Page last updated: 2024-12-10

chartreusin

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

Description

chartreusin: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5281394
CHEMBL ID1554674
CHEBI ID3580
SCHEMBL ID973723
MeSH IDM0042680

Synonyms (32)

Synonym
brn 0075649
benzo(h)(1)benzopyrano(5,4,3-cde)(1)benzopyran-5,12-dione, 10-((6-deoxy-2-o-(6-deoxy-3-o-methyl-alpha-d-galactopyranosyl)-beta-d-galactopyranosyl)oxy)-6-hydroxy-1-methyl-
nsc 5159
u-7257
nsc-5159
x 465a
lambdamycin
antibiotic x-465a
[(2s,3r,4s,5r,6r)-3-[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-hydroxy-methyl-[?]dione
10-{3-[2-(3,5-dihydroxy-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-ethoxy]-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy}-6-hydroxy-1-methyl-benzo[h!chromeno[5,4,3-cde!chromene-5,12-dione
chartreusin, dihydrate
C09181
chartreusin
6377-18-0
NCGC00163668-01
M01618
CHEMBL1554674
chebi:3580 ,
4-19-00-03078 (beilstein handbook reference)
unii-hs0h395e3o
hs0h395e3o ,
CCG-208644
PONPPNYZKHNPKZ-RYBWXQSLSA-N
SCHEMBL973723
benzo(h)(1)benzopyrano(5,4,3-cde)(1)benzopyran-5,12-dione, 10-((6-deoxy-2-o-(6-deoxy-3-o-methyl-.alpha.-d-galactopyranosyl)-.beta.-d-galactopyranosyl)oxy)-6-hydroxy-1-methyl-
chartreusin, (-)-
chartreusin [mi]
DTXSID20930431
Q15410881
3-[(2s,3r,4s,5r,6r)-3-[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-8-hydroxy-15-methyl-11,18-dioxapentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(19),2(7),3,5,8,12(20),13,15-octaene-10,17-dione
benzo(h)(1)benzopyrano(5,4,3-cde)(1)benzopyran-5,12-dione, 10-((6-deoxy-2-o-(6-deoxy-3-o-methyl-alpha-d-galactopyranosyl)-beta-d-galactopyranosyl)oxy)-6-hydroxy-1-methyl- (9ci)
AKOS040745662

Research Excerpts

Overview

Chartreusin (1) is a potent antitumor polyketide that contains a unique rearranged pentacyclic aromatic bilactone aglycone derived from a type II PKS. It is produced by Streptomyces chartreusis.

ExcerptReferenceRelevance
"Chartreusin (1) is a potent antitumor polyketide that contains a unique rearranged pentacyclic aromatic bilactone aglycone derived from a type II PKS."( Molecular Basis for the Final Oxidative Rearrangement Steps in Chartreusin Biosynthesis.
Ge, HM; Guo, Y; Huang, H; Jiao, RH; Liang, Y; Liu, CL; Liu, F; Tan, RX; Wang, YS; Yang, CL; Zhang, B; Zhao, S; Zhu, J, 2018
)
1.44
"Chartreusin is a potent antitumor agent with a mixed polyketide-carbohydrate structure produced by Streptomyces chartreusis. "( Biosynthesis of the antitumor agent chartreusin involves the oxidative rearrangement of an anthracyclic polyketide.
Hertweck, C; Jakobi, K; Welzel, K; Xu, Z, 2005
)
2.05

Effects

ExcerptReferenceRelevance
"Chartreusin has exhibited significant therapeutic activity against three experimental mouse tumors (ascitic P388, L1210 leukemia, and B16 melanoma) when tumor cells were inoculated i.p. "( Antitumor activity and preliminary drug disposition studies on chartreusin (NSC 5159).
Crampton, SL; Douros, JD; McGovren, JP; Neil, GL; Robinson, MI, 1977
)
1.94

Bioavailability

ExcerptReferenceRelevance
" The drug is well absorbed from small intestine."( [Topoisomerase inhibitors developing in Japan].
Furue, H, 1993
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
glycosideA glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.
benzochromenoneA benzochromene in which the heterotricyclic ring system is substituted by an oxo group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency7.06270.140911.194039.8107AID2451
Chain A, Ferritin light chainEquus caballus (horse)Potency35.48135.623417.292931.6228AID485281
chromobox protein homolog 1Homo sapiens (human)Potency100.00000.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency18.35640.00419.984825.9290AID504444
flap endonuclease 1Homo sapiens (human)Potency10.00000.133725.412989.1251AID588795
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency19.95260.050127.073689.1251AID588590
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency23.35070.00798.23321,122.0200AID2546; AID2551
DNA polymerase kappa isoform 1Homo sapiens (human)Potency35.48130.031622.3146100.0000AID588579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID697853Inhibition of horse BChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID1503774Cytotoxicity against human HL cells assessed as cell viability at 50 uM after 72 hrs by resazurin dye based fluorescence assay relative to control2017Journal of natural products, 10-27, Volume: 80, Issue:10
Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy.
AID697852Inhibition of electric eel AChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (42)

TimeframeStudies, This Drug (%)All Drugs %
pre-199018 (42.86)18.7374
1990's10 (23.81)18.2507
2000's8 (19.05)29.6817
2010's4 (9.52)24.3611
2020's2 (4.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.87

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 Index19.87 (24.57)
Research Supply Index3.78 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.87)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (2.38%)5.53%
Reviews3 (7.14%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other38 (90.48%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]