Page last updated: 2024-11-12

cladosporin

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Description

cladosporin: antifungal metabolite from Cladosporium cladosporioides; toxic, minor metabolite of Aspersillus flavus; inhibits tRNA synthetase in Plasmodium falciparum [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID13990016
CHEMBL ID448685
MeSH IDM0040628

Synonyms (21)

Synonym
1h-2-benzopyran-1-one, 3,4-dihydro-6,8-dihydroxy-3-((tetrahydro-6-methyl-2h-pyran-2-yl)methyl)-, (2r-(2-alpha(r*),6-beta))-
cladosporin
3,4-dihydro-6,8-dihydroxy-3-(tetrahydro-6-methyl-2h-pyran-2-yl)methylisocoumarin
CHEMBL448685
35818-31-6
unii-81pr0d5fi4
81pr0d5fi4 ,
bdbm50434379
KRS ,
1h-2-benzopyran-1-one, 3,4-dihydro-6,8-dihydroxy-3-(((2r,6s)-tetrahydro-6-methyl-2h-pyran-2-yl)methyl)-, (3r)-
(3r)-3,4-dihydro-6,8-dihydroxy-3-(((2r,6s)-tetrahydro-6-methyl-2h-pyran-2-yl)methyl)-1h-2-benzopyran-1-one
1h-2-benzopyran-1-one, 3,4-dihydro-6,8-dihydroxy-3-((tetrahydro-6-methyl-2h-pyran-2-yl)methyl)-, (2r-(2.alpha.(r*),6.beta.))-
4PG3
(3r)-6,8-dihydroxy-3-{[(2r,6s)-6-methyltetrahydro-2h-pyran-2-yl]methyl}-3,4-dihydro-1h-isochromen-1-one
(3r)-6,8-dihydroxy-3-[[(2r,6s)-6-methyloxan-2-yl]methyl]-3,4-dihydroisochromen-1-one
(3r)-3-[[(2r,6s)-6-methyloxan-2-yl]methyl]-6,8-bis(oxidanyl)-3,4-dihydroisochromen-1-one
gtpl10247
(r)-6,8-dihydroxy-3-(((2r,6s)-6-methyltetrahydro-2h-pyran-2-yl)methyl)isochroman-1-one
Q27269262
HY-136767
CS-0133554

Research Excerpts

Overview

Cladosporin is a naturally occurring fungal metabolite mainly isolated from the endophytic fungus Cladosporium cladosporioides. It kills the malaria parasite via inhibiting its cytoplasmic lysyl-tRNA synthetase (KRS)

ExcerptReferenceRelevance
"Cladosporin is a naturally occurring fungal metabolite mainly isolated from the endophytic fungus Cladosporium cladosporioides."( Chemical and Biological Study of Cladosporin, an Antimicrobial Inhibitor: A Review.
Cutler, SJ; Wang, X; Wedge, DE, 2016
)
1.44
"Cladosporin (CLD) is a fungal metabolite that kills the malaria parasite via inhibiting its cytoplasmic lysyl-tRNA synthetase (KRS) and abrogating protein translation. "( Side chain rotameric changes and backbone dynamics enable specific cladosporin binding in Plasmodium falciparum lysyl-tRNA synthetase.
Chhibber-Goel, J; Sharma, A, 2019
)
2.19
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Lysine--tRNA ligaseHomo sapiens (human)IC50 (µMol)62.50000.00090.30731.4740AID1380935; AID748887
Lysine--tRNA ligase Plasmodium falciparum 3D7IC50 (µMol)0.12000.12000.12000.1200AID1380934
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
basophil activation involved in immune responseLysine--tRNA ligaseHomo sapiens (human)
positive regulation of inflammatory response to antigenic stimulusLysine--tRNA ligaseHomo sapiens (human)
lysyl-tRNA aminoacylationLysine--tRNA ligaseHomo sapiens (human)
tRNA processingLysine--tRNA ligaseHomo sapiens (human)
response to X-rayLysine--tRNA ligaseHomo sapiens (human)
diadenosine tetraphosphate biosynthetic processLysine--tRNA ligaseHomo sapiens (human)
positive regulation of macrophage activationLysine--tRNA ligaseHomo sapiens (human)
positive regulation of DNA-templated transcriptionLysine--tRNA ligaseHomo sapiens (human)
ERK1 and ERK2 cascadeLysine--tRNA ligaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
tRNA bindingLysine--tRNA ligaseHomo sapiens (human)
ATP:ADP adenylyltransferase activityLysine--tRNA ligaseHomo sapiens (human)
lysine-tRNA ligase activityLysine--tRNA ligaseHomo sapiens (human)
protein bindingLysine--tRNA ligaseHomo sapiens (human)
ATP bindingLysine--tRNA ligaseHomo sapiens (human)
amino acid bindingLysine--tRNA ligaseHomo sapiens (human)
identical protein bindingLysine--tRNA ligaseHomo sapiens (human)
protein homodimerization activityLysine--tRNA ligaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
extracellular spaceLysine--tRNA ligaseHomo sapiens (human)
nucleusLysine--tRNA ligaseHomo sapiens (human)
mitochondrionLysine--tRNA ligaseHomo sapiens (human)
mitochondrial matrixLysine--tRNA ligaseHomo sapiens (human)
cytosolLysine--tRNA ligaseHomo sapiens (human)
plasma membraneLysine--tRNA ligaseHomo sapiens (human)
aminoacyl-tRNA synthetase multienzyme complexLysine--tRNA ligaseHomo sapiens (human)
extracellular spaceLysine--tRNA ligaseHomo sapiens (human)
cytosolLysine--tRNA ligaseHomo sapiens (human)
nucleusLysine--tRNA ligaseHomo sapiens (human)
mitochondrionLysine--tRNA ligaseHomo sapiens (human)
nucleoplasmLysine--tRNA ligaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1274573Antiinflammatory activity in LPS-induced human BV2 cells assessed as reduction in NO production pretreated for 30 mins followed by LPS stimulation measured for 24 hrs by Greiss assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Dihydroisocoumarin Derivatives from Marine-Derived Fungal Isolates and Their Anti-inflammatory Effects in Lipopolysaccharide-Induced BV2 Microglia.
AID748889Antiplasmodial activity against liver stage of drug-sensitive Plasmodium falciparum D102013Bioorganic & medicinal chemistry letters, May-15, Volume: 23, Issue:10
Recent advances in malaria drug discovery.
AID1274572Cytotoxicity against human BV2 cells at 10 to 80 uM by MTT assay2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Dihydroisocoumarin Derivatives from Marine-Derived Fungal Isolates and Their Anti-inflammatory Effects in Lipopolysaccharide-Induced BV2 Microglia.
AID748888Antiplasmodial activity against liver stage of drug-sensitive Plasmodium falciparum 3D72013Bioorganic & medicinal chemistry letters, May-15, Volume: 23, Issue:10
Recent advances in malaria drug discovery.
AID1274571Inhibition of LPS-induced iNOS expression in human BV2 cells pretreated for 30 mins followed by LPS stimulation measured for 24 hrs by Western blot analysis2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Dihydroisocoumarin Derivatives from Marine-Derived Fungal Isolates and Their Anti-inflammatory Effects in Lipopolysaccharide-Induced BV2 Microglia.
AID1274574Antiinflammatory activity in LPS-induced human BV2 cells assessed as reduction in PGE2 production pretreated for 30 mins followed by LPS stimulation measured for 24 hrs by ELISA2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Dihydroisocoumarin Derivatives from Marine-Derived Fungal Isolates and Their Anti-inflammatory Effects in Lipopolysaccharide-Induced BV2 Microglia.
AID1380936Antiparasitic activity against Plasmodium falciparum 3D7 infected in human erythrocytes after 48 hrs by SYBR green-1 staining based assay2018Journal of medicinal chemistry, 07-12, Volume: 61, Issue:13
Specific Stereoisomeric Conformations Determine the Drug Potency of Cladosporin Scaffold against Malarial Parasite.
AID1380935Inhibition of human KRS expressed in Escherichia coli BL21 using tRNA(Lys) as substrate after 1 hr in presence of L-lysine by AMP-GLO assay2018Journal of medicinal chemistry, 07-12, Volume: 61, Issue:13
Specific Stereoisomeric Conformations Determine the Drug Potency of Cladosporin Scaffold against Malarial Parasite.
AID1380934Inhibition of Plasmodium falciparum KRS expressed in Escherichia coli BL21 using tRNA(Lys) as substrate after 45 mins in presence of L-lysine by AMP-GLO assay2018Journal of medicinal chemistry, 07-12, Volume: 61, Issue:13
Specific Stereoisomeric Conformations Determine the Drug Potency of Cladosporin Scaffold against Malarial Parasite.
AID1380937Selectivity ratio of IC50 for human KRS to IC50 for Plasmodium falciparum KRS2018Journal of medicinal chemistry, 07-12, Volume: 61, Issue:13
Specific Stereoisomeric Conformations Determine the Drug Potency of Cladosporin Scaffold against Malarial Parasite.
AID1274570Inhibition of LPS-induced COX2 expression in human BV2 cells pretreated for 30 mins followed by LPS stimulation measured for 24 hrs by Western blot analysis2015Journal of natural products, Dec-24, Volume: 78, Issue:12
Dihydroisocoumarin Derivatives from Marine-Derived Fungal Isolates and Their Anti-inflammatory Effects in Lipopolysaccharide-Induced BV2 Microglia.
AID1380932Binding affinity to Plasmodium falciparum KRS expressed in Escherichia coli BL21 by thermal shift assay2018Journal of medicinal chemistry, 07-12, Volume: 61, Issue:13
Specific Stereoisomeric Conformations Determine the Drug Potency of Cladosporin Scaffold against Malarial Parasite.
AID748887Inhibition of human recombinant cytoplasmic lysyl-tRNA synthetase2013Bioorganic & medicinal chemistry letters, May-15, Volume: 23, Issue:10
Recent advances in malaria drug discovery.
AID1380933Binding affinity to human KRS expressed in Escherichia coli BL21 by thermal shift assay2018Journal of medicinal chemistry, 07-12, Volume: 61, Issue:13
Specific Stereoisomeric Conformations Determine the Drug Potency of Cladosporin Scaffold against Malarial Parasite.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2014Journal of structural and functional genomics, Jun, Volume: 15, Issue:2
Structural basis of malaria parasite lysyl-tRNA synthetase inhibition by cladosporin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.85)18.7374
1990's2 (7.69)18.2507
2000's0 (0.00)29.6817
2010's19 (73.08)24.3611
2020's4 (15.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.11

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 Index30.11 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index6.25 (4.65)
Search Engine Demand Index34.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.11)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (11.11%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]