Eseroline (BioDeep_00000397872)

   


代谢物信息卡片


(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol

  化学式: C13H18N2O (218.1419)
中文名称:
  谱图信息: 最多检出来源 () %

分子结构信息

SMILES: CC12CCN(C1N(C3=C2C=C(C=C3)O)C)C
InChI: InChI=1S/C13H18N2O/c1-13-6-7-14(2)12(13)15(3)11-5-4-9(16)8-10(11)13/h4-5,8,12,16H,6-7H2,1-3H3


描述信息

A pyrroloindole that is 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole substituted by methyl groups at positions 1, 3a and 8 and a hydroxy group at position 5. It is a metabolite of physostigmine and causes neuronal cell death by a mechanism involving loss of cell ATP.
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3583

同义名列表

23 个代谢物同义名

Eseroline; Eseroline; (-)-Eseroline; (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrol[2,3-b]indol-7-ol;maleate; (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol; (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol;(Z)-2-butenedioate; (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol;(Z)-but-2-enedioate; (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-ol; (3AS,8AR)-1,2,3,3A,8,8A-HEXAHYDRO-1,3A,8-TRIMETHYLPYRROLO(2,3-B)INDOL-5-OL; (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indol-5-ol; (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol; Eseroline (-)-Eseroline (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol; eseroline monohydrochloride, (3aS-cis)-isomer; eseroline-(-); ESEROLINE, (-)-; eseroline, (+)-; eseroline, (3aR-cis)-isomer; PYRROLO(2,3-B)INDOL-5-OL, 1,2,3,3A,8,8A-HEXAHYDRO-1,3A,8-TRIMETHYL-, (3AS-CIS)-; Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS,8aR)-; Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS-cis)-; Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS,8aR)-; Q22H41O18D; UNII-Q22H41O18D



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome()

BioCyc()

PlantCyc()

代谢反应

个相关的代谢反应过程信息。

Reactome()

BioCyc()

WikiPathways()

Plant Reactome()

INOH()

PlantCyc()

COVID-19 Disease Map()

PathBank()

PharmGKB()

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

  • Nadine Pinder, Johannes B Zimmermann, Stefan Hofer, Thorsten Brenner, Markus A Weigand, Ute Gubbe, Torsten Hoppe-Tichy, Stefanie Swoboda. Revival of physostigmine - a novel HPLC assay for simultaneous determination of physostigmine and its metabolite eseroline designed for a pharmacokinetic study of septic patients. Clinical chemistry and laboratory medicine. 2015 Jul; 53(8):1259-64. doi: 10.1515/cclm-2014-0834. [PMID: 25565546]
  • Bin Zhao, Shabbir M Moochhala, Cheng Shu Chaw, Yi Yan Yang. Simple liquid chromatographic method for the determination of physostigmine and its metabolite eseroline in rat plasma: application to a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Feb; 784(2):323-9. doi: 10.1016/s1570-0232(02)00817-6. [PMID: 12505780]
  • A Galli, E Ranaudo, L Giannini, C Costagli. Reversible inhibition of cholinesterases by opioids: possible pharmacological consequences. The Journal of pharmacy and pharmacology. 1996 Nov; 48(11):1164-8. doi: 10.1111/j.2042-7158.1996.tb03914.x. [PMID: 8961166]
  • K D Quinn, J T Stewart. A high performance liquid chromatographic post-column fluorescent ion pair extraction system: application to physostigmine and its metabolite eseroline in human serum. Biomedical chromatography : BMC. 1991 Jan; 5(1):8-13. doi: 10.1002/bmc.1130050104. [PMID: 2032023]
  • G D Lawrence, N Yatim. Extraction of physostigmine from biologic fluids and analysis by liquid chromatography with electrochemical detection. Journal of pharmacological methods. 1990 Sep; 24(2):137-43. doi: 10.1016/0160-5402(90)90024-f. [PMID: 2232817]
  • Q S Yu, J R Atack, S I Rapoport, A Brossi. Carbamate analogues of (-)-physostigmine: in vitro inhibition of acetyl- and butyrylcholinesterase. FEBS letters. 1988 Jul; 234(1):127-30. doi: 10.1016/0014-5793(88)81317-6. [PMID: 3391264]
  • E Giacobini, S Somani, M McIlhany, M Downen, M Hallak. Pharmacokinetics and pharmacodynamics of physostigmine after intravenous administration in beagle dogs. Neuropharmacology. 1987 Jul; 26(7B):831-6. doi: 10.1016/0028-3908(87)90059-1. [PMID: 3658115]
  • S M Somani, A Khalique. Determination of physostigmine in plasma and brain by HPLC. Journal of analytical toxicology. 1985 Mar; 9(2):71-5. doi: 10.1093/jat/9.2.71. [PMID: 3921763]
  • A Galli, P Malmberg Aiello, G Renzi, A Bartolini. In-vitro and in-vivo protection of acetylcholinesterase by eseroline against inactivation by diisopropyl fluorophosphate and carbamates. The Journal of pharmacy and pharmacology. 1985 Jan; 37(1):42-8. doi: 10.1111/j.2042-7158.1985.tb04928.x. [PMID: 2858526]
  • A Galli, G Renzi, E Grazzini, R Bartolini, P Aiello-Malmberg, A Bartolini. Reversible inhibition of acetylcholinesterase by eseroline, an opioid agonist structurally related to physostigmine (eserine) and morphine. Biochemical pharmacology. 1982 Apr; 31(7):1233-8. doi: 10.1016/0006-2952(82)90009-0. [PMID: 7092918]