Tosylphenylalanyl chloromethyl ketone (BioDeep_00001868281)
Main id: BioDeep_00000004843
代谢物信息卡片
Tosyl phenylalanyl chloromethyl ketone
化学式: C17H18ClNO3S (351.0696)
中文名称: N-(对甲苯磺酰基)-L-苯丙氨酰甲基氯酮(TPCK)
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(CC2=CC=CC=C2)C(=O)CCl
InChI: InChI=1S/C17H18ClNO3S/c1-13-7-9-15(10-8-13)23(21,22)19-16(17(20)12-18)11-14-5-3-2-4-6-14/h2-10,16,19H,11-12H2,1H3/t16-/m0/s1
描述信息
D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D015842 - Serine Proteinase Inhibitors
D009676 - Noxae > D000477 - Alkylating Agents > D000590 - Amino Acid Chloromethyl Ketones
D004791 - Enzyme Inhibitors > D011500 - Protein Synthesis Inhibitors
同义名列表
数据库引用编号
12 个数据库交叉引用编号
- ChEBI: CHEBI:9642
- KEGG: C02088
- PubChem: 439647
- ChEMBL: CHEMBL60718
- MeSH: Tosylphenylalanyl Chloromethyl Ketone
- CAS: 130021-38-4
- CAS: 402-71-1
- ChEBI: CHEBI:195780
- PubChem: 5173
- PDB-CCD: TQ8
- NIKKAJI: J59.695G
- KNApSAcK: 9642
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)
2 个相关的物种来源信息
- 38033 - Chaetomium globosum: 10.1016/J.BMCL.2015.08.063
- 1883 - Streptomyces: 10.1021/NP4006635
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
- X M Souto, L S Ramos, S S C Oliveira, M H Branquinha, A L S Santos. The serine peptidase inhibitor N-ρ-tosyl-l-phenylalanine chloromethyl ketone (TPCK) affects the cell biology of Candida haemulonii species complex.
Fungal biology.
2021 05; 125(5):378-388. doi:
10.1016/j.funbio.2020.12.004. [PMID: 33910679] - Rafael M Gandra, Laura N Silva, Xênia M Souto, Leandro S Sangenito, Lucas P S Cruz, Lys A Braga-Silva, Diego S Gonçalves, Sergio H Seabra, Marta H Branquinha, André L S Santos. The serine peptidase inhibitor TPCK induces several morphophysiological changes in the opportunistic fungal pathogen Candida parapsilosis sensu stricto.
Medical mycology.
2019 Nov; 57(8):1024-1037. doi:
10.1093/mmy/myz008. [PMID: 30753649] - Mayuramas Sang-Ngern, Ui Joung Youn, Eun-Jung Park, Tamara P Kondratyuk, Charles J Simmons, Marisa M Wall, Michael Ruf, Sam E Lorch, Ethyn Leong, John M Pezzuto, Leng Chee Chang. Withanolides derived from Physalis peruviana (Poha) with potential anti-inflammatory activity.
Bioorganic & medicinal chemistry letters.
2016 Jun; 26(12):2755-2759. doi:
10.1016/j.bmcl.2016.04.077. [PMID: 27210437] - Hui Bao, Yan Ge, Ai Peng, Rujun Gong. Fine-tuning of NFκB by glycogen synthase kinase 3β directs the fate of glomerular podocytes upon injury.
Kidney international.
2015 Jun; 87(6):1176-90. doi:
10.1038/ki.2014.428. [PMID: 25629551] - C Reuther, G K Ganjam, A M Dolga, C Culmsee. The serine protease inhibitor TLCK attenuates intrinsic death pathways in neurons upstream of mitochondrial demise.
Apoptosis : an international journal on programmed cell death.
2014 Nov; 19(11):1545-58. doi:
10.1007/s10495-014-1027-7. [PMID: 25146045] - Sayyed Mohammad Hadi Alavi, Pavla Postlerová-Maňásková, Azadeh Hatef, Martin Pšenička, Jana Pěknicová, Kazuo Inaba, Andrzej Ciereszko, Otomar Linhart. Protease in sturgeon sperm and the effects of protease inhibitors on sperm motility and velocity.
Fish physiology and biochemistry.
2014 Oct; 40(5):1393-8. doi:
10.1007/s10695-014-9933-8. [PMID: 24677048] - Feng Wang, Hongyan Cai, Qing Zhao, Tao Xing, Junhui Li, Niansong Wang. Epinephrine evokes renalase secretion via α-adrenoceptor/NF-κB pathways in renal proximal tubular epithelial cells.
Kidney & blood pressure research.
2014; 39(4):252-9. doi:
10.1159/000355802. [PMID: 25171187] - Ui Joung Youn, Eun-Jung Park, Tamara P Kondratyuk, Charles J Simmons, Robert P Borris, Patcharawan Tanamatayarat, Supakit Wongwiwatthananukit, Onoomar Toyama, Thanapat Songsak, John M Pezzuto, Leng Chee Chang. Anti-inflammatory sesquiterpene lactones from the flower of Vernonia cinerea.
Bioorganic & medicinal chemistry letters.
2012 Sep; 22(17):5559-62. doi:
10.1016/j.bmcl.2012.07.010. [PMID: 22850207] - Lian Chen, Martin Conda-Sheridan, P V Narasimha Reddy, Andrew Morrell, Eun-Jung Park, Tamara P Kondratyuk, John M Pezzuto, Richard B van Breemen, Mark Cushman. Identification, synthesis, and biological evaluation of the metabolites of 3-amino-6-(3'-aminopropyl)-5H-indeno[1,2-c]isoquinoline-5,11-(6H)dione (AM6-36), a promising rexinoid lead compound for the development of cancer chemotherapeutic and chemopreventive agents.
Journal of medicinal chemistry.
2012 Jun; 55(12):5965-81. doi:
10.1021/jm3006806. [PMID: 22712432] - Salman Khan, Omer Shehzad, Hong-Guang Jin, Eun-Rhan Woo, Sam Sik Kang, Sa Wang Baek, Jinwoong Kim, Yeong Shik Kim. Anti-inflammatory mechanism of 15,16-epoxy-3α-hydroxylabda-8,13(16),14-trien-7-one via inhibition of LPS-induced multicellular signaling pathways.
Journal of natural products.
2012 Jan; 75(1):67-71. doi:
10.1021/np200666t. [PMID: 22233348] - Loredan S Niculescu, Marius R Robciuc, Gabriela M Sanda, Anca V Sima. Apolipoprotein A-I stimulates cholesteryl ester transfer protein and apolipoprotein E secretion from lipid-loaded macrophages; the role of NF-κB and PKA signaling pathways.
Biochemical and biophysical research communications.
2011 Nov; 415(3):497-502. doi:
10.1016/j.bbrc.2011.10.101. [PMID: 22056562] - Liuqiang Zhang, Li Feng, Qi Jia, Jinwen Xu, Rui Wang, Zhengtao Wang, Yingchun Wu, Yiming Li. Effects of β-glucosidase hydrolyzed products of harpagide and harpagoside on cyclooxygenase-2 (COX-2) in vitro.
Bioorganic & medicinal chemistry.
2011 Aug; 19(16):4882-6. doi:
10.1016/j.bmc.2011.06.069. [PMID: 21775152] - Jian-Hong Yang, Tamara P Kondratyuk, Katherine C Jermihov, Laura E Marler, Xi Qiu, Yongsoo Choi, Hongmei Cao, Rui Yu, Megan Sturdy, Rong Huang, Ying Liu, Li-Qin Wang, Andrew D Mesecar, Richard B van Breemen, John M Pezzuto, Harry H S Fong, Ye-Gao Chen, Hong-Jie Zhang. Bioactive compounds from the fern Lepisorus contortus.
Journal of natural products.
2011 Feb; 74(2):129-36. doi:
10.1021/np100373f. [PMID: 21261296] - M Deppe, J Risopatrón, R Sánchez. Trypsin and chymotrypsin are involved in the progesterone-induced acrosome reaction in canine spermatozoa.
Reproduction in domestic animals = Zuchthygiene.
2010 Jun; 45(3):453-7. doi:
10.1111/j.1439-0531.2008.01225.x. [PMID: 18954392] - Jia-hong Xue, Zuyi Yuan, Yue Wu, Yan Liu, Yan Zhao, Wei-ping Zhang, Yu-ling Tian, Wei-min Liu, Yu Liu, Chiharu Kishimoto. High glucose promotes intracellular lipid accumulation in vascular smooth muscle cells by impairing cholesterol influx and efflux balance.
Cardiovascular research.
2010 Apr; 86(1):141-50. doi:
10.1093/cvr/cvp388. [PMID: 20007688] - Hongling Han, Yu Xia, Min Yang, Scott A McLuckey. Rapidly alternating transmission mode electron-transfer dissociation and collisional activation for the characterization of polypeptide ions.
Analytical chemistry.
2008 May; 80(9):3492-7. doi:
10.1021/ac7022734. [PMID: 18396915] - Elena Dragomir, Magdalena Tircol, Ileana Manduteanu, Manuela Voinea, Maya Simionescu. Aspirin and PPAR-alpha activators inhibit monocyte chemoattractant protein-1 expression induced by high glucose concentration in human endothelial cells.
Vascular pharmacology.
2006 Jun; 44(6):440-9. doi:
10.1016/j.vph.2006.02.006. [PMID: 16600694] - A Neşe Cokuğraş, Doğan Cengiz, E Ferhan Tezcan. Do alkylating agents modify the histidine residue of the desensitized butyrylcholinesterase?.
The protein journal.
2004 Nov; 23(8):495-500. doi:
10.1007/s10930-004-7876-0. [PMID: 15648971] - Yeo Dae Yoon, Sang Bae Han, Jong Soon Kang, Chang Woo Lee, Song-Kyu Park, Hyun Sun Lee, Jong Seong Kang, Hwan Mook Kim. Toll-like receptor 4-dependent activation of macrophages by polysaccharide isolated from the radix of Platycodon grandiflorum.
International immunopharmacology.
2003 Dec; 3(13-14):1873-82. doi:
10.1016/j.intimp.2003.09.005. [PMID: 14636836] - Yujiro Watanabe, Masahito Tamura, Akihiko Osajima, Hirofumi Anai, Narutoshi Kabashima, Ryota Serino, Yasuhide Nakashima. Integrins induce expression of monocyte chemoattractant protein-1 via focal adhesion kinase in mesangial cells.
Kidney international.
2003 Aug; 64(2):431-40. doi:
10.1046/j.1523-1755.2003.00122.x. [PMID: 12846738] - Hyun-Ja Jeong, Hwan-Suck Chung, Seung-Heon Hong, Ho-Jeong Na, Hye-Young Koo, Sang-Bong Seo, Kyung-Suk Kim, Yung-Sun Song, Hyung-Min Kim. CancerB increases production of nitric oxide and tumor necrosis factor-alpha in peritoneal macrophages.
Clinica chimica acta; international journal of clinical chemistry.
2002 Aug; 322(1-2):149-56. doi:
10.1016/s0009-8981(02)00171-7. [PMID: 12104094] - Irina Baranova, Tatyana Vishnyakova, Alexander Bocharov, Zhigang Chen, Alan T Remaley, John Stonik, Thomas L Eggerman, Amy P Patterson. Lipopolysaccharide down regulates both scavenger receptor B1 and ATP binding cassette transporter A1 in RAW cells.
Infection and immunity.
2002 Jun; 70(6):2995-3003. doi:
10.1128/iai.70.6.2995-3003.2002. [PMID: 12010990] - Y F Xia, L P Liu, C P Zhong, J G Geng. NF-kappaB activation for constitutive expression of VCAM-1 and ICAM-1 on B lymphocytes and plasma cells.
Biochemical and biophysical research communications.
2001 Dec; 289(4):851-6. doi:
10.1006/bbrc.2001.6067. [PMID: 11735124] - R Zemel, S Gerechet, H Greif, L Bachmatove, Y Birk, A Golan-Goldhirsh, M Kunin, Y Berdichevsky, I Benhar, R Tur-Kaspa. Cell transformation induced by hepatitis C virus NS3 serine protease.
Journal of viral hepatitis.
2001 Mar; 8(2):96-102. doi:
10.1046/j.1365-2893.2001.00283.x. [PMID: 11264729] - V A Movsesyan, A G Yakovlev, L Fan, A I Faden. Effect of serine protease inhibitors on posttraumatic brain injury and neuronal apoptosis.
Experimental neurology.
2001 Feb; 167(2):366-75. doi:
10.1006/exnr.2000.7567. [PMID: 11161625] - K Shibata, H Yoshino, N Mizuno, H Shinohara, K Morita, S Kitayama, H Kurihara, T Dohi. Mediation by platelet-activating factor of 12-hydroxyeicosatetraenoic acid-induced cytosolic free calcium concentration elevation in neutrophils.
Prostaglandins & other lipid mediators.
2000 Oct; 62(4):385-94. doi:
10.1016/s0090-6980(00)00090-3. [PMID: 11060901] - J H Choi, W J Chung, S J Han, H B Lee, I W Choi, H K Lee, K Y Jang, D G Lee, S S Han, K H Park, S Y IM. Selective involvement of reactive oxygen intermediates in platelet-activating factor-mediated activation of NF-kappaB.
Inflammation.
2000 Oct; 24(5):385-98. doi:
10.1023/a:1007068010645. [PMID: 10921504] - H D Guthrie, W M Garrett, B S Cooper. Inhibition of apoptosis in cultured porcine granulosa cells by inhibitors of caspase and serine protease activity.
Theriogenology.
2000 Sep; 54(5):731-40. doi:
10.1016/s0093-691x(00)00386-1. [PMID: 11101034] - W H Mueller, D Kleefeld, B Khattab, J D Meissner, R J Scheibe. Effects of retinoic acid on N-glycosylation and mRNA stability of the liver/bone/kidney alkaline phosphatase in neuronal cells.
Journal of cellular physiology.
2000 Jan; 182(1):50-61. doi:
10.1002/(sici)1097-4652(200001)182:1<50::aid-jcp6>3.0.co;2-6. [PMID: 10567916] - A Abate, S Oberle, H Schröder. Lipopolysaccharide-induced expression of cyclooxygenase-2 in mouse macrophages is inhibited by chloromethylketones and a direct inhibitor of NF-kappa B translocation.
Prostaglandins & other lipid mediators.
1998 Aug; 56(5-6):277-90. doi:
10.1016/s0090-6980(98)00061-6. [PMID: 9990673] - Y Bayón, A Alonso, M Sánchez Crespo. Immunoglobulin-E/dinitrophenyl complexes induce nitric oxide synthesis in rat peritoneal macrophages by a mechanism involving CD23 and NF-kappa B activation.
Biochemical and biophysical research communications.
1998 Jan; 242(3):570-4. doi:
10.1006/bbrc.1997.8011. [PMID: 9464257] - D Cengiz, A N Cokuğraş, K Kilinç, E F Tezcan. Histidine modification of human serum butyrylcholinesterase.
Biochemical and molecular medicine.
1997 Jun; 61(1):52-7. doi:
10.1006/bmme.1997.2578. [PMID: 9232197] - H Ruetten, C Thiemermann. Effect of calpain inhibitor I, an inhibitor of the proteolysis of I kappa B, on the circulatory failure and multiple organ dysfunction caused by endotoxin in the rat.
British journal of pharmacology.
1997 Jun; 121(4):695-704. doi:
10.1038/sj.bjp.0701180. [PMID: 9208136] - D A Bagarozzi, R Pike, J Potempa, J Travis. Purification and characterization of a novel endopeptidase in ragweed (Ambrosia artemisiifolia) pollen.
The Journal of biological chemistry.
1996 Oct; 271(42):26227-32. doi:
10.1074/jbc.271.42.26227. [PMID: 8824272] - B H Rovin, J A Dickerson, L C Tan, C A Hebert. Activation of nuclear factor-kappa B correlates with MCP-1 expression by human mesangial cells.
Kidney international.
1995 Oct; 48(4):1263-71. doi:
10.1038/ki.1995.410. [PMID: 8569088] - L Wikström, H F Lodish. Unfolded H2b asialoglycoprotein receptor subunit polypeptides are selectively degraded within the endoplasmic reticulum.
The Journal of biological chemistry.
1993 Jul; 268(19):14412-6. doi:
. [PMID: 8314799] - M V Kolodzeĭs'ka. [Enzymatic activity of chymopsin of various origin].
Ukrainskii biokhimicheskii zhurnal (1978).
1992 Jan; 64(1):60-5. doi:
NULL. [PMID: 1519348] - L N Su, W A Toscano, A R Kennedy. Suppression of phorbol ester-enhanced radiation-induced malignancy in vitro by protease inhibitors is independent of protein kinase C.
Biochemical and biophysical research communications.
1991 Apr; 176(1):18-24. doi:
10.1016/0006-291x(91)90883-9. [PMID: 2018516] - A G Stewart, T Harris. Involvement of platelet-activating factor in endotoxin-induced priming of rabbit polymorphonuclear leukocytes.
Journal of lipid mediators.
1991 Mar; 3(2):125-38. doi:
". [PMID: 1665713] - E C Conseiller, D Schott, F Lederer. Inhibition by aminoacyl-chloromethane protease inhibitors of superoxide anion production by phorbol-ester-stimulated human neutrophils. The labeled target is a membrane protein.
European journal of biochemistry.
1990 Oct; 193(2):345-50. doi:
10.1111/j.1432-1033.1990.tb19344.x. [PMID: 2171934] - P A Rood, R M Lorence, K W Kelley. Serum protease inhibitor abrogation of Newcastle disease virus enhancement of cytolysis by recombinant tumor necrosis factors alpha and beta.
Journal of the National Cancer Institute.
1990 Feb; 82(3):213-7. doi:
10.1093/jnci/82.3.213. [PMID: 2296051] - H Nakagawa, K Watanabe, K Sato. Inhibitory action of synthetic proteinase inhibitors and substrates on the chemotaxis of rat polymorphonuclear leukocytes in vitro.
Journal of pharmacobio-dynamics.
1988 Oct; 11(10):674-8. doi:
10.1248/bpb1978.11.674. [PMID: 3065473] - J Tumen, B Meyrick, L Berry, K L Brigham. Antiproteinases protect cultured lung endothelial cells from endotoxin injury.
Journal of applied physiology (Bethesda, Md. : 1985).
1988 Aug; 65(2):835-43. doi:
10.1152/jappl.1988.65.2.835. [PMID: 2844719] - M M Dawson, U Shipton, M Moore. Involvement of cell surface macromolecules sensitive to alkylating ketones in lysis by human peripheral blood NK cells.
Clinical and experimental immunology.
1985 Jan; 59(1):91-100. doi:
. [PMID: 3971601] - B A Lessley, D L Garner. Identification and preliminary characterization of two distinct bovine seminal Pz-peptidases.
Biology of reproduction.
1984 Sep; 31(2):353-69. doi:
10.1095/biolreprod31.2.353. [PMID: 6383489] - R Hiller, A Schaefer, R Zibirre, H R Kaback, G Koch. Factors influencing the accumulation of tetraphenylphosphonium cation in HeLa cells.
Molecular and cellular biology.
1984 Jan; 4(1):199-202. doi:
10.1128/mcb.4.1.199-202.1984. [PMID: 6700585] - M C Herzberg, K L Brintzenhofe, C C Clawson. Cell-free released components of Streptococcus sanguis inhibit human platelet aggregation.
Infection and immunity.
1983 Oct; 42(1):394-401. doi:
10.1128/iai.42.1.394-401.1983. [PMID: 6618669] - R E Duque, S H Phan, M C Sulavik, P A Ward. Inhibition by tosyl-L-phenylalanyl chloromethyl ketone of membrane potential changes in rat neutrophils. Correlation with the inhibition of biological activity.
The Journal of biological chemistry.
1983 Jul; 258(13):8123-8. doi:
. [PMID: 6863281] - B Damerau, E Grünefeld, W Vogt. Aggregation of leukocytes induced by the complement-derived peptides C3a and C5a and by three synthetic formyl-methionyl peptides.
International archives of allergy and applied immunology.
1980; 63(2):159-69. doi:
10.1159/000232622. [PMID: 7419283] - B Szajáni, A Kiss, L Boross. Investigation of the active center and catalytic mechanism of porcine kidney aminoacylase: a model of the active center.
Acta biochimica et biophysica; Academiae Scientiarum Hungaricae.
1980; 15(1):29-37. doi:
NULL. [PMID: 6779500] - C W Lui, S Meizel. Further evidence in support of a role for hamster sperm hydrolytic enzymes in the acrosome reaction.
The Journal of experimental zoology.
1979 Feb; 207(2):173-85. doi:
10.1002/jez.1402070202. [PMID: 571894] - R Vainionpää. Measles virus-specified polypeptides in infected cells.
Archives of virology.
1979; 60(3-4):239-48. doi:
10.1007/bf01317495. [PMID: 116624] - C Mukherjee, W S Lynn. Role of ions and extracellular protein in leukocyte motility and membrane ruffling.
The American journal of pathology.
1978 Nov; 93(2):369-81. doi:
NULL. [PMID: 717536] - G Jay, F T Jay, R M Friedman, A S Levine. Biosynthesis, immunological specificity, and intracellular distribution of the simian virus 40-specific protein induced by the nondefective hybrid Ad2+ND1.
Journal of virology.
1978 May; 26(2):411-9. doi:
10.1128/jvi.26.2.411-419.1978. [PMID: 207895] - M E Baker, D D Fanestil. Effect of protease inhibitors and substrates on deoxycorticosterone binding to its receptor in dog MDCK kidney cells.
Nature.
1977 Oct; 269(5631):810-2. doi:
10.1038/269810a0. [PMID: 927506] - D Cavanagh, D V Sangar, D J Rowlands, F Brown. Immunogenic and cell attachment sites of FMDV: further evidence for their location in a single capsid polypeptide.
The Journal of general virology.
1977 Apr; 35(1):149-58. doi:
10.1099/0022-1317-35-1-149. [PMID: 192841] - R O Hynes, E S Pearistein. Investigations of the possible role of proteases in altering surface proteins of virally transformed hamster fibroblasts.
Journal of supramolecular structure.
1976; 4(1):1-14. doi:
10.1002/jss.400040102. [PMID: 1256058] - E J Goetzl. Modulation of human neutrophil polymorphonuclear leucocyte migration by human plasma alpha-globulin inhibitors and synthetic esterase inhibitors.
Immunology.
1975 Jul; 29(1):163-74. doi:
. [PMID: 49293]
