2,3-Epoxyaflatoxin B1 (BioDeep_00000012938)

 

Secondary id: BioDeep_00001869028

human metabolite Endogenous Volatile Flavor Compounds


代谢物信息卡片


(3R,4R,6S,8S)-12-methoxy-5,7,9,20-tetraoxahexacyclo[11.7.0.0^{2,10}.0^{3,8}.0^{4,6}.0^{14,18}]icosa-1(13),2(10),11,14(18)-tetraene-17,19-dione

化学式: C17H12O7 (328.05830019999996)
中文名称: 黄曲霉素B1 8,9-环氧化物
谱图信息: 最多检出来源 Viridiplantae(plant) 4.67%

分子结构信息

SMILES: COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C5C6C(O6)OC5OC4=C1
InChI: InChI=1S/C17H12O7/c1-20-7-4-8-11(12-14-17(23-14)24-16(12)21-8)13-10(7)5-2-3-6(18)9(5)15(19)22-13/h4,12,14,16-17H,2-3H2,1H3/t12-,14-,16+,17+/m1/s1

描述信息

2,3-Epoxyaflatoxin B1 is formed due to the metabolism of aflatoxin B1 (AFB1) by CYP2A13, an enzyme predominantly expressed in the human respiratory tract. There is no detectable AFB1 epoxide formation by CYP2A6, which was also reported to be involved in the metabolic activation of AFB1 (PMID: 16385575). Aflatoxins are naturally occurring mycotoxins that are produced by many species of Aspergillus, a fungus. At least 13 different types of aflatoxin are produced in nature. Aflatoxin B1 is considered the most toxic and is produced by both Aspergillus flavus and Aspergillus parasiticus. The native habitat of Aspergillus is in soil, decaying vegetation, hay, and grains undergoing microbiological deterioration and it invades all types of organic substrates whenever conditions are favourable for its growth. Favourable conditions include high moisture content (at least 7\\%) and high temperature. Aflatoxins B1 (AFB1) are contaminants of improperly stored foods; they are potent genotoxic and carcinogenic compounds, exerting their effects through damage to DNA. They can also induce mutations that increase oxidative damage (PMID: 17214555). Crops which are frequently affected by Aspergillus contamination include cereals (maize, sorghum, pearl millet, rice, wheat), oilseeds (peanut, soybean, sunflower, cotton), spices (chile peppers, black pepper, coriander, turmeric, ginger), and tree nuts (almond, pistachio, walnut, coconut, brazil nut). BioTransformer predicts that 2,3-epoxyaflatoxin B1 is a product of aflatoxin B1 metabolism via an epoxidation-of-vinyl-ether reaction catalyzed by CYP1A2 and CYP3A4 enzymes (PMID: 30612223).
D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins
D009676 - Noxae > D011042 - Poisons > D000348 - Aflatoxins
Prob. ultimate carcinogen of Aflatoxin B1
D009676 - Noxae > D002273 - Carcinogens

同义名列表

21 个代谢物同义名

(3R,4R,6S,8S)-12-methoxy-5,7,9,20-tetraoxahexacyclo[11.7.0.0^{2,10}.0^{3,8}.0^{4,6}.0^{14,18}]icosa-1(13),2(10),11,14(18)-tetraene-17,19-dione; [6AS-(6aa,7ab,8ab,8ba)]-2,3,6a,7a,8a,8b-hexahydro-4-methoxy-cyclopent[c]oxireno[4,5]furo[3,2:4,5]furo[2,3-H][1]benzopyran-1,10-dione; (6AS,7as,8ar,8BR)-2,3,6a,7a,8a,8b-hexahydro-4-methoxy-cyclopent[c]oxireno[4,5]furo[3,2:4,5]furo[2,3-H][1]benzopyran-1,10-dione; exo-Aflatoxin b1-8,9-epoxide; aflatoxin B1 exo-8,9-epoxide; Aflatoxin b1 exo-8,9-oxide; Aflatoxin b1-8,9-epoxide; Aflatoxin b1 8,9-epoxide; Aflatoxin b1 2,3-epoxide; Aflatoxin b1, 2,3-oxide; Aflatoxin b1 8,9-oxide; 8,9-Epoxy-aflatoxin b1; Aflatoxin b1-2,3-oxide; 2,3-Epoxyaflatoxin B1; 8,9-Epoxyaflatoxin B1; Aflatoxin b1 epoxide; AFB1 8,9-oxide; AFB1-2,3-oxide; AFB epoxide; SCHEMBL13811696; Aflatoxin B1-exo-8,9-epoxide



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(6)

BioCyc(0)

PlantCyc(0)

代谢反应

82 个相关的代谢反应过程信息。

Reactome(81)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

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

  • Taofeek O Ajiboye, Musa T Yakubu, Adenike T Oladiji. Lophirones B and C extenuate AFB1-mediated oxidative onslaught on cellular proteins, lipids, and DNA through Nrf-2 expression. Journal of biochemical and molecular toxicology. 2014 Dec; 28(12):558-67. doi: 10.1002/jbt.21598. [PMID: 25154877]
  • F Peter Guengerich, Kyle O Arneson, Kevin M Williams, Zhengwu Deng, Thomas M Harris. Reaction of aflatoxin B(1) oxidation products with lysine. Chemical research in toxicology. 2002 Jun; 15(6):780-92. doi: 10.1021/tx010156s. [PMID: 12067245]