Docebenone (BioDeep_00000004675)
Secondary id: BioDeep_00000629866
human metabolite blood metabolite Volatile Flavor Compounds
代谢物信息卡片
2-(12-hydroxydodeca-5,10-diyn-1-yl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
化学式: C21H26O3 (326.1881846)
中文名称: 多西苯醌
谱图信息:
最多检出来源 Rattus norvegicus(blood) 92.31%
分子结构信息
SMILES: CC1=C(C(=O)C(=C(C1=O)C)CCCCC#CCCCC#CCO)C
InChI: InChI=1S/C21H26O3/c1-16-17(2)21(24)19(18(3)20(16)23)14-12-10-8-6-4-5-7-9-11-13-15-22/h22H,5,7-10,12,14-15H2,1-3H3
描述信息
D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors
C471 - Enzyme Inhibitor > C1322 - Lipooxygenase Inhibitor
Docebenone (AA 861) is a potent, selective and orally active 5-LO (5-lipoxygenase) inhibitor.
同义名列表
13 个代谢物同义名
2-(12-hydroxydodeca-5,10-diyn-1-yl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione; 6-(12-Hydroxydodeca-5,10-diyn-1-yl)-2,3,5-trimethyl-1,4-benzoquinone; 2,3,5-Trimethyl-6-(12-hydroxy-5,10-dodecadiynyl)-1,4-benzoquinone; 2-(12-Hydroxydodeca-5,10-diynyl)-3,5,6-trimethyl-1,4-benzoquinone; 2-(12-Hydroxy-5,10-dodecadiynyl)-3,5,6-trimethyl-p-benzoquinone; AA861; Docebenone; Docebenonum; docebenone; Docebenona; AA-861; AA861; AA 861; AA861
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:2340
- KEGG: C01349
- KEGGdrug: D03882
- PubChem: 1967
- HMDB: HMDB0247732
- Metlin: METLIN65586
- chemspider: 1891
- CAS: 80809-81-0
- PMhub: MS000017224
- PubChem: 4554
- LipidMAPS: LMFA05000652
- NIKKAJI: J20.558C
- RefMet: Docebenone
- medchemexpress: HY-12886
- KNApSAcK: 2340
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
- Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040. [PMID: 33910017] - 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] - Jia Xiao, Emily C Liong, Hai Huang, Wing On Tse, Kam Shing Lau, Jingfei Pan, Amin A Nanji, Man Lung Fung, Feiyue Xing, George L Tipoe. Cyclooxygenase-1 serves a vital hepato-protective function in chemically induced acute liver injury.
Toxicological sciences : an official journal of the Society of Toxicology.
2015 Feb; 143(2):430-40. doi:
10.1093/toxsci/kfu244. [PMID: 25432964] - Lu Li, Yi-Rong Liu, Shan Gao, Jun-Feng Li, Shan-Shan Li, Dan-Dan Zhang, Shuang Liu, Li Bai, Su-Jun Zheng, Zhong-Ping Duan, Min Qi, Yu Chen. Inhibition of 5-lipoxygenase pathway attenuates acute liver failure by inhibiting macrophage activation.
Journal of immunology research.
2014; 2014(?):697560. doi:
10.1155/2014/697560. [PMID: 24987711] - Young Hee Nam, Arim Min, Seong Hoon Kim, Young Ah Lee, Kyeong Ah Kim, Kyoung-Ju Song, Myeong Heon Shin. Leukotriene B(4) receptors BLT1 and BLT2 are involved in interleukin-8 production in human neutrophils induced by Trichomonas vaginalis-derived secretory products.
Inflammation research : official journal of the European Histamine Research Society ... [et al.].
2012 Feb; 61(2):97-102. doi:
10.1007/s00011-011-0425-3. [PMID: 22215047] - Grzegorz A Czapski, Kinga Czubowicz, Robert P Strosznajder. Evaluation of the antioxidative properties of lipoxygenase inhibitors.
Pharmacological reports : PR.
2012; 64(5):1179-88. doi:
10.1016/s1734-1140(12)70914-3. [PMID: 23238474] - Sònia Roig-Pérez, Núria Cortadellas, Miquel Moretó, Ruth Ferrer. Intracellular mechanisms involved in docosahexaenoic acid-induced increases in tight junction permeability in Caco-2 cell monolayers.
The Journal of nutrition.
2010 Sep; 140(9):1557-63. doi:
10.3945/jn.109.120469. [PMID: 20660281] - Masamichi Okubo, Hiroki Yamanaka, Kimiko Kobayashi, Koichi Noguchi. Leukotriene synthases and the receptors induced by peripheral nerve injury in the spinal cord contribute to the generation of neuropathic pain.
Glia.
2010 Apr; 58(5):599-610. doi:
10.1002/glia.20948. [PMID: 19908283] - Christoph Andreas Reichel, Markus Rehberg, Max Lerchenberger, Nina Berberich, Peter Bihari, Alexander Georg Khandoga, Stefan Zahler, Fritz Krombach. Ccl2 and Ccl3 mediate neutrophil recruitment via induction of protein synthesis and generation of lipid mediators.
Arteriosclerosis, thrombosis, and vascular biology.
2009 Nov; 29(11):1787-93. doi:
10.1161/atvbaha.109.193268. [PMID: 19608967] - Flavia Radogna, Silvia Nuccitelli, Fabio Mengoni, Lina Ghibelli. Neuroprotection by melatonin on astrocytoma cell death.
Annals of the New York Academy of Sciences.
2009 Aug; 1171(?):509-13. doi:
10.1111/j.1749-6632.2009.04900.x. [PMID: 19723097] - Gláucia C Mello, Ivani A Desouza, Nádia S Mariano, Tatiane Ferreira, Maria Lígia R Macedo, Edson Antunes. Mechanisms involved in the rat peritoneal leukocyte migration induced by a Kunitz-type inhibitor isolated from Dimorphandra mollis seeds.
Toxicon : official journal of the International Society on Toxinology.
2009 Mar; 53(3):323-9. doi:
10.1016/j.toxicon.2008.12.002. [PMID: 19103216] - Ivani A Desouza, Carla F Franco-Penteado, Enilton A Camargo, Carmen S P Lima, Simone A Teixeira, Marcelo N Muscará, Gilberto De Nucci, Edson Antunes. Acute pulmonary inflammation induced by exposure of the airways to staphylococcal enterotoxin type B in rats.
Toxicology and applied pharmacology.
2006 Nov; 217(1):107-13. doi:
10.1016/j.taap.2006.07.001. [PMID: 16920168] - Tuan Trang, Benjamin McNaull, Remi Quirion, Khem Jhamandas. Involvement of spinal lipoxygenase metabolites in hyperalgesia and opioid tolerance.
European journal of pharmacology.
2004 Apr; 491(1):21-30. doi:
10.1016/j.ejphar.2004.03.022. [PMID: 15102529] - Jennifer L Walker, Joseph Loscalzo, Ying-Yi Zhang. 5-Lipoxygenase and human pulmonary artery endothelial cell proliferation.
American journal of physiology. Heart and circulatory physiology.
2002 Feb; 282(2):H585-93. doi:
10.1152/ajpheart.00003.2001. [PMID: 11788406] - G Hardy, F Stanke-Labesque, M Peoc'h, A Hakim, P Devillier, F Caron, S Morel, P Faure, S Halimi, G Bessard. Cysteinyl leukotrienes modulate angiotensin II constrictor effects on aortas from streptozotocin-induced diabetic rats.
Arteriosclerosis, thrombosis, and vascular biology.
2001 Nov; 21(11):1751-8. doi:
10.1161/hq1201.098769. [PMID: 11701461] - H Nomura, E Sato, S Koyama, M Haniuda, K Kubo, S Nagai, T Izumi. Histamine stimulates alveolar macrophages to release neutrophil and monocyte chemotactic activity.
The Journal of laboratory and clinical medicine.
2001 Oct; 138(4):226-35. doi:
10.1067/mlc.2001.117988. [PMID: 11574816] - G O Daglar, N A Kama, M Atli, Y N Yuksek, E Reis, M Doganay, M Dolapci, M Kologlu. Effect of 5-lipoxygenase inhibition on Kupffer cell clearance capacity in obstructive jaundiced rats.
The Journal of surgical research.
2001 Apr; 96(2):158-62. doi:
10.1006/jsre.2000.6058. [PMID: 11266267] - G Le Filliatre, S Sayah, V Latournerie, J F Renaud, M Finet, R Hanf. Cyclo-oxygenase and lipoxygenase pathways in mast cell dependent-neurogenic inflammation induced by electrical stimulation of the rat saphenous nerve.
British journal of pharmacology.
2001 Apr; 132(7):1581-9. doi:
10.1038/sj.bjp.0703950. [PMID: 11264253] - K Lutnicki, E Szpringer, K Czerny, A Ledwozyw. Effects of ethanol and arachidonic acid pathway inhibitors on the effectiveness of gastric mucosa cytoprotection.
Folia morphologica.
2001; 60(1):47-56. doi:
". [PMID: 11234698] - J K Huang, C R Jan. AA-861-induced Ca(2+) mobilization in Madin Darby canine kidney cells.
Toxicology and applied pharmacology.
1999 Dec; 161(2):202-8. doi:
10.1006/taap.1999.8802. [PMID: 10581214] - M Takami, W Tsukada. In vitro effect of DP-1904, a novel anti-asthma agent, against antigen-induced constriction and TXB2 release from the isolated guinea-pig lung parenchymal tissue.
Pharmacological research.
1998 Aug; 38(2):141-7. doi:
10.1006/phrs.1998.0346. [PMID: 9721602] - J Takasaki, Y Kawauchi, Y Masuho. Synergistic effect of type II phospholipase A2 and platelet-activating factor on Mac-1 surface expression and exocytosis of gelatinase granules in human neutrophils: evidence for the 5-lipoxygenase-dependent mechanism.
Journal of immunology (Baltimore, Md. : 1950).
1998 May; 160(10):5066-72. doi:
. [PMID: 9590257] - T Yamazaki, K Higuchi, S Kominami, S Takemori. 15-lipoxygenase metabolite(s) of arachidonic acid mediates adrenocorticotropin action in bovine adrenal steroidogenesis.
Endocrinology.
1996 Jul; 137(7):2670-5. doi:
10.1210/endo.137.7.8770885. [PMID: 8770885] - M Urade, R Izumi, H Kitagawa. Inhibition of 5-lipoxygenase promotes the regeneration of the liver after partial hepatectomy in normal and icteric rats.
Hepatology (Baltimore, Md.).
1996 Mar; 23(3):544-8. doi:
10.1053/jhep.1996.v23.pm0008617435. [PMID: 8617435] - T Nagao, T Kubo, R Fujimoto, H Nishio, T Takeuchi, F Hata. Ca(2+)-independent fusion of secretory granules with phospholipase A2-treated plasma membranes in vitro.
The Biochemical journal.
1995 Apr; 307 ( Pt 2)(?):563-9. doi:
10.1042/bj3070563. [PMID: 7537492] - S Kasayama, M Koga, H Kouhara, S Sumitani, K Wada, T Kishimoto, B Sato. Unsaturated fatty acids are required for continuous proliferation of transformed androgen-dependent cells by fibroblast growth factor family proteins.
Cancer research.
1994 Dec; 54(24):6441-5. doi:
NULL. [PMID: 7987840] - K Inoue, K Hamada, F Ueda, Y Shibata, K Kimura. Effect of anti-inflammatory agent etodolac on antigen-induced contractions of the trachea and lung parenchyma of guinea pigs.
Prostaglandins, leukotrienes, and essential fatty acids.
1994 Dec; 51(6):451-5. doi:
10.1016/0952-3278(94)90064-7. [PMID: 7708811] - T S Rao, S S Yu, S W Djuric, P C Isakson. Phorbol ester-induced dermal inflammation in mice: evaluation of inhibitors of 5-lipoxygenase and antagonists of leukotriene B4 receptor.
Journal of lipid mediators and cell signalling.
1994 Sep; 10(3):213-28. doi:
. [PMID: 7812673] - T Kobayashi, K Furukawa, M Onda. [The effect of arachidonic acid metabolite inhibitors on liver injury in endotoxin shock, with special reference to the role of polymorphonuclear leukocytes (PMNs)].
Nihon Ika Daigaku zasshi.
1994 Jun; 61(3):200-8. doi:
10.1272/jnms1923.61.200. [PMID: 8045994] - C R Chen, N F Voelkel, S W Chang. Platelet-activating factor potentiates protamine-induced lung edema. Role of eicosanoids.
American journal of respiratory and critical care medicine.
1994 Jan; 149(1):34-40. doi:
10.1164/ajrccm.149.1.8111595. [PMID: 8111595] - M Watanabe, Y Arakida, J Tanabe, A Sugidachi, N Hirasawa, S Mue, K Ohuchi. Pharmacological analysis of neutrophil chemotactic factor production by leucocytes and roles of PAF in allergic inflammation in rats.
British journal of pharmacology.
1994 Jan; 111(1):123-30. doi:
10.1111/j.1476-5381.1994.tb14033.x. [PMID: 8012688] - M Kiriyama, R Izumi, I Miyazaki. Protective effect of AA-861 (5-lipoxygenase inhibitor) on experimental acute necrotizing pancreatitis in rats.
International journal of pancreatology : official journal of the International Association of Pancreatology.
1993 Jun; 13(3):201-8. doi:
10.1007/bf02924441. [PMID: 7690378] - Y C Huang, T P Kennedy, Y F Su, W D Watkins, A R Whorton, C A Piantadosi. Protection against platelet-activating factor-induced injury by interferon inducer in perfused rabbit lung.
Journal of applied physiology (Bethesda, Md. : 1985).
1993 Jan; 74(1):251-8. doi:
10.1152/jappl.1993.74.1.251. [PMID: 8444700] - J M Dickenson, S J Hill. Adenosine A1-receptor stimulated increases in intracellular calcium in the smooth muscle cell line, DDT1MF-2.
British journal of pharmacology.
1993 Jan; 108(1):85-92. doi:
10.1111/j.1476-5381.1993.tb13444.x. [PMID: 8428218] - M Yoshikawa, E Uchida, N Chatani, N Murakami, J Yamahara. Thunberginols A, B, and F, new antiallergic and antimicrobial principles from hydrangeae dulcis folium.
Chemical & pharmaceutical bulletin.
1992 Nov; 40(11):3121-3. doi:
10.1248/cpb.40.3121. [PMID: 1477932] - J H Musser, A F Kreft. 5-lipoxygenase: properties, pharmacology, and the quinolinyl(bridged)aryl class of inhibitors.
Journal of medicinal chemistry.
1992 Jul; 35(14):2501-24. doi:
10.1021/jm00092a001. [PMID: 1635053] - T Yoshikawa, H Ichikawa, Y Naito, M Kondo. Role of leukotrienes in gastric mucosal injury induced by ischemia-reperfusion in rats.
Journal of clinical gastroenterology.
1992; 14 Suppl 1(?):S68-70. doi:
10.1097/00004836-199206001-00012. [PMID: 1629580] - B L Spangelo, W D Jarvis, A M Judd, R M MacLeod. Induction of interleukin-6 release by interleukin-1 in rat anterior pituitary cells in vitro: evidence for an eicosanoid-dependent mechanism.
Endocrinology.
1991 Dec; 129(6):2886-94. doi:
10.1210/endo-129-6-2886. [PMID: 1954875] - C A Herbert, D Edwards, J R Boot, C Robinson. In vitro modulation of the eosinophil-dependent enhancement of the permeability of the bronchial mucosa.
British journal of pharmacology.
1991 Oct; 104(2):391-8. doi:
10.1111/j.1476-5381.1991.tb12441.x. [PMID: 1797305] - W Ren, R Dziak. Effects of leukotrienes on osteoblastic cell proliferation.
Calcified tissue international.
1991 Sep; 49(3):197-201. doi:
10.1007/bf02556118. [PMID: 1657327] - S Miura, M Suematsu, S Tanaka, H Nagata, S Houzawa, M Suzuki, I Kurose, H Serizawa, M Tsuchiya. Microcirculatory disturbance in indomethacin-induced intestinal ulcer.
The American journal of physiology.
1991 Aug; 261(2 Pt 1):G213-9. doi:
10.1152/ajpgi.1991.261.2.g213. [PMID: 1651657] - F D Beusenberg, A van Schaik, J G van Amsterdam, I L Bonta. Involvement of eicosanoids in platelet-activating factor-induced modulation of adenylyl cyclase activity in alveolar macrophages.
Journal of lipid mediators.
1991 May; 3(3):301-9. doi:
". [PMID: 1663403] - Y Sakuma, H Tsunoda, S Katayama, S Abe, I Yamatsu, K Katayama. Determination of plasma leukotrienes in antigen-induced bronchoconstrictive guinea pigs.
Prostaglandins.
1991 Apr; 41(4):315-29. doi:
10.1016/0090-6980(91)90002-w. [PMID: 1651545] - S Ohkawa, S Terao, Z Terashita, Y Shibouta, K Nishikawa. Dual inhibitors of thromboxane A2 synthase and 5-lipoxygenase with scavenging activity of active oxygen species. Synthesis of a novel series of (3-pyridylmethyl)benzoquinone derivatives.
Journal of medicinal chemistry.
1991 Jan; 34(1):267-76. doi:
10.1021/jm00105a042. [PMID: 1992126] - N Kawada, Y Mizoguchi, K Kobayashi, S Yamamoto, S Morisawa. Arachidonic acid metabolites in carbon tetrachloride-induced liver injury.
Gastroenterologia Japonica.
1990 Jun; 25(3):363-8. doi:
10.1007/bf02779452. [PMID: 2113499] - T Shimazawa, H Nagai, A Koda, M Kasahara. The effects of thromboxane A2 inhibitors (OKY-046 and ONO-3708) and leukotriene inhibitors (AA-861 and LY-171883) on CCl4-induced chronic liver injury in mice.
Prostaglandins, leukotrienes, and essential fatty acids.
1990 May; 40(1):67-71. doi:
10.1016/0952-3278(90)90119-6. [PMID: 2119043] - M Watanabe, A Sugidachi, M Omata, N Hirasawa, S Mue, S Tsurufuji, K Ohuchi. Possible role for platelet-activating factor in neutrophil infiltration in allergic inflammation in rats.
International archives of allergy and applied immunology.
1990; 92(4):396-403. doi:
10.1159/000235171. [PMID: 2083975] - H Nagai, T Shimazawa, I Yakuo, M Aoki, A Koda, M Kasahara. Role of peptide-leukotrienes in liver injury in mice.
Inflammation.
1989 Dec; 13(6):673-80. doi:
10.1007/bf00914311. [PMID: 2575600] - T Imai, M Adachi, K Idaira, S Konno, T Takahashi, H Yamaguchi, C Saito, M Maeda, A Tuzi. [The effect of a selective 5-lipoxygenase inhibitor, AA-861 on airway hyperresponsiveness induced by ozone exposure in dogs].
Arerugi = [Allergy].
1989 Jul; 38(7):532-41. doi:
. [PMID: 2510702] - H Kato, M Inoue, Y Yamamura, M Tanigawa, H Sano, S Sugino, M Kondo. Mechanism of polymorphonuclear leukocytes accumulation examined using inhibitors of complement and arachidonic acid cascade in rats treated with OK-432.
Natural immunity and cell growth regulation.
1989; 8(5):290-300. doi:
. [PMID: 2512482] - J A van Hilten, G R Elliott, I L Bonta. Endogenous lipoxygenase metabolites mediate A23187 induced macrophage cytostasis towards P815 tumor cells in vitro.
Agents and actions.
1989 Jan; 26(1-2):170-2. doi:
10.1007/bf02126597. [PMID: 2496588] - M S Rohrbach, T Kreofsky, R A Rolstad, J A Russell. Tannin-mediated secretion of a neutrophil chemotactic factor from alveolar macrophages. Potential contribution to the acute pulmonary inflammatory reaction associated with byssinosis.
The American review of respiratory disease.
1989 Jan; 139(1):39-45. doi:
10.1164/ajrccm/139.1.39. [PMID: 2492174] - K Katayama, Y Sakuma, S Katayama. Generation of leukotrienes in guinea-pigs in vivo during antigen-induced bronchospasm.
Agents and actions. Supplements.
1988; 23(?):129-33. doi:
10.1007/978-3-0348-9156-1_9. [PMID: 3262988] - W Hagmann, A M Steffan, A Kirn, D Keppler. Leukotrienes as mediators in frog virus 3-induced hepatitis in rats.
Hepatology (Baltimore, Md.).
1987 Jul; 7(4):732-6. doi:
10.1002/hep.1840070419. [PMID: 3111968] - R Kato, S Yamamoto, T Nakadate. [Factors controlling tumor promotion induced by TPA].
Gan to kagaku ryoho. Cancer & chemotherapy.
1986 Mar; 13(3 Pt 2):782-9. doi:
NULL. [PMID: 3083783] - H Uzumaki, S Yamamoto, R Kato. Effects of lipoxygenase and cyclooxygenase inhibitors on the induction of ornithine decarboxylase by 12-O-tetradecanoylphorbol-13-acetate and isoproterenol in mouse tissues in vivo.
Carcinogenesis.
1986 Feb; 7(2):289-94. doi:
10.1093/carcin/7.2.289. [PMID: 3081271] - H Saito, A Hirai, Y Tamura, S Yoshida. The 5-lipoxygenase products can modulate the synthesis of platelet-activating factor (alkyl-acetyl GPC) in Ca-ionophore A23187-stimulated rat peritoneal macrophages.
Prostaglandins, leukotrienes, and medicine.
1985 Jun; 18(3):271-86. doi:
10.1016/0262-1746(85)90059-9. [PMID: 3927314]