Bicuculline (BioDeep_00000000317)

 

Secondary id: BioDeep_00000015568, BioDeep_00000398567, BioDeep_00000859957

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


(bicuculline) 6-Methyl-5-(8-oxo-6,8-dihydro-furo[3,4:3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium

化学式: C20H17NO6 (367.1055822)
中文名称: 毕扣扣灵碱, 右旋比扣扣灵碱, 必扣扣灵, 比枯枯灵, 山乌龟碱, (+)-荷包牡丹碱, 右旋荷包牡丹碱, 毕枯枯林
谱图信息: 最多检出来源 Viridiplantae(plant) 1.15%

Reviewed

Last reviewed on 2024-07-09.

Cite this Page

Bicuculline. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/bicuculline (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000000317). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CN1CCC2=CC3=C(C=C2C1C4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3
InChI: InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1

描述信息

Bicuculline is a benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species. It has a role as an agrochemical, a central nervous system stimulant, a GABA-gated chloride channel antagonist, a neurotoxin and a GABAA receptor antagonist. It is an isoquinoline alkaloid, a member of isoquinolines and a benzylisoquinoline alkaloid.
Bicuculline is a light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.
Bicuculline is a natural product found in Fumaria capreolata, Fumaria densiflora, and other organisms with data available.
Bicuculline is a light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species. Since it blocks the inhibitory action of GABA receptors, the action of bicuculline mimics epilepsy. This property is utilized in laboratories across the world in the in vitro study of epilepsy, generally in hippocampal or cortical neurons in prepared brain slices from rodents. This compound is also routinely used to isolate glutamatergic (excitatory amino acid) receptor function.
An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.
A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.

Bicuculline. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=485-49-4 (retrieved 2024-07-09) (CAS RN: 485-49-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Bicuculline ((+)-Bicuculline; d-Bicuculline), as a convulsant alkaloid, is a competitive neurotransmitter GABAA receptor antagonist (IC50=2 μM). Bicuculline also blocks Ca2+-activated potassium (SK) channels and subsequently blocks the slow afterhyperpolarization (slow AHP) [1][2][3].
Bicuculline ((+)-Bicuculline) is A competing neurotransmitter GABAA receptor antagonist (IC50=2 μM). Bicuculline also blocks Ca2+ activating potassium (SK) channels and subsequently blocks slow post-hyperpolarization (slow AHP). Bicuculline has anticonvulsant activity. Bicuculline can be used to induce seizures in mice[1][2][3][4].
Bicuculline ((+)-Bicuculline; d-Bicuculline), as a convulsant alkaloid, is a competitive neurotransmitter GABAA receptor antagonist (IC50=2 μM). Bicuculline also blocks Ca2+-activated potassium (SK) channels and subsequently blocks the slow afterhyperpolarization (slow AHP) [1][2][3].

同义名列表

49 个代谢物同义名

(bicuculline) 6-Methyl-5-(8-oxo-6,8-dihydro-furo[3,4:3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium; (6R)-6-((5S)-6-methyl(5,6,7,8-tetrahydro-2H-1,3-dioxolano[4,5-g]isoquinolin-5- yl))-6-hydro-2H-1,3-dioxoleno[4,5-e]isobenzofuran-8-one; 6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3,4:3,4]benzo[1,2-d][1,3]dioxol-8-one (Bicuculline); 6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3,4:3,4]benzo[1,2-d][1,3]dioxol-8-one(bicuculline); (R)-6-((S)-6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3,4:3,4]benzo[1,2-d][1,3]dioxol-8-one; Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (R-(R*,S*))-; Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-((5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (6R)-; Furo[3,4-e]-1,3-benzodioxol-8(6H)-one, 6-[(5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (6R)-; (R)-6-((S)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-[1,3]dioxolo[4,5-e]isobenzofuran-8(6H)-one; [R-(R*,S*)]-6-(5,6,7,8-Tetrahydro-6 -methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)furo[3, 4-e]-1,3-benzodioxol-8(6H)-one; [R-(R*,S*)]-6-(5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)furo[3,4-e]-1,3-benzodioxol-8(6H)-one; (R)-6-((S)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuro[5,4-d][1,3]dioxol-8(6H)-one; (6R)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]lisoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one; (6R)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one; 6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3,4:3,4]benzo[1,2-d][1,3]dioxol-8-one; Furo[3,3-benzodioxol-8(6H)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [R-(R*,S*)]-; (6R)-6-((5S)-6-METHYL-5,6,7,8-TETRAHYDRO(1,3)DIOXOLO(4,5-G)ISOQUINOLIN-5-YL)FURO(3,4-E)(1,3BENZODIOXOL-8(6H)-ONE; (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one; (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[4,3-g][1,3]benzodioxol-8-one; 6-(5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)furo(3,4-e)1,3-benzodioxol-8(6H)one; 4-27-00-06900 (Beilstein Handbook Reference); (+)-Bicuculline, >=97.0\\% (TLC); (+)-Bicuculline- Bio-X; (+)-Bicuculline, 98\\%; Prestwick0_000589; Prestwick1_000589; Prestwick2_000589; Prestwick3_000589; BICUCULLINE [MI]; Bicuculline (+); bicuculline-(+); Bicuculline,(+); (+)-Bicuculline; Lopac0_000234; BPBio1_000482; BPBio1_000794; d-Bicuculline; DivK1c_000609; Prestwick_96; PDSP2_000138; KBio1_000609; Bicuculline; IDI1_000609; Bicucullin; Bicculine; H0Z; (+-)-Bicuculline; Capnoidine; Bicuculline



数据库引用编号

34 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

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149 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

  • Weikang Chen, Yangbin Zheng, Yanyan Zhu, Dehong Liu, Lianghui Zhu. Pharmacokinetics, tissue distribution, and plasma protein binding ratio of bicuculline following intragastric and intravenous administration in rats using ultra-high-performance liquid chromatography-tandem mass spectrometry. Biomedical chromatography : BMC. 2023 Dec; ?(?):e5802. doi: 10.1002/bmc.5802. [PMID: 38110194]
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  • Magdalena Olga Ciechanowska, Magdalena Łapot, Marek Kowalczyk, Tadeusz Malewski, Marek Brytan, Bożena Antkowiak, Franciszek Przekop. Does kisspeptin participate in GABA-mediated modulation of GnRH and GnRH receptor biosynthesis in the hypothalamic-pituitary unit of follicular-phase ewes?. Pharmacological reports : PR. 2019 Aug; 71(4):636-643. doi: 10.1016/j.pharep.2019.02.019. [PMID: 31176893]
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  • Simonas Masiulis, Rooma Desai, Tomasz Uchański, Itziar Serna Martin, Duncan Laverty, Dimple Karia, Tomas Malinauskas, Jasenko Zivanov, Els Pardon, Abhay Kotecha, Jan Steyaert, Keith W Miller, A Radu Aricescu. GABAA receptor signalling mechanisms revealed by structural pharmacology. Nature. 2019 01; 565(7740):454-459. doi: 10.1038/s41586-018-0832-5. [PMID: 30602790]
  • Yuntao Ou, Man Su, Yong Ling, Qianqian Wei, Fei Pan, Jiejia Li, Jun-Xu Li, Qing Zhu. Anti-allodynic effects of N-demethylsinomenine, an active metabolite of sinomenine, in a mouse model of postoperative pain. European journal of pharmacology. 2018 Mar; 823(?):105-109. doi: 10.1016/j.ejphar.2018.01.044. [PMID: 29408089]
  • Gisele Claudine Nkamguie Nkantchoua, Jacqueline Stephanie Kameni Njapdounke, Jean Jules Fifen, Germain Sotoing Taiwe, Lucie Josiane Ojong, Antoine Kavaye Kandeda, Elisabeth Ngo Bum. Anticonvulsant effects of Senna spectabilis on seizures induced by chemicals and maximal electroshock. Journal of ethnopharmacology. 2018 Feb; 212(?):18-28. doi: 10.1016/j.jep.2017.09.042. [PMID: 28986332]
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