Lasiocarpine (BioDeep_00000395551)

Main id: BioDeep_00000004086

 

PANOMIX_OTCML-2023


代谢物信息卡片


2-BUTENOIC ACID, 2-METHYL-, 7-((2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)-2,3,5,7A-TETRAHYDRO-1H-PYRROLIZIN-1-YL ESTER, (1S-(1.ALPHA.(Z),7(S*(R*)),7A.ALPHA.))-

化学式: C21H33NO7 (411.22569080000005)
中文名称: 毛果天芥菜碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC=C(C)C(=O)OC1CCN2C1C(=CC2)COC(=O)C(C(C)OC)(C(C)(C)O)O
InChI: InChI=1S/C21H33NO7/c1-7-13(2)18(23)29-16-9-11-22-10-8-15(17(16)22)12-28-19(24)21(26,14(3)27-6)20(4,5)25/h7-8,14,16-17,25-26H,9-12H2,1-6H3/b13-7-/t14-,16-,17+,21-/m0/s1

描述信息

Lasiocarpine appears as colorless plates or beige crystalline solid. (NTP, 1992)
Lasiocarpine is a natural product found in Heliotropium arbainense, Heliotropium suaveolens, and other organisms with data available.
See also: Comfrey Leaf (part of); Comfrey Root (part of).

同义名列表

37 个代谢物同义名

2-BUTENOIC ACID, 2-METHYL-, 7-((2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)-2,3,5,7A-TETRAHYDRO-1H-PYRROLIZIN-1-YL ESTER, (1S-(1.ALPHA.(Z),7(S*(R*)),7A.ALPHA.))-; 2-BUTENOIC ACID, 2-METHYL-, 7-((2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)--2,3,5,7A-TETRAHYDRO-1H-PYRROLIZIN-1-YL ESTER, (1S-(1ALPHA(Z),7(2S*,3R*),7AALPHA))-; 2-Butenoic acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, (1S-(1alpha(Z),7(2S*,3R*),7a alpha))-; 2-Butenoic acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, (1S-(1alpha(Z),7(2S*,3R*),7aalpha))-; 2-BUTENOIC ACID, 2-METHYL-, 7-((2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)-2,3,5,7A-TETRAHYDRO-1H-PYRROLIZIN-1-YL ESTER, (1S-(1alpha(Z),7(S*(R*)),7Aalpha))-; 2-BUTENOIC ACID-2-METHYL-7((2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)-2,3,5,7A-TETRAHYDRO-1H-PYRROLIZIN-1-YL-ESTER(1S-1-ALPHA (Z),-7(2S,3R)7-A-ALPHA)); 2-Butenoic acid, 7-[[2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy]methyl]-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, [1S-[1.alpha.(Z),7(2S*,3R*),7a.alpha.]]-; (1S,7aR)-7-((((R)-2,3-dihydroxy-2-((S)-1-methoxyethyl)-3-methylbutanoyl)oxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (Z)-2-methylbut-2-enoate; 2-Butenoic acid, 2-methy-,(1S,7aR)-7-(((2R)-2,3-dihydroxy-2-((1S)-1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-ester, (2Z)-; stereoisomer of 7-(2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)-methyl-2,3,5,7alpha-tetrahydro-1H-pyrrolizin-1-yl-2-methyl-2-butenoate; 2-methyl-2-butenoic acid 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester; 2,3,5,7ALPHA, BETA-TETRAHYDRO-1-HYDROXYL-1H-PYRROLIZINE-7-METHANOL-1-ANGELATE-7-(2,3-DIHYDROXY)-2(1-METHOXYETHYL)-3-METHYLBUTYRATE; 2,3,5,7alphabeta-Tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol-1-angelate-7-(2,3-dihydroxy-2(1-methoxyethyl))-3-methyl-butyrate; (7-ALPHA-ANGELYLOXY-5,6,7,8-ALPHA-TETRAHYDRO-3H-PYRROLIZIN-1-YL)METHYL-2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYLBUTYRATE; (7alpha-Angelyloxy-5,6,7,8alpha-tetrahydro-3H-pyrrolizin-1-yl)methyl-2,3-dihydroxy-2-(1-methoxyethyl)-3-methylbutyrate; (Z)-2-METHYL-CROTONIC ACID, 2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYLBUTYRATE (ESTER); (Z)-2-Methylcrotonic acid, 2,3-dihydroxy-2-(1-methoxyethyl)-3-methylbutyrate (ester); (Z)-2-METHYLCROTONIC ACID-2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYLBUTYRATE (ESTER); lasiocarpine hydrochloride, (1S-(1alpha(Z),7(2S*,3R*),7aalpha))-isomer; lasiocarpine sulfate, (1S-(1alpha(Z),7(2S*,3R*),7aalpha))-isomer; Heliotridine ester with lasiocarpum and angelic acid; WLN: T55 AN CUTJ D1OVXQXQ1 & 1 & Y1 & O1 FOVY1 & U2; Heliotridine ester with lasiocarpum & angelic acid; 7-Angelyl-9-lasiocarpylheliotridine; Lasiocarpine (7-Angelyleuropine); HELIOSUPINE METHYL ETHER [MI]; HELIOSUPINE METHYL ETHER; LASIOCARPINE (IARC); LASIOCARPINE [HSDB]; Europine 7-angelate; LASIOCARPINE [IARC]; LASIOCARPINE [MI]; 7-Angelyleuropine; (-)-Lasiocarpine; Lasiocarpine; AI3-51770; 1ST14169



数据库引用编号

6 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

5 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

  • Yueyang Pan, Jiang Ma, Hui Zhao, Peter P Fu, Ge Lin. Hepatotoxicity screening and ranking of structurally different pyrrolizidine alkaloids in zebrafish. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2023 Jun; 178(?):113903. doi: 10.1016/j.fct.2023.113903. [PMID: 37390955]
  • Naji Said Aboud Hadi, Ezgi Eyluel Bankoglu, Helga Stopper. Genotoxicity of pyrrolizidine alkaloids in metabolically inactive human cervical cancer HeLa cells co-cultured with human hepatoma HepG2 cells. Archives of toxicology. 2023 01; 97(1):295-306. doi: 10.1007/s00204-022-03394-z. [PMID: 36273350]
  • Sara Abdelfatah, Janine Naß, Caroline Knorz, Sabine M Klauck, Jan-Heiner Küpper, Thomas Efferth. Pyrrolizidine alkaloids cause cell cycle and DNA damage repair defects as analyzed by transcriptomics in cytochrome P450 3A4-overexpressing HepG2 clone 9 cells. Cell biology and toxicology. 2022 04; 38(2):325-345. doi: 10.1007/s10565-021-09599-9. [PMID: 33884520]
  • Julia Buchmueller, Heike Sprenger, Johanna Ebmeyer, Josef Daniel Rasinger, Otto Creutzenberg, Dirk Schaudien, Jan G Hengstler, Georgia Guenther, Albert Braeuning, Stefanie Hessel-Pras. Pyrrolizidine alkaloid-induced transcriptomic changes in rat lungs in a 28-day subacute feeding study. Archives of toxicology. 2021 08; 95(8):2785-2796. doi: 10.1007/s00204-021-03108-x. [PMID: 34185104]
  • Lukas Rutz, Lan Gao, Jan-Heiner Küpper, Dieter Schrenk. Structure-dependent genotoxic potencies of selected pyrrolizidine alkaloids in metabolically competent HepG2 cells. Archives of toxicology. 2020 12; 94(12):4159-4172. doi: 10.1007/s00204-020-02895-z. [PMID: 32910235]
  • Suparmi Suparmi, Sebastiaan Wesseling, Ivonne M C M Rietjens. Monocrotaline-induced liver toxicity in rat predicted by a combined in vitro physiologically based kinetic modeling approach. Archives of toxicology. 2020 09; 94(9):3281-3295. doi: 10.1007/s00204-020-02798-z. [PMID: 32518961]
  • Johanna Ebmeyer, Josef Daniel Rasinger, Jan G Hengstler, Dirk Schaudien, Otto Creutzenberg, Alfonso Lampen, Albert Braeuning, Stefanie Hessel-Pras. Hepatotoxic pyrrolizidine alkaloids induce DNA damage response in rat liver in a 28-day feeding study. Archives of toxicology. 2020 05; 94(5):1739-1751. doi: 10.1007/s00204-020-02779-2. [PMID: 32419051]
  • Johanna Ebmeyer, Jessica Behrend, Mario Lorenz, Georgia Günther, Raymond Reif, Jan G Hengstler, Albert Braeuning, Alfonso Lampen, Stefanie Hessel-Pras. Pyrrolizidine alkaloid-induced alterations of prostanoid synthesis in human endothelial cells. Chemico-biological interactions. 2019 Jan; 298(?):104-111. doi: 10.1016/j.cbi.2018.11.007. [PMID: 30465738]
  • Vidushi Mahajan, Sanjay D'Cruz, Ritambara Nada, Atul Sachdev. Successful Use of Entecavir in Hepatitis B-associated Membranous Nephropathy. Journal of tropical pediatrics. 2018 Jun; 64(3):249-252. doi: 10.1093/tropej/fmx058. [PMID: 28977667]
  • Claudia Luckert, Albert Braeuning, Alfonso Lampen, Stefanie Hessel-Pras. PXR: Structure-specific activation by hepatotoxic pyrrolizidine alkaloids. Chemico-biological interactions. 2018 May; 288(?):38-48. doi: 10.1016/j.cbi.2018.04.017. [PMID: 29665350]
  • Kristina Forsch, Verena Schöning, Lucia Disch, Beate Siewert, Matthias Unger, Jürgen Drewe. Development of an in vitro screening method of acute cytotoxicity of the pyrrolizidine alkaloid lasiocarpine in human and rodent hepatic cell lines by increasing susceptibility. Journal of ethnopharmacology. 2018 May; 217(?):134-139. doi: 10.1016/j.jep.2018.02.018. [PMID: 29454024]
  • Rosalind R Dalefield, Michelle A Gosse, Utz Mueller. A 28-day oral toxicity study of echimidine and lasiocarpine in Wistar rats. Regulatory toxicology and pharmacology : RTP. 2016 Nov; 81(?):146-154. doi: 10.1016/j.yrtph.2016.08.006. [PMID: 27546169]
  • Reuel A Field, Bryan L Stegelmeier, Steven M Colegate, Ammon W Brown, Benedict T Green. An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides. Toxicon : official journal of the International Society on Toxinology. 2015 Apr; 97(?):36-45. doi: 10.1016/j.toxicon.2015.02.001. [PMID: 25666399]
  • Feng Liu, Sow Yin Wan, Zhangjian Jiang, Sam Fong Yau Li, Eng Shi Ong, Jhon Carlos Castaño Osorio. Determination of pyrrolizidine alkaloids in comfrey by liquid chromatography-electrospray ionization mass spectrometry. Talanta. 2009 Dec; 80(2):916-23. doi: 10.1016/j.talanta.2009.08.020. [PMID: 19836573]
  • Y Eröksüz, H Eröksüz, H Ozer, B Sener, F Tosun, C Akyüz. Toxicity of dietary Heliotropium dolosum seed to mice. Veterinary and human toxicology. 2001 Jun; 43(3):152-5. doi: . [PMID: 11383655]