argifin: possible lead insecticide; isolated from Gliocladium; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 449124 |
| CHEMBL ID | 197199 |
| MeSH ID | M0370150 |
| Synonym |
|---|
| argifin |
| cyclo[d-alanyl-n5-[imino[[(methylamino)carbonyl]amino]methyl]-l-ornithyl-n-methyl-l-phenylalanyl-l-beta-aspartyl-l-beta-aspartyl] (9ci) |
| 243975-37-3 |
| ftd 0668 |
| (2r,5s,8s,11s,15s)-8-benzyl-2,7-dimethyl-5-[3-({[(methylcarbamoyl)amino]methanimidoyl}amino)propyl]-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaazacycloheptadecane-11,15-dicarboxylic acid |
| 1WB0 |
| 1W9V |
| DB03632 |
| bdbm10853 |
| (2r,5s,8s,11s,15s)-5-[3-[[amino-(methylcarbamoylamino)methylidene]amino]propyl]-8-benzyl-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentazacycloheptadecane-11,15-dicarboxylic acid |
| CHEMBL197199 , |
| 5-[3-[amino-(methylcarbamoylamino)methylidene]aminopropyl]-8-benzyl-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentazacycloheptadecane-11,15-dicarboxylic acid |
| bdbm50173286 |
| DTXSID00332297 |
| CS-0121055 |
| HY-P2274 |
Argifin is a cyclic pentapeptide that was originally isolated as a fungal natural product.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Argifin is a cyclic pentapeptide that was originally isolated as a fungal natural product." | ( Natural product-guided discovery of a fungal chitinase inhibitor. Blair, DE; Desvergnes, S; Eggleston, IM; Hurtado-Guerrero, R; Ibrahim, AF; Rush, CL; Schüttelkopf, AW; van Aalten, DM, 2010) | 1.08 |
Argifin shows strong inhibitory activity against chitinases. Argifin has properties that render it unsuitable as a drug development candidate.
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chitinase A | Serratia marcescens | IC50 (µMol) | 0.0250 | 0.0250 | 0.0250 | 0.0250 | AID414640 |
| Chitinase B | Serratia marcescens | IC50 (µMol) | 4.7125 | 0.0034 | 2.9492 | 6.4000 | AID1227264; AID1227265; AID1796549; AID381960; AID414641; AID424940; AID499655 |
| Chitinase B | Serratia marcescens | Ki | 33.0000 | 0.0200 | 0.0200 | 0.0200 | AID1796549 |
| Chitotriosidase-1 | Homo sapiens (human) | IC50 (µMol) | 2.5318 | 0.0130 | 1.7733 | 4.5000 | AID1796549; AID1799533 |
| Chitotriosidase-1 | Homo sapiens (human) | Ki | 33.0000 | 0.0200 | 0.0200 | 0.0200 | AID1796549 |
| Endochitinase B1 | Aspergillus fumigatus | IC50 (µMol) | 2.5318 | 0.0130 | 1.7733 | 4.5000 | AID1796549; AID1799533 |
| Endochitinase B1 | Aspergillus fumigatus | Ki | 16.5085 | 0.0170 | 0.0185 | 0.0200 | AID1796549; AID254471 |
| Acidic mammalian chitinase | Homo sapiens (human) | IC50 (µMol) | 4.5000 | 0.0400 | 2.2700 | 4.5000 | AID451293 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chitinase B | Serratia marcescens | Kd | 5.9975 | 0.4600 | 2.9453 | 9.3900 | AID1796549; AID499655 |
| Chitotriosidase-1 | Homo sapiens (human) | Kd | 2.1400 | 0.4600 | 2.9453 | 9.3900 | AID1796549 |
| Endochitinase B1 | Aspergillus fumigatus | Kd | 2.1400 | 0.4600 | 2.9453 | 9.3900 | AID1796549 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| hydrolase activity, hydrolyzing O-glycosyl compounds | Chitotriosidase-1 | Homo sapiens (human) |
| chitinase activity | Chitotriosidase-1 | Homo sapiens (human) |
| chitin binding | Chitotriosidase-1 | Homo sapiens (human) |
| endochitinase activity | Chitotriosidase-1 | Homo sapiens (human) |
| chitinase activity | Acidic mammalian chitinase | Homo sapiens (human) |
| protein binding | Acidic mammalian chitinase | Homo sapiens (human) |
| kinase binding | Acidic mammalian chitinase | Homo sapiens (human) |
| chitin binding | Acidic mammalian chitinase | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| extracellular region | Chitotriosidase-1 | Homo sapiens (human) |
| extracellular space | Chitotriosidase-1 | Homo sapiens (human) |
| lysosome | Chitotriosidase-1 | Homo sapiens (human) |
| specific granule lumen | Chitotriosidase-1 | Homo sapiens (human) |
| tertiary granule lumen | Chitotriosidase-1 | Homo sapiens (human) |
| extracellular region | Chitotriosidase-1 | Homo sapiens (human) |
| extracellular region | Acidic mammalian chitinase | Homo sapiens (human) |
| extracellular space | Acidic mammalian chitinase | Homo sapiens (human) |
| cytoplasm | Acidic mammalian chitinase | Homo sapiens (human) |
| extracellular region | Acidic mammalian chitinase | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID424940 | Inhibition of Serratia marcescens chitinase B | 2009 | Bioorganic & medicinal chemistry letters, May-15, Volume: 19, Issue:10 | Computer-aided rational molecular design of argifin-derivatives with increased inhibitory activity against chitinase B from Serratia marcescens. |
| AID254573 | Michaelis constant for compound binding to Chitinase B1 | 2005 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 15, Issue:21 | An efficient synthesis of argifin: a natural product chitinase inhibitor with chemotherapeutic potential. |
| AID254471 | Inhibitory activity against Chitinase B1 (AfChiB1) using fuorometric assay with 4-methylumbelliferyl-b-D-N,N0-diacetylchitobiose as substrate | 2005 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 15, Issue:21 | An efficient synthesis of argifin: a natural product chitinase inhibitor with chemotherapeutic potential. |
| AID499655 | Inhibition of Serratia marcescens chitinase B | 2010 | Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16 | NMR spectroscopy and computational analysis of interaction between Serratia marcescens chitinase B and a dipeptide derived from natural-product cyclopentapeptide chitinase inhibitor argifin. |
| AID253796 | Maximum rate of metabolism of compound | 2005 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 15, Issue:21 | An efficient synthesis of argifin: a natural product chitinase inhibitor with chemotherapeutic potential. |
| AID381960 | Binding affinity to Serratia marcescens chitinase B | 2008 | Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7 | Computational analysis of the binding affinities of the natural-product cyclopentapeptides argifin and argadin to chitinase B from Serratia marcescens. |
| AID414640 | Displacement of 4-methylumbelliferydiacetyl-chitobiose from Serratia marcescens ChiA | 2009 | Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7 | Argifin; efficient solid phase total synthesis and evaluation of analogues of acyclic peptide. |
| AID451293 | Inhibition of human acidic mammalian chitinase | 2009 | Bioorganic & medicinal chemistry, Sep-01, Volume: 17, Issue:17 | Molecular modeling of human acidic mammalian chitinase in complex with the natural-product cyclopentapeptide chitinase inhibitor argifin. |
| AID414641 | Displacement of 4-methylumbelliferydiacetyl-chitobiose from Serratia marcescens ChiB | 2009 | Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7 | Argifin; efficient solid phase total synthesis and evaluation of analogues of acyclic peptide. |
| AID1227265 | Inhibition of Serratia marcescens chitinase ChiB assessed as reduction in chitinolytic activity using 4MU-(GlcNAc)2 substrate by fluorescence based assay | 2015 | Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12 | Creation of Customized Bioactivity within a 14-Membered Macrolide Scaffold: Design, Synthesis, and Biological Evaluation Using a Family-18 Chitinase. |
| AID381961 | Inhibition of Lucilia cuprina chitinase B | 2008 | Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7 | Computational analysis of the binding affinities of the natural-product cyclopentapeptides argifin and argadin to chitinase B from Serratia marcescens. |
| AID1227264 | Inhibition of Serratia marcescens chitinase ChiB | 2015 | Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12 | Creation of Customized Bioactivity within a 14-Membered Macrolide Scaffold: Design, Synthesis, and Biological Evaluation Using a Family-18 Chitinase. |
| AID414642 | Displacement of 4-methylumbelliferydiacetyl-chitobiose from Serratia marcescens ChiC | 2009 | Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7 | Argifin; efficient solid phase total synthesis and evaluation of analogues of acyclic peptide. |
| AID1796549 | Enzyme Inhibition Assay from Article 10.1016/j.chembiol.2004.10.013: \\Specificity and affinity of natural product cyclopentapeptide inhibitors against A. fumigatus, human, and bacterial chitinases.\\ | 2005 | Chemistry & biology, Jan, Volume: 12, Issue:1 | Specificity and affinity of natural product cyclopentapeptide inhibitors against A. fumigatus, human, and bacterial chitinases. |
| AID1799533 | Inhibition Assay from Article 10.1016/j.chembiol.2008.02.015: \\Structure-based dissection of the natural product cyclopentapeptide chitinase inhibitor argifin.\\ | 2008 | Chemistry & biology, Mar, Volume: 15, Issue:3 | Structure-based dissection of the natural product cyclopentapeptide chitinase inhibitor argifin. |
| AID1799552 | Enzyme Inhibition Assay from Article 10.1016/j.chembiol.2010.07.018: \\Natural product-guided discovery of a fungal chitinase inhibitor.\\ | 2010 | Chemistry & biology, Dec-22, Volume: 17, Issue:12 | Natural product-guided discovery of a fungal chitinase inhibitor. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 15 (68.18) | 29.6817 |
| 2010's | 7 (31.82) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (23.71) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 4 (18.18%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 18 (81.82%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||