Page last updated: 2024-12-11

fumarprotocetraric acid

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Description

fumarprotocetraric acid: RN given refers to (E)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5317419
CHEMBL ID366861
CHEBI ID144157
SCHEMBL ID717507
MeSH IDM0086546

Synonyms (37)

Synonym
10-formyl-3,9-dihydroxy-4-[[(e)-4-hydroxy-4-oxo-but-2-enoyl]oxymethyl]-1,7-dimethyl-6-oxo-benzo[b][1,4]benzodioxepine-2-carboxylic acid
9-[((2e)-3-carboxyprop-2-enoyloxy)methyl]-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxodibenzo[b,e]1,4-dioxepin-7-carboxylic acid
nsc249984
(e)-2-butenedioic acid,8-dihydroxy-1,6-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepin-9-yl)methyl] ester
nsc-249984
BSPBIO_002497
SPECTRUM5_000885
9-(3-carboxy-acryloyloximethyl)-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepin-7-carboxylic acid
but-2-enedioic acid mono-(7-carboxy-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepin-9-ylmethyl) ester
2-butenedioic acid, mono[(7-carboxy-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepin-9-yl)methyl] ester, (2e)-
489-50-9
9-({[(2e)-3-carboxyprop-2-enoyl]oxy}methyl)-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepine-7-carboxylic acid
inchi=1/c22h16o12/c1-8-5-12(24)10(6-23)19-15(8)22(31)34-20-11(7-32-14(27)4-3-13(25)26)17(28)16(21(29)30)9(2)18(20)33-19/h3-6,24,28h,7h2,1-2h3,(h,25,26)(h,29,30)/b4-3
fumarprotocetraric acid
nsc-685588
NCGC00095467-01
SPECTRUM200054
NCGC00095467-02
CHEMBL366861 ,
(e)-but-2-enedioic acid mono-(7-carboxy-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepin-9-ylmethyl) ester
bdbm50056933
CHEBI:144157
5vj6j3a960 ,
CCG-38658
SCHEMBL717507
fumaric acid, 9-monoester with 4-formyl-3,8-dihydroxy-9-(hydroxymethyl)-1,6-dimethyl-11-oxo-11h-dibenzo(b,e)(1,4)dioxepin-7-carboxylic acid
2-butenedioic acid (2e)-, 1-((7-carboxy-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11h-dibenzo(b,e)(1,4)dioxepin-9-yl)methyl) ester
sr-05000002702
SR-05000002702-1
Q27896597
(e)-9-((3-carboxyacryloyloxy)methyl)-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepine-7-carboxylic acid
4-[[(e)-3-carboxyprop-2-enoyl]oxymethyl]-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxo-benzo[b][1,4]benzodioxepine-2-carboxylic acid
4-[[(e)-3-carboxyprop-2-enoyl]oxymethyl]-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylic acid
4-(3-carboxyprop-2-enoyloxymethyl)-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylic acid
DTXSID801313939
fumarprotocetraricacid
AKOS040734853
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
carbonyl compoundAny compound containing the carbonyl group, C=O. The term is commonly used in the restricted sense of aldehydes and ketones, although it actually includes carboxylic acids and derivatives.
[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 (41)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency6.23950.003245.467312,589.2998AID2517; AID2572
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency21.48650.004023.8416100.0000AID485290; AID489007
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency19.90540.140911.194039.8107AID2451
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency28.18380.177814.390939.8107AID2147
Chain A, ATP-DEPENDENT DNA HELICASE Q1Homo sapiens (human)Potency3.98110.125919.1169125.8920AID2549
15-lipoxygenase, partialHomo sapiens (human)Potency25.11890.012610.691788.5700AID887
USP1 protein, partialHomo sapiens (human)Potency56.23410.031637.5844354.8130AID504865
Microtubule-associated protein tauHomo sapiens (human)Potency6.23030.180013.557439.8107AID1460; AID1468
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency4.46680.011212.4002100.0000AID1030
polyunsaturated fatty acid lipoxygenase ALOX12Homo sapiens (human)Potency15.84891.000012.232631.6228AID1452
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency1.41250.001815.663839.8107AID894
runt-related transcription factor 1 isoform AML1bHomo sapiens (human)Potency19.70200.02007.985839.8107AID504374; AID504375
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency6.30960.354828.065989.1251AID504847
thyroid hormone receptor beta isoform aHomo sapiens (human)Potency19.35120.010039.53711,122.0200AID1469; AID1479
core-binding factor subunit beta isoform 2Homo sapiens (human)Potency19.70200.02007.985839.8107AID504374; AID504375
ubiquitin carboxyl-terminal hydrolase 2 isoform aHomo sapiens (human)Potency25.11890.65619.452025.1189AID927
DNA polymerase kappa isoform 1Homo sapiens (human)Potency3.54810.031622.3146100.0000AID588579
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency39.81070.031610.279239.8107AID884; AID885
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency19.95260.251215.843239.8107AID504327
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Glutamate receptor 1Rattus norvegicus (Norway rat)Potency11.22020.01418.602439.8107AID2572
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency11.22020.001551.739315,848.9004AID2572
Glutamate receptor 3Rattus norvegicus (Norway rat)Potency11.22020.01418.602439.8107AID2572
Glutamate receptor 4Rattus norvegicus (Norway rat)Potency11.22020.01418.602439.8107AID2572
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Disintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)Potency25.11891.584913.004325.1189AID927
GABA theta subunitRattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency39.81071.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Integrase Human immunodeficiency virus 1IC50 (µMol)5.26000.00051.544310.0000AID397605; AID397758; AID93701; AID93706; AID93707
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
positive regulation of epidermal growth factor receptor signaling pathwayDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
response to hypoxiaDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
neutrophil mediated immunityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
germinal center formationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of leukocyte chemotaxisDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
proteolysisDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
membrane protein ectodomain proteolysisDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cell adhesionDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
Notch receptor processingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of cell population proliferationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
response to xenobiotic stimulusDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of T cell chemotaxisDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
protein processingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
signal releaseDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
B cell differentiationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of cell growthDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of cell migrationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathwayDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
response to lipopolysaccharideDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of chemokine productionDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of tumor necrosis factor productionDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
regulation of mast cell apoptotic processDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
T cell differentiation in thymusDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cell adhesion mediated by integrinDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
wound healing, spreading of epidermal cellsDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
amyloid precursor protein catabolic processDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of blood vessel endothelial cell migrationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of cyclin-dependent protein serine/threonine kinase activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of epidermal growth factor-activated receptor activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of epidermal growth factor receptor signaling pathwayDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
spleen developmentDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cell motilityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
defense response to Gram-positive bacteriumDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cellular response to high density lipoprotein particle stimulusDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
commissural neuron axon guidanceDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
negative regulation of cold-induced thermogenesisDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of G1/S transition of mitotic cell cycleDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of tumor necrosis factor-mediated signaling pathwayDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of vascular endothelial cell proliferationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
Notch signaling pathwayDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
endopeptidase activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
metalloendopeptidase activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
Notch bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
interleukin-6 receptor bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
integrin bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
protein bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
peptidase activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
metallopeptidase activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
SH3 domain bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cytokine bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
PDZ domain bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
tumor necrosis factor bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
metal ion bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
metalloendopeptidase activity involved in amyloid precursor protein catabolic processDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor 1Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
cell-cell junctionDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
focal adhesionDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
ruffle membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
Golgi membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cytoplasmDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
endoplasmic reticulum lumenDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cytosolDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
plasma membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cell surfaceDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
actin cytoskeletonDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
apical plasma membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
membrane raftDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
plasma membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID93701Inhibitory concentration of compound against 3'-processing of HIV-1 integrase in experiment 1&21997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID397758Inhibition of HIV1 integrase 3' processing activity2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID292619DPPH radical scavenging activity at 3000 uM2007Journal of natural products, Jul, Volume: 70, Issue:7
Stictic acid derivatives from the lichen Usnea articulata and their antioxidant activities.
AID93707Inhibitory concentration of compound against strand transfer of HIV-1 integrase in experiment 21997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID91562Percentage inhibition against strand transfer of HIV-1 integrase at 100 ug/mL1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID292620Superoxide radical scavenging activity2007Journal of natural products, Jul, Volume: 70, Issue:7
Stictic acid derivatives from the lichen Usnea articulata and their antioxidant activities.
AID93706Inhibitory concentration of compound against strand transfer of HIV-1 integrase in experiment 1&21997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID91561Percentage inhibition of compound against 3'-processing of HIV-1 integrase at 100 ug/mL1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID397605Inhibition of HIV1 integrase strand transfer activity2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID397604Therapeutic index, ratio of cytotoxicity against human MT2 cells to EC50 for HIV1 RF2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID397603Antiviral activity against HIV1 RF in human MT2 cells assessed as virus-induced cytopathic effect after 72 hrs2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (10.00)18.7374
1990's1 (10.00)18.2507
2000's4 (40.00)29.6817
2010's3 (30.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.05

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 Index23.05 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.95 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.05)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]