Naphthalene epoxide (BioDeep_00000010142)

 

Secondary id: BioDeep_00001884412

human metabolite Endogenous


代谢物信息卡片


1,2-Epoxy-1,2-dihydro-naphthalene

化学式: C10H8O (144.0575118)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 0.47%

分子结构信息

SMILES: C1=CC2OC2c2ccccc21
InChI: InChI=1S/C10H8O/c1-2-4-8-7(3-1)5-6-9-10(8)11-9/h1-6,9-10H

描述信息

Naphthalene epoxide is an epoxide derivative of naphthalene. The toxicity of naphthalene has to do with the Phase I metabolism of this compound by cytochrome P450 monooxygenases. Deactivation of naphthalene involves epoxidation followed by glutathione conjugation and mercapturic acid formation. Naphthalene is stereoselectively metabolized to form (1R,2S)-Naphthalene epoxide and (1S,2R)-Naphthalene epoxide in the presence of CYP1A1 and CYP1A2, CYP2E1,CYP3A4 and CYP2A6. (PMID: 16959878) [HMDB]
Naphthalene epoxide is an epoxide derivative of naphthalene. The toxicity of naphthalene has to do with the Phase I metabolism of this compound by cytochrome P450 monooxygenases. Deactivation of naphthalene involves epoxidation followed by glutathione conjugation and mercapturic acid formation. Naphthalene is stereoselectively metabolized to form (1R,2S)-Naphthalene epoxide and (1S,2R)-Naphthalene epoxide in the presence of CYP1A1 and CYP1A2, CYP2E1,CYP3A4 and CYP2A6. (PMID: 16959878).

同义名列表

11 个代谢物同义名

1,2-Epoxy-1,2-dihydro-naphthalene; 1,2-Epoxy-1,2-dihydronaphthalene; 1aH,7bH-naphtho[1,2-b]oxirene; (1R,2S)-Naphthalene 1,2-oxide; (1S,2R)-Naphthalene epoxide; (1R,2S)-Naphthalene epoxide; Naphthalene 1,2-epoxide; Naphthalene-1,2-oxide; Naphthalene 1,2-oxide; Naphthalene epoxide; Naphthalene oxide



数据库引用编号

15 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

2 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(2)

  • Glutathione Metabolism: -Glutamylcysteine + Adenosine triphosphate + Glycine ⟶ Adenosine diphosphate + Glutathione + Hydrogen Ion + Phosphate
  • Glutathione Metabolism: Hydrogen Ion + NADPH + Oxidized glutathione ⟶ Glutathione + NADP

PharmGKB(0)

2 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

  • Suramya Waidyanatha, Melissa A Troester, Andrew B Lindstrom, Stephen M Rappaport. Measurement of hemoglobin and albumin adducts of naphthalene-1,2-oxide, 1,2-naphthoquinone and 1,4-naphthoquinone after administration of naphthalene to F344 rats. Chemico-biological interactions. 2002 Oct; 141(3):189-210. doi: 10.1016/s0009-2797(02)00048-0. [PMID: 12385719]
  • L S Tsuruda, M W Lamé, A D Jones. Formation of epoxide and quinone protein adducts in B6C3F1 mice treated with naphthalene, sulfate conjugate of 1,4-dihydroxynaphthalene and 1,4-naphthoquinone. Archives of toxicology. 1995; 69(6):362-7. doi: 10.1007/s002040050185. [PMID: 7495373]
  • S Kanekal, C Plopper, D Morin, A Buckpitt. Metabolism and cytotoxicity of naphthalene oxide in the isolated perfused mouse lung. The Journal of pharmacology and experimental therapeutics. 1991 Jan; 256(1):391-401. doi: . [PMID: 1988668]
  • M Buonarati, A D Jones, A Buckpitt. In vivo metabolism of isomeric naphthalene oxide glutathione conjugates. Drug metabolism and disposition: the biological fate of chemicals. 1990 Mar; 18(2):183-9. doi: NULL. [PMID: 1971571]
  • P R Richieri, A R Buckpitt. Glutathione depletion by naphthalene in isolated hepatocytes and by naphthalene oxide in vivo. Biochemical pharmacology. 1988 Jun; 37(12):2473-8. doi: 10.1016/0006-2952(88)90376-0. [PMID: 3390209]
  • A L Misra, R Bloch, J Vardy, S J Mulé, K Verebely. Disposition of (15,16-3H)naltrexone in the central nervous system of the rat. Drug metabolism and disposition: the biological fate of chemicals. 1976 May; 4(3):276-80. doi: NULL. [PMID: 6233]