Page last updated: 2024-12-09

benzylidenephthalide

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Description

benzylidenephthalide: contaminant of phenindione tablets considered as potentially immunogenic substance [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID700611
CHEMBL ID1562463
SCHEMBL ID5433929
MeSH IDM0057694
PubMed CID642371
CHEMBL ID67365
CHEBI ID113035
SCHEMBL ID214423
MeSH IDM0057694

Synonyms (90)

Synonym
smr000217194
MLS000589956
3-[1-phenyl-meth-(e)-ylidene]-3h-isobenzofuran-1-one
einecs 209-388-8
1(3h)-isobenzofuranane, 3-(phenylmethylene)-
3-(phenylmethylene)-1(3h)-isobenzofuranone
nsc 2824
brn 0083797
benzylidenephthalide
ai3-17979
escalol 547
AKOS003614531
NCGC00246296-01
HMS2533B05
unii-n2s40871lm
ec 209-388-8
n2s40871lm ,
5-17-10-00577 (beilstein handbook reference)
SCHEMBL5433929
CHEMBL1562463
c9e8s3agyq ,
trans-3-benzylidenephthalide
4767-55-9
1(3h)-isobenzofuranone, 3-(phenylmethylene)-, (3e)-
trans-3-(phenylmethylene)phthalide
unii-c9e8s3agyq
benzalphthalide, (e)-
J-519667
(e)-3-benzylidenephthalide
1,4-diaminopiperazinehydrate
(e)-benzalphthalide
Q27275358
3-(phenylmethylidene)-1,3-dihydro-2-benzofuran-1-one
EN300-13345571
(e)-3-benzylideneisobenzofuran-1(3h)-one
HMS2619E19
phthalide, 3-benzylidene-
1(3h)-isobenzofuranone, 3-(phenylmethylene)-
nsc2824
3-benzylidenephthalide
575-61-1
3-benzalphthalide
nsc-2824
benzalphthalide
MLS000584766
smr000203729
1(3h)-isobenzofuranone, 3-(phenyl)methylene]-, (3z)-
(3z)-3-benzylideneisobenzofuran-1-one
inchi=1/c15h10o2/c16-15-13-9-5-4-8-12(13)14(17-15)10-11-6-2-1-3-7-11/h1-10h/b14-10
1(3h)-isobenzofuranone, 3-(phenylmethylene)-, (3z)-
(3z)-3-benzylidene-2-benzofuran-1(3h)-one
CHEBI:113035
AC-11676
B1214 ,
CHEMBL67365 ,
(3z)-3-benzylidene-2-benzofuran-1-one
3-benzylidene-2-benzofuran-1(3h)-one
HMS1610I16
AKOS000567737
STK862417
3-benzylideneisobenzofuran-1(3h)-one
A831503
NCGC00245849-01
4767-56-0
SCHEMBL214423
AE-641/05032029
bdbm50441021
BBL027545
benzalphthalid
YRTPZXMEBGTPLM-UVTDQMKNSA-N
(3z)-3-benzylidene-2-benzofuran-1(3h)-one #
benzalphthalide, (z)-
r93gn14k61 ,
unii-r93gn14k61
(z)-3-benzylidenephthalide
AC-31127
mfcd00005929
sr-01000438153
SR-01000438153-1
(3z)-3-(phenylmethylidene)-1,3-dihydro-2-benzofuran-1-one
VS-08562
3-benzylidene-3h-isobenzofuran-1-one
(z)-3-benzylideneisobenzofuran-1(3h)-one
AT15806
Q27287989
(z)-benzalphthalide
3-[1-phenyl-meth-(z)-ylidene]-3h-isobenzofuran-1-one
PD119248
CS-0067707
HY-118659
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (21)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency22.38720.004023.8416100.0000AID485290
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency56.23410.631035.7641100.0000AID504339
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency28.18380.177814.390939.8107AID2147
Chain A, Ferritin light chainEquus caballus (horse)Potency25.11895.623417.292931.6228AID485281
LuciferasePhotinus pyralis (common eastern firefly)Potency11.99550.007215.758889.3584AID588342
T cell receptor, partialHomo sapiens (human)Potency5.62340.99603.64016.2841AID504894
ClpPBacillus subtilisPotency25.11891.995322.673039.8107AID651965
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency39.81070.707912.194339.8107AID720542
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency25.11890.011212.4002100.0000AID1030
glucocerebrosidaseHomo sapiens (human)Potency50.11870.01268.156944.6684AID2101
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency56.23410.707936.904389.1251AID504333
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency28.18380.001815.663839.8107AID894
chromobox protein homolog 1Homo sapiens (human)Potency89.12510.006026.168889.1251AID540317
DNA polymerase eta isoform 1Homo sapiens (human)Potency0.19950.100028.9256213.3130AID588591
lethal(3)malignant brain tumor-like protein 1 isoform IHomo sapiens (human)Potency31.62280.075215.225339.8107AID485360
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency63.09570.631035.7641100.0000AID504339
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency31.62280.177814.390939.8107AID2147
LuciferasePhotinus pyralis (common eastern firefly)Potency11.99550.007215.758889.3584AID588342
chaperonin-containing TCP-1 beta subunit homologHomo sapiens (human)Potency17.78283.981127.764939.8107AID504842
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency39.81070.707912.194339.8107AID720542
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency37.65050.011212.4002100.0000AID1030
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency56.23410.707936.904389.1251AID504333
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency50.11870.035520.977089.1251AID504332
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency35.48130.001815.663839.8107AID894
chromobox protein homolog 1Homo sapiens (human)Potency50.11870.006026.168889.1251AID540317
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency33.58750.168316.404067.0158AID720504
lethal(3)malignant brain tumor-like protein 1 isoform IHomo sapiens (human)Potency22.38720.075215.225339.8107AID485360
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency39.81070.00419.962528.1838AID2675
[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)
Transient receptor potential cation channel subfamily A member 1Rattus norvegicus (Norway rat)IC50 (µMol)2.90000.45003.42437.5000AID772955
Transient receptor potential cation channel subfamily M member 8Rattus norvegicus (Norway rat)IC50 (µMol)9.25000.05802.65048.3000AID772951; AID772952
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Transient receptor potential cation channel subfamily A member 1Rattus norvegicus (Norway rat)EC50 (µMol)3.00000.06002.22238.4000AID772956
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (42)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID772957Agonist activity at rat recombinant TRPA1 overexpressed in HEK293 cells assessed as induction of intracellular calcium influx by Fluo-4-AM dye-based spectrofluorimetric analysis relative to allyl isothiocyanate2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID772956Agonist activity at rat recombinant TRPA1 overexpressed in HEK293 cells assessed as induction of intracellular calcium influx by Fluo-4-AM dye-based spectrofluorimetric analysis2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID772955Antagonist activity at rat recombinant TRPA1 overexpressed in HEK293 cells assessed as inhibition of allyl isothiocyanate-induced intracellular calcium influx preincubated for 5 mins followed by allyl isothiocyanate challenge by Fluo-4-AM dye-based spectr2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID772952Antagonist activity at rat recombinant TRPM8 overexpressed in HEK293 cells assessed as inhibition of icilin-induced intracellular calcium influx preincubated for 5 mins followed by icilin challenge by Fluo-4-AM dye-based spectrofluorimetric analysis2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID99864In vitro inhibitory activity against Leishmania amazonensis (PH8)2001Bioorganic & medicinal chemistry letters, Aug-20, Volume: 11, Issue:16
Leishmanicidal activity of some stilbenoids and related heterocyclic compounds.
AID213788Inhibitory concentration against epimastigotes (Tulahuen strain) of Trypanosoma cruzi; Inactive2001Bioorganic & medicinal chemistry letters, Oct-22, Volume: 11, Issue:20
Anti-Trypanosoma activity of some natural stilbenoids and synthetic related heterocyclic compounds.
AID100420In vitro inhibitory activity against Leishmania donovani (PP75)2001Bioorganic & medicinal chemistry letters, Aug-20, Volume: 11, Issue:16
Leishmanicidal activity of some stilbenoids and related heterocyclic compounds.
AID772954Agonist activity at rat recombinant TRPM8 overexpressed in HEK293 cells assessed as induction of intracellular calcium influx by Fluo-4-AM dye-based spectrofluorimetric analysis relative to ionomycin2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID772953Agonist activity at rat recombinant TRPM8 overexpressed in HEK293 cells assessed as induction of intracellular calcium influx by Fluo-4-AM dye-based spectrofluorimetric analysis2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID213787Inhibitory concentration against Epimastigotes (Tulahuen strain) of Trypanosoma cruzi2001Bioorganic & medicinal chemistry letters, Oct-22, Volume: 11, Issue:20
Anti-Trypanosoma activity of some natural stilbenoids and synthetic related heterocyclic compounds.
AID99990In vitro inhibitory activity against Leishmania braziliensis (M2903)2001Bioorganic & medicinal chemistry letters, Aug-20, Volume: 11, Issue:16
Leishmanicidal activity of some stilbenoids and related heterocyclic compounds.
AID772951Antagonist activity at rat recombinant TRPM8 overexpressed in HEK293 cells assessed as inhibition of menthol-induced intracellular calcium influx preincubated for 5 mins followed by menthol challenge by Fluo-4-AM dye-based spectrofluorimetric analysis2013Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators.
AID229349Ratio of inhibitory concentration to that of reference drug was determined2001Bioorganic & medicinal chemistry letters, Oct-22, Volume: 11, Issue:20
Anti-Trypanosoma activity of some natural stilbenoids and synthetic related heterocyclic compounds.
AID213793Inhibitory concentration against trypomastigotes (Y strain) of Trypanosoma cruzi; Inactive2001Bioorganic & medicinal chemistry letters, Oct-22, Volume: 11, Issue:20
Anti-Trypanosoma activity of some natural stilbenoids and synthetic related heterocyclic compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (8.33)18.7374
1990's0 (0.00)18.2507
2000's3 (25.00)29.6817
2010's7 (58.33)24.3611
2020's1 (8.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.91

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.91 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.91)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]