Chelidonine (BioDeep_00000003017)

 

Secondary id: BioDeep_00000374167

natural product PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


(1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol

化学式: C20H19NO5 (353.1263)
中文名称: 白屈菜宁, 白屈菜碱
谱图信息: 最多检出来源 Viridiplantae(plant) 46.15%

分子结构信息

SMILES: CN1CC2=C(C=CC3=C2OCO3)C4C1C5=CC6=C(C=C5CC4O)OCO6
InChI: InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3

描述信息

Chelidonine is an alkaloid fundamental parent, a benzophenanthridine alkaloid and an alkaloid antibiotic.
Chelidonine is a natural product found in Sarcocapnos baetica, Sarcocapnos saetabensis, and other organisms with data available.
Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.
See also: Chelidonium majus flowering top (part of).
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2255
Chelidonine, an isoquinoline alkaloid, can be isolated from Chelidonium majus L.. Chelidonine causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, and prevents cell cycle progression of stem cells in Dugesia japonica. Chelidonine has cytotoxic activity against melanoma cell lines. with anticancer and antiviral activity[1][2][3].
Chelidonine, an isoquinoline alkaloid, can be isolated from Chelidonium majus L.. Chelidonine causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, and prevents cell cycle progression of stem cells in Dugesia japonica. Chelidonine has cytotoxic activity against melanoma cell lines. with anticancer and antiviral activity[1][2][3].

同义名列表

50 个代谢物同义名

(1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol; (5BR-(5B.ALPHA.,6.BETA.,12B.ALPHA.))-5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL(1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL; (5BR-(5Balpha,6beta,12Balpha))-5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL(1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL; Rel-(5bR,6R,12bS)-13-methyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4,5:4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol; (5bR,6S,12bS)-13-Methyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4,5:4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol; (1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL, 5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL-, (5BR,6S,12BS)-REL-; [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5bR,6S,12bS)-rel-; (1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL, 5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL-, (5BR,6S,12BS)-; [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5bR,6S,12bS)-; 5b,6,7,12b,13,14-Hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenan-thridin-6-ol; Chelidonine ((+)-Chelidonine); Chelidonine, >=97.0\\% (HPLC); GHKISGDRQRSCII-ZOCIIQOWSA-N; CHELIDONINE (+/-)-FORM [MI]; chelidonine hydrochloride; CHELIDONINE (+)-FORM [MI]; DIPHYLLINE (ALKALOID); chelidonine bisulfate; chelidonine tartrate; CHELIDONINE (+)-FORM; Chelidoniny [Polish]; CHELIDONINE [WHO-DD]; chelidonine sulfate; Chelidonin [German]; CHELIDONINE, (+/-)-; CHELIDONINE [INCI]; Prestwick1_000587; Chelidonine (+-)-; Prestwick0_000587; Prestwick2_000587; Prestwick3_000587; (+/-)-chelidonine; CHELIDONINE (+); (1)-Chelidonine; UNII-8K7EK8446J; (+)-Chelidonine; UNII-4UDG3LY0GT; MEGxp0_001421; BPBio1_000478; Stylophorine; ACon1_000007; Stylophorin; Chelidonine; Chelidoniny; 8K7EK8446J; Khelidonin; 4UDG3LY0GT; Helidonine; Chelidonin; Chelidonine



数据库引用编号

60 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)

81 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 16 ABCB1, AIMP2, ANXA5, BCL2, BCL2L1, BIRC5, CASP3, CASP8, CASP9, CAT, CCNB1, PLK1, PTGS2, RELA, STAT3, TUBB4B
Peripheral membrane protein 4 ACHE, ANXA5, CYP1B1, PTGS2
Endoplasmic reticulum membrane 3 BCL2, CYP1B1, PTGS2
Mitochondrion membrane 1 BCL2L1
Nucleus 13 ACHE, AIMP2, BCL2, BIRC5, CASP3, CASP8, CASP9, CCNB1, FOXM1, PLK1, RELA, STAT3, TUBB4B
cytosol 14 AIMP2, ANXA5, BCL2, BCL2L1, BIRC5, CASP3, CASP8, CASP9, CAT, CCNB1, PLK1, RELA, STAT3, TUBB4B
centrosome 3 BCL2L1, CCNB1, PLK1
nucleoplasm 8 BIRC5, CASP3, CASP8, CCNB1, FOXM1, PLK1, RELA, STAT3
RNA polymerase II transcription regulator complex 1 STAT3
Cell membrane 3 ABCB1, ACHE, TNF
Cytoplasmic side 1 BCL2L1
lamellipodium 1 CASP8
Multi-pass membrane protein 1 ABCB1
Synapse 1 ACHE
cell surface 3 ABCB1, ACHE, TNF
glutamatergic synapse 2 CASP3, RELA
Golgi apparatus 1 ACHE
mitochondrial inner membrane 1 BCL2L1
neuromuscular junction 1 ACHE
neuronal cell body 2 CASP3, TNF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 AIMP2, BCL2L1
plasma membrane 4 ABCB1, ACHE, STAT3, TNF
synaptic vesicle membrane 1 BCL2L1
Membrane 8 ABCB1, ACHE, AIMP2, ANXA5, BCL2, CAT, CCNB1, CYP1B1
apical plasma membrane 1 ABCB1
caveola 1 PTGS2
extracellular exosome 4 ABCB1, ANXA5, CAT, TUBB4B
endoplasmic reticulum 3 BCL2, BCL2L1, PTGS2
extracellular space 2 ACHE, TNF
perinuclear region of cytoplasm 1 ACHE
mitochondrion 6 BCL2, BCL2L1, CASP8, CASP9, CAT, CYP1B1
protein-containing complex 6 BCL2, BIRC5, CASP8, CASP9, CAT, PTGS2
intracellular membrane-bounded organelle 2 CAT, CYP1B1
Microsome membrane 2 CYP1B1, PTGS2
postsynaptic density 1 CASP3
Secreted 1 ACHE
extracellular region 5 ACHE, ANXA5, CAT, TNF, TUBB4B
Mitochondrion outer membrane 2 BCL2, BCL2L1
Single-pass membrane protein 2 BCL2, BCL2L1
mitochondrial outer membrane 3 BCL2, BCL2L1, CASP8
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 3 BCL2L1, CAT, CCNB1
Extracellular side 1 ACHE
transcription regulator complex 2 RELA, STAT3
centriolar satellite 1 PLK1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 BCL2L1, PLK1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 2 BCL2, BCL2L1
Bcl-2 family protein complex 2 BCL2, BCL2L1
nuclear membrane 2 BCL2, BCL2L1
external side of plasma membrane 2 ANXA5, TNF
Extracellular vesicle 1 TUBB4B
microtubule cytoskeleton 3 BIRC5, PLK1, TUBB4B
midbody 2 BIRC5, PLK1
recycling endosome 1 TNF
spindle midzone 1 PLK1
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 ABCB1
Cell projection, lamellipodium 1 CASP8
Membrane raft 1 TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 TUBB4B
Cytoplasm, cytoskeleton, spindle 2 BIRC5, PLK1
focal adhesion 2 ANXA5, CAT
microtubule 2 BIRC5, TUBB4B
spindle 2 BIRC5, PLK1
Peroxisome 1 CAT
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 ANXA5
interphase microtubule organizing center 1 BIRC5
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
chromatin 4 FOXM1, PLK1, RELA, STAT3
phagocytic cup 1 TNF
mitotic spindle 1 TUBB4B
Chromosome 1 BIRC5
cytoskeleton 2 CASP8, TUBB4B
centriole 2 BIRC5, PLK1
spindle pole 2 CCNB1, PLK1
nuclear chromosome 1 BIRC5
Lipid-anchor, GPI-anchor 1 ACHE
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
Chromosome, centromere 1 BIRC5
Chromosome, centromere, kinetochore 1 BIRC5
axonemal microtubule 1 TUBB4B
cell body 1 CASP8
side of membrane 1 ACHE
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 1 PTGS2
kinetochore 2 BIRC5, PLK1
mitotic spindle pole 1 PLK1
azurophil granule lumen 1 TUBB4B
apoptosome 1 CASP9
chromosome, centromeric region 1 BIRC5
outer kinetochore 2 CCNB1, PLK1
vesicle membrane 1 ANXA5
chromosome passenger complex 1 BIRC5
cytoplasmic microtubule 1 BIRC5
synaptic cleft 1 ACHE
spindle microtubule 1 BIRC5
survivin complex 1 BIRC5
external side of apical plasma membrane 1 ABCB1
synaptonemal complex 1 PLK1
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
cyclin B1-CDK1 complex 1 CCNB1
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
NF-kappaB p50/p65 complex 1 RELA
[Isoform H]: Cell membrane 1 ACHE
NF-kappaB complex 1 RELA
caspase complex 1 CASP9
[Isoform Bcl-X(L)]: Mitochondrion inner membrane 1 BCL2L1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • 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]
  • Ling Qian, Kun Chen, Changhong Wang, Zhen Chen, Zhiqiang Meng, Peng Wang. Targeting NRAS-Mutant Cancers with the Selective STK19 Kinase Inhibitor Chelidonine. Clinical cancer research : an official journal of the American Association for Cancer Research. 2020 07; 26(13):3408-3419. doi: 10.1158/1078-0432.ccr-19-2604. [PMID: 32156748]
  • Zhong-Min Zhao, Xiao-Fei Shang, Raymond Kobla Lawoe, Ying-Qian Liu, Rui Zhou, Yu Sun, Yin-Fang Yan, Jun-Cai Li, Guan-Zhou Yang, Cheng-Jie Yang. Anti-phytopathogenic activity and the possible mechanisms of action of isoquinoline alkaloid sanguinarine. Pesticide biochemistry and physiology. 2019 Sep; 159(?):51-58. doi: 10.1016/j.pestbp.2019.05.015. [PMID: 31400784]
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  • Cuiting Wu, Xin Wang, Ming Xu, Youping Liu, Xin Di. Intracellular Accumulation as an Indicator of Cytotoxicity to Screen Hepatotoxic Components of Chelidonium majus L. by LC-MS/MS. Molecules (Basel, Switzerland). 2019 Jun; 24(13):. doi: 10.3390/molecules24132410. [PMID: 31261913]
  • Yuyang Liu, Tiantian Cui, Ying Peng, Mingshan Ji, Jiang Zheng. Mechanism-based inactivation of cytochrome P450 2D6 by chelidonine. Journal of biochemical and molecular toxicology. 2019 Feb; 33(2):e22251. doi: 10.1002/jbt.22251. [PMID: 30368994]
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  • Okhwa Kim, Cheol Hwangbo, Junhyeong Kim, Dong-Hao Li, Byung-Sun Min, Jeong-Hyung Lee. Chelidonine suppresses migration and invasion of MDA-MB-231 cells by inhibiting formation of the integrin-linked kinase/PINCH/α-parvin complex. Molecular medicine reports. 2015 Aug; 12(2):2161-8. doi: 10.3892/mmr.2015.3621. [PMID: 25890994]
  • Avijit Paul, Jayeeta Das, Sreemanti Das, Asmita Samadder, Anisur Rahman Khuda-Bukhsh. Poly (lactide-co-glycolide) nano-encapsulation of chelidonine, an active bioingredient of greater celandine (Chelidonium majus), enhances its ameliorative potential against cadmium induced oxidative stress and hepatic injury in mice. Environmental toxicology and pharmacology. 2013 Nov; 36(3):937-47. doi: 10.1016/j.etap.2013.08.008. [PMID: 24035924]
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