Picrotoxinin (BioDeep_00001867546)
Main id: BioDeep_00000000752
PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C15H16O6 (292.0947)
中文名称: （1R，3R，5S，8S，9S，12S，13R，14R）-1-羟基-13-甲基-14-丙-1-烯-2-基-4,7,10-三氧杂五环[6.4.1.19，12.03,5.05,13]十四烷-6,11-二酮, 木防己苦毒宁
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(=C)C1C2C3C4(C(C1C(=O)O2)(CC5C4(O5)C(=O)O3)O)C
InChI: InChI=1S/C15H16O6/c1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h6-10,18H,1,4H2,2-3H3/t6-,7+,8-,9-,10-,13-,14-,15+/m1/s1
描述信息
Picrotoxinin is a picrotoxane sesquiterpenoid that is 3a,4,5,6,7,7a-hexahydro-1H-indene-3,7-dicarboxylic acid which is substituted at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy groups, respectively; in which the double bond at position 2-3 has been epoxidised; and in which the carboxy groups at positions 3 and 7 have undergone gamma-lactone formation by O-alkylation to positions 4 and 5, respectively. A component of picrotoxin. It has a role as a plant metabolite, a GABA antagonist and a serotonergic antagonist. It is an organic heteropentacyclic compound, an epoxide, a tertiary alcohol, a gamma-lactone and a picrotoxane sesquiterpenoid.
Picrotoxinin is a natural product found in Picrodendron baccatum and Anamirta cocculus with data available.
A picrotoxane sesquiterpenoid that is 3a,4,5,6,7,7a-hexahydro-1H-indene-3,7-dicarboxylic acid which is substituted at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy groups, respectively; in which the double bond at position 2-3 has been epoxidised; and in which the carboxy groups at positions 3 and 7 have undergone gamma-lactone formation by O-alkylation to positions 4 and 5, respectively. A component of picrotoxin.
D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018756 - GABA Antagonists
Picrotoxinin, a potent convulsant, is a chloride channel blocker. Picrotoxinin is a noncompetitive GABAA receptor antagonist, which negatively modulates the action of GABA on GABAA receptors. Picrotoxinin inhibits α1β2γ2L GABAA receptor with an IC50 of 1.15 μM[1].
Picrotoxinin, a potent convulsant, is a chloride channel blocker. Picrotoxinin is a noncompetitive GABAA receptor antagonist, which negatively modulates the action of GABA on GABAA receptors. Picrotoxinin inhibits α1β2γ2L GABAA receptor with an IC50 of 1.15 μM[1].
同义名列表
40 个代谢物同义名
3,6-Methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-, (1aR-(1a-alpha,2a-beta,3-beta,6-beta,6a-beta,8as*,8b-beta,9R*))-; (1aR-(1aalpha,2abeta,3beta,6beta,6abeta,8aS*,8bbeta,9R*))-Hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-3,6-methano-8H-1,5,7-trioxa cyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione; 3,6-Methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-, (1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-; 3,6-Methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-, (1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-; PICROTOXININ1-hydroxy-14-isopropenyl-13-methyl-(1R,3R,5S,8S,9R,12S,13R,14R)-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione(picrotoxinin); (1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-2a-hydroxy-8b-methyl-9-(prop-1-en-2-yl)hexahydro-3,6-methano-1,5,7-trioxacyclopenta[ij]c yclopropa[a]azulene-4,8(3H)-dione; (1ar,2ar,3s,6r,6as,8as,8br,9r)-2a-Hydroxy-8b-Methyl-9-(Prop-1-En-2-Yl)hexahydro-3,6-Methano-1,5,7-Trioxacyclopenta[ij]cyclopropa[a]azulene-4,8(3h)-Dione; 1-hydroxy-14-isopropenyl-13-methyl-(1R,3R,5S,8S,9R,12S,13R,14R)-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione(picrotoxin); (1R,3R,5S,8S,9R,12S,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1(9,12).0(3,5).0(5,13)]tetradecane-6,11-dione; (5S,8S,12S,1R,3R,9R,13R,14R)-1-hydroxy-13-methyl-14-(1-methylvinyl)-4,7,10-tri oxapentacyclo[6.4.1.1<9,12>.0<3,5>.0<5,13>]tetradecane-6,11-dione; (1R,3R,5S,8S,9R,12S,13R,14R)-1-hydroxy-13-methyl-14-prop-1-en-2-yl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione; 1-hydroxy-14-isopropenyl-13-methyl-(1R,3R,5S,8S,9R,12S,13R,14R)-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione; (1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-2a-hydroxy-8b-methyl-9-(prop-1-en-2-yl)hexahydro-3,6-methano-1,5,7-trioxacyclopenta[ij]c; Picrotoxinin (from Anamirta cocculus seed); 3-(1-Methyl-pyrrolidin-2-yl)-pyridine; yclopropa[a]azulene-4,8(3H)-dione; PIMZUZSSNYHVCU-YKWPQBAZSA-N; Picrotoxin (Part b); PICROTOXININ [MI]; Spectrum2_001085; Spectrum3_001437; Spectrum5_001313; Spectrum4_000911; (-)-Picrotoxinin; UNII-9K011NUF0R; BPBio1_001035; DivK1c_000595; picrotoxinine; KBio2_001772; Picrotoxinin; KBio3_002394; KBio2_004340; KBio2_006908; KBio1_000595; IDI1_000595; 9K011NUF0R; AI3-41571; RI5; Picrotoxinin; (1R,3R,5S,8S,9S,12S,13R,14R)-1-hydroxy-13-methyl-14-prop-1-en-2-yl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:8206
- KEGG: C09529
- PubChem: 442292
- ChEMBL: CHEMBL47244
- LipidMAPS: LMPR0103540001
- MeSH: picrotoxinin
- ChemIDplus: 0017617457
- CAS: 17617-45-7
- medchemexpress: HY-B1494
- MetaboLights: MTBLC8206
- PubChem: 11720
- KNApSAcK: C00003350
- PDB-CCD: RI5
- 3DMET: B03051
- NIKKAJI: J10.347K
- KNApSAcK: 8206
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)
3 个相关的物种来源信息
- 432627 - Anamirta cocculus: 10.1016/S0031-9422(98)00692-X
- 212329 - Picrodendron baccatum: 10.1248/BPB.22.1310
- 33090 - Plants: -
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
- Guanghu Tong, Ryan A Shenvi. Revision of the Unstable Picrotoxinin Hydrolysis Product.
Angewandte Chemie (International ed. in English).
2021 08; 60(35):19113-19116. doi:
10.1002/anie.202107785. [PMID: 34236745] - Monaj Kumar Sarkar, Vellingiri Vadivel, Mamilla R Charan Raja, Santanu Kar Mahapatra. Investigation of phytochemical constituents of anti-leukemic herbal drugs used by the traditional healers of Purulia, Birbhum and Bankura districts of West Bengal.
Natural product research.
2020 Dec; 34(23):3388-3393. doi:
10.1080/14786419.2019.1566818. [PMID: 30764661] - Brandon Pressly, Natalia Vasylieva, Bogdan Barnych, Vikrant Singh, Latika Singh, Donald A Bruun, Sung Hee Hwang, Yi-Je Chen, James C Fettinger, Stephanie Johnnides, Pamela J Lein, Jun Yang, Bruce D Hammock, Heike Wulff. Comparison of the toxicokinetics of the convulsants picrotoxinin and tetramethylenedisulfotetramine (TETS) in mice.
Archives of toxicology.
2020 06; 94(6):1995-2007. doi:
10.1007/s00204-020-02728-z. [PMID: 32239239] - Min-Shan Lin, Wen-Chao Xiong, Shu-Ji Li, Zhi Gong, Xiong Cao, Xiao-Jing Kuang, Yuan Zhang, Tian-Ming Gao, Naguib Mechawar, Ce Liu, Xin-Hong Zhu. α2-glycine receptors modulate adult hippocampal neurogenesis and spatial memory.
Developmental neurobiology.
2017 12; 77(12):1430-1441. doi:
10.1002/dneu.22549. [PMID: 29057625] - Shun-Fan Wu, Xi-Chao Mu, Yao-Xue Dong, Li-Xiang Wang, Qi Wei, Cong-Fen Gao. Expression pattern and pharmacological characterisation of two novel alternative splice variants of the glutamate-gated chloride channel in the small brown planthopper Laodelphax striatellus.
Pest management science.
2017 Mar; 73(3):590-597. doi:
10.1002/ps.4340. [PMID: 27302648] - R A Shenvi. Neurite outgrowth enhancement by jiadifenolide: possible targets.
Natural product reports.
2016 Apr; 33(4):535-9. doi:
10.1039/c5np00160a. [PMID: 26891462] - Janhvi Mishra Rawat, Balwant Rawat, Shakti Mehrotra. Plant regeneration, genetic fidelity, and active ingredient content of encapsulated hairy roots of Picrorhiza kurrooa Royle ex Benth.
Biotechnology letters.
2013 Jun; 35(6):961-8. doi:
10.1007/s10529-013-1152-3. [PMID: 23397268] - Andrew J Thompson, Gavin E Jarvis, Rujee K Duke, Graham A R Johnston, Sarah C R Lummis. Ginkgolide B and bilobalide block the pore of the 5-HT₃receptor at a location that overlaps the picrotoxin binding site.
Neuropharmacology.
2011 Feb; 60(2-3):488-95. doi:
10.1016/j.neuropharm.2010.11.003. [PMID: 21059362] - T Ikeda, Y Ozoe, E Okuyama, K Nagata, H Honda, T Shono, T Narahashi. Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons.
British journal of pharmacology.
1999 Aug; 127(7):1567-76. doi:
10.1038/sj.bjp.0702700. [PMID: 10455311] - L Giménez-Llort, E Martínez, L Camón, N de Vera. Concentration of putrescine in plasma, frontal cortex and hippocampus of rats after systemic administration of the convulsants N-methyl-D-aspartate, pentylentetrazol, picrotoxinine, lindane and 4-aminopyridine.
Neuroscience letters.
1996 Oct; 217(1):1-4. doi:
. [PMID: 8905725] - T McIntyre, P Skolnick. t-[35S]butylbicyclophosphorothionate binding under equilibrium and nonequilibrium conditions: differential effects of barbiturates and gamma-aminobutyric acid in the long-sleep and short-sleep selected mouse lines.
Journal of neurochemistry.
1991 Jan; 56(1):287-93. doi:
10.1111/j.1471-4159.1991.tb02594.x. [PMID: 1846173] - R Soto-Otero, E Mendez-Alvarez, G Sierra-Paredes, J Galan-Valiente, E Aguilar-Veiga, G Sierra-Marcuño. Simultaneous determination of the two components of picrotoxin in serum by reversed-phase high-performance liquid chromatography with application to a pharmacokinetic study in rats.
Journal of pharmaceutical and biomedical analysis.
1989; 7(3):369-75. doi:
10.1016/0731-7085(89)80104-9. [PMID: 2488637] - M K Ticku, T P Burch, W C Davis. The interactions of ethanol with the benzodiazepine-GABA receptor-ionophore complex.
Pharmacology, biochemistry, and behavior.
1983; 18 Suppl 1(?):15-8. doi:
10.1016/0091-3057(83)90140-5. [PMID: 6138771] - K Matsumoto, H Fukuda. Anisatin modulation of GABA- and pentobarbital-induced enhancement of diazepam binding in rat brain.
Neuroscience letters.
1982 Oct; 32(2):175-9. doi:
10.1016/0304-3940(82)90270-1. [PMID: 6292798]
