Isoquinoline (BioDeep_00000002906)
Secondary id: BioDeep_00001867984
human metabolite
代谢物信息卡片
Isoquinoline conjugate acid
化学式: C9H7N (129.0578462)
中文名称: 异喹啉
谱图信息:
最多检出来源 Homo sapiens(blood) 9.04%
分子结构信息
SMILES: c(c2)cc(c1)c(c2)cnc1
InChI: InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
描述信息
Isoquinoline is a flavouring agent Being an analog of pyridine, isoquinoline is a weak base, with a pKb of 8.6. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3. Isoquinoline is a colorless hygroscopic liquid at room temperature with a penetrating, unpleasant odor. Impure samples can appear brownish, as is typical for nitrogen heterocycles. It crystallizes platelets that have a low solubility in water but dissolve well in ethanol, acetone, diethyl ether, carbon disulfide, and other common organic solvents. It is also soluble in dilute acids as the protonated derivative. Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in naturally occurring alkaloids including papaverine and morphine. The isoquinoline ring in these natural compound derives from the aromatic amino acid tyrosine
Flavouring agent
KEIO_ID I067
同义名列表
18 个代谢物同义名
Isoquinoline conjugate acid; Isoquinoline hydrochloride; Isoquinoline sulfate (1:1); Isoquinoline hydrobromide; Isoquinoline hydroiodide; 3,4-Benzopyridine; Benzo[c]pyridine; benzo(c)Pyridine; 2-Azanaphthalene; beta -Quinoline; beta-Quinoline; Benzopyridine; ISOQUINOLINE; Isochinolin; 2-Benzanine; 2-Benzazine; FEMA 2978; ISQ
数据库引用编号
25 个数据库交叉引用编号
- ChEBI: CHEBI:16092
- KEGG: C06323
- PubChem: 8405
- HMDB: HMDB0034244
- Metlin: METLIN44763
- DrugBank: DB04329
- ChEMBL: CHEMBL12315
- Wikipedia: Isoquinoline
- MetaCyc: ISOQUINOLINE
- KNApSAcK: C00055955
- foodb: FDB012557
- chemspider: 8098
- CAS: 2241982-85-2
- CAS: 119-65-3
- MoNA: KO003252
- MoNA: KO003255
- MoNA: KO003253
- MoNA: KO003254
- MoNA: KO003256
- PMhub: MS000006897
- PubChem: 8559
- PDB-CCD: ISQ
- 3DMET: B00931
- NIKKAJI: J43.394B
- RefMet: Isoquinoline
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)
6 个相关的物种来源信息
- 105884 Lonicera japonica: 10.3390/MOLECULES18021368
- 88149 Saccharina japonica: 10.3390/MOLECULES200712093
- 105884 Lonicera japonica: 10.3390/MOLECULES18021368
- 88149 Saccharina japonica: 10.3390/MOLECULES200712093
- 9606 Homo sapiens: -
- 569774 金线莲: -
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
- Erika Plazas, Mónica C Avila M, Diego R Muñoz, Luis E Cuca S. Natural isoquinoline alkaloids: Pharmacological features and multi-target potential for complex diseases.
Pharmacological research.
2022 03; 177(?):106126. doi:
10.1016/j.phrs.2022.106126. [PMID: 35151857] - Emmanoel V Costa, Liviane do N Soares, Jamal da Silva Chaar, Valdenizia R Silva, Luciano de S Santos, Hector H F Koolen, Felipe M A da Silva, Josean F Tavares, Gokhan Zengin, Milena B P Soares, Daniel P Bezerra. Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities.
Molecules (Basel, Switzerland).
2021 Jun; 26(12):. doi:
10.3390/molecules26123714. [PMID: 34207059] - Yang Huang, Tiejie Wang, Zhengjin Jiang. Fast analysis of alkaloids from different parts of Mahonia bealei (Fort.) Carr. studied for their anti-Alzheimer's activity using supercritical fluid chromatography.
Journal of separation science.
2021 May; 44(9):2006-2014. doi:
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Chemico-biological interactions.
2021 Jan; 334(?):109300. doi:
10.1016/j.cbi.2020.109300. [PMID: 33098838] - Huan Xia, Yitong Liu, Guiyang Xia, Yi Liu, Sheng Lin, Lijia Guo. Novel Isoquinoline Alkaloid Litcubanine A - A Potential Anti-Inflammatory Candidate.
Frontiers in immunology.
2021; 12(?):685556. doi:
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2020 10; 22(19):7439-7442. doi:
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Bioorganic chemistry.
2020 05; 98(?):103722. doi:
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2018 Oct; 130(?):6-16. doi:
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Electrophoresis.
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Die Pharmazie.
2012 Jul; 67(7):571-85. doi:
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Journal of medicinal chemistry.
2012 Jun; 55(12):5965-81. doi:
10.1021/jm3006806. [PMID: 22712432] - Phurpa Wangchuk, Paul A Keller, Stephen G Pyne, Thanapat Sastraruji, Malai Taweechotipatr, Roonglawan Rattanajak, Aunchalee Tonsomboon, Sumalee Kamchonwongpaisan. Phytochemical and biological activity studies of the Bhutanese medicinal plant Corydalis crispa.
Natural product communications.
2012 May; 7(5):575-80. doi:
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Bioorganic & medicinal chemistry.
2012 Apr; 20(8):2498-505. doi:
10.1016/j.bmc.2012.03.006. [PMID: 22459209] - Wei-Han Chueh, Jin-Yuarn Lin. Protective effect of berberine on serum glucose levels in non-obese diabetic mice.
International immunopharmacology.
2012 Mar; 12(3):534-8. doi:
10.1016/j.intimp.2012.01.003. [PMID: 22266065] - Fabien Caillé, Célia S Bonnet, Frédéric Buron, Sandrine Villette, Lothar Helm, Stéphane Petoud, Franck Suzenet, Eva Tóth. Isoquinoline-based lanthanide complexes: bright NIR optical probes and efficient MRI agents.
Inorganic chemistry.
2012 Feb; 51(4):2522-32. doi:
10.1021/ic202446e. [PMID: 22233349] - Jeong-Seok Hong, Yeun-Kyung Chu, Hyung Lee, Byung-Hoon Ahn, Jae-Hyung Park, Mi-Jung Kim, Sunghye Lee, Ho-Sang Ryoo, Jung-Hee Jang, Seong-Ryong Lee, Jong-Wook Park. Effects of berberine on hippocampal neuronal damage and matrix metalloproteinase-9 activity following transient global cerebral ischemia.
Journal of neuroscience research.
2012 Feb; 90(2):489-97. doi:
10.1002/jnr.22756. [PMID: 22052603] - Philip J Jensen, Noemi Halbrendt, Gennaro Fazio, Izabela Makalowska, Naomi Altman, Craig Praul, Siela N Maximova, Henry K Ngugi, Robert M Crassweller, James W Travis, Timothy W McNellis. Rootstock-regulated gene expression patterns associated with fire blight resistance in apple.
BMC genomics.
2012 Jan; 13(?):9. doi:
10.1186/1471-2164-13-9. [PMID: 22229964] - Yaou Shen, Zhou Jiang, Xiadong Yao, Zhiming Zhang, Haijian Lin, Maojun Zhao, Hailan Liu, Huanwei Peng, Shujun Li, Guangtang Pan. Genome expression profile analysis of the immature maize embryo during dedifferentiation.
PloS one.
2012; 7(3):e32237. doi:
10.1371/journal.pone.0032237. [PMID: 22448216] - Angela I Calderón, Johayra Simithy-Williams, Mahabir P Gupta. Antimalarial natural products drug discovery in Panama.
Pharmaceutical biology.
2012 Jan; 50(1):61-71. doi:
10.3109/13880209.2011.602417. [PMID: 22196582] - Takashi Sugane, Takahiko Tobe, Wataru Hamaguchi, Itsuro Shimada, Kyoichi Maeno, Junji Miyata, Takeshi Suzuki, Tetsuya Kimizuka, Takuma Morita, Shuichi Sakamoto, Shin-ichi Tsukamoto. Synthesis and biological evaluation of (4H-1,2,4-triazol-4-yl)isoquinoline derivatives as selective glycine transporter 1 inhibitors.
Bioorganic & medicinal chemistry.
2012 Jan; 20(1):34-41. doi:
10.1016/j.bmc.2011.11.038. [PMID: 22177408] - Wei Wei, Hongmin Zhao, Aili Wang, Ming Sui, Kun Liang, Haiyun Deng, Yukun Ma, Yajuan Zhang, Hongxiu Zhang, Yuanyuan Guan. A clinical study on the short-term effect of berberine in comparison to metformin on the metabolic characteristics of women with polycystic ovary syndrome.
European journal of endocrinology.
2012 Jan; 166(1):99-105. doi:
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Frontiers in oncology.
2012; 2(?):58. doi:
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TheScientificWorldJournal.
2012; 2012(?):859210. doi:
10.1100/2012/859210. [PMID: 22645460] - Qiao-Qin Huang, Jun-Long Bi, Qian-Yun Sun, Fu-Mei Yang, Yue-Hu Wang, Gui-Hua Tang, Fu-Wei Zhao, Huan Wang, Jin-Jin Xu, Edward J Kennelly, Chun-Lin Long, Ge-Fen Yin. Bioactive isoquinoline alkaloids from Corydalis saxicola.
Planta medica.
2012 Jan; 78(1):65-70. doi:
10.1055/s-0031-1280126. [PMID: 21858757] - Md Sarfaraj Hussain, Sheeba Fareed, Saba Ansari, Md Akhlaquer Rahman, Iffat Zareen Ahmad, Mohd Saeed. Current approaches toward production of secondary plant metabolites.
Journal of pharmacy & bioallied sciences.
2012 Jan; 4(1):10-20. doi:
10.4103/0975-7406.92725. [PMID: 22368394] - Sharanappa M Bagale, Adrienne S Brown, Melissa M Carballosa Gonzalez, Alberto Vitores, Teresa L Micotto, N S Saleesh Kumar, Ian D Hentall, James N Wilson. Fluorescent reporters of monoamine transporter distribution and function.
Bioorganic & medicinal chemistry letters.
2011 Dec; 21(24):7387-91. doi:
10.1016/j.bmcl.2011.10.007. [PMID: 22047697] - Tianjiong Lou, Zhongai Zhang, Zhilei Xi, Kang Liu, Lin Li, Baolin Liu, Fang Huang. Berberine inhibits inflammatory response and ameliorates insulin resistance in hepatocytes.
Inflammation.
2011 Dec; 34(6):659-67. doi:
10.1007/s10753-010-9276-2. [PMID: 21110076] - Chad E Cecil, Jeanine M Davis, Nadja B Cech, Scott M Laster. Inhibition of H1N1 influenza A virus growth and induction of inflammatory mediators by the isoquinoline alkaloid berberine and extracts of goldenseal (Hydrastis canadensis).
International immunopharmacology.
2011 Nov; 11(11):1706-14. doi:
10.1016/j.intimp.2011.06.002. [PMID: 21683808] - Yasuyuki Yamada, Tomotsugu Koyama, Fumihiko Sato. Basic helix-loop-helix transcription factors and regulation of alkaloid biosynthesis.
Plant signaling & behavior.
2011 Nov; 6(11):1627-30. doi:
10.4161/psb.6.11.17599. [PMID: 22067108] - Z-J Huang, Y Zeng, P Lan, P-H Sun, W-M Chen. Advances in structural modifications and biological activities of berberine: an active compound in traditional Chinese medicine.
Mini reviews in medicinal chemistry.
2011 Nov; 11(13):1122-9. doi:
10.2174/138955711797655362. [PMID: 22353221] - Ying Guo, Chad Pope, Xingguo Cheng, Honghao Zhou, Curtis D Klaassen. Dose-response of berberine on hepatic cytochromes P450 mRNA expression and activities in mice.
Journal of ethnopharmacology.
2011 Oct; 138(1):111-8. doi:
10.1016/j.jep.2011.08.058. [PMID: 21920422] - Mayurkumar B Patel, Shrihari Mishra. Hypoglycemic activity of alkaloidal fraction of Tinospora cordifolia.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2011 Sep; 18(12):1045-52. doi:
10.1016/j.phymed.2011.05.006. [PMID: 21665451] - Marianna A Patrauchan, J Jacob Parnell, Michael P McLeod, Christine Florizone, James M Tiedje, Lindsay D Eltis. Genomic analysis of the phenylacetyl-CoA pathway in Burkholderia xenovorans LB400.
Archives of microbiology.
2011 Sep; 193(9):641-50. doi:
10.1007/s00203-011-0705-x. [PMID: 21519854] - Tae Ho Lee, Ki Hyun Kim, Sung Ok Lee, Kang Ro Lee, Miwon Son, Mirim Jin. Tetrahydroberberine, an isoquinoline alkaloid isolated from corydalis tuber, enhances gastrointestinal motor function.
The Journal of pharmacology and experimental therapeutics.
2011 Sep; 338(3):917-24. doi:
10.1124/jpet.111.182048. [PMID: 21659472] - Waranya Chatuphonprasert, Thewtas Sangkawat, Nobuo Nemoto, Kanokwan Jarukamjorn. Suppression of beta-naphthoflavone induced CYP1A expression and lipid-peroxidation by berberine.
Fitoterapia.
2011 Sep; 82(6):889-95. doi:
10.1016/j.fitote.2011.05.002. [PMID: 21624442] - Maria Kulp, Olga Bragina, Priit Kogerman, Mihkel Kaljurand. Capillary electrophoresis with LED-induced native fluorescence detection for determination of isoquinoline alkaloids and their cytotoxicity in extracts of Chelidonium majus L.
Journal of chromatography. A.
2011 Aug; 1218(31):5298-304. doi:
10.1016/j.chroma.2011.06.016. [PMID: 21726876] - Wei-Han Chueh, Jin-Yuarn Lin. Berberine, an isoquinoline alkaloid in herbal plants, protects pancreatic islets and serum lipids in nonobese diabetic mice.
Journal of agricultural and food chemistry.
2011 Jul; 59(14):8021-7. doi:
10.1021/jf201627w. [PMID: 21696141] - Wen Tan, Jinjian Lu, Mingqing Huang, Yingbo Li, Meiwan Chen, Guosheng Wu, Jian Gong, Zhangfeng Zhong, Zengtao Xu, Yuanye Dang, Jiajie Guo, Xiuping Chen, Yitao Wang. Anti-cancer natural products isolated from chinese medicinal herbs.
Chinese medicine.
2011 Jul; 6(1):27. doi:
10.1186/1749-8546-6-27. [PMID: 21777476] - Hao Wu, Li-Bing Zhang, Li-Ming Du. Ionic liquid sensitized fluorescence determination of four isoquinoline alkaloids.
Talanta.
2011 Jul; 85(1):787-93. doi:
10.1016/j.talanta.2011.04.076. [PMID: 21645774] - Yasuyuki Yamada, Yasuhisa Kokabu, Kaori Chaki, Tadashi Yoshimoto, Mai Ohgaki, Sayumi Yoshida, Nobuhiko Kato, Tomotsugu Koyama, Fumihiko Sato. Isoquinoline alkaloid biosynthesis is regulated by a unique bHLH-type transcription factor in Coptis japonica.
Plant & cell physiology.
2011 Jul; 52(7):1131-41. doi:
10.1093/pcp/pcr062. [PMID: 21576193] - Qian Hou, Xu Tang, Hanqiang Liu, Junqi Tang, Ying Yang, Xiaohong Jing, Qian Xiao, Wen Wang, Xingchun Gou, Zongren Wang. Berberine induces cell death in human hepatoma cells in vitro by downregulating CD147.
Cancer science.
2011 Jul; 102(7):1287-92. doi:
10.1111/j.1349-7006.2011.01933.x. [PMID: 21443647] - Guo-Ying Zuo, Fan-Yan Meng, Jun Han, Xiao-Yan Hao, Gen-Chun Wang, Yun-Ling Zhang, Qing Zhang. In vitro activity of plant extracts and alkaloids against clinical isolates of extended-spectrum β-lactamase (ESBL)-producing strains.
Molecules (Basel, Switzerland).
2011 Jun; 16(7):5453-9. doi:
10.3390/molecules16075453. [PMID: 21712759] - Pravinkumar Bhutada, Yogita Mundhada, Kuldeep Bansod, Santosh Tawari, Shaktipal Patil, Pankaj Dixit, Sudhir Umathe, Dharmendra Mundhada. Protection of cholinergic and antioxidant system contributes to the effect of berberine ameliorating memory dysfunction in rat model of streptozotocin-induced diabetes.
Behavioural brain research.
2011 Jun; 220(1):30-41. doi:
10.1016/j.bbr.2011.01.022. [PMID: 21262264] - Ferenc Zsila, Judit Kámán, Borbála Bogányi, Dávid Józsvai. Binding of alkaloids into the S1 specificity pocket of α-chymotrypsin: evidence from induced circular dichroism spectra.
Organic & biomolecular chemistry.
2011 Jun; 9(11):4127-37. doi:
10.1039/c0ob01221a. [PMID: 21483967] - Nan Dong, Li-na Cheng, Xiu-lin Wang, Qin Li, Chuan-yu Dai, Zhu Tao. Significant fluorescence enhancement by supramolecular complex formation between berberine chloride and cucurbit(n=7)uril and its analytical application.
Talanta.
2011 May; 84(3):684-9. doi:
10.1016/j.talanta.2011.01.071. [PMID: 21482268] - Jakub Chlebek, Katerina Macáková, Lucie Cahlíkovi, Milan Kurfürst, Jirí Kunes, Lubomir Opletal. Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Corydalis cava (Fumariaceae).
Natural product communications.
2011 May; 6(5):607-10. doi:
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Biochimica et biophysica acta.
2011 May; 1814(5):657-63. doi:
10.1016/j.bbapap.2011.03.002. [PMID: 21420512] - Kristýna Pěnčíková, Jana Urbanová, Pavel Musil, Eva Táborská, Jana Gregorová. Seasonal variation of bioactive alkaloid contents in Macleaya microcarpa (Maxim.) Fedde.
Molecules (Basel, Switzerland).
2011 Apr; 16(4):3391-401. doi:
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Phytomedicine : international journal of phytotherapy and phytopharmacology.
2011 Apr; 18(6):533-8. doi:
10.1016/j.phymed.2010.08.012. [PMID: 20851588] - Sutapa Mahata, Alok C Bharti, Shirish Shukla, Abhishek Tyagi, Syed A Husain, Bhudev C Das. Berberine modulates AP-1 activity to suppress HPV transcription and downstream signaling to induce growth arrest and apoptosis in cervical cancer cells.
Molecular cancer.
2011 Apr; 10(?):39. doi:
10.1186/1476-4598-10-39. [PMID: 21496227] - Sean M Watts, Craig D Dodson, O J Reichman. The roots of defense: plant resistance and tolerance to belowground herbivory.
PloS one.
2011 Apr; 6(4):e18463. doi:
10.1371/journal.pone.0018463. [PMID: 21494690] - Weicheng Hu, Lingling Yu, Myeong-Hyeon Wang. Antioxidant and antiproliferative properties of water extract from Mahonia bealei (Fort.) Carr. leaves.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2011 Apr; 49(4):799-806. doi:
10.1016/j.fct.2010.12.001. [PMID: 21130829] - Philippe Rasoanaivo, Colin W Wright, Merlin L Willcox, Ben Gilbert. Whole plant extracts versus single compounds for the treatment of malaria: synergy and positive interactions.
Malaria journal.
2011 Mar; 10 Suppl 1(?):S4. doi:
10.1186/1475-2875-10-s1-s4. [PMID: 21411015]