Lasiocarpine (BioDeep_00000395551)

Main id: BioDeep_00000004086

 

PANOMIX_OTCML-2023 natural product


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 (411.2257)
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: C/C=C(/C)C(=O)O[C@H]1CCN2CC=C(COC(=O)[C@@](O)([C@@H](C)OC)C(C)(C)O)[C@H]12
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

38 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; Lasiocarpine



数据库引用编号

10 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)

16 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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 CASP3, CASP7, CAT, CES2, CYP1A1, CYP2D6, CYP3A4, FAS, RARA
Peripheral membrane protein 2 CRAT, CYP1A1
Endoplasmic reticulum membrane 4 CYP1A1, CYP2D6, CYP3A4, CYP3A5
Nucleus 7 CASP3, CASP7, FASLG, H2AX, NR1I2, PBK, RARA
cytosol 9 AP1AR, CASP3, CASP7, CAT, CES2, CRAT, FAS, RARA, TDO2
dendrite 1 RARA
nuclear body 2 FAS, NR1I2
centrosome 1 H2AX
nucleoplasm 5 CASP3, CASP7, H2AX, NR1I2, RARA
RNA polymerase II transcription regulator complex 1 RARA
Cell membrane 3 FAS, FASLG, SLC22A1
Multi-pass membrane protein 1 SLC22A1
cell surface 1 FAS
glutamatergic synapse 1 CASP3
Golgi apparatus 2 AP1AR, FAS
mitochondrial inner membrane 2 CRAT, CYP1A1
neuronal cell body 1 CASP3
Cytoplasm, cytosol 1 CASP7
Presynapse 1 SLC22A1
endosome 1 AP1AR
plasma membrane 4 FAS, FASLG, RARA, SLC22A1
Membrane 7 CAT, CYP2D6, CYP3A4, CYP3A5, FAS, FASLG, SLC22A1
apical plasma membrane 1 SLC22A1
basolateral plasma membrane 1 SLC22A1
caveola 1 FASLG
extracellular exosome 5 CAT, CES2, FAS, FASLG, H2AX
endoplasmic reticulum 3 CES2, CRAT, CYP2D6
extracellular space 2 CASP7, FASLG
lysosomal lumen 1 FASLG
perinuclear region of cytoplasm 2 FASLG, RARA
mitochondrion 4 CAT, CRAT, CYP1A1, CYP2D6
protein-containing complex 2 CAT, RARA
intracellular membrane-bounded organelle 6 CAT, CES2, CYP1A1, CYP2D6, CYP3A4, CYP3A5
Microsome membrane 4 CYP1A1, CYP2D6, CYP3A4, CYP3A5
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 FAS
Secreted 1 FASLG
extracellular region 2 CAT, FASLG
Single-pass membrane protein 1 CYP2D6
mitochondrial matrix 1 CAT
Cytoplasmic vesicle lumen 1 FASLG
transcription regulator complex 2 NR1I2, RARA
external side of plasma membrane 2 FAS, FASLG
actin cytoskeleton 1 RARA
nucleolus 1 RARA
Early endosome 1 AP1AR
Single-pass type II membrane protein 1 FASLG
Apical cell membrane 1 SLC22A1
Mitochondrion inner membrane 2 CRAT, CYP1A1
Matrix side 1 CRAT
Membrane raft 1 FAS
focal adhesion 1 CAT
cis-Golgi network 1 GOLGA6A
Peroxisome 2 CAT, CRAT
Peroxisome matrix 1 CAT
peroxisomal matrix 2 CAT, CRAT
peroxisomal membrane 1 CAT
lateral plasma membrane 1 SLC22A1
nuclear speck 1 H2AX
Late endosome 1 AP1AR
chromatin 2 NR1I2, RARA
Chromosome 1 H2AX
Secreted, extracellular space 1 CASP7
[Isoform 1]: Mitochondrion 1 CRAT
Basolateral cell membrane 1 SLC22A1
site of double-strand break 1 H2AX
Lipid droplet 1 CES2
Melanosome 1 FAS
Golgi cisterna membrane 1 GOLGA6A
replication fork 1 H2AX
intermediate filament cytoskeleton 1 NR1I2
basal plasma membrane 1 SLC22A1
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 1 CES2
male germ cell nucleus 1 H2AX
XY body 1 H2AX
transport vesicle 1 AP1AR
Lysosome lumen 1 FASLG
condensed nuclear chromosome 1 H2AX
Basal cell membrane 1 SLC22A1
Lateral cell membrane 1 SLC22A1
CD95 death-inducing signaling complex 1 FAS
death-inducing signaling complex 2 CASP3, FAS
[Isoform 1]: Cell membrane 1 FAS
nucleosome 1 H2AX
site of DNA damage 1 H2AX
catalase complex 1 CAT
[Isoform 2]: Peroxisome 1 CRAT
[Tumor necrosis factor ligand superfamily member 6, soluble form]: Secreted 1 FASLG
[FasL intracellular domain]: Nucleus 1 FASLG
glycogen granule 1 FAS
Golgi cis cisterna 1 GOLGA6A


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]