Page last updated: 2024-11-07

allosamidin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Allosamidin is a natural product isolated from the culture broth of the bacterium Streptomyces griseus. It is a potent and selective inhibitor of chitin synthase, an enzyme involved in the synthesis of chitin. Chitin is a major structural component of the cell walls of fungi and the exoskeletons of insects and crustaceans. Allosamidin exhibits antifungal and insecticidal activities. Its unique mechanism of action and potential for agricultural applications have made it a subject of extensive research.'

allosamidin: Anti-Asthmatic [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID119339
CHEMBL ID1230997
SCHEMBL ID118668
MeSH IDM0154700

Synonyms (30)

Synonym
CHEMBL1230997 ,
103782-08-7
allosamidine
C05346
DB04628
allosamidin
a 82516
beta-d-allopyranoside, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-6-(hydroxymethyl)-4h-cyclopentoxazol-5-yl 2-(acetylamino)-4-o-(2-(acetylamino)-2-deoxy-beta-d-allopyranosyl)-2-deoxy-, (3aalpha,4beta,5beta,6alpha,6aalpha)-
a82516
a-82516
1,2-dideoxy-2'-dimethylamino-alpha-d-glucopyranoso-[2,1-d]-delta2'-thiazoline
n-[(2s,3r,4s,5s,6r)-2-[(2r,3s,4s,5r,6r)-6-[[(3ar,4r,5r,6s,6as)-2-(dimethylamino)-4-hydroxy-6-(hydroxymethyl)-4,5,6,6a-tetrahydro-3ah-cyclopenta[d][1,3]oxazol-5-yl]oxy]-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxa
bdbm50331851
5udj46528k ,
unii-5udj46528k
n-[(2s,3r,4s,5s,6r)-2-[(2r,3s,4s,5r,6r)-6-[[(3ar,4r,5r,6s,6as)-2-(dimethylamino)-4-hydroxy-6-(hydroxymethyl)-4,5,6,6a-tetrahydro-3ah-cyclopenta[d]oxazol-5-yl]oxy]-5-acetamido-4-hydroxy-2-(hydroxymethyl)tetrahydropyran-3-yl]oxy-4,5-dihydroxy-6-(hydroxymeth
{(3ar,4r,5r,6s,6as)-2-(dimethylamino)-4-hydroxy-6-(hydroxymethyl)-4,5,6,6a-tetrahydro-3ah-cyclopenta[d][1,3]oxazol-5-yl}-2-(acetylamino)-4-o-[2-(acetylamino)-2-deoxy-beta-d-allopyranosyl]-2-deoxy-beta-d-allopyranoside
SCHEMBL118668
W-200706
(3ar,4r,5r,6s,6as)-2-(dimethylamino)-4-hydroxy-6-(hydroxymethyl)-4,5,6,6a-tetrahydro-3ah-cyclopenta[d][1,3]oxazol-5-yl 2-(acetylamino)-4-o-[2-(acetylamino)-2-deoxy-beta-d-allopyranosyl]-2-deoxy-beta-d-allopyranoside
DTXSID90883122
Q27095365
(-)-allosamidine
allosamidin [iso]
.beta.-d-allopyranoside, (3ar,4r,5r,6s,6as)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-6-(hydroxymethyl)-4h-cyclopentoxazol-5-yl 2-(acetylamino)-4-o-(2-(acetylamino)-2-deoxy-.beta.-d-allopyranosyl)-2-deoxy-
(3ar,4r,5r,6s,6as)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-6-(hydroxymethyl)-4h-cyclopentoxazol-5-yl 2-(acetylamino)-4-o-(2-(acetylamino)-2-deoxy-.beta.-d-allopyranosyl)-2-deoxy-.beta.-d-allopyranoside
(-)-allosamidin
HY-120827
CS-0079267
AKOS040747793

Research Excerpts

Overview

Allosamidin is a family 18 chitinase inhibitor produced by Streptomyces. It was found to be a competitive inhibitor with a K(i) of 3.1 microM.

ExcerptReferenceRelevance
"Allosamidin is a strong inhibitor of family 18 chitinases. "( Nucleotide sequences of genes encoding allosamidin-sensitive and -insensitive chitinases produced by allosamidin-producing Streptomyces.
Anamnart, S; Kuzuyama, T; Matsuura, H; Nagasawa, H; Nakayama, J; Nihira, T; Okamoto, S; Sakuda, S; Seto, H; Suzuki, A; Wang, Q; Yamada, Y; Zhou, ZY, 2003
)
2.03
"Allosamidin is a family 18 chitinase inhibitor produced by Streptomyces. "( Chitinase inhibitor allosamidin promotes chitinase production of Streptomyces generally.
Furihata, K; Horinouchi, S; Miyamoto, K; Nagasawa, H; Nakanishi, E; Ohnishi, Y; Sakuda, S; Suzuki, S; Tsujibo, H; Watanabe, T, 2008
)
2.11
"Allosamidin is a substrate analog that strongly inhibits the class 18 enzymes."( The X-ray structure of a chitinase from the pathogenic fungus Coccidioides immitis.
Bortone, K; Cox, R; Ernst, S; Hollis, T; Monzingo, AF; Robertus, JD, 2000
)
1.03
"Allosamidin was found to be a competitive inhibitor with a K(i) of 3.1 microM."( Enzyme kinetics of hevamine, a chitinase from the rubber tree Hevea brasiliensis.
Barends, T; Beintema, JJ; Bokma, E; Dijkstr, BW; Terwissch van Scheltingab, AC, 2000
)
1.03
"Allosamidin is a known inhibitor of class 18 chitinases. "( The structure of an allosamidin complex with the Coccidioides immitis chitinase defines a role for a second acid residue in substrate-assisted mechanism.
Bortone, K; Ernst, S; Monzingo, AF; Robertus, JD, 2002
)
2.08

Effects

ExcerptReferenceRelevance
"Allosamidins have been used as chitinase inhibitors to investigate the physiological roles of chitinases in a variety of organisms."( Novel biological activities of allosamidins.
Inoue, H; Nagasawa, H; Sakuda, S, 2013
)
1.4

Actions

ExcerptReferenceRelevance
"Allosamidin is likely to enhance abiotic stress tolerance, probably through crosstalk between the two signaling pathways for biotic and abiotic stress responses."( Chitinase gene expression in response to environmental stresses in Arabidopsis thaliana: chitinase inhibitor allosamidin enhances stress tolerance.
Fukamizo, T; Nakano, S; Sakuda, S; Takenaka, Y; Tamoi, M, 2009
)
1.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pathways (2)

PathwayProteinsCompounds
chitin degradation III (Serratia)510
chitin degradation II (Vibrio)87

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chitinase BSerratia marcescensIC50 (µMol)0.09000.00342.94926.4000AID1227265
EndochitinaseSaccharomyces cerevisiae S288CKi0.61000.61001.90503.2000AID539001
Acidic mammalian chitinaseHomo sapiens (human)IC50 (µMol)0.04000.04002.27004.5000AID539003
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
polysaccharide catabolic processAcidic mammalian chitinaseHomo sapiens (human)
immune system processAcidic mammalian chitinaseHomo sapiens (human)
production of molecular mediator involved in inflammatory responseAcidic mammalian chitinaseHomo sapiens (human)
chitin metabolic processAcidic mammalian chitinaseHomo sapiens (human)
chitin catabolic processAcidic mammalian chitinaseHomo sapiens (human)
apoptotic processAcidic mammalian chitinaseHomo sapiens (human)
positive regulation of chemokine productionAcidic mammalian chitinaseHomo sapiens (human)
polysaccharide digestionAcidic mammalian chitinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
chitinase activityAcidic mammalian chitinaseHomo sapiens (human)
protein bindingAcidic mammalian chitinaseHomo sapiens (human)
kinase bindingAcidic mammalian chitinaseHomo sapiens (human)
chitin bindingAcidic mammalian chitinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
extracellular regionAcidic mammalian chitinaseHomo sapiens (human)
extracellular spaceAcidic mammalian chitinaseHomo sapiens (human)
cytoplasmAcidic mammalian chitinaseHomo sapiens (human)
extracellular regionAcidic mammalian chitinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1227265Inhibition of Serratia marcescens chitinase ChiB assessed as reduction in chitinolytic activity using 4MU-(GlcNAc)2 substrate by fluorescence based assay2015Journal 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.
AID539001Inhibition of Saccharomyces cerevisiae CTS12010Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23
Acetazolamide-based fungal chitinase inhibitors.
AID610637Inhibition of Trichoderma chitinase T1 using [4MU-(GlcNAc)3] as substrate2011Bioorganic & medicinal chemistry, May-15, Volume: 19, Issue:10
Preparation of allosamidin and demethylallosamidin photoaffinity probes and analysis of allosamidin-binding proteins in asthmatic mice.
AID539002Inhibition of Aspergillus fumigatus ChiA1 expressed in Pichia pastoris after 70 mins2010Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23
Acetazolamide-based fungal chitinase inhibitors.
AID539003Inhibition of human chitinase2010Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23
Acetazolamide-based fungal chitinase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (88)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (5.68)18.7374
1990's29 (32.95)18.2507
2000's37 (42.05)29.6817
2010's16 (18.18)24.3611
2020's1 (1.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.26

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.

MetricThis Compound (vs All)
Research Demand Index22.26 (24.57)
Research Supply Index4.49 (2.92)
Research Growth Index5.11 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews8 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other80 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]