • B C Baguley, G Cole, L L Thomsen, Z Li. Serotonin involvement in the antitumour and host effects of flavone-8-acetic acid and 5,6-dimethylxanthenone-4-acetic acid. Cancer chemotherapy and pharmacology. 1993; 33(1):77-81. doi: 10.1007/bf00686027. [PMID: 8269593]
  • H Futami, L Eader, T T Back, E Gruys, H A Young, R H Wiltrout, B C Baguley. Cytokine induction and therapeutic synergy with interleukin-2 against murine renal and colon cancers by xanthenone-4-acetic acid derivatives. Journal of immunotherapy : official journal of the Society for Biological Therapy. 1992 Nov; 12(4):247-55. doi: 10.1097/00002371-199211000-00005. [PMID: 1477076]
  • L L Thomsen, B C Baguley, G J Rustin, S M O'Reilly. Flavone acetic acid (FAA) with recombinant interleukin-2 (TIL-2) in advanced malignant melanoma. II: Induction of nitric oxide production. British journal of cancer. 1992 Oct; 66(4):723-7. doi: 10.1038/bjc.1992.346. [PMID: 1419615]
  • T S Maughan, R Ward, I Dennis, D J Honess, P Workman, N M Bleehen. Tumour concentrations of flavone acetic acid (FAA) in human melanoma: comparison with mouse data. British journal of cancer. 1992 Sep; 66(3):579-82. doi: 10.1038/bjc.1992.317. [PMID: 1520597]
  • L L Thomsen, L M Ching, W R Joseph, B C Baguley, J B Gavin. Nitric oxide production in endotoxin-resistant C3H/HeJ mice stimulated with flavone-8-acetic acid and xanthenone-4-acetic acid analogues. Biochemical pharmacology. 1992 Jun; 43(11):2401-6. doi: 10.1016/0006-2952(92)90319-e. [PMID: 1610403]
  • R R Salup, D C Sicker, N Wolmark, R B Herberman, T R Hakala. Chemoimmunotherapy of metastatic murine renal cell carcinoma using flavone acetic acid and interleukin 2. The Journal of urology. 1992 Apr; 147(4):1120-3. doi: 10.1016/s0022-5347(17)37499-2. [PMID: 1552607]
  • I N Olver, L K Webster, J F Bishop, K H Stokes. A phase I and pharmacokinetic study of 12-h infusion of flavone acetic acid. Cancer chemotherapy and pharmacology. 1992; 29(5):354-60. doi: 10.1007/bf00686003. [PMID: 1551173]
  • G Thurston, K A Smith, J C Murray. Anticoagulant treatment does not affect the action of flavone acetic acid in tumour-bearing mice. British journal of cancer. 1991 Oct; 64(4):689-92. doi: 10.1038/bjc.1991.382. [PMID: 1911218]
  • J C Murray, M Clauss, J Denekamp, D Stern. Selective induction of endothelial cell tissue factor in the presence of a tumour-derived mediator: a potential mechanism of flavone acetic acid action in tumour vasculature. International journal of cancer. 1991 Sep; 49(2):254-9. doi: 10.1002/ijc.2910490219. [PMID: 1879970]
  • E Galligioni, M Quaia, A Spada, D Crivellari, D Favaro, R Sorio, R Talamini, M D'Incalci, P Allavena, G Damia. Natural killer (NK) and lymphokine activated killer (LAK) cell activity in patients (PTS) treated with flavone acetic acid (FAA). Annals of oncology : official journal of the European Society for Medical Oncology. 1991 Feb; 2(2):145-50. doi: 10.1093/oxfordjournals.annonc.a057879. [PMID: 2054317]
  • K A Havlin, J G Kuhn, J B Craig, D H Boldt, G R Weiss, J Koeller, G Harman, R Schwartz, G N Clark, D D Von Hoff. Phase I clinical and pharmacokinetic trial of flavone acetic acid. Journal of the National Cancer Institute. 1991 Jan; 83(2):124-8. doi: 10.1093/jnci/83.2.124. [PMID: 1703237]
  • L L Thomsen, L M Ching, L Zhuang, J B Gavin, B C Baguley. Tumor-dependent increased plasma nitrate concentrations as an indication of the antitumor effect of flavone-8-acetic acid and analogues in mice. Cancer research. 1991 Jan; 51(1):77-81. doi: NULL. [PMID: 1988109]
  • J C Murray, K A Smith, D M Stern. Flavone acetic acid potentiates the induction of endothelial procoagulant activity by tumour necrosis factor. European journal of cancer (Oxford, England : 1990). 1991; 27(6):765-70. doi: 10.1016/0277-5379(91)90185-g. [PMID: 1829921]
  • M J McKeage, P Kestell, W A Denny, B C Baguley. Plasma pharmacokinetics of the antitumour agents 5,6-dimethylxanthenone-4-acetic acid, xanthenone-4-acetic acid and flavone-8-acetic acid in mice. Cancer chemotherapy and pharmacology. 1991; 28(6):409-13. doi: 10.1007/bf00685815. [PMID: 1934244]
  • M C Bibby, R M Phillips, J A Double, G Pratesi. Anti-tumour activity of flavone acetic acid (NSC 347512) in mice--influence of immune status. British journal of cancer. 1991 Jan; 63(1):57-62. doi: 10.1038/bjc.1991.12. [PMID: 1989665]
  • H Futami, R L Hornung, T T Back, R Bull, E Gruys, R H Wiltrout. Systemic alkalinization inhibits the ability of flavone acetic acid to augment natural killer activity, induce cytokine gene expression, and synergize with interleukin 2 for the treatment of murine renal cancer. Cancer research. 1990 Dec; 50(24):7926-31. doi: NULL. [PMID: 2253233]
  • V Mahadevan, S T Malik, A Meager, W Fiers, G P Lewis, I R Hart. Role of tumor necrosis factor in flavone acetic acid-induced tumor vasculature shutdown. Cancer research. 1990 Sep; 50(17):5537-42. doi: NULL. [PMID: 2386959]
  • T J Sayers, T A Wiltrout, K McCormick, C Husted, R H Wiltrout. Antitumor effects of alpha-interferon and gamma-interferon on a murine renal cancer (Renca) in vitro and in vivo. Cancer research. 1990 Sep; 50(17):5414-20. doi: NULL. [PMID: 2117482]
  • K F Mace, R L Hornung, R H Wiltrout, H A Young. Correlation between in vivo induction of cytokine gene expression by flavone acetic acid and strict dose dependency and therapeutic efficacy against murine renal cancer. Cancer research. 1990 Mar; 50(6):1742-7. doi: NULL. [PMID: 1689611]
  • J Brodfuehrer, F Valeriote, K Chan, L Heilbrun, T Corbett. Flavone acetic acid and plasma protein binding. Cancer chemotherapy and pharmacology. 1990; 27(1):27-32. doi: 10.1007/bf00689272. [PMID: 2245490]
  • J C Murray, K A Smith, G Thurston. Flavone acetic acid induces a coagulopathy in mice. British journal of cancer. 1989 Nov; 60(5):729-33. doi: 10.1038/bjc.1989.348. [PMID: 2803949]
  • J Cummings, J A Double, M C Bibby, P Farmer, S Evans, D J Kerr, S B Kaye, J F Smyth. Characterization of the major metabolites of flavone acetic acid and comparison of their disposition in humans and mice. Cancer research. 1989 Jul; 49(13):3587-93. doi: NULL. [PMID: 2731178]
  • M C Bibby, J A Double, P M Loadman, C V Duke. Reduction of tumor blood flow by flavone acetic acid: a possible component of therapy. Journal of the National Cancer Institute. 1989 Feb; 81(3):216-20. doi: 10.1093/jnci/81.3.216. [PMID: 2911084]
  • G G Chabot, M C Bissery, T H Corbett, K Rutkowski, L H Baker. Pharmacodynamics and causes of dose-dependent pharmacokinetics of flavone-8-acetic acid (LM-975; NSC-347512) in mice. Cancer chemotherapy and pharmacology. 1989; 24(1):15-22. doi: 10.1007/bf00254099. [PMID: 2597279]
  • J Cassidy, D J Kerr, A Setanoians, D S Zaharko, S B Kaye. Could interspecies differences in the protein binding of flavone acetic acid contribute to the failure to predict lack of efficacy in patients?. Cancer chemotherapy and pharmacology. 1989; 23(6):397-400. doi: 10.1007/bf00435845. [PMID: 2713962]
  • G G Chabot, M C Bissery, A Gouyette. Flavone acetic acid (LM-975; NSC-347512) activation to cytotoxic species in vivo and in vitro. Cancer chemotherapy and pharmacology. 1989; 24(5):273-6. doi: 10.1007/bf00304757. [PMID: 2758556]
  • M C Bibby, R M Phillips, J A Double. Influence of site on the chemosensitivity of transplantable murine colon tumours to flavone acetic acid (LM975, NSC 347512). Cancer chemotherapy and pharmacology. 1989; 24(2):87-94. doi: 10.1007/bf00263126. [PMID: 2731316]
  • R L Hornung, T C Back, D S Zaharko, W J Urba, D L Longo, R H Wiltrout. Augmentation of natural killer activity, induction of IFN and development tumor immunity during the successful treatment of established murine renal cancer using flavone acetic acid and IL-2. Journal of immunology (Baltimore, Md. : 1950). 1988 Nov; 141(10):3671-9. doi: NULL. [PMID: 2460546]
  • R B Weiss, R F Greene, R D Knight, J M Collins, J J Pelosi, A Sulkes, G A Curt. Phase I and clinical pharmacology study of intravenous flavone acetic acid (NSC 347512). Cancer research. 1988 Oct; 48(20):5878-82. doi: NULL. [PMID: 3167843]
  • R L Hornung, H A Young, W J Urba, R H Wiltrout. Immunomodulation of natural killer cell activity by flavone acetic acid: occurrence via induction of interferon alpha/beta. Journal of the National Cancer Institute. 1988 Oct; 80(15):1226-31. doi: 10.1093/jnci/80.15.1226. [PMID: 3418728]
  • J Cummings, D J Kerr, S B Kaye, J F Smyth. Optimisation of a reversed-phase high-performance liquid chromatographic method for the determination of flavone acetic acid and its major human metabolites in plasma and urine. Journal of chromatography. 1988 Sep; 431(1):77-85. doi: 10.1016/s0378-4347(00)83071-6. [PMID: 3235538]
  • G Pratesi, C Manzotti, G Damia, M D'Incalci. Response of chemically induced primary colon tumours of the mouse to flavone acetic acid (NSC 347 512). British journal of cancer. 1988 Aug; 58(2):144-6. doi: 10.1038/bjc.1988.181. [PMID: 3166904]
  • R H Wiltrout, M R Boyd, T C Back, R R Salup, J A Arthur, R L Hornung. Flavone-8-acetic acid augments systemic natural killer cell activity and synergizes with IL-2 for treatment of murine renal cancer. Journal of immunology (Baltimore, Md. : 1950). 1988 May; 140(9):3261-5. doi: NULL. [PMID: 3258894]
  • G Damia, M L Zanette, C Rossi, R Mandelli, A Ferrari, M D'Incalci. Dose-dependent pharmacokinetics of flavone acetic acid in mice. Cancer chemotherapy and pharmacology. 1988; 22(1):47-50. doi: 10.1007/bf00254180. [PMID: 3396145]
  • D J Kerr, S B Kaye, J Cassidy, C Bradley, E M Rankin, L Adams, A Setanoians, T Young, G Forrest, M Soukop. Phase I and pharmacokinetic study of flavone acetic acid. Cancer research. 1987 Dec; 47(24 Pt 1):6776-81. doi: NULL. [PMID: 3677106]
  • L S Capolongo, G Balconi, P Ubezio, R Giavazzi, G Taraboletti, A Regonesi, O C Yoder, M D'Incalci. Antiproliferative properties of flavone acetic acid (NSC 347512) (LM 975), a new anticancer agent. European journal of cancer & clinical oncology. 1987 Oct; 23(10):1529-35. doi: 10.1016/0277-5379(87)90096-4. [PMID: 3678316]
  • W A Schroyens, P F Dodion, C Sanders, M Loos, N E Dethier, A R Delforge, P A Stryckmans, Y Kenis. In vitro chemosensitivity testing of flavone acetic acid (LM975; NSC 347512) and its diethylaminoethyl ester derivative (LM985; NSC 293015). European journal of cancer & clinical oncology. 1987 Aug; 23(8):1135-9. doi: 10.1016/0277-5379(87)90146-5. [PMID: 3653209]
  • M C Bibby, J A Double, R M Phillips, P M Loadman. Factors involved in the anti-cancer activity of the investigational agents LM985 (flavone acetic acid ester) and LM975 (flavone acetic acid). British journal of cancer. 1987 Feb; 55(2):159-63. doi: 10.1038/bjc.1987.32. [PMID: 3814485]
  • D S Zaharko, C K Grieshaber, J Plowman, J C Cradock. Therapeutic and pharmacokinetic relationships of flavone acetic acid: an agent with activity against solid tumors. Cancer treatment reports. 1986 Dec; 70(12):1415-21. doi: NULL. [PMID: 3791254]