Guineensine (BioDeep_00000227712)

   

human metabolite


代谢物信息卡片


(2E,4E,12E)-13-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide

  化学式: C24H33NO3 (383.246)
中文名称:
  谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C)CNC(=O)/C=C/C=C/CCCCCC/C=C/C1=CC2=C(C=C1)OCO2
InChI: InChI=1S/C24H33NO3/c1-20(2)18-25-24(26)14-12-10-8-6-4-3-5-7-9-11-13-21-15-16-22-23(17-21)28-19-27-22/h8,10-17,20H,3-7,9,18-19H2,1-2H3,(H,25,26)/b10-8+,13-11+,14-12+


描述信息

Guineensine, also known as pipyahyine, is a member of the class of compounds known as benzodioxoles. Benzodioxoles are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Guineensine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Guineensine can be found in pepper (spice), which makes guineensine a potential biomarker for the consumption of this food product. Guineesine (or guineensine) is an alkaloid isolated from long pepper (Piper longum) and black pepper (Piper nigrum) .

同义名列表

16 个代谢物同义名

(2E,4E,12E)-13-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide; (2E,4E,12E)-13-(Benzo(D)(1,3)dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide); 13-(Benzo(D)(1,3)dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide; Guineensine; Guineesine; Pipyahyine; (2E,4E,12E)-13-(1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)-2,4,12-tridecatrienamide; (2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide; (2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-isobutyl-trideca-2,4,12-trienamide; (2E,4E,12E)-13-(benzo(d)(1,3)dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide; (2E,4E,12E)-13-(benzo[d][1,3]dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide; (E,E,E)-Guineensine; 2,4,12-Tridecatrienamide, 13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (2E,4E,12E)-; 2,4,12-Tridecatrienamide, 13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (E,E,E)-; 7DK8DMU9JX; UNII-7DK8DMU9JX



数据库引用编号

11 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)

1 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


文献列表

  • Ruben Bartholomäus, Simon Nicolussi, Alice Baumann, Mark Rau, Ana Catarina Simão, Jürg Gertsch, Karl-Heinz Altmann. Total Synthesis of the Endocannabinoid Uptake Inhibitor Guineensine and SAR Studies. ChemMedChem. 2019 09; 14(17):1590-1596. doi: 10.1002/cmdc.201900390. [PMID: 31322825]
  • Christopher W Cunningham. Plant-Based Modulators of Endocannabinoid Signaling. Journal of natural products. 2019 03; 82(3):636-646. doi: 10.1021/acs.jnatprod.8b00874. [PMID: 30816712]
  • Inés Reynoso-Moreno, Israel Najar-Guerrero, Noé Escareño, Mario Eduardo Flores-Soto, Jürg Gertsch, Juan Manuel Viveros-Paredes. An Endocannabinoid Uptake Inhibitor from Black Pepper Exerts Pronounced Anti-Inflammatory Effects in Mice. Journal of agricultural and food chemistry. 2017 Nov; 65(43):9435-9442. doi: 10.1021/acs.jafc.7b02979. [PMID: 28942644]
  • Simon Nicolussi, Juan Manuel Viveros-Paredes, María Salomé Gachet, Mark Rau, Mario Eduardo Flores-Soto, Martina Blunder, Jürg Gertsch. Guineensine is a novel inhibitor of endocannabinoid uptake showing cannabimimetic behavioral effects in BALB/c mice. Pharmacological research. 2014 Feb; 80(?):52-65. doi: 10.1016/j.phrs.2013.12.010. [PMID: 24412246]
  • Zhi-Yong Jiang, Wen-Feng Liu, Xue-Mei Zhang, Jie Luo, Yun-Bao Ma, Ji-Jun Chen. Anti-HBV active constituents from Piper longum. Bioorganic & medicinal chemistry letters. 2013 Apr; 23(7):2123-7. doi: 10.1016/j.bmcl.2013.01.118. [PMID: 23434420]
  • Weng Ieong Tou, Su-Sen Chang, Cheng-Chun Lee, Calvin Yu-Chian Chen. Drug design for neuropathic pain regulation from traditional Chinese medicine. Scientific reports. 2013; 3(?):844. doi: 10.1038/srep00844. [PMID: 23378894]
  • Saksit Nobsathian, Patoomratana Tuchinda, Darunee Soorukram, Manat Pohmakotr, Vichai Reutrakul, Chalobon Yoosook, Jitra Kasisit, Chanita Napaswad. A new conjugated amide-dimer from the aerial parts of Piper submultinerve. Natural product research. 2012; 26(19):1824-30. doi: 10.1080/14786419.2011.639071. [PMID: 22117113]
  • Bruno Ndjakou Lenta, Ferdinand Tantangmo, Krishna Prasad Devkota, Jean Duplex Wansi, Jean Rodolphe Chouna, Rene Cosme Fongang Soh, Beate Neumann, Hans-Georg Stammler, Etienne Tsamo, Norbert Sewald. Bioactive constituents of the stem bark of Beilschmiedia zenkeri. Journal of natural products. 2009 Dec; 72(12):2130-4. doi: 10.1021/np900341f. [PMID: 19904919]
  • Seung Woong Lee, Young Kook Kim, Koanhoi Kim, Hyun Sun Lee, Jung Ho Choi, Woo Song Lee, Chang-Duk Jun, Jee Hun Park, Jeong Min Lee, Mun-Chual Rho. Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition. Bioorganic & medicinal chemistry letters. 2008 Aug; 18(16):4544-6. doi: 10.1016/j.bmcl.2008.07.045. [PMID: 18672369]
  • Hisashi Matsuda, Kiyofumi Ninomiya, Toshio Morikawa, Daisuke Yasuda, Itadaki Yamaguchi, Masayuki Yoshikawa. Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes. Bioorganic & medicinal chemistry letters. 2008 Mar; 18(6):2038-42. doi: 10.1016/j.bmcl.2008.01.101. [PMID: 18289853]
  • Seung Woong Lee, Mun-Chual Rho, Jung Yeon Nam, Eun Hee Lim, Oh Eok Kwon, Young Ho Kim, Hyun Sun Lee, Young Kook Kim. Guineensine, an Acyl-CoA: cholesterol acyltransferase inhibitor, from the fruits of Piper longum. Planta medica. 2004 Jul; 70(7):678-9. doi: 10.1055/s-2004-827193. [PMID: 15254860]