Ellipticine (BioDeep_00000017215)

 

Secondary id: BioDeep_00000867284

human metabolite PANOMIX_OTCML-2023 blood metabolite natural product


代谢物信息卡片


5,11-dimethyl-6H-pyrido[4,3-b]carbazole

化学式: C17H14N2 (246.1156924)
中文名称: 玫瑰树碱, 椭圆玫瑰树碱, 椭圆玫瑰树碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.56%

Reviewed

Last reviewed on 2024-06-29.

Cite this Page

Ellipticine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/ellipticine (retrieved 2024-11-03) (BioDeep RN: BioDeep_00000017215). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC1=C(C=NC=C2)C2=C(C)C(N3)=C1C4=C3C=CC=C4
InChI: InChI=1S/C17H14N2/c1-10-14-9-18-8-7-12(14)11(2)17-16(10)13-5-3-4-6-15(13)19-17/h3-9,19H,1-2H3

描述信息

Ellipticine is a organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11. It has a role as an antineoplastic agent and a plant metabolite. It is an organic heterotetracyclic compound, an organonitrogen heterocyclic compound, a polycyclic heteroarene and an indole alkaloid.
Ellipticine is a potent antineoplastic agent.
Ellipticine is a natural product found in Asparagus cochinchinensis, Aspergillus sclerotiorum, and other organisms with data available.
A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.

Ellipticine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=519-23-3 (retrieved 2024-06-29) (CAS RN: 519-23-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Ellipticine (NSC 71795) is a potent antineoplastic agent; inhibits DNA topoisomerase II activities.
Ellipticine (NSC 71795) is a potent antineoplastic agent; inhibits DNA topoisomerase II activities.

同义名列表

31 个代谢物同义名

5-23-09-00417 (Beilstein Handbook Reference); 6H-Pyrido[4,3-b]carbazole, 5,11-dimethyl-; 6H-Pyrido(4,3-b)carbazole, 5,11-dimethyl-; 5,11-dimethyl-2H-pyrido[4,3-b]carbazole; 5,11-dimethyl-6H-pyrido(4,3-b)carbazole; 5,11-Dimethyl-6H-pyrido[4,3-b]carbazole; 5,11-Dimethylpyrido[4,3-b]carbazole; WLN: T D6 B656 FN LMJ C1 J1; CTSPAMFJBXKSOY-UHFFFAOYSA-N; ellipticine hydrochloride; Ellipticine, synthetic; ellipticine tartrate; Prestwick3_000614; Prestwick1_000614; Prestwick0_000614; Prestwick2_000614; ELLIPTICINE [MI]; ellipticine, HCl; 5,3-b]carbazole; Probes2_000130; Probes1_000152; BPBio1_000604; Lopac0_000531; NCI60_040685; Tox21_500531; Elliptisine; Ellipticine; elliptecine; Ellipticin; CP 5; NSC 71795



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

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)

31 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]
  • Hongyan Ma, Huiyun Liang, Shengxin Cai, Barry R O'Keefe, Susan L Mooberry, Robert H Cichewicz. An Integrated Strategy for the Detection, Dereplication, and Identification of DNA-Binding Biomolecules from Complex Natural Product Mixtures. Journal of natural products. 2021 03; 84(3):750-761. doi: 10.1021/acs.jnatprod.0c00946. [PMID: 33226219]
  • Patcharee Arsakhant, Uthaiwan Sirion, Arthit Chairoungdua, Kanoknetr Suksen, Pawinee Piyachaturawat, Apichart Suksamrarn, Rungnapha Saeeng. Design and synthesis of C-12 dithiocarbamate andrographolide analogues as an anticancer agent. Bioorganic & medicinal chemistry letters. 2020 07; 30(14):127263. doi: 10.1016/j.bmcl.2020.127263. [PMID: 32527561]
  • Xingli Li, Chenxian Ye, Mubarak Mulati, Lei Sun, Feng Qian. Ellipticine blocks synergistic effects of IL-17A and TNF-α in epithelial cells and alleviates severe acute pancreatitis-associated acute lung injury. Biochemical pharmacology. 2020 07; 177(?):113992. doi: 10.1016/j.bcp.2020.113992. [PMID: 32335141]
  • Jittra Kornsakulkarn, Somporn Palasarn, Wilunda Choowong, Tienthong Thongpanchang, Nattawut Boonyuen, Rattaket Choeyklin, Thitiya Boonpratuang, Masahiko Isaka, Chawanee Thongpanchang. Antimalarial 9-Methoxystrobilurins, Oudemansins, and Related Polyketides from Cultures of Basidiomycete Favolaschia Species. Journal of natural products. 2020 04; 83(4):905-917. doi: 10.1021/acs.jnatprod.9b00647. [PMID: 32193929]
  • Zhi Xu, Shi-Jia Zhao, Yi Liu. 1,2,3-Triazole-containing hybrids as potential anticancer agents: Current developments, action mechanisms and structure-activity relationships. European journal of medicinal chemistry. 2019 Dec; 183(?):111700. doi: 10.1016/j.ejmech.2019.111700. [PMID: 31546197]
  • Parichat Suebsakwong, Jie Wang, Phorntip Khetkam, Natthida Weerapreeyakul, Jing Wu, Yun Du, Zhu-Jun Yao, Jian-Xin Li, Apichart Suksamrarn. A Bioreductive Prodrug of Cucurbitacin B Significantly Inhibits Tumor Growth in the 4T1 Xenograft Mice Model. ACS medicinal chemistry letters. 2019 Oct; 10(10):1400-1406. doi: 10.1021/acsmedchemlett.9b00161. [PMID: 31620225]
  • Yao-Hao Xu, Wei Li, Yong Rao, Zhi-Shu Huang, Sheng Yin. Pyridocarbazole alkaloids from Ochrosia borbonica: lipid-lowering agents inhibit the cell proliferation and adipogenesis of 3T3-L1 adipocyte via intercalating into supercoiled DNA. Chinese journal of natural medicines. 2019 Sep; 17(9):663-671. doi: 10.1016/s1875-5364(19)30080-9. [PMID: 31526501]
  • Lei Zhang, Jiang Xu, Feng Wang, Yong Ding, Toby Wang, Grace Jin, Matthew Martz, Zhongzheng Gui, Pingkai Ouyang, P Chen. Histidine-Rich Cell-Penetrating Peptide for Cancer Drug Delivery and Its Uptake Mechanism. Langmuir : the ACS journal of surfaces and colloids. 2019 03; 35(9):3513-3523. doi: 10.1021/acs.langmuir.8b03175. [PMID: 30673275]
  • Sudarat Sombut, Rada Bunthawong, Uthaiwan Sirion, Teerapich Kasemsuk, Pawinee Piyachaturawat, Kanoknetr Suksen, Apichart Suksamrarn, Rungnapha Saeeng. Synthesis of 14-deoxy-11,12-didehydroandrographolide analogues as potential cytotoxic agents for cholangiocarcinoma. Bioorganic & medicinal chemistry letters. 2017 12; 27(23):5139-5143. doi: 10.1016/j.bmcl.2017.10.063. [PMID: 29097170]
  • Sara Cruz-Morales, Jhon Castañeda-Gómez, Daniel Rosas-Ramírez, Mabel Fragoso-Serrano, Gabriela Figueroa-González, Argelia Lorence, Rogelio Pereda-Miranda. Resin Glycosides from Ipomoea alba Seeds as Potential Chemosensitizers in Breast Carcinoma Cells. Journal of natural products. 2016 Dec; 79(12):3093-3104. doi: 10.1021/acs.jnatprod.6b00782. [PMID: 28006904]
  • Sakchai Hongthong, Jatuporn Meesin, Phanruethai Pailee, Darunee Soorukram, Palangpon Kongsaeree, Samran Prabpai, Pawinee Piyachaturawat, Surawat Jariyawat, Kanoknetr Suksen, Thaworn Jaipetch, Narong Nuntasaen, Vichai Reutrakul, Chutima Kuhakarn. Cytotoxic lanostanes from fruits of Garcinia wallichii Choisy (Guttiferae). Bioorganic & medicinal chemistry letters. 2016 12; 26(23):5773-5779. doi: 10.1016/j.bmcl.2016.10.045. [PMID: 27793565]
  • Thanika Promchai, Atchara Jaidee, Sarot Cheenpracha, Kongkiat Trisuwan, Roonglawan Rattanajak, Sumalee Kamchonwongpaisan, Surat Laphookhieo, Stephen G Pyne, Thunwadee Ritthiwigrom. Antimalarial Oxoprotoberberine Alkaloids from the Leaves of Miliusa cuneata. Journal of natural products. 2016 Apr; 79(4):978-83. doi: 10.1021/acs.jnatprod.5b01054. [PMID: 26928423]
  • Lei Zhang, W F Drew Bennett, Tao Zheng, Ping-Kai Ouyang, Xinping Ouyang, Xueqing Qiu, Anqi Luo, Mikko Karttunen, P Chen. Effect of Cholesterol on Cellular Uptake of Cancer Drugs Pirarubicin and Ellipticine. The journal of physical chemistry. B. 2016 Mar; 120(12):3148-56. doi: 10.1021/acs.jpcb.5b12337. [PMID: 26937690]
  • Sheng Lu, W F Drew Bennett, Yong Ding, Lei Zhang, Helen Y Fan, Danyang Zhao, Tao Zheng, Ping-Kai Ouyang, Jason Li, Yan Wu, Wen Xu, Dafeng Chu, Yongfang Yuan, Heiko Heerklotz, Mikko Karttunen, P Chen. Design and Characterization of a Multifunctional pH-Triggered Peptide C8 for Selective Anticancer Activity. Advanced healthcare materials. 2015 Dec; 4(17):2709-18. doi: 10.1002/adhm.201500636. [PMID: 26474414]
  • Ha T T Nguyen, Ngan B Truong, Huong T M Doan, Marc Litaudon, Pascal Retailleau, Thao T Do, Hung V Nguyen, Minh V Chau, Cuong V Pham. Cytotoxic Clerodane Diterpenoids from the Leaves of Casearia grewiifolia. Journal of natural products. 2015 Nov; 78(11):2726-30. doi: 10.1021/acs.jnatprod.5b00677. [PMID: 26516994]
  • Aneta Żabka, Konrad Winnicki, Justyna Teresa Polit, Janusz Maszewski. The effects of anti-DNA topoisomerase II drugs, etoposide and ellipticine, are modified in root meristem cells of Allium cepa by MG132, an inhibitor of 26S proteasomes. Plant physiology and biochemistry : PPB. 2015 Nov; 96(?):72-82. doi: 10.1016/j.plaphy.2015.07.016. [PMID: 26233708]
  • Raina Thakur, Anupam Das, Vandna Sharma, Chandan Adhikari, Kalyan Sundar Ghosh, Anjan Chakraborty. Interaction of different prototropic species of an anticancer drug ellipticine with HSA and IgG proteins: multispectroscopic and molecular modeling studies. Physical chemistry chemical physics : PCCP. 2015 Jul; 17(26):16937-46. doi: 10.1039/c4cp05734a. [PMID: 26060925]
  • Amrita Banerjee, Sulagna Sanyal, Parijat Majumder, Payal Chakraborty, Kuladip Jana, Chandrima Das, Dipak Dasgupta. Recognition of chromatin by the plant alkaloid, ellipticine as a dual binder. Biochemical and biophysical research communications. 2015 Jul; 462(4):352-7. doi: 10.1016/j.bbrc.2015.04.140. [PMID: 25960297]
  • Martin Studenovský, Ondřej Sedláček, Martin Hrubý, Jiří Pánek, Karel Ulbrich. Multi-responsive polymer micelles as ellipticine delivery carriers for cancer therapy. Anticancer research. 2015 Feb; 35(2):753-7. doi: NULL. [PMID: 25667454]
  • Jittra Suthiwong, Siripit Pitchuanchom, Wareeporn Wattanawongdon, Chariya Hahnvajanawong, Chavi Yenjai. Terpenoids from the root bark of Pterolobium macropterum. Journal of natural products. 2014 Nov; 77(11):2432-7. doi: 10.1021/np500476h. [PMID: 25337628]
  • Tuyet Anh Dang Thi, Nguyen Thi Kim Tuyet, Chinh Pham The, Ha Thanh Nguyen, Cham Ba Thi, Tien Doan Duy, Matthias D'hooghe, Tuyen Van Nguyen. Synthesis and cytotoxic evaluation of novel ester-triazole-linked triterpenoid-AZT conjugates. Bioorganic & medicinal chemistry letters. 2014 Nov; 24(22):5190-4. doi: 10.1016/j.bmcl.2014.09.079. [PMID: 25442310]
  • Ondrej Sedlacek, Jan Kucka, Jana Mattova, Martin Parizek, Martin Studenovsky, Marie Zadinova, Pavla Pouckova, Martin Hruby. Multistage-targeted pH-responsive polymer conjugate of Auger electron emitter: optimized design and in vivo activity. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2014 Oct; 63(?):216-25. doi: 10.1016/j.ejps.2014.07.012. [PMID: 25110352]
  • Andreia Montoia, Luiz F Rocha E Silva, Zelina E Torres, David S Costa, Marycleuma C Henrique, Emerson S Lima, Marne C Vasconcellos, Rita C Z Souza, Monica R F Costa, Andriy Grafov, Iryna Grafova, Marcos N Eberlin, Wanderli P Tadei, Rodrigo C N Amorim, Adrian M Pohlit. Antiplasmodial activity of synthetic ellipticine derivatives and an isolated analog. Bioorganic & medicinal chemistry letters. 2014 Jun; 24(12):2631-4. doi: 10.1016/j.bmcl.2014.04.070. [PMID: 24813729]
  • Raj Kumar Koninti, Abhigyan Sengupta, Krishna Gavvala, Nirmalya Ballav, Partha Hazra. Loading of an anti-cancer drug onto graphene oxide and subsequent release to DNA/RNA: a direct optical detection. Nanoscale. 2014 Mar; 6(5):2937-44. doi: 10.1039/c3nr06081k. [PMID: 24477816]
  • Abhigyan Sengupta, Raj Kumar Koninti, Krishna Gavvala, Nirmalya Ballav, Partha Hazra. An anticancer drug to probe non-specific protein-DNA interactions. Physical chemistry chemical physics : PCCP. 2014 Mar; 16(9):3914-7. doi: 10.1039/c3cp54422b. [PMID: 24448495]
  • Raina Thakur, Anupam Das, Anjan Chakraborty. The fate of anticancer drug, ellipticine in DPPC and DMPC liposomes upon interaction with HSA: a photophysical approach. Journal of photochemistry and photobiology. B, Biology. 2014 Jan; 130(?):122-31. doi: 10.1016/j.jphotobiol.2013.10.016. [PMID: 24322006]
  • Santhi Latha Pandrangi, Rajasekhar Chikati, Pradeep Singh Chauhan, Chitta Suresh Kumar, Anropa Banarji, Sunita Saxena. Effects of ellipticine on ALDH1A1-expressing breast cancer stem cells--an in vitro and in silico study. Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine. 2014 Jan; 35(1):723-37. doi: 10.1007/s13277-013-1099-y. [PMID: 23982874]
  • Phurpa Wangchuk, Wangchuk Phurpa, Paul A Keller, Stephen G Pyne, Wilford Lie, Anthony C Willis, Roonglawan Rattanajak, Sumalee Kamchonwongpaisan. A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain. Journal of ethnopharmacology. 2013 Dec; 150(3):953-9. doi: 10.1016/j.jep.2013.09.052. [PMID: 24120516]
  • Prapairat Seephonkai, Stephen G Pyne, Anthony C Willis, Wilford Lie. Bioactive compounds from the roots of Strophioblachia fimbricalyx. Journal of natural products. 2013 Jul; 76(7):1358-64. doi: 10.1021/np400268d. [PMID: 23806014]
  • Saptaparni Ghosh, Anirban Kar, Shantanu Chowdhury, Dipak Dasgupta. Ellipticine binds to a human telomere sequence: an additional mode of action as a putative anticancer agent?. Biochemistry. 2013 Jun; 52(24):4127-37. doi: 10.1021/bi400080t. [PMID: 23697684]
  • Naowarat Kongkum, Patoomratana Tuchinda, Manat Pohmakotr, Vichai Reutrakul, Pawinee Piyachaturawat, Surawat Jariyawat, Kanoknetr Suksen, Radeekorn Akkarawongsapat, Jitra Kasisit, Chanita Napaswad. Cytotoxic, antitopoisomerase IIα, and anti-HIV-1 activities of triterpenoids isolated from leaves and twigs of Gardenia carinata. Journal of natural products. 2013 Apr; 76(4):530-7. doi: 10.1021/np3006887. [PMID: 23550966]
  • Sarot Cheenpracha, Thunwadee Ritthiwigrom, Surat Laphookhieo. Alstoniaphyllines A-C, unusual nitrogenous derivatives from the bark of Alstonia macrophylla. Journal of natural products. 2013 Apr; 76(4):723-6. doi: 10.1021/np3006937. [PMID: 23806072]
  • L F Rocha e Silva, A Montoia, R C N Amorim, M R Melo, M C Henrique, S M Nunomura, M R F Costa, V F Andrade Neto, D S Costa, G Dantas, J Lavrado, R Moreira, A Paulo, A C Pinto, W P Tadei, R S Zacardi, M N Eberlin, A M Pohlit. Comparative in vitro and in vivo antimalarial activity of the indole alkaloids ellipticine, olivacine, cryptolepine and a synthetic cryptolepine analog. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2012 Dec; 20(1):71-6. doi: 10.1016/j.phymed.2012.09.008. [PMID: 23092722]
  • Wisanu Maneerat, Thunwadee Ritthiwigrom, Sarot Cheenpracha, Trinop Promgool, Kulsiri Yossathera, Suwanna Deachathai, Wong Phakhodee, Surat Laphookhieo. Bioactive carbazole alkaloids from Clausena wallichii roots. Journal of natural products. 2012 Apr; 75(4):741-6. doi: 10.1021/np3000365. [PMID: 22482432]
  • Weina Ma, Sheng Lu, Pei Pan, Parisa Sadatmousavi, Yongfang Yuan, P Chen. Pharmacokinetics of peptide mediated delivery of anticancer drug ellipticine. PloS one. 2012; 7(8):e43684. doi: 10.1371/journal.pone.0043684. [PMID: 22952737]
  • Volker M Arlt, Kateřina Levová, František Bárta, Zhanquan Shi, James D Evans, Eva Frei, Heinz H Schmeiser, Daniel W Nebert, David H Phillips, Marie Stiborová. Role of P450 1A1 and P450 1A2 in bioactivation versus detoxication of the renal carcinogen aristolochic acid I: studies in Cyp1a1-/-, Cyp1a2-/-, and Cyp1a1/1a2-/- mice. Chemical research in toxicology. 2011 Oct; 24(10):1710-9. doi: 10.1021/tx200259y. [PMID: 21932800]
  • Charlotte Passemar, Mariette Saléry, Patrice Njomnang Soh, Marie-Denise Linas, Alain Ahond, Christiane Poupat, Françoise Benoit-Vical. Indole and aminoimidazole moieties appear as key structural units in antiplasmodial molecules. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2011 Oct; 18(13):1118-25. doi: 10.1016/j.phymed.2011.03.010. [PMID: 21612900]
  • Sanghamitra Banerjee, Ashok Pabbathi, M Chandra Sekhar, Anunay Samanta. Dual fluorescence of ellipticine: excited state proton transfer from solvent versus solvent mediated intramolecular proton transfer. The journal of physical chemistry. A. 2011 Aug; 115(33):9217-25. doi: 10.1021/jp206232b. [PMID: 21812494]
  • 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]
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