OCHRATOXIN B (BioDeep_00000408575)

   


代谢物信息卡片


2-[(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)formamido]-3-phenylpropanoic acid

化学式: C20H19NO6 (369.12123140000006)
中文名称: 赭曲霉素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1CC2=C(C(=C(C=C2)C(=O)NC(CC3=CC=CC=C3)C(=O)O)O)C(=O)O1
InChI: InChI=1S/C20H19NO6/c1-11-9-13-7-8-14(17(22)16(13)20(26)27-11)18(23)21-15(19(24)25)10-12-5-3-2-4-6-12/h2-8,11,15,22H,9-10H2,1H3,(H,21,23)(H,24,25)/t11-,15+/m1/s1

描述信息

A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid. Ochratoxin B differs from the more naturally abundant ochratoxin A in the absence of the dihydroisocoumarin chlorine atom. It has cytotoxic effects on kidney and liver cells in vitro but only minor effects in vivo, due to its rapid metabolism and excretion. It inhibits cell proliferation of human liver HepG2 cells at doses as low as 1 mug/ ml but lacks the genotoxic activity of ochratoxin A, even at higher concentrations.
D009676 - Noxae > D011042 - Poisons > D009793 - Ochratoxins
D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins
CONFIDENCE Penicillium verrucosum

同义名列表

2 个代谢物同义名

OCHRATOXIN B; 2-[(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)formamido]-3-phenylpropanoic acid



数据库引用编号

10 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)

0 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

  • Beatriz Arce-López, Elena Lizarraga, Reyes López de Mesa, Elena González-Peñas. Assessment of Exposure to Mycotoxins in Spanish Children through the Analysis of Their Levels in Plasma Samples. Toxins. 2021 02; 13(2):. doi: 10.3390/toxins13020150. [PMID: 33672088]
  • Zelma Faisal, Virág Vörös, Eszter Fliszár-Nyúl, Beáta Lemli, Sándor Kunsági-Máté, Rita Csepregi, Tamás Kőszegi, Ferenc Zsila, Miklós Poór. Probing the Interactions of Ochratoxin B, Ochratoxin C, Patulin, Deoxynivalenol, and T-2 Toxin with Human Serum Albumin. Toxins. 2020 06; 12(6):. doi: 10.3390/toxins12060392. [PMID: 32545742]
  • Victor Limay-Rios, J David Miller, Arthur W Schaafsma. Occurrence of Penicillium verrucosum, ochratoxin A, ochratoxin B and citrinin in on-farm stored winter wheat from the Canadian Great Lakes Region. PloS one. 2017; 12(7):e0181239. doi: 10.1371/journal.pone.0181239. [PMID: 28749978]
  • Simona Marianna Sanzani, Massimo Reverberi, Corrado Fanelli, Antonio Ippolito. Detection of ochratoxin A using molecular beacons and real-time PCR thermal cycler. Toxins. 2015 Mar; 7(3):812-20. doi: 10.3390/toxins7030812. [PMID: 25760080]
  • Lukas Vaclavik, Marta Vaclavikova, Timothy H Begley, Alexander J Krynitsky, Jeanne I Rader. Determination of multiple mycotoxins in dietary supplements containing green coffee bean extracts using ultrahigh-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS). Journal of agricultural and food chemistry. 2013 May; 61(20):4822-30. doi: 10.1021/jf401139u. [PMID: 23631685]
  • Zheng Han, Yunliang Zheng, Lianjun Luan, Yiping Ren, Yongjiang Wu. Analysis of ochratoxin A and ochratoxin B in traditional Chinese medicines by ultra-high-performance liquid chromatography-tandem mass spectrometry using [(13)C(20)]-ochratoxin A as an internal standard. Journal of chromatography. A. 2010 Jun; 1217(26):4365-74. doi: 10.1016/j.chroma.2010.04.052. [PMID: 20483416]
  • Alexandra H Heussner, Simon Ausländer, Daniel R Dietrich. Development and characterization of a monoclonal antibody against Ochratoxin B and its application in ELISA. Toxins. 2010 06; 2(6):1582-94. doi: 10.3390/toxins2061582. [PMID: 22069651]
  • C Boesch-Saadatmandi, A Loboda, A Jozkowicz, P Huebbe, R Blank, S Wolffram, J Dulak, G Rimbach. Effect of ochratoxin A on redox-regulated transcription factors, antioxidant enzymes and glutathione-S-transferase in cultured kidney tubulus cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2008 Aug; 46(8):2665-71. doi: 10.1016/j.fct.2008.04.023. [PMID: 18547704]
  • A H Heussner, E O'Brien, D R Dietrich. Effects of repeated ochratoxin exposure on renal cells in vitro. Toxicology in vitro : an international journal published in association with BIBRA. 2007 Feb; 21(1):72-80. doi: 10.1016/j.tiv.2006.08.007. [PMID: 17045452]
  • A H Heussner, D R Dietrich, E O'Brien. In vitro investigation of individual and combined cytotoxic effects of ochratoxin A and other selected mycotoxins on renal cells. Toxicology in vitro : an international journal published in association with BIBRA. 2006 Apr; 20(3):332-41. doi: 10.1016/j.tiv.2005.08.003. [PMID: 16140496]
  • Angela Mally, Heike Keim-Heusler, Alexander Amberg, Michael Kurz, Herbert Zepnik, Peter Mantle, Wolfgang Völkel, Gordon C Hard, Wolfgang Dekant. Biotransformation and nephrotoxicity of ochratoxin B in rats. Toxicology and applied pharmacology. 2005 Aug; 206(1):43-53. doi: 10.1016/j.taap.2004.11.007. [PMID: 15963343]
  • Angela Mally, Gaetano Pepe, Srivani Ravoori, Mario Fiore, Ramesh C Gupta, Wolfgang Dekant, Pasquale Mosesso. Ochratoxin a causes DNA damage and cytogenetic effects but no DNA adducts in rats. Chemical research in toxicology. 2005 Aug; 18(8):1253-61. doi: 10.1021/tx049650x. [PMID: 16097798]
  • Ralf Blank, Siegfried Wolffram. Alkalinization of urinary pH accelerates renal excretion of ochratoxin A in pigs. The Journal of nutrition. 2004 Sep; 134(9):2355-8. doi: 10.1093/jn/134.9.2355. [PMID: 15333728]
  • E O'Brien, A H Heussner, D R Dietrich. Species-, sex-, and cell type-specific effects of ochratoxin A and B. Toxicological sciences : an official journal of the Society of Toxicology. 2001 Oct; 63(2):256-64. doi: 10.1093/toxsci/63.2.256. [PMID: 11568369]
  • V G Curtui, M Gareis, E Usleber, E Märtlbauer. Survey of Romanian slaughtered pigs for the occurrence of mycotoxins ochratoxins A and B, and zearalenone. Food additives and contaminants. 2001 Aug; 18(8):730-8. doi: 10.1080/02652030116824. [PMID: 11469329]
  • D R Dietrich, E O'Brien, M E Stack, A H Heussner. Species- and sex-specific renal cytotoxicity of ochratoxin A and B in vitro. Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie. 2001 Jun; 53(2-3):215-25. doi: 10.1078/0940-2993-00184. [PMID: 11484842]
  • G S Bondy, C L Armstrong. Cytotoxicity of nephrotoxic fungal toxins to kidney-derived LLC-PK1 and OK cell lines. Cell biology and toxicology. 1998 Oct; 14(5):323-32. doi: 10.1023/a:1007581606944. [PMID: 9808360]
  • A Bruinink, T Rasonyi, C Sidler. Reduction of ochratoxin A toxicity by heat-induced epimerization. In vitro effects of ochratoxins on embryonic chick meningeal and other cell cultures. Toxicology. 1997 Mar; 118(2-3):205-10. doi: 10.1016/s0300-483x(96)03615-3. [PMID: 9129174]
  • F E Würgler, U Friederich, J Schlatter. Lack of mutagenicity of ochratoxin A and B, citrinin, patulin and cnestine in Salmonella typhimurium TA102. Mutation research. 1991 Nov; 261(3):209-16. doi: 10.1016/0165-1218(91)90069-x. [PMID: 1719413]
  • F C Størmer, P Kolsaker, H Holm, S Rogstad, F Elling. Metabolism of ochratoxin B and its possible effects upon the metabolism and toxicity of ochratoxin A in rats. Applied and environmental microbiology. 1985 May; 49(5):1108-12. doi: 10.1128/aem.49.5.1108-1112.1985. [PMID: 4004232]
  • H Isaacs, J J Heffron, M Badenhorst. 'Picture frame' fibres in a carrier of the trait for malignant hyperpyrexia. South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde. 1975 Nov; 49(46):1923-6. doi: NULL. [PMID: 795]