2,2':5',2'-Terthiophene (BioDeep_00000000862)

 

Secondary id: BioDeep_00000861718, BioDeep_00001867560

human metabolite PANOMIX_OTCML-2023 blood metabolite Volatile Flavor Compounds


代谢物信息卡片


2,2 inverted exclamation mark :5 inverted exclamation mark ,2 inverted exclamation mark inverted exclamation mark -Terthiophene

化学式: C12H8S3 (247.97881280000001)
中文名称: 三噻吩, 2,2:5,2-三噻吩, α-三噻吩, 2,2′:5′,2′′-三噻吩
谱图信息: 最多检出来源 Homo sapiens(blood) 0.33%

分子结构信息

SMILES: C1(C2=CC=C(C3=CC=CS3)S2)=CC=CS1
InChI: InChI=1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H

描述信息

2,2:5,2-terthiophene is a terthiophene.
2,2:5,2-Terthiophene is a natural product found in Schoenia cassiniana, Lawrencella rosea, and other organisms with data available.
D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
D010575 - Pesticides > D007306 - Insecticides
D003879 - Dermatologic Agents
D016573 - Agrochemicals
2,2':5',2''-Terthiophene (α-Terthiophene) is an oligomer of the heterocycle thiophene. 2,2':5',2''-Terthiophene has been employed as building block for the organic semi-conductor polythiophene.
2,2':5',2''-Terthiophene (α-Terthiophene) is an oligomer of the heterocycle thiophene. 2,2':5',2''-Terthiophene has been employed as building block for the organic semi-conductor polythiophene.

同义名列表

44 个代谢物同义名

2,2 inverted exclamation mark :5 inverted exclamation mark ,2 inverted exclamation mark inverted exclamation mark -Terthiophene; InChI=1/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8; 2,2:5,2-Terthiophene (purified by sublimation); alpha-Terthienyl, 2,5-Di(2-thienyl)thiophene; 2,2:5,2-Terthiophene, (=alpha-Terthienyl); alpha-Terthienyl (2,2,5,2-Terthiophene); 5-(thiophen-2-yl)-2,2-bithiophene; 2,5-bis(thiophen-2-yl)thiophene; 2,2-Bithiophene, 5-(2-thienyl)-; 2,5-dithiophen-2-ylthiophene; 2,5-dithiophen-2-ylthiophen; 2,5-bis(2-thienyl)thiophene; 2,5-Di(2-thienyl)thiophene; 2,2:5,2-Terthiophene, 99\\%; .ALPHA.-TERTHIENYL [MI]; 2,2:5,2"-Terthiophene; 2,2:5,2-Terthiophene; 2,2,5,2-terthiophene; 2,2-5,2-Terthiophene; .alpha.-Terthiophene; 2,2:52-Terthiophene; 2,2:5,2-Terthienyl; TERTHIENYL, ALPHA-; 2,2,5,2-Terthienyl; .alpha.-Terthienyl; alpha-terthiophene; Maybridge1_007704; alpha-terthienyl; I+/--Terthienyl; UNII-0P77RAU2RR; Α-terthiophene; a-Terthiophene; .a.-Terthienyl; MEGxp0_001543; Trithiophene; terthiophene; Tox21_300648; Α-terthienyl; a-terthienyl; 0P77RAU2RR; C12H8S3; alpha-Terthienyl; α-?Terthiophene; 2,2':5',2''-Terthiophene



数据库引用编号

18 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)

33 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

  • Sabrin R M Ibrahim, Gamal A Mohamed, Rwaida A Al Haidari, Amal A El-Kholy, Mohamed F Zayed, Maan T Khayat. Tagetnoic acid, a new lipoxygenase inhibitor peroxy fatty acid from Tagetes minuta growing in Saudi Arabia. Natural product research. 2020 Feb; 34(4):474-481. doi: 10.1080/14786419.2018.1488712. [PMID: 30295511]
  • Jie Zhang, Shakil Ahmad, Lan-Ying Wang, Qian Han, Jian-Chun Zhang, Yan-Ping Luo. Cell death induced by α-terthienyl via reactive oxygen species-mediated mitochondrial dysfunction and oxidative stress in the midgut of Aedes aegypti larvae. Free radical biology & medicine. 2019 06; 137(?):87-98. doi: 10.1016/j.freeradbiomed.2019.04.021. [PMID: 31022448]
  • Jeffrey D Weidenhamer, Tricia M Montgomery, Donald F Cipollini, Paul A Weston, Brian K Mohney. Plant Density and Rhizosphere Chemistry: Does Marigold Root Exudate Composition Respond to Intra- and Interspecific Competition?. Journal of chemical ecology. 2019 Jun; 45(5-6):525-533. doi: 10.1007/s10886-019-01073-5. [PMID: 31134522]
  • Bin Zhao, Jingqian Huo, Ning Liu, Jinlin Zhang, Jingao Dong. Transketolase Is Identified as a Target of Herbicidal Substance α-Terthienyl by Proteomics. Toxins. 2018 01; 10(1):. doi: 10.3390/toxins10010041. [PMID: 29329271]
  • Umma Hafsa Preya, Kyung-Tae Lee, Nam-Jung Kim, Jung-Yun Lee, Dae Sik Jang, Jung-Hye Choi. The natural terthiophene α-terthienylmethanol induces S phase cell cycle arrest of human ovarian cancer cells via the generation of ROS stress. Chemico-biological interactions. 2017 Jun; 272(?):72-79. doi: 10.1016/j.cbi.2017.05.011. [PMID: 28506552]
  • Yijing Wang, Ashton Partridge, Yinqiu Wu. Comparison of a carboxylated terthiophene surface with carboxymethylated dextran layer for surface plasmon resonance detection of progesterone. Analytical biochemistry. 2016 09; 508(?):46-9. doi: 10.1016/j.ab.2016.05.027. [PMID: 27288558]
  • Seung-Min Choi, Dong-Min Kim, Ok-Sang Jung, Yoon-Bo Shim. A disposable chronocoulometric sensor for heavy metal ions using a diaminoterthiophene-modified electrode doped with graphene oxide. Analytica chimica acta. 2015 Sep; 892(?):77-84. doi: 10.1016/j.aca.2015.08.037. [PMID: 26388477]
  • Yun Wei, Kai Zhang, Li Yin, Jilin Du, Guoliang Zhang. Isolation of bioactive components from Flaveria bidentis (L.) Kuntze using high-speed counter-current chromatography and time-controlled collection method. Journal of separation science. 2012 Apr; 35(7):869-74. doi: 10.1002/jssc.201101027. [PMID: 22532356]
  • Hui-Bog Noh, Pranjal Chandra, Jeon Ok Moon, Yoon-Bo Shim. In vivo detection of glutathione disulfide and oxidative stress monitoring using a biosensor. Biomaterials. 2012 Mar; 33(9):2600-7. doi: 10.1016/j.biomaterials.2011.12.026. [PMID: 22209642]
  • Hiroshi Nakano, Charles L Cantrell, Leonid K Mamonov, Weste L A Osbrink, Samir A Ross. Echinopsacetylenes A and B, new thiophenes from Echinops transiliensis. Organic letters. 2011 Dec; 13(23):6228-31. doi: 10.1021/ol202680a. [PMID: 22066834]
  • Shaheen Faizi, Shahina Fayyaz, Samina Bano, Erum Yawar Iqbal, Lubna, Humaira Siddiqi, Aneela Naz. Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae. Journal of agricultural and food chemistry. 2011 Sep; 59(17):9080-93. doi: 10.1021/jf201611b. [PMID: 21780738]
  • Yoshinori Kadoma, Seiichiro Fujisawa. Radical-scavenging activity of melatonin, either alone or in combination with vitamin E, ascorbate or 2-mercaptoethanol as co-antioxidants, using the induction period method. In vivo (Athens, Greece). 2011 Jan; 25(1):49-53. doi: . [PMID: 21282734]
  • Ilaria Marotti, Mauro Marotti, Roberta Piccaglia, Anna Nastri, Silvia Grandi, Giovanni Dinelli. Thiophene occurrence in different Tagetes species: agricultural biomasses as sources of biocidal substances. Journal of the science of food and agriculture. 2010 May; 90(7):1210-7. doi: 10.1002/jsfa.3950. [PMID: 20394003]
  • Qingchun Huang, Yang Liu, Taisong Zhan, Yunfei Deng, Yuan He. Comparable susceptibilities of human 293 cells and insect Tn-5B1-4 cells to photoactivated alpha-terthienyl. Journal of agricultural and food chemistry. 2010 Mar; 58(5):2637-42. doi: 10.1021/jf902204q. [PMID: 20014764]
  • Xue Qiao, Jian Han, Wen-ni He, Tao Wu, Bao-rong Wang, Min Ye, De-an Guo. Chemical fingerprint of commercial Radix Echinopsis and quantitative analysis of alpha-terthienyl. Journal of separation science. 2010 Mar; 33(4-5):530-8. doi: 10.1002/jssc.200900613. [PMID: 20112306]
  • Ling-min Zhang, Jia-mei Sun, Hui-fang Lv, Hai-ying Shi. [Effect of alpha-terthienyl on protein, esterase and lipid peroxidation of Aedes albopictus larvae]. Zhongguo ji sheng chong xue yu ji sheng chong bing za zhi = Chinese journal of parasitology & parasitic diseases. 2010 Feb; 28(1):46-9. doi: ". [PMID: 20411751]
  • Brian K Mohney, Tricia Matz, Jessica Lamoreaux, David S Wilcox, Anne Louise Gimsing, Philipp Mayer, Jeffrey D Weidenhamer. In situ silicone tube microextraction: a new method for undisturbed sampling of root-exuded thiophenes from marigold (Tagetes erecta L.) in soil. Journal of chemical ecology. 2009 Nov; 35(11):1279-87. doi: 10.1007/s10886-009-9711-8. [PMID: 19902302]
  • Md Aminur Rahman, Kyung-Sun Lee, Deog-Su Park, Mi-Sook Won, Yoon-Bo Shim. An amperometric bilirubin biosensor based on a conductive poly-terthiophene-Mn(II) complex. Biosensors & bioelectronics. 2008 Jan; 23(6):857-64. doi: 10.1016/j.bios.2007.09.005. [PMID: 17964773]
  • Supinya Tewtrakul, Sanan Subhadhirasakul, Sarot Cheenpracha, Chatchanok Karalai. HIV-1 protease and HIV-1 integrase inhibitory substances from Eclipta prostrata. Phytotherapy research : PTR. 2007 Nov; 21(11):1092-5. doi: 10.1002/ptr.2252. [PMID: 17696192]
  • Nikolas Fokialakis, Weste L A Osbrink, Leonid K Mamonov, Nadejda G Gemejieva, Amelia B Mims, Alexios L Skaltsounis, Alan R Lax, Charles L Cantrell. Antifeedant and toxicity effects of thiophenes from four Echinops species against the Formosan subterranean termite, Coptotermes formosanus. Pest management science. 2006 Sep; 62(9):832-8. doi: 10.1002/ps.1237. [PMID: 16791907]
  • Nikolas Fokialakis, Charles L Cantrell, Stephen O Duke, Alexios L Skaltsounis, David E Wedge. Antifungal activity of thiophenes from Echinops ritro. Journal of agricultural and food chemistry. 2006 Mar; 54(5):1651-5. doi: 10.1021/jf052702j. [PMID: 16506815]
  • Lilla Margl, Andreas Tei, István Gyurján, Michael Wink. GLC and GLC-mS analysis of thiophene derivatives in plants and in in vitro cultures of Tagetes patula L. (Asteraceae). Zeitschrift fur Naturforschung. C, Journal of biosciences. 2002 Jan; 57(1-2):63-71. doi: 10.1515/znc-2002-1-211. [PMID: 11926545]
  • T M Brennan, E Lee, P R Battaglia. Participation of the photosensitizer alpha-terthienyl in the peroxidase-catalyzed oxidation of indole-3-acetic acid. Photochemistry and photobiology. 2000 Apr; 71(4):355-60. doi: 10.1562/0031-8655(2000)071<0355:potpat>2.0.co;2. [PMID: 10824584]
  • G Guillet, J Harmatha, T G Waddell, B J Philogène, J T Arnason. Synergistic insecticidal mode of action between sesquiterpene lactones and a phototoxin, alpha-terthienyl. Photochemistry and photobiology. 2000 Feb; 71(2):111-5. doi: 10.1562/0031-8655(2000)071<0111:sipsim>2.0.co;2. [PMID: 10687381]
  • R Boch, N Mohtat, Y Lear, J T Arnason, T Durst, J C Scaiano. Study of photoinduced energy and electron transfer in alpha-terthienyl-bovine serum albumin conjugates: a laser flash photolysis study. Photochemistry and photobiology. 1996 Jul; 64(1):92-9. doi: 10.1111/j.1751-1097.1996.tb02426.x. [PMID: 8787021]
  • M Nivsarkar, G P Kumar, M Laloraya. Metal binding and resultant loss of phototoxicity of alpha-terthienyl: metal detoxification versus alpha-terthienyl inactivation. Bulletin of environmental contamination and toxicology. 1996 Feb; 56(2):183-9. doi: 10.1007/s001289900028. [PMID: 8720089]
  • D C Chauret, C B Bernard, J T Arnason, T Durst, H G Krishnamurty, P Sanchez-Vindas, N Moreno, L S Roman, L Poveda. Insecticidal neolignans from Piper decurrens. Journal of natural products. 1996 Feb; 59(2):152-5. doi: 10.1021/np960036y. [PMID: 8991948]
  • R Marles, T Durst, M Kobaisy, C Soucy-Breau, M Abou-Zaid, J T Arnason, S Kacew, D Kanjanapothi, C Rujjanawate, M Meckes. Pharmacokinetics, metabolism and toxicity of the plant-derived photoxin alpha-terthienyl. Pharmacology & toxicology. 1995 Sep; 77(3):164-8. doi: 10.1111/j.1600-0773.1995.tb01007.x. [PMID: 8884878]
  • J B Hudson, R J Marles, C Soucy-Breau, L Harris, J T Arnason. Photoactive terthiophenes: the influence of serum on anti-HIV (human immunodeficiency virus) activities. Photochemistry and photobiology. 1994 Dec; 60(6):591-3. doi: 10.1111/j.1751-1097.1994.tb05153.x. [PMID: 7870765]
  • A Sharma, H C Goel. Some naturally occurring phytophototoxins for mosquito control. Indian journal of experimental biology. 1994 Oct; 32(10):745-51. doi: ". [PMID: 7821985]
  • J B Hudson, F Balza, L Harris, G H Towers. Light-mediated activities of thiarubrines against human immunodeficiency virus. Photochemistry and photobiology. 1993 Apr; 57(4):675-80. doi: 10.1111/j.1751-1097.1993.tb02936.x. [PMID: 8389484]
  • J B Hudson, L Harris, A Teeple, G H Towers. The anti-HIV activity of the phytochemical alpha-terthienyl. Antiviral research. 1993 Jan; 20(1):33-43. doi: 10.1016/0166-3542(93)90057-p. [PMID: 8457146]
  • M Nivsarkar, G P Kumar, M Laloraya, M M Laloraya. Generation of superoxide anion radical by alpha-terthienyl in the anal gills of mosquito larvae Aedes aegypti: a new aspect in alpha-terthienyl phototoxicity. Archives of insect biochemistry and physiology. 1992; 19(4):261-70. doi: 10.1002/arch.940190405. [PMID: 1318115]
  • D Mares, M P Fasulo, A Bruni. Ultraviolet-mediated antimycotic activity of alpha-terthienyl on Microsporum cookei. Journal of medical and veterinary mycology : bi-monthly publication of the International Society for Human and Animal Mycology. 1990; 28(6):469-77. doi: . [PMID: 2093120]
  • B M Hasspieler, J T Arnason, A E Downe. Toxicity, localization and elimination of the phototoxin, alpha-terthienyl, in mosquito larvae. Journal of the American Mosquito Control Association. 1988 Dec; 4(4):479-84. doi: . [PMID: 2906359]
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  • J Bakker, F J Gommers, I Nieuwenhuis, H Wynberg. Photoactivation of the nematicidal compound alpha-terthienyl from roots of marigolds (Tagetes species). A possible singlet oxygen role. The Journal of biological chemistry. 1979 Mar; 254(6):1841-4. doi: . [PMID: 422557]