Securinine (BioDeep_00000003873)

 

Secondary id: BioDeep_00000396437

natural product PANOMIX_OTCML-2023


代谢物信息卡片


6,10-METHANOPYRIDO(1,2-A)AZEPINE-.GAMMA.9(6H),.ALPHA.-ACETIC ACID,1,2,3,4,10,10A-HEXAHYDRO-10-HYDROXY-, .GAMMA.-LACTONE

化学式: C13H15NO2 (217.1103)
中文名称: 一叶秋碱, 别一叶萩碱, 一叶萩碱
谱图信息: 最多检出来源 Viridiplantae(plant) 11.71%

分子结构信息

SMILES: C1CCN2C(C1)C34CC2C=CC3=CC(=O)O4
InChI: InChI=1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2

描述信息

Securinine is a member of indolizines.
Securinine is a natural product found in Flueggea suffruticosa, Flueggea virosa, and other organisms with data available.
See also: Phyllanthus amarus top (part of).
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.052
(-)-Securinine is plant-derived alkaloid and also a GABAA receptor antagonist.
(-)-Securinine is plant-derived alkaloid and also a GABAA receptor antagonist.
(-)-Securinine is plant-derived alkaloid and also a GABAA receptor antagonist.
(-)-Securinine is plant-derived alkaloid and also a GABAA receptor antagonist.
(-)-Securinine is plant-derived alkaloid and also a GABAA receptor antagonist.
(-)-Securinine is plant-derived alkaloid and also a GABAA receptor antagonist.
Allosecurinine (Phyllochrysine) is a Securinega alkaloid isolated from Phyllanthus glaucus [1].

同义名列表

42 个代谢物同义名

6,10-METHANOPYRIDO(1,2-A)AZEPINE-.GAMMA.9(6H),.ALPHA.-ACETIC ACID,1,2,3,4,10,10A-HEXAHYDRO-10-HYDROXY-, .GAMMA.-LACTONE; 6,10-METHANOPYRIDO(1,2-A)AZEPINE-gamma9(6H),alpha-ACETIC ACID,1,2,3,4,10,10A-HEXAHYDRO-10-HYDROXY-, gamma-LACTONE; REL-(6R,11AS,11BR)-9,10,11,11A-TETRAHYDRO-8H-6,11B-METHANOFURO[2,3-C]PYRIDO[1,2-A]AZEPIN-2(6H)-ONE; rel-(6S,11AR,11bS)-6,8,9,10,11,11a-hexahydro-2H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2-one; (6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro[2,3-c]-pyrido[1,2-a]azepin-2(6H)-one; (6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro(2,3-c)pyrido(1,2-a)azepin-2(6H)-one; (6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one; rac-(1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.0~1,11~.0~2,7~]pentadeca-9,11-dien-13-one; (1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.0^{1,11}.0^{2,7}]pentadeca-9,11-dien-13-one; (1S,8S,14R)-2-oxa-9-azatetracyclo[6.6.1.0<1,5>.0<9,14>]pentadeca-4,6-dien-3-on e; 2-Oxo-2,6,9,10,11,11a-hexahydro-8H-6,11b-methanofuro(2,3-c)pyrido(1,2-a)azepin; (1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-one; Securinine, >=98\\% (HPLC); Securinina [INN-Spanish]; Securininum [INN-Latin]; securinine methiodide; SECURININE [WHO-DD]; Viroallosecurinine; securinine nitrate; allonorsecurinine; Spectrum3_001977; securinan-11-one; Spectrum2_000669; Securinine [INN]; Securinine, (-)-; UNII-G4VS580P5E; SECURININE [MI]; (-)-Securinine; Virosecurinine; (a?-Securinine; allosecurinine; Tox21_111468; l-Securinine; KBio3_002957; Securininum; Securinine; G4VS580P5E; Securinina; Securinin; Securinine; Phyllochrysine; Securinine



数据库引用编号

51 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)

44 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 12 ABCB1, AIMP2, AKT1, ANXA5, BCL2, MAPK8, MTOR, NFATC1, PIK3CA, PML, TNFSF11, TXN
Peripheral membrane protein 3 ANXA5, MTOR, PML
Endosome membrane 1 CD14
Endoplasmic reticulum membrane 3 BCL2, MTOR, PML
Nucleus 12 AIMP2, AKT1, BCL2, CEBPA, FOS, MAPK8, MTOR, NFATC1, PAX2, PML, SPI1, TXN
cytosol 12 AIMP2, AKT1, ANXA5, BCL2, BCR, FOS, MAPK8, MTOR, NFATC1, PIK3CA, PML, TXN
dendrite 1 MTOR
nuclear body 1 NFATC1
phagocytic vesicle 1 MTOR
nucleoplasm 10 AKT1, CEBPA, FOS, MAPK8, MTOR, NFATC1, PAX2, PML, SPI1, TXN
RNA polymerase II transcription regulator complex 2 CEBPA, FOS
Cell membrane 5 ABCB1, AGTR1, AKT1, CD14, TNFSF11
Cytoplasmic side 2 MTOR, PML
lamellipodium 2 AKT1, PIK3CA
Cell projection, axon 1 BCR
Early endosome membrane 1 PML
Multi-pass membrane protein 2 ABCB1, AGTR1
Golgi apparatus membrane 1 MTOR
Synapse 2 BCR, MAPK8
cell cortex 1 AKT1
cell surface 1 ABCB1
glutamatergic synapse 2 AKT1, BCR
Golgi apparatus 1 CD14
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
postsynapse 1 AKT1
sarcolemma 1 ANXA5
Cytoplasm, cytosol 1 AIMP2
Lysosome 1 MTOR
plasma membrane 7 ABCB1, AGTR1, AKT1, BCR, CD14, PIK3CA, TNFSF11
Membrane 10 ABCB1, AGTR1, AIMP2, AKT1, ANXA5, BCL2, BCR, MTOR, SPI1, TNFSF11
apical plasma membrane 1 ABCB1
axon 3 BCR, CCK, MAPK8
extracellular exosome 5 ABCB1, ANXA5, BCR, CD14, TXN
Lysosome membrane 1 MTOR
endoplasmic reticulum 2 BCL2, FOS
extracellular space 3 CCK, CD14, TNFSF11
perinuclear region of cytoplasm 2 NFATC1, PIK3CA
Schaffer collateral - CA1 synapse 1 BCR
intercalated disc 1 PIK3CA
mitochondrion 1 BCL2
protein-containing complex 4 AKT1, BCL2, BCR, PAX2
intracellular membrane-bounded organelle 1 CEBPA
Microsome membrane 1 MTOR
postsynaptic density 1 BCR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 4 CCK, CD14, TNFSF11, TXN
extracellular region 5 ANXA5, CCK, CD14, TNFSF11, TXN
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, MTOR
transcription regulator complex 3 CEBPA, NFATC1, SPI1
centriolar satellite 1 PAX2
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, PML
external side of plasma membrane 2 ANXA5, CD14
dendritic spine 1 BCR
microtubule cytoskeleton 1 AKT1
nucleolus 2 CEBPA, PML
sarcoplasm 1 NFATC1
cell-cell junction 1 AKT1
Single-pass type II membrane protein 1 TNFSF11
vesicle 1 AKT1
Apical cell membrane 1 ABCB1
Membrane raft 1 CD14
pore complex 1 BCL2
focal adhesion 1 ANXA5
spindle 1 AKT1
Cell projection, dendritic spine 1 BCR
Nucleus, PML body 2 MTOR, PML
PML body 2 MTOR, PML
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 1 ANXA5
Zymogen granule membrane 1 ANXA5
ciliary basal body 1 AKT1
chromatin 5 CEBPA, FOS, NFATC1, PAX2, SPI1
chromosome, telomeric region 1 PML
Lipid-anchor, GPI-anchor 1 CD14
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
microtubule organizing center 1 PAX2
side of membrane 1 CD14
myelin sheath 1 BCL2
lipopolysaccharide receptor complex 1 CD14
secretory granule membrane 1 CD14
nuclear matrix 2 FOS, PML
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
[Isoform 2]: Cytoplasm 1 TNFSF11
[Tumor necrosis factor ligand superfamily member 11, soluble form]: Secreted 1 TNFSF11
vesicle membrane 1 ANXA5
protein-DNA complex 2 FOS, PAX2
external side of apical plasma membrane 1 ABCB1
basal dendrite 1 MAPK8
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
Cytoplasmic vesicle, phagosome 1 MTOR
transcription factor AP-1 complex 1 FOS
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
C/EBP complex 1 CEBPA
CHOP-C/EBP complex 1 CEBPA
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[Isoform 4]: Nucleus, nucleolus 1 CEBPA


文献列表

  • Xin-Liang Xu, Jin-Xia Lan, Hao Huang, Wei Dai, Xiao-Peng Peng, Sheng-Lan Liu, Wei-Ming Chen, Le-Jun Huang, Jun Liu, Xiao-Jun Li, Jun-Lin Zeng, Xian-Hua Huang, Guan-Nan Zhao, Wen Hou. Synthesis, biological activity and mechanism of action of novel allosecurinine derivatives as potential antitumor agents. Bioorganic & medicinal chemistry. 2023 03; 82(?):117234. doi: 10.1016/j.bmc.2023.117234. [PMID: 36906964]
  • Shabeeba M Ashraf, Susobhan Mahanty, Krishnan Rathinasamy. Securinine induces mitotic block in cancer cells by binding to tubulin and inhibiting microtubule assembly: A possible mechanistic basis for its anticancer activity. Life sciences. 2021 Dec; 287(?):120105. doi: 10.1016/j.lfs.2021.120105. [PMID: 34756929]
  • Hanlin Xiao, Qinghua Zhang, Peiyun Zhong, Genyun Tang, Lijun Tao, Zhengyi Huang, Daji Guo, Yumei Liao, Yinghui Peng, Zhen-Long Wu, Ying Wang, Wen-Cai Ye, Lei Shi. Securinine Promotes Neuronal Development and Exhibits Antidepressant-like Effects via mTOR Activation. ACS chemical neuroscience. 2021 10; 12(19):3650-3661. doi: 10.1021/acschemneuro.1c00381. [PMID: 34541857]
  • Yun Jung Lee, Byung Hyuk Han, Jung Joo Yoon, Hye Yoom Kim, You Mee Ahn, Mi Hyeon Hong, Chan Ok Son, Dae Gill Kang, Ho Sub Lee. Identification of securinine as vascular protective agent targeting atherosclerosis in vascular endothelial cells, smooth muscle cells, and apolipoprotein E deficient mice. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Jan; 81(?):153430. doi: 10.1016/j.phymed.2020.153430. [PMID: 33341451]
  • Wen Hou, Ying Meng, Xiao-Fang Xu, Zhi-Xing Huang, Jun Liu, Zhen-Ya Wang, Jing Lin, Wei-Min Chen. Novel virosecurinine bivalent mimetics as potent reversal agents against P-glycoprotein-mediated multidrug resistance. European journal of medicinal chemistry. 2019 Dec; 183(?):111726. doi: 10.1016/j.ejmech.2019.111726. [PMID: 31585275]
  • Kyoung Jin Park, Chung Sub Kim, Zahra Khan, Joonseok Oh, Sun Yeou Kim, Sang Un Choi, Kang Ro Lee. Securinega Alkaloids from the Twigs of Securinega suffruticosa and Their Biological Activities. Journal of natural products. 2019 05; 82(5):1345-1353. doi: 10.1021/acs.jnatprod.9b00142. [PMID: 31082231]
  • Zhen-Long Wu, Xiao-Jun Huang, Ming-Tao Xu, Xuanyue Ma, Liuren Li, Lei Shi, Wen-Jing Wang, Ren-Wang Jiang, Wen-Cai Ye, Ying Wang. Flueggeacosines A-C, Dimeric Securinine-Type Alkaloid Analogues with Neuronal Differentiation Activity from Flueggea suffruticosa. Organic letters. 2018 12; 20(23):7703-7707. doi: 10.1021/acs.orglett.8b03432. [PMID: 30484660]
  • Dmitri Leonoudakis, Anand Rane, Suzanne Angeli, Gordon J Lithgow, Julie K Andersen, Shankar J Chinta. Anti-Inflammatory and Neuroprotective Role of Natural Product Securinine in Activated Glial Cells: Implications for Parkinson's Disease. Mediators of inflammation. 2017; 2017(?):8302636. doi: 10.1155/2017/8302636. [PMID: 28473732]
  • Justyna Stefanowicz-Hajduk, Barbara Sparzak-Stefanowska, Mirosława Krauze-Baranowska, J Renata Ochocka. Securinine from Phyllanthus glaucus Induces Cell Cycle Arrest and Apoptosis in Human Cervical Cancer HeLa Cells. PloS one. 2016; 11(10):e0165372. doi: 10.1371/journal.pone.0165372. [PMID: 27792748]
  • Danuta Raj, Adam Kokotkiewicz, Maria Luczkiewicz. Production of therapeutically relevant indolizidine alkaloids in Securinega suffruticosa in vitro shoots maintained in liquid culture systems. Applied biochemistry and biotechnology. 2015 Feb; 175(3):1576-87. doi: 10.1007/s12010-014-1386-0. [PMID: 25413794]
  • Eqor Chirkin, William Atkatlian, François-Hugues Porée. The Securinega alkaloids. The Alkaloids. Chemistry and biology. 2015; 74(?):1-120. doi: 10.1016/bs.alkal.2014.11.001. [PMID: 25845059]
  • Egor Chirkin, William Atkatlian, Quyên Do, Thomas Gaslonde, Thi-Hanh Dufat, Sylvie Michel, Pascale Lemoine, Grégory Genta-Jouve, François-Hugues Porée. Chiroptical study and absolute configuration of securinine oxidation products. Natural product research. 2015; 29(13):1235-42. doi: 10.1080/14786419.2015.1023727. [PMID: 25790256]
  • Gang Zhang, Maidong Li, Shuwen Han, Dongyun Chen, Ying Wang, Wencai Ye, Zhaoning Ji. Induction of human chronic myeloid leukemia K562 cell apoptosis by virosecurinine and its molecular mechanism. Molecular medicine reports. 2014 Nov; 10(5):2365-71. doi: 10.3892/mmr.2014.2531. [PMID: 25189629]
  • Simuli L Wabuyele, David Wald, Yan Xu. Development and validation of LC-MS/MS method for quantitative determination of (-)-securinine in mouse plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jun; 960(?):19-26. doi: 10.1016/j.jchromb.2014.04.011. [PMID: 24786218]
  • Shuwen Han, Gang Zhang, Maidong Li, Dongyun Chen, Ying Wang, Wencai Ye, Zhaoning Ji. L-securinine induces apoptosis in the human promyelocytic leukemia cell line HL-60 and influences the expression of genes involved in the PI3K/AKT/mTOR signaling pathway. Oncology reports. 2014 May; 31(5):2245-51. doi: 10.3892/or.2014.3101. [PMID: 24676995]
  • Matt Shipman, Kirk Lubick, David Fouchard, Rajani Guram, Paul Grieco, Mark Jutila, Edward A Dratz. Proteomic and systems biology analysis of monocytes exposed to securinine, a GABA(A) receptor antagonist and immune adjuvant. PloS one. 2012; 7(9):e41278. doi: 10.1371/journal.pone.0041278. [PMID: 23028424]
  • Yong-Hui Xia, Chuan-Rong Cheng, Shu-Yan Yao, Qing Zhang, Ying Wang, Zhao-Ning Ji. L-securinine induced the human colon cancer SW480 cell autophagy and its molecular mechanism. Fitoterapia. 2011 Dec; 82(8):1258-64. doi: 10.1016/j.fitote.2011.08.015. [PMID: 21907765]
  • Kalpana Gupta, Amitabha Chakrabarti, Sonia Rana, Ritu Ramdeo, Bryan L Roth, Munna L Agarwal, William Tse, Mukesh K Agarwal, David N Wald. Securinine, a myeloid differentiation agent with therapeutic potential for AML. PloS one. 2011; 6(6):e21203. doi: 10.1371/journal.pone.0021203. [PMID: 21731671]
  • Ayumi Ohsaki, Yukino Kobayashi, Kaisuke Yoneda, Akio Kishida, Haruaki Ishiyama. Securinega alkaloids from the wood of Securinega suffruticosa var. amamiensis. Journal of natural products. 2007 Dec; 70(12):2003-5. doi: 10.1021/np0780102. [PMID: 18052029]
  • Wei Yuan, Ping Zhu, Kedi Cheng, Chao Meng, Lin Ma, Feng Wu, Huixin Zhu. Callus of Securinega suffruticosa, a cell line accumulates dextro Securinega alkaloids. Natural product research. 2007 Mar; 21(3):234-42. doi: 10.1080/14786410701189781. [PMID: 17365714]
  • Hai-yan Wu, Jin-yun Zhou. [Studies on chemical constituents from leaves of Securinega suffruticosa]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2004 Jun; 29(6):535-7. doi: . [PMID: 15706917]
  • Xiao-hai Li, Jin-lin Zhang, Tong-hui Zhou. [The metabolic transformation of (-)-securinine]. Yao xue xue bao = Acta pharmaceutica Sinica. 2002 Apr; 37(4):288-93. doi: NULL. [PMID: 12579826]
  • Xiao-hai Li, Jin-lan Zhang, Tong-hui Zhou. [Study on the chiral separation of securinine by high-performance capillary electrophoresis and its stereoselective metabolism in rat]. Yao xue xue bao = Acta pharmaceutica Sinica. 2002 Jan; 37(1):50-3. doi: NULL. [PMID: 12579900]
  • X Y Zhao, Z Y Jiang, J Z Peng. [Cardiovascular effects of lateral intracerebroventricular injection of L-securinine]. Sheng li xue bao : [Acta physiologica Sinica]. 2000 Dec; 52(6):473-8. doi: . [PMID: 11941410]
  • F S Yan, G B Li, F X Li. [Comparative study of applying tiaoxue yisui recipe and SSL regimen in treating infantile chronic aplastic anemia and analysis of its therapeutical mechanism]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 1997 Jun; 17(6):331-3. doi: ". [PMID: 9863123]
  • NULL. The metabolic fate of securinine. Chinese medical journal. 1975 May; 1(3):205-15. doi: NULL. [PMID: 219]