Haemanthamine (BioDeep_00000000636)

   

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


(1S,13S,15S,18R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol

化学式: C17H19NO4 (301.1314014)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.72%

分子结构信息

SMILES: COC1C=CC23c4cc5c(cc4CN(CC2O)C3C1)OCO5
InChI: InChI=1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3

描述信息

Haemanthamine is an alkaloid.
Hemanthamine is a natural product found in Sternbergia clusiana, Cyrtanthus elatus, and other organisms with data available.

同义名列表

25 个代谢物同义名

(1S,13S,15S,18R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol; 3H,6H-5,11b-Ethano[1,3]dioxolo[4,5-j]phenanthridin-12-ol, 4,4a-dihydro-3-methoxy-, (3S,4aS,5S,11bS,12R)-; (3S,4aS,5S,11bS,12R)-4,4a-Dihydro-3-methoxy-3H,6H-5,11b-ethano[1,3]dioxolo[4,5-j]phenanthridin-12-ol; Crinan-11-ol,2-didehydro-3-methoxy-, (3.beta.,5.alpha.,11R,13.beta.,19.alpha.)-; Crinan-18-ol,2-didehydro-3-methoxy-, (3.beta.,5.beta.,6.alpha.,17.alpha.,18R)-; Crinan-11-ol, 1,2-didehydro-3-methoxy-, (3beta,5alpha,11R,13beta,19alpha)-; 4abeta,5alpha,11balpha-Crinan-12-ol, 1,2-didehydro-3beta-methoxy-, (12R)-; 4a.beta.,11b.alpha.-Crinan-12-ol, 1,2-didehydro-3.beta.-methoxy-, (12R)-; (3beta,5alpha,11R,13beta,19alpha)-1,2-Didehydro-3-methoxycrinan-11-ol; Haemanthamin; Natalensin; 3-Epicrinamine; Natalensine (+)-Haemanthamine; (+)-Haemanthamine; 3-epi-Crinamine; 3-Epicrinamine; Haemanthamine; NCI60_003793; hemanthamine; Haemanthamin; Hemeanthamin; Natalensine; Natalensin; VBL6HZX2ZB; HN8; Crinamine; Haemanthamine



数据库引用编号

22 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)

165 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

  • Deborah Kimie Yonamine, Vitor Eduardo Narciso Dos Reis, Amanda Eiriz Feu, Warley de Souza Borges, Carmen Lúcia Cardoso, Taisa Magnani Dinamarco. Ligand fishing approach to explore Amaryllidaceae alkaloids as potential antiviral candidates targeting SARS-CoV-2 Nsp4. Journal of pharmaceutical and biomedical analysis. 2023 Dec; 240(?):115935. doi: 10.1016/j.jpba.2023.115935. [PMID: 38181554]
  • Christine J Kempthorne, Suresh Borra, Manoj Kumar, Chanti Babu Dokuburra, David K Liscombe, James McNulty. Identification of haemanthamine as a phytotoxic alkaloid in Narcissus pseudonarcissus L. (Daffodil) emerging buds. Natural product research. 2023 Feb; ?(?):1-7. doi: 10.1080/14786419.2023.2174536. [PMID: 36744673]
  • Veronique Mathieu, Breana Laguera, Marco Masi, Sara Adriana Dulanto, Tanner W Bingham, Lucas W Hernandez, David Sarlah, Antonio Evidente, Denis L J Lafontaine, Alexander Kornienko, Michelle A Lane. Amaryllidaceae Alkaloids Decrease the Proliferation, Invasion, and Secretion of Clinically Relevant Cytokines by Cultured Human Colon Cancer Cells. Biomolecules. 2022 09; 12(9):. doi: 10.3390/biom12091267. [PMID: 36139106]
  • Sneha Singh, Nandini Pathak, Eram Fatima, Arvind Singh Negi. Plant isoquinoline alkaloids: Advances in the chemistry and biology of berberine. European journal of medicinal chemistry. 2021 Dec; 226(?):113839. doi: 10.1016/j.ejmech.2021.113839. [PMID: 34536668]
  • Daniel Zaragoza-Puchol, Javier E Ortiz, Alejandro A Orden, Marianela Sanchez, Jorge Palermo, Alejandro Tapia, Jaume Bastida, Gabriela E Feresin. Alkaloids Analysis of Habranthus cardenasianus (Amaryllidaceae), Anti-Cholinesterase Activity and Biomass Production by Propagation Strategies. Molecules (Basel, Switzerland). 2021 Jan; 26(1):. doi: 10.3390/molecules26010192. [PMID: 33401696]
  • Darja Koutová, Negar Maafi, Radim Havelek, Lubomír Opletal, Gerald Blunden, Martina Řezáčová, Lucie Cahlíková. Chemical and Biological Aspects of Montanine-Type Alkaloids Isolated from Plants of the Amaryllidaceae Family. Molecules (Basel, Switzerland). 2020 May; 25(10):. doi: 10.3390/molecules25102337. [PMID: 32429491]
  • D Naidoo, A Roy, L Poštová Slavětínská, J C Chukwujekwu, S Gupta, J Van Staden. New role for crinamine as a potent, safe and selective inhibitor of human monoamine oxidase B: In vitro and in silico pharmacology and modeling. Journal of ethnopharmacology. 2020 Feb; 248(?):112305. doi: 10.1016/j.jep.2019.112305. [PMID: 31639490]
  • Deepali Katoch, Dharmesh Kumar, Yogendra S Padwad, Bikram Singh, Upendra Sharma. Narciclasine-4-O-β-D-xylopyranoside, a new narciclasine glycoside from Zephyranthes minuta. Natural product research. 2020 Jan; 34(2):233-240. doi: 10.1080/14786419.2018.1527836. [PMID: 30636443]
  • Jerald J Nair, Johannes van Staden. Antiprotozoal alkaloid principles of the plant family Amaryllidaceae. Bioorganic & medicinal chemistry letters. 2019 10; 29(20):126642. doi: 10.1016/j.bmcl.2019.126642. [PMID: 31515186]
  • You-Sheng Cai, Cong Wang, Congkui Tian, Wen-Ting Sun, Ling Chen, Di Xiao, Si-Yuan Zhou, Guofu Qiu, Jianqing Yu, Kongkai Zhu, Sheng-Ping Yang. Octahydro-Protoberberine and Protoemetine-Type Alkaloids from the Stems of Alangium salviifolium and Their Cytotoxicity. Journal of natural products. 2019 09; 82(9):2645-2652. doi: 10.1021/acs.jnatprod.9b00670. [PMID: 31513408]
  • Phattharachanok Khumkhrong, Kitiya Piboonprai, Waraluck Chaichompoo, Wittaya Pimtong, Mattaka Khongkow, Katawut Namdee, Angkana Jantimaporn, Deanpen Japrung, Udom Asawapirom, Apichart Suksamrarn, Tawin Iempridee. Crinamine Induces Apoptosis and Inhibits Proliferation, Migration, and Angiogenesis in Cervical Cancer SiHa Cells. Biomolecules. 2019 09; 9(9):. doi: 10.3390/biom9090494. [PMID: 31527550]
  • Tonino G Adessi, José L Borioni, Natalia B Pigni, Jaume Bastida, Valeria Cavallaro, Ana P Murray, Marcelo Puiatti, Juan C Oberti, Segundo Leiva, Viviana E Nicotra, Manuela E Garcia. Clinanthus microstephium, an Amaryllidaceae Species with Cholinesterase Inhibitor Alkaloids: Structure-Activity Analysis of Haemanthamine Skeleton Derivatives. Chemistry & biodiversity. 2019 May; 16(5):e1800662. doi: 10.1002/cbdv.201800662. [PMID: 30801949]
  • Sarah S Takla, Eman Shawky, Hala M Hammoda, Fikria A Darwish. Green techniques in comparison to conventional ones in the extraction of Amaryllidaceae alkaloids: Best solvents selection and parameters optimization. Journal of chromatography. A. 2018 Sep; 1567(?):99-110. doi: 10.1016/j.chroma.2018.07.009. [PMID: 30033169]
  • Suresh Borra, Ringaile Lapinskaite, Christine Kempthorne, David Liscombe, James McNulty, Tomas Hudlicky. Isolation, Synthesis, and Semisynthesis of Amaryllidaceae Constituents from Narcissus and Galanthus sp.: De Novo Total Synthesis of 2- epi-Narciclasine. Journal of natural products. 2018 06; 81(6):1451-1459. doi: 10.1021/acs.jnatprod.8b00218. [PMID: 29787267]
  • Devashan Naidoo, Lenka Poštová Slavětínská, Adeyemi O Aremu, Jiri Gruz, Ondrej Biba, Karel Doležal, Johannes Van Staden, Jeffrey F Finnie. Metabolite profiling and isolation of biologically active compounds from Scadoxus puniceus, a highly traded South African medicinal plant. Phytotherapy research : PTR. 2018 Apr; 32(4):625-630. doi: 10.1002/ptr.6000. [PMID: 29226479]
  • Sean Henry, Ria Kidner, Mary R Reisenauer, Igor V Magedov, Robert Kiss, Véronique Mathieu, Florence Lefranc, Ramesh Dasari, Antonio Evidente, Xiaojie Yu, Xiuye Ma, Alexander Pertsemlidis, Regina Cencic, Jerry Pelletier, David A Cavazos, Andrew J Brenner, Alexander V Aksenov, Snezna Rogelj, Alexander Kornienko, Liliya V Frolova. 5,10b-Ethanophenanthridine amaryllidaceae alkaloids inspire the discovery of novel bicyclic ring systems with activity against drug resistant cancer cells. European journal of medicinal chemistry. 2016 Sep; 120(?):313-28. doi: 10.1016/j.ejmech.2016.05.004. [PMID: 27218860]
  • Miloš Hroch, Stanislav Mičuda, Radim Havelek, Jolana Cermanová, Lucie Cahlíková, Anna Hošťálková, Daniela Hulcová, Martina Řezáčová. LC-MS/MS method for the determination of haemanthamine in rat plasma, bile and urine and its application to a pilot pharmacokinetic study. Biomedical chromatography : BMC. 2016 Jul; 30(7):1083-1091. doi: 10.1002/bmc.3653. [PMID: 26577707]
  • Zhi-Ming Liu, Xiao-Yun Huang, Mao-Rong Cui, Xiao-De Zhang, Zhao Chen, Ben-Shou Yang, Xiao-Kun Zhao. Amaryllidaceae alkaloids from the bulbs of Lycoris radiata with cytotoxic and anti-inflammatory activities. Fitoterapia. 2015 Mar; 101(?):188-93. doi: 10.1016/j.fitote.2015.01.003. [PMID: 25596094]
  • Radim Havelek, Martina Seifrtova, Karel Kralovec, Lenka Bruckova, Lucie Cahlikova, Marketa Dalecka, Jirina Vavrova, Martina Rezacova, Lubomir Opletal, Zuzana Bilkova. The effect of Amaryllidaceae alkaloids haemanthamine and haemanthidine on cell cycle progression and apoptosis in p53-negative human leukemic Jurkat cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Mar; 21(4):479-90. doi: 10.1016/j.phymed.2013.09.005. [PMID: 24182986]
  • Andrea Lubbe, Henk Gude, Robert Verpoorte, Young Hae Choi. Seasonal accumulation of major alkaloids in organs of pharmaceutical crop Narcissus Carlton. Phytochemistry. 2013 Apr; 88(?):43-53. doi: 10.1016/j.phytochem.2012.12.008. [PMID: 23318143]
  • Deepali Katoch, Shiv Kumar, Neeraj Kumar, Bikram Singh. Simultaneous quantification of Amaryllidaceae alkaloids from Zephyranthes grandiflora by UPLC-DAD/ESI-MS/MS. Journal of pharmaceutical and biomedical analysis. 2012 Dec; 71(?):187-92. doi: 10.1016/j.jpba.2012.08.001. [PMID: 22939505]
  • Jian-Sai Yang, Xu Feng, Yu Chen, Xing-Zeng Zhao, Ming Wang, Qi-Zhi Wang, Yun-Fa Dong. [Study on the chemical constituents from the bulbs of Zephyranthes candida]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2010 Nov; 33(11):1730-2. doi: . [PMID: 21434434]
  • Strahil Berkov, Jaume Bastida, Reneta Tsvetkova, Francesc Viladomat, Carles Codina. Alkaloids from Sternbergia colchiciflora. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2009 May; 64(5-6):311-6. doi: 10.1515/znc-2009-5-601. [PMID: 19678530]
  • Kirandeep Kaur, Meenakshi Jain, Tarandeep Kaur, Rahul Jain. Antimalarials from nature. Bioorganic & medicinal chemistry. 2009 May; 17(9):3229-56. doi: 10.1016/j.bmc.2009.02.050. [PMID: 19299148]
  • James McNulty, Jerald J Nair, Jaume Bastida, Siyaram Pandey, Carly Griffin. Structure activity studies on the crinane alkaloid apoptosis-inducing pharmacophore. Natural product communications. 2009 Apr; 4(4):483-8. doi: ". [PMID: 19475990]
  • Yue-Hu Wang, Zhong-Kai Zhang, Fu-Mei Yang, Qian-Yun Sun, Hong-Ping He, Ying-Tong Di, Shu-Zhen Mu, Yang Lu, Ying Chang, Qi-Tai Zheng, Ming Ding, Jia-Hong Dong, Xiao-Jiang Hao. Benzylphenethylamine alkaloids from Hosta plantaginea with inhibitory activity against tobacco mosaic virus and acetylcholinesterase. Journal of natural products. 2007 Sep; 70(9):1458-61. doi: 10.1021/np0702077. [PMID: 17822295]
  • László Szlávik, Agnes Gyuris, János Minárovits, Peter Forgo, József Molnár, Judit Hohmann. Alkaloids from Leucojum vernum and antiretroviral activity of Amaryllidaceae alkaloids. Planta medica. 2004 Sep; 70(9):871-3. doi: 10.1055/s-2004-827239. [PMID: 15386196]
  • Susana López, Jaume Bastida, Francesc Viladomat, Carles Codina. Solid-phase extraction and reversed-phase high-performance liquid chromatography of the five major alkaloids in Narcissus confusus. Phytochemical analysis : PCA. 2002 Nov; 13(6):311-5. doi: 10.1002/pca.660. [PMID: 12494748]
  • Judit Hohmann, Peter Forgo, Joseph Molnár, Krisztina Wolfard, Annamária Molnár, Theresia Thalhammer, Imre Máthé, Derek Sharples. Antiproliferative amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis. Planta medica. 2002 May; 68(5):454-7. doi: 10.1055/s-2002-32068. [PMID: 12058326]