canthinone (BioDeep_00001867566)

PANOMIX_OTCML-2023 Chemicals and Drugs Volatile Flavor Compounds

代谢物信息卡片

1,6-diazatetracyclo[7.6.1.0^{5,16.0^{10,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one

化学式: C14H8N2O (220.06365979999998)
中文名称: 铁屎米酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC=C2C(=C1)C3=C4N2C(=O)C=CC4=NC=C3
InChI: InChI=1S/C14H8N2O/c17-13-6-5-11-14-10(7-8-15-11)9-3-1-2-4-12(9)16(13)14/h1-8H

描述信息

Canthin-6-one is an indole alkaloid that is 6H-indolo[3,2,1-de][1,5]naphthyridine substituted by an oxo group at position 6. It has a role as a metabolite and an antimycobacterial drug. It is an indole alkaloid, an organic heterotetracyclic compound and an enone.
Canthin-6-one is a natural product found in Zanthoxylum mayu, Zanthoxylum ovalifolium, and other organisms with data available.
An indole alkaloid that is 6H-indolo[3,2,1-de][1,5]naphthyridine substituted by an oxo group at position 6.
D016573 - Agrochemicals
D010575 - Pesticides
Canthin-6-one displays a wide range of biological activities, such as antimycobacterial activity[1].
Canthin-6-one displays a wide range of biological activities, such as antimycobacterial activity[1].

同义名列表

16 个代谢物同义名

1,6-diazatetracyclo[7.6.1.0^{5,16.0^{10,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one; 1,6-diazatetracyclo[7.6.1.0?,??.0??,??]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one; 1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one; 6H-Indolo[3,2,1-de][1,5]naphthyridin-6-one; 6H-Indolo(3,2,1-de)(1,5)naphthyridin-6-one; Indolo[3,2,1-de][1,5]naphthyridin-6-one; ZERVJPYNQLONEK-UHFFFAOYSA-N; NCIOpen2_007333; UNII-3FK17S759N; Canthin-6-one; MEGxp0_000046; ACon0_001416; canthinone; 3FK17S759N; Canthin-6-one; Canthin-6-one

数据库引用编号

15 个数据库交叉引用编号

ChEBI: CHEBI:3363
KEGG: C15843
KEGG: C09098
PubChem: 97176
ChEMBL: CHEMBL156897
MeSH: canthin-6-one
ChemIDplus: 0000479436
CAS: 479-43-6
medchemexpress: HY-N3536
MetaboLights: MTBLC3363
PubChem: 11290
KNApSAcK: C00001701
3DMET: B02681
NIKKAJI: J12.535K
KNApSAcK: 3363

分类词条

生物碱

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)

32 个相关的物种来源信息

74896 - Allium neapolitanum: 10.1002/PTR.2136
459111 - Brucea antidysenterica:
210348 - Brucea javanica:
43723 - Brucea mollis: 10.1016/S0031-9422(00)89758-7
458531 - Eurycoma longifolia:
1762910 - Fagaropsis angolensis: 10.1017/S174275840001345X
106335 - Hibiscus syriacus: 10.1248/YAKUSHI1947.98.11_1508
459150 - Homalolepis ferruginea: 10.1016/J.JEP.2011.01.009
1226098 - Pentaceras australe: 10.1016/0305-1978(91)90117-I
68554 - Phellodendron amurense:
354508 - Phellodendron chinense:
459138 - Picrasma crenata: 10.1515/ZNB-2001-0316
459139 - Picrasma excelsa: 10.1055/S-0028-1097250
210334 - Picrasma quassioides: 10.1248/CPB.31.3198
459145 - Pierreodendron africanum: 10.1055/S-2006-960941
33090 - Plants: -
279516 - Pulveroboletus curtisii: 10.1002/EJOC.200400519
459167 - Quassia africana: 10.1021/NP50047A037
1899180 - Quassia undulata: 10.1055/S-2006-961467
459154 - Simaba orinocensis: 10.1016/S0031-9422(00)82492-9
459155 - Simaba polyphylla: 10.1590/1809-43921997274272
43729 - Simarouba glauca: 10.1002/PTR.1642
23808 - Simaroubaceae: 10.1055/S-0043-123349
2839964 - Zanthoxylum dimorphophyllum: 10.1515/ZNC-2001-7-802
1336649 - Zanthoxylum dipetalum:
681508 - Zanthoxylum ekmanii:
1056472 - Zanthoxylum mayu: 10.1055/S-2007-969890
1056474 - Zanthoxylum ovalifolium:
1056474 - Zanthoxylum ovalifolium: -
1752150 - Zanthoxylum piasezkii: 10.1007/S10600-018-2544-3
2099547 - Zanthoxylum viride:
2099548 - Zanthoxylum zanthoxyloides: 10.1055/S-0028-1097271

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

Rattanathorn Choonong, Jiranan Chaingam, Ruttanaporn Chantakul, Sirikan Mukda, Prapapan Temkitthawon, Kornkanok Ingkaninan, Thaweesak Juengwatanatrakul, Gorawit Yusakul, Tripetch Kanchanapoom, Waraporn Putalun. Phosphodiesterase-5 Inhibitory Activity of Canthin-6-One Alkaloids and the Roots of Eurycoma longifolia and Eurycoma harmandiana. Chemistry & biodiversity. 2022 Jul; 19(7):e202200121. doi: 10.1002/cbdv.202200121. [PMID: 35652145]
Bo Luo, Xinqiang Song. A comprehensive overview of β-carbolines and its derivatives as anticancer agents. European journal of medicinal chemistry. 2021 Nov; 224(?):113688. doi: 10.1016/j.ejmech.2021.113688. [PMID: 34332400]
Jiranan Chaingam, Thaweesak Juengwatanatrakul, Gorawit Yusakul, Tripetch Kanchanapoom, Waraporn Putalun. HPLC-UV-Based Simultaneous Determination of Canthin-6-One Alkaloids, Quassinoids, and Scopoletin: The Active Ingredients in Eurycoma Longifolia Jack and Eurycoma Harmandiana Pierre, and Their Anti-Inflammatory Activities. Journal of AOAC International. 2021 Jun; 104(3):802-810. doi: 10.1093/jaoacint/qsaa141. [PMID: 33064798]
Karuppusamy Arunachalam, Amilcar Sabino Damazo, Antonio Macho, Monica Steffi Matchado, Eduarda Pavan, Fabiana de Freitas Figueiredo, Darley Maria Oliveira, Carrie A Duckworth, Parimelazhagan Thangaraj, Marco Leonti, Domingos Tabajara de Oliveira Martins. Canthin-6-one ameliorates TNBS-induced colitis in rats by modulating inflammation and oxidative stress. An in vivo and in silico approach. Biochemical pharmacology. 2021 04; 186(?):114490. doi: 10.1016/j.bcp.2021.114490. [PMID: 33647259]
Leonidah Kerubo Omosa, Gacheru Martin Mbogo, Eric Korir, Ruth Omole, Ean-Jeong Seo, Abiy Yenesew, Matthias Heydenreich, Jacob Ogweno Midiwo, Thomas Efferth. Cytotoxicity of fagaramide derivative and canthin-6-one from Zanthoxylum (Rutaceae) species against multidrug resistant leukemia cells. Natural product research. 2021 Feb; 35(4):579-586. doi: 10.1080/14786419.2019.1587424. [PMID: 30896260]
Yongchun Li, Meirong Zhao, Zhi Zhang. Quantitative proteomics reveals the antifungal effect of canthin-6-one isolated from Ailanthus altissima against Fusarium oxysporum f. sp. cucumerinum in vitro. PloS one. 2021; 16(4):e0250712. doi: 10.1371/journal.pone.0250712. [PMID: 33891670]
Ying Zhang, Wei Zhao, Jingya Ruan, Nuttapong Wichai, Zheng Li, Lifeng Han, Yi Zhang, Tao Wang. Anti-inflammatory canthin-6-one alkaloids from the roots of Thailand Eurycoma longifolia Jack. Journal of natural medicines. 2020 Sep; 74(4):804-810. doi: 10.1007/s11418-020-01433-6. [PMID: 32638295]
Rafael Dos Santos Costa, Renan Fernandes do Espírito-Santo, Lucas Silva Abreu, Leonardo de Oliveira Aguiar, Dara Leite Fontes, Josean Fechine Tavares, Marcelo Sobral da Silva, Milena Botelho Pereira Soares, Eudes da Silva Velozo, Cristiane Flora Villarreal. Fluorescent Canthin-6-one Alkaloids from Simaba bahiensis: Isolation, Identification, and Cell-Labeling Properties. ChemPlusChem. 2019 03; 84(3):260-267. doi: 10.1002/cplu.201800591. [PMID: 31950762]
Vanessa Fátima Gazoni, Sikiru Olaitan Balogun, Karuppusamy Arunachalam, Darley Maria Oliveira, Valdir Cechinel Filho, Samara Rosolem Lima, Edson Moleta Colodel, Ilsamar Mendes Soares, Sérgio Donizeti Ascêncio, Domingos Tabajara de Oliveira Martins. Assessment of toxicity and differential antimicrobial activity of methanol extract of rhizome of Simaba ferruginea A. St.-Hil. and its isolate canthin-6-one. Journal of ethnopharmacology. 2018 Sep; 223(?):122-134. doi: 10.1016/j.jep.2018.05.014. [PMID: 29772356]
Carlos López, Manuel Pastrana, Alexandra Ríos, Alvaro Cogollo, Adriana Pabón. Huberine, a New Canthin-6-One Alkaloid from the Bark of Picrolemma huberi. Molecules (Basel, Switzerland). 2018 Apr; 23(4):. doi: 10.3390/molecules23040934. [PMID: 29673229]
Navriti Chadha, Om Silakari. Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view. European journal of medicinal chemistry. 2017 Jul; 134(?):159-184. doi: 10.1016/j.ejmech.2017.04.003. [PMID: 28412530]
Norazwana Samat, Mei Fong Ng, Hui Mei Lee, Sui Kiong Ling, Pei Jean Tan, Vyomesh Patel. Canthin-6-one Isolated from Bruceajavanica Root Blocks Cancer Cells in the G2/M phase and Synergizes with Cisplatin. Natural product communications. 2017 May; 12(5):771-778. doi: . [PMID: 30496663]
Gerardo Cebrián-Torrejón, Antonio Doménech-Carbó, Bruno Figadère, Erwan Poupon, Alain Fournet. Phytoelectrochemical analysis of Zanthoxylum chiloperone. Phytochemical analysis : PCA. 2017 May; 28(3):171-175. doi: 10.1002/pca.2657. [PMID: 27995663]
Heron F Vieira Torquato, Antonio C Ribeiro-Filho, Marcus V Buri, Roberto T Araújo Júnior, Renata Pimenta, José Salvador R de Oliveira, Valdir C Filho, Antonio Macho, Edgar J Paredes-Gamero, Domingos T de Oliveira Martins. Canthin-6-one induces cell death, cell cycle arrest and differentiation in human myeloid leukemia cells. Biochimica et biophysica acta. General subjects. 2017 Apr; 1861(4):958-967. doi: 10.1016/j.bbagen.2017.01.033. [PMID: 28161479]
Hong-Xia Fan, Zheng-Qun Zhou, Jun Peng, Bao-Jian Wu, He-Ru Chen, Xue-Feng Bao, Zhen-Qiang Mu, Wei-Hua Jiao, Xin-Sheng Yao, Hao Gao. A microbial model of mammalian metabolism: biotransformation of 4,5-dimethoxyl-canthin-6-one using Cunninghamella blakesleeana CGMCC 3.970. Xenobiotica; the fate of foreign compounds in biological systems. 2017 Apr; 47(4):284-289. doi: 10.1080/00498254.2016.1184774. [PMID: 27237303]
Hye Mi Kim, Su Jung Kim, Ha-Yeong Kim, Byeol Ryu, Hokwang Kwak, Jonghyun Hur, Jung-Hye Choi, Dae Sik Jang. Constituents of the stem barks of Ailanthus altissima and their potential to inhibit LPS-induced nitric oxide production. Bioorganic & medicinal chemistry letters. 2015 Mar; 25(5):1017-20. doi: 10.1016/j.bmcl.2015.01.034. [PMID: 25666824]
Chong Wu, Gui-Hua Deng, Chao-Zhan Lin, Chen-Chen Zhu. [Simultaneous determination of 4 alkaloids and a flavonoid in Picrasmae Ramulus et Folium by RP-HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 May; 39(9):1656-9. doi: . [PMID: 25095379]
Thi Van Anh Tran, Clemens Malainer, Stefan Schwaiger, Atanas G Atanasov, Elke H Heiss, Verena M Dirsch, Hermann Stuppner. NF-κB inhibitors from Eurycoma longifolia. Journal of natural products. 2014 Mar; 77(3):483-8. doi: 10.1021/np400701k. [PMID: 24467387]
Hui Chen, M A Shuang-Gang, Zhen-Feng Fang, Gui-Jie Zhang, Shi-Shan Yu, Xiao-Guang Chen. [A new indole alkaloid from the stems of Brucea mollis]. Yao xue xue bao = Acta pharmaceutica Sinica. 2014 Feb; 49(2):225-9. doi: . [PMID: 24761613]
Camille Dejos, Matthieu Régnacq, Marianne Bernard, Pierre Voisin, Thierry Bergès. The MFS-type efflux pump Flr1 induced by Yap1 promotes canthin-6-one resistance in yeast. FEBS letters. 2013 Sep; 587(18):3045-51. doi: 10.1016/j.febslet.2013.07.040. [PMID: 23912082]
H D Hollis Showalter. Progress in the synthesis of canthine alkaloids and ring-truncated congeners. Journal of natural products. 2013 Mar; 76(3):455-67. doi: 10.1021/np300753z. [PMID: 23311415]
Suzye Mireille Moladje Donkwe, Emmanuel Ngeufa Happi, Jean Duplex Wansi, Bruno Ndjakou Lenta, Krishna Prasad Devkota, Beate Neumann, Hans-Georg Stammler, Norbert Sewald. Oxidative burst inhibitory and cytotoxic activity of constituents of the fruits of Odyendyea gabonensis. Planta medica. 2012 Dec; 78(18):1949-56. doi: 10.1055/s-0032-1327878. [PMID: 23136063]
Elisângela Saturnino de Souza Almeida, Valdir Cechinel Filho, Rivaldo Niero, Bruna Kurz Clasen, Sikiru Olaitan Balogun, Domingos Tabajara de Oliveira Martins. Pharmacological mechanisms underlying the anti-ulcer activity of methanol extract and canthin-6-one of Simaba ferruginea A. St-Hil. in animal models. Journal of ethnopharmacology. 2011 Apr; 134(3):630-6. doi: 10.1016/j.jep.2011.01.009. [PMID: 21236329]
Mei-Xiang Jiang, Ying-Jun Zhou. Canthin-6-one alkaloids from Picrasma quassioides and their cytotoxic activity. Journal of Asian natural products research. 2008 Nov; 10(11-12):1009-12. doi: 10.1080/10286020802277956. [PMID: 19031238]
D Lagoutte, V Nicolas, E Poupon, A Fournet, R Hocquemiller, D Libong, P Chaminade, P M Loiseau. Antifungal canthin-6-one series accumulate in lipid droplets and affect fatty acid metabolism in Saccharomyces cerevisiae. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2008 Feb; 62(2):99-103. doi: 10.1016/j.biopha.2007.07.014. [PMID: 17888617]
Ping-Chung Kuo, Li-Shian Shi, Amooru G Damu, Chung-Ren Su, Chieh-Hung Huang, Chih-Huang Ke, Jin-Bin Wu, Ai-Jeng Lin, Kenneth F Bastow, Kuo-Hsiung Lee, Tian-Shung Wu. Cytotoxic and antimalarial beta-carboline alkaloids from the roots of Eurycoma longifolia. Journal of natural products. 2003 Oct; 66(10):1324-7. doi: 10.1021/np030277n. [PMID: 14575431]
Céline Thouvenel, Jean-Charles Gantier, Philippe Duret, Christophe Fourneau, Reynald Hocquemiller, Maria-Elena Ferreira, Antonieta Rojas de Arias, Alain Fournet. Antifungal compounds from Zanthoxylum chiloperone var. angustifolium. Phytotherapy research : PTR. 2003 Jun; 17(6):678-80. doi: 10.1002/ptr.1137. [PMID: 12820240]
M E Ferreira, A Rojas de Arias, S Torres de Ortiz, A Inchausti, H Nakayama, C Thouvenel, R Hocquemiller, A Fournet. Leishmanicidal activity of two canthin-6-one alkaloids, two major constituents of Zanthoxylum chiloperone var. angustifolium. Journal of ethnopharmacology. 2002 May; 80(2-3):199-202. doi: 10.1016/s0378-8741(02)00025-9. [PMID: 12007711]
Weidong He, Luc Van Puyvelde, Norbert De Kimpe, Luc Verbruggen, Kristel Anthonissen, Mark Van der Flaas, Jan Bosselaers, Simon G Mathenge, Francis P Mudida. Chemical constituents and biological activities of Zanthoxylum usambarense. Phytotherapy research : PTR. 2002 Feb; 16(1):66-70. doi: 10.1002/ptr.849. [PMID: 11807969]
L A Anderson, A Harris, J D Phillipson. Production of cytotoxic canthin-6-one alkaloids by Ailanthus altissima plant cell cultures. Journal of natural products. 1983 May; 46(3):374-8. doi: 10.1021/np50027a014. [PMID: 6619885]
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