Gliotoxin (BioDeep_00000008190)
Secondary id: BioDeep_00000900900
Toxin
代谢物信息卡片
化学式: C13H14N2O4S2 (326.0394964)
中文名称: 胶霉毒素
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CN1C(=O)C23CC4=CC=CC(C4N2C(=O)C1(SS3)CO)O
InChI: InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1
描述信息
Gliotoxin is a pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi. It has a role as a mycotoxin, an immunosuppressive agent, an EC 2.5.1.58 (protein farnesyltransferase) inhibitor, a proteasome inhibitor and an antifungal agent. It is an organic disulfide, a pyrazinoindole, an organic heterotetracyclic compound and a dipeptide.
Gliotoxin is a natural product found in Streptomyces, Aspergillus cejpii, and other organisms with data available.
Gliotoxin is a sulfur-containing antibiotic produced by several species of fungi, some of which are pathogens of humans such as Aspergillus, and also by species of Trichoderma, and Penicillium. Gliotoxin possesses immunosuppressive properties as it may suppress and cause apoptosis in certain types of cells of the immune system, including neutrophils, eosinophils, granulocytes, macrophages, and thymocytes. (L1941)
A fungal toxin produced by various species of Trichoderma, Gladiocladium fimbriatum, Aspergillus fumigatus, and Penicillium. It is used as an immunosuppressive agent.
A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi.
D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents
D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins
C308 - Immunotherapeutic Agent > C574 - Immunosuppressant
同义名列表
23 个代谢物同义名
10H-3,10a-Epidithiopyrazino(1,2-a)indole-1,4-dione, 2,3,5a,6-hydroxy-3- (hydroxymethyl)-2-methyl-, (3R-(3-alpha,5a-beta,6-beta,10a-alpha))-; (1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-diene-10,14-dione; 10H-3,10A-EPIDITHIOPYRAZINO(1,2-A)INDOLE-1,4-DIONE, 2,3,5A,6-TETRAHYDRO-6-HYDROXY-3-(HYDROXYMETHYL)-2-METHYL-, (3R,5AS,6S,10AR)-; 10H-3,10a-Epidithiopyrazino[1,2-a]indole-1,4-dione,2,3,5a,6-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-, (3R,5aS,6S,10aR)-; (3R,5aS,6S,10aR)-2,3,5a,6-Tetrahydr o-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-e pidithiopyrazino[1,2-a]indole-1,4-dione; (3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5aH-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione; (3R,5aS,6S,10aR)-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione; (3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,5a,6-tetrahydro-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione; 7-hydroxy-11-hydroxymethyl-12-methyl-14,15-dithia-9,12-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-diene-10,13-dione; 10H-3,10a-Epidithiopyrazino(1,2-a)indole-1,4-dione, 2,3,5a,6-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-; 2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4 dione; 6-Hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5aH-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione; 4-27-00-08902 (Beilstein Handbook Reference); Gliotoxin from Gliocladium fimbriatum; UNII-5L648PH06K; GLIOTOXIN [MI]; C13H14N2O4S2; QTL1_000040; Aspergillin; 5L648PH06K; Gliotoxins; AI3-62383; Gliotoxin
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:5385
- KEGG: C10595
- PubChem: 6223
- Metlin: METLIN68415
- ChEMBL: CHEMBL331627
- Wikipedia: Gliotoxin
- MeSH: Gliotoxin
- ChemIDplus: 0000067992
- KNApSAcK: C00002340
- CAS: 67-99-2
- PMhub: MS000021760
- MetaboLights: MTBLC5385
- PubChem: 12778
- 3DMET: B03986
- NIKKAJI: J9.768C
- RefMet: Gliotoxin
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)
9 个相关的物种来源信息
- 1884262 - Aspergillus cejpii: 10.1021/JF00099A014
- 5059 - Aspergillus flavus: 10.1271/BBB.56.2085
- 746128 - Aspergillus fumigatus:
- 5073 - Penicillium:
- 69773 - Penicillium glabrum:
- 1883 - Streptomyces: 10.1080/14786419.2019.1611814
- 29861 - Trichoderma deliquescens:
- 29875 - Trichoderma virens:
- 5547 - Trichoderma viride:
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
- Yaojie Guo, Jian-Zi Liu, Jarukitt Limwachiranon, Fan Xu, Yi Han, Liru Xu, Zhenzhen Xiong, Nan Zhang, Gang Ding, Daniel H Scharf. Reconstitution of the Early Stage of Chetomin Biosynthesis in Aspergillus fumigatus Leads to the Production of Epipolythiodioxopiperazines.
Organic letters.
2024 May; 26(21):4469-4474. doi:
10.1021/acs.orglett.4c01274
. [PMID: 38767929] - Jun Fu, Xiaowei Luo, Miaoping Lin, Zimin Xiao, Lishan Huang, Jiaxi Wang, Yongyan Zhu, Yonghong Liu, Huaming Tao. Marine-Fungi-Derived Gliotoxin Promotes Autophagy to Suppress Mycobacteria tuberculosis Infection in Macrophage.
Marine drugs.
2023 Nov; 21(12):. doi:
10.3390/md21120616
. [PMID: 38132937] - Hyewon Seo, Suzie Kang, Dongho Lee, Cheol-Won Yun. Regulation of pseurotin A biosynthesis by GliZ and zinc in Aspergillus fumigatus.
Scientific reports.
2023 Feb; 13(1):2431. doi:
10.1038/s41598-023-29753-z
. [PMID: 36765124] - Huabin Chen, Ruiyun Zhao, Meng Ge, Ying Sun, Yaru Li, Lihong Shan. Gliotoxin, a natural product with ferroptosis inducing properties.
Bioorganic chemistry.
2023 Feb; 133(?):106415. doi:
10.1016/j.bioorg.2023.106415
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Journal of gastroenterology and hepatology.
2022 Oct; 37(10):1946-1954. doi:
10.1111/jgh.15974
. [PMID: 35933582] - Shengqiang Zhang, Jida Guo, Hongyan Zhang, Lu Tong, Linyou Zhang. Gliotoxin Induced Ferroptosis by Downregulating SUV39H1 Expression in Esophageal Cancer Cells.
Recent patents on anti-cancer drug discovery.
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mBio.
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Phytopathology.
2021 Oct; 111(10):1720-1725. doi:
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Mycoses.
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Analytical chemistry.
2019 01; 91(2):1610-1618. doi:
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Mycoses.
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Scientific reports.
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Natural product research.
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. [PMID: 28068839] - Antonio Pereira-Neves, Rubem F S Menna-Barreto, Marlene Benchimol. The fungal metabolite gliotoxin inhibits proteasome proteolytic activity and induces an irreversible pseudocystic transformation and cell death in Tritrichomonas foetus.
Parasitology research.
2016 Aug; 115(8):3057-69. doi:
10.1007/s00436-016-5061-y
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Environmental microbiology.
2016 Apr; 18(4):1096-109. doi:
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European journal of medicinal chemistry.
2016 Jan; 108(?):553-563. doi:
10.1016/j.ejmech.2015.12.003
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Applied biochemistry and biotechnology.
2015 Apr; 175(7):3458-67. doi:
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International journal of medical microbiology : IJMM.
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Microbiology (Reading, England).
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PloS one.
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Diagnostic microbiology and infectious disease.
2012 May; 73(1):57-64. doi:
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BMC evolutionary biology.
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