Page last updated: 2024-12-11

ascofuranone

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

Description

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

ascofuranone : A dihydroxybenzaldehyde that is 2,4-dihydroxybenzaldehyde which is substituted by a (2E,6E)-7-[(2S)-5,5-dimethyl-4-oxotetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl group at position 3, chlorine at position 5, and a methyl group at position 6. A meroterpenoid produced by the soil fungus, Acremonium sclerotigenum. It is a promising drug candidate against the tropical disease, African trypanosomiasis. [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]

Cross-References

ID SourceID
PubMed CID6434242
CHEMBL ID133046
CHEBI ID156148
SCHEMBL ID639391
MeSH IDM0049272

Synonyms (21)

Synonym
ascofuranone
benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadienyl)-, (s-(e,e))-
ascofuranon
CHEMBL133046
CHEBI:156148
3-chloro-5-{(2e,6e)-7-[(2s)-5,5-dimethyl-4-oxotetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl}-4,6-dihydroxy-2-methylbenzaldehyde
(s)-ascofuranone
(-)-ascofuranone
38462-04-3
(s-(e,e))-3-chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadienyl)-benzaldehyde
5-chloro-3-[(2e,6e)-7-[(2s)-5,5-dimethyl-4-oxooxolan-2-yl]-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde
unii-i31efb9515
i31efb9515 ,
SCHEMBL639391
VGYPZLGWVQQOST-JUERRSSISA-N
3-chloro-4,6-dihydroxy-2-methyl-5-((2e,6e)-3-methyl-7-((2s)-tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadien-1-yl)benzaldehyde
benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-((2e,6e)-3-methyl-7-((2s)-tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadien-1-yl)-
DTXSID60903967
Q4803989
5-chloro-3-[(2e,6e)-7-[(2s)-5,5-dimethyl-4-oxo-tetrahydrofuran-2-yl]-3-methyl-octa-2,6-dienyl]-2,4-dihydroxy-6-methyl benzaldehyde
bdbm50459778

Research Excerpts

Overview

Ascofuranone is an antiviral antibiotic that is known to exert multiple anti-tumor effects, including cell cycle arrest and inhibition of mitochondrial respiration.

ExcerptReferenceRelevance
"Ascofuranone is an antiviral antibiotic that is known to exert multiple anti-tumor effects, including cell cycle arrest, inhibition of mitochondrial respiration, and inhibition of angiogenesis. "( Ascofuranone suppresses invasion and F-actin cytoskeleton organization in cancer cells by inhibiting the mTOR complex 1 signaling pathway.
Chang, YC; Hwang, SK; Jeong, YJ; Magae, J, 2020
)
3.44

Effects

Ascofuranone has been shown to have antitumor activity. The precise molecular mechanism by which it inhibits the proliferation of cancer cells remains unclear.

ExcerptReferenceRelevance
"Ascofuranone has been shown to have antitumor activity, but the precise molecular mechanism by which it inhibits the proliferation of cancer cells remains unclear. "( p53-independent induction of G1 arrest and p21WAF1/CIP1 expression by ascofuranone, an isoprenoid antibiotic, through downregulation of c-Myc.
Chang, HW; Chang, YC; Jeong, JH; Kang, SS; Magae, J; Park, KK, 2010
)
2.04
"Ascofuranone (AF) has antitumor protective property on experimental tumors. "( Effects of an antitumor agent, ascofuranone, on the macromolecular syntheses of intact cells.
Ando, K; Magae, J; Nagai, K; Tamura, G; Yamasaki, M, 1983
)
1.99

Treatment

ExcerptReferenceRelevance
"Treatment with ascofuranone also increased splenic cytotoxicity and phagocytic activity of host animal cells."( Antitumor and antimetastatic activity of an antibiotic, ascofuranone, and activation of phagocytes.
Ando, K; Hayasaki, J; Hosokawa, T; Hotta, M; Magae, J; Matsuda, Y; Nagai, K; Suzuki, S; Tamura, G, 1988
)
0.86
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
angiogenesis inhibitorAn agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antilipemic drugA substance used to treat hyperlipidemia (an excess of lipids in the blood).
fungal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antiprotozoal drugAny antimicrobial drug which is used to treat or prevent protozoal infections.
[role 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]

Drug Classes (7)

ClassDescription
dihydroxybenzaldehydeAny member of the class of benzaldehydes in which the phenyl ring is substituted by two hydroxy groups.
monochlorobenzenesAny member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine.
olefinic compoundAny organic molecular entity that contains at least one C=C bond.
resorcinolsAny benzenediol in which the two hydroxy groups are meta to one another.
meroterpenoidMeroterpenoids are complex organooxygen natural products produced from polyketide and terpenoid precursors.
sesquiterpenoidAny terpenoid derived from a sesquiterpene. The term includes compounds in which the C15 skeleton of the parent sesquiterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
tetrahydrofuranoneAny oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)IC50 (µMol)5.40000.00050.742710.0000AID1773961
Alternative oxidase, mitochondrialTrypanosoma brucei bruceiIC50 (µMol)0.00200.00201.48455.9300AID1387615
Alternative oxidase, mitochondrialTrypanosoma brucei bruceiKi0.00010.00010.00010.0001AID1401087
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Nuclear receptor subfamily 1 group I member 2Homo sapiens (human)MEC3.00001.00001.66673.0000AID161437
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
negative regulation of DNA-templated transcriptionNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
regulation of DNA-templated transcriptionNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
xenobiotic metabolic processNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
signal transductionNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
steroid metabolic processNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
positive regulation of gene expressionNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
intracellular receptor signaling pathwayNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
xenobiotic catabolic processNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
xenobiotic transportNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
positive regulation of DNA-templated transcriptionNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
positive regulation of transcription by RNA polymerase IINuclear receptor subfamily 1 group I member 2Homo sapiens (human)
cell differentiationNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
negative regulation of transcription by RNA polymerase IINuclear receptor subfamily 1 group I member 2Homo sapiens (human)
UDP biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
'de novo' UMP biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
pyrimidine ribonucleotide biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
'de novo' pyrimidine nucleobase biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
RNA polymerase II transcription regulatory region sequence-specific DNA bindingNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
nuclear receptor activityNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
protein bindingNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
zinc ion bindingNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
nuclear receptor bindingNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
sequence-specific double-stranded DNA bindingNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
dihydroorotase activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
protein bindingDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
dihydroorotate dehydrogenase (quinone) activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
dihydroorotate dehydrogenase activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
nucleoplasmNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
transcription regulator complexNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
nuclear bodyNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
intermediate filament cytoskeletonNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
chromatinNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
nucleusNuclear receptor subfamily 1 group I member 2Homo sapiens (human)
nucleoplasmDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrionDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrial inner membraneDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
cytosolDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrial inner membraneDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID1808254Inhibition of recombinant Trypanosoma brucei brucei delta MTS TAO using ubiquinol as substrate measured at 10 uM after 2 mins by UV-vis spectrophotometry2022ACS medicinal chemistry letters, Feb-10, Volume: 13, Issue:2
Imidazoline- and Benzamidine-Based Trypanosome Alternative Oxidase Inhibitors: Synthesis and Structure-Activity Relationship Studies.
AID38996Minimum effective concentration required to inhibit androgen receptor (AR)2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Ascochlorin derivatives as ligands for nuclear hormone receptors.
AID156958Minimum effective concentration required to inhibit Peroxisome proliferator activated receptor gamma (PPAR gamma).2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Ascochlorin derivatives as ligands for nuclear hormone receptors.
AID1772158Antibacterial activity against Staphylococcus aureus ATCC 29213 assessed as inhibition of bacterial growth incubated for 16 hrs by microdilution method
AID156284Minimum effective concentration required to inhibit Peroxisome proliferator activated receptor alpha (PPAR alpha); Not detected2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Ascochlorin derivatives as ligands for nuclear hormone receptors.
AID422388Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced TNFalpha production at 100 uM after 24 hrs by ELISA relative to control2009Journal of natural products, Feb-27, Volume: 72, Issue:2
Anti-inflammatory sesquiterpenoids from a sponge-derived Fungus Acremonium sp.
AID44172Concentration required for inhibition of C3H10T1/2 progenitor cell growth2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Ascochlorin derivatives as ligands for nuclear hormone receptors.
AID1772166Antifungal activity against Candida albicans ATCC 10231 assessed as inhibition of fungal growth incubated for 16 hrs by microdilution method
AID1387621Antiparasitic activity against bloodstream trypomastigote stage of wild type Trypanosoma brucei brucei Lister 427 after 48 hrs in presence of glycerol by resazurin dye based fluorescence assay2018ACS medicinal chemistry letters, Sep-13, Volume: 9, Issue:9
SAR of 4-Alkoxybenzoic Acid Inhibitors of the Trypanosome Alternative Oxidase.
AID70032Minimum effective concentration required to inhibit Estrogen receptor 2 (ER beta); Not detected2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Ascochlorin derivatives as ligands for nuclear hormone receptors.
AID1773960Cytotoxicity against human MDA-MB-468 cells assessed as reduction in cell viability incubated for 24 hrs by CellTiter-Glo luminescent assay
AID1394618Inhibition of recombinant N-terminal His6 tagged SUMO-fused Trypanosoma brucei brucei TC221 TAO MTS deletion mutant expressed in Escherichia coli FN102 preincubated for 2 mins followed by ubiquinol-1 addition measured over 2 mins by double beam-dual wavel2018European journal of medicinal chemistry, Apr-25, Volume: 150Inhibition of trypanosome alternative oxidase without its N-terminal mitochondrial targeting signal (ΔMTS-TAO) by cationic and non-cationic 4-hydroxybenzoate and 4-alkoxybenzaldehyde derivatives active against T. brucei and T. congolense.
AID1394668Non-competitive inhibition of Trypanosoma brucei brucei TC221 TAO expressed in Escherichia coli FN102 assessed as reduction in ubiquinoldependent oxygen consumption by spectrophotometry2018European journal of medicinal chemistry, Apr-25, Volume: 150Inhibition of trypanosome alternative oxidase without its N-terminal mitochondrial targeting signal (ΔMTS-TAO) by cationic and non-cationic 4-hydroxybenzoate and 4-alkoxybenzaldehyde derivatives active against T. brucei and T. congolense.
AID1387615Inhibition of recombinant Trypanosoma brucei brucei alternative oxidase using ubiquinol-1 as substrate incubated for 2 mins followed by substrate addition by spectrophotometric method2018ACS medicinal chemistry letters, Sep-13, Volume: 9, Issue:9
SAR of 4-Alkoxybenzoic Acid Inhibitors of the Trypanosome Alternative Oxidase.
AID1772168Cytotoxicity against human HepG2 cells assessed as reduction in cell viability incubated for 48 hrs by CCK8 assay
AID1773961Inhibition of recombinant N-terminal His-tagged human DHODH (31 to 395 residues) expressed in Escherichia coli using DL-dihydroorotic acid as substrate and Q0 as coenzyme by DCIP based assay
AID475975Antitrypanosomal activity against Trypanosoma brucei brucei 427-221a after 40 hrs by bioluminescence assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Assessing the trypanocidal potential of natural and semi-synthetic diketopiperazines from two deep water marine-derived fungi.
AID1772163Antibacterial activity against vancomycin-resistant Enterococcus faecalis 21-07 assessed as inhibition of bacterial growth incubated for 16 hrs by microdilution method
AID422387Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production at 100 uM after 24 hrs by Griess reagent method relative to control2009Journal of natural products, Feb-27, Volume: 72, Issue:2
Anti-inflammatory sesquiterpenoids from a sponge-derived Fungus Acremonium sp.
AID1772159Antibacterial activity against Staphylococcus aureus ATCC 25923 assessed as inhibition of bacterial growth incubated for 16 hrs by microdilution method
AID69869Minimum effective concentration required to inhibit Estrogen receptor 1 (ER alpha); Not detected2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Ascochlorin derivatives as ligands for nuclear hormone receptors.
AID1773959Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability incubated for 24 hrs by CellTiter-Glo luminescent assay
AID1772167Cytotoxicity against human A549 cells assessed as reduction in cell viability incubated for 48 hrs by CCK8 assay
AID1394622Anti-parasitic activity against bloodstream trypomastigote stage of wild-type Trypanosoma brucei brucei Lister 427 after 48 hrs in presence of 5 mM glycerol by resazurin-based assay2018European journal of medicinal chemistry, Apr-25, Volume: 150Inhibition of trypanosome alternative oxidase without its N-terminal mitochondrial targeting signal (ΔMTS-TAO) by cationic and non-cationic 4-hydroxybenzoate and 4-alkoxybenzaldehyde derivatives active against T. brucei and T. congolense.
AID1772165Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 assessed as inhibition of bacterial growth incubated for 16 hrs by microdilution method
AID1394665Anti-parasitic activity against bloodstream trypomastigote stage of wild-type Trypanosoma brucei brucei Lister 4272018European journal of medicinal chemistry, Apr-25, Volume: 150Inhibition of trypanosome alternative oxidase without its N-terminal mitochondrial targeting signal (ΔMTS-TAO) by cationic and non-cationic 4-hydroxybenzoate and 4-alkoxybenzaldehyde derivatives active against T. brucei and T. congolense.
AID1772164Antibacterial activity against Escherichia coli ATCC 25922 assessed as inhibition of bacterial growth incubated for 16 hrs by microdilution method
AID1772161Antibacterial activity against Staphylococcus epidermidis ATCC 12228 assessed as inhibition of bacterial growth incubated for 16 hrs by microdilution method
AID1401087Inhibition of Trypanosoma brucei alternative oxidase expressed in Escherichia coli FN102 using ubiquinol-1 as substrate preincubated for 2 mins followed by substrate addition by spectrophotometric method2017European journal of medicinal chemistry, Dec-01, Volume: 141African trypanosomiasis: Synthesis & SAR enabling novel drug discovery of ubiquinol mimics for trypanosome alternative oxidase.
AID1772160Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 33591 assessed as inhibition of bacterial growth incubated for 16 hrs by microdilution method
AID161437Minimum effective concentration required to inhibit pregnane X receptor (PXR)2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Ascochlorin derivatives as ligands for nuclear hormone receptors.
AID1387616Antiparasitic activity against bloodstream trypomastigote stage of wild type Trypanosoma brucei brucei Lister 427 after 48 hrs by resazurin dye based fluorescence assay2018ACS medicinal chemistry letters, Sep-13, Volume: 9, Issue:9
SAR of 4-Alkoxybenzoic Acid Inhibitors of the Trypanosome Alternative Oxidase.
AID1772162Antibacterial activity against Bacillus subtilis ATCC 6633 assessed as inhibition of bacterial growth incubated for 16 hrs by microdilution method
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (58)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (13.79)18.7374
1990's5 (8.62)18.2507
2000's18 (31.03)29.6817
2010's19 (32.76)24.3611
2020's8 (13.79)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.48

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 Index21.48 (24.57)
Research Supply Index4.08 (2.92)
Research Growth Index4.98 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.48)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews8 (13.79%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other50 (86.21%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]