Page last updated: 2024-09-23

isocoumarins

Description

Isocoumarins: Compounds that differ from COUMARINS in having the positions of the ring and ketone oxygens reversed so the keto oxygen is at the 1-position of the molecule. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

isocoumarin : The simplest member of the class of isocoumarins that is 1H-isochromene which is substituted by an oxo group at position 1. [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 CID68108
CHEMBL ID457811
CHEBI ID38759
SCHEMBL ID76183
MeSH IDM0471145

Synonyms (23)

Synonym
1h-2-benzopyran-1-one
isocoumarin
isochromen-1-one
CHEMBL457811
chebi:38759 ,
491-31-6
AKOS006285714
benzoic acid, 2-(2-hydroxyethenyl)-, delta-lactone
sr89982s3e ,
unii-sr89982s3e
isocoumarins
3,4-benzo-2-pyrone
1h-isochromen-1-one
FT-0607868
SCHEMBL76183
DTXSID8060080
IQZZFVDIZRWADY-UHFFFAOYSA-N
N10038
Q412756
mfcd08061387
AS-76786
EN300-6487432
Z1198175817

Effects

ExcerptReference
"Four isocoumarins have been isolated from the terrestrial Streptomyces sp. "( Abdalla, MA; Islam, MT; Laatsch, H; Schüffler, A; Shaaban, KA; Zinad, DS, 2011)

Drug Classes (1)

ClassDescription
isocoumarins
[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]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID399186Antifungal activity against Cladosporium herbarum assessed as inhibition zone in mycelial layer assessed per spot by TLC bioautography assay2004Journal of natural products, Jan, Volume: 67, Issue:1
Antifungal 3-butylisocoumarins from Asteraceae-Anthemideae.
AID399185Antifungal activity against Pyricularia grisea assessed as inhibition of germ-tube development by microdilution method2004Journal of natural products, Jan, Volume: 67, Issue:1
Antifungal 3-butylisocoumarins from Asteraceae-Anthemideae.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (545)

TimeframeStudies, This Drug (%)All Drugs %
pre-199019 (3.49)18.7374
1990's94 (17.25)18.2507
2000's110 (20.18)29.6817
2010's247 (45.32)24.3611
2020's75 (13.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.18%)5.53%
Reviews20 (3.60%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other534 (96.22%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (6)

ArticleYear
New isocoumarins from a cold-adapted fungal strain mucor sp. and their developmental toxicity to zebrafish embryos.
Chemistry & biodiversity, Volume: 11, Issue: 7
2014
Topoisomerase I inactivation by reticulol and its in vivo cytotoxicity against B16F10 melanoma.
Chemotherapy, Volume: 49, Issue: 5
2003
NM-3, an isocoumarin, increases the antitumor effects of radiotherapy without toxicity.
Cancer research, Dec-15, Volume: 60, Issue: 24
2000
Acute myeloblastic leukemic cells acquire cellular cytotoxicity under genotoxic stress: implication of granzyme B and perforin.
Blood, Sep-01, Volume: 96, Issue: 5
2000
Differences in neurotoxic effects of ochratoxin A, ochracin and ochratoxin-alpha in vitro.
Natural toxins, Volume: 6, Issue: 5
1998
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (1)

ArticleYear
Pharmacokinetics, pharmacodynamics, and efficacy of a small-molecule SMN2 splicing modifier in mouse models of spinal muscular atrophy.
Human molecular genetics, 05-15, Volume: 25, Issue: 10
2016
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (4)

ArticleYear
Design and Synthesis of Metabolically Stable tRNA Synthetase Inhibitors Derived from Cladosporin.
Chembiochem : a European journal of chemical biology, 03-01, Volume: 20, Issue: 5
2019
The angiogenesis inhibitor NM-3 is active against human NSCLC xenografts alone and in combination with docetaxel.
Cancer chemotherapy and pharmacology, Volume: 56, Issue: 6
2005
2-(8-Hydroxy-6-methoxy-1-oxo-1H-2-benzopyran-3-yl)propionic acid, a small molecule isocoumarin, potentiates dexamethasone-induced apoptosis of human multiple myeloma cells.
Cancer research, Dec-01, Volume: 64, Issue: 23
2004
NM-3, an isocoumarin, increases the antitumor effects of radiotherapy without toxicity.
Cancer research, Dec-15, Volume: 60, Issue: 24
2000
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (5)

ArticleYear
Pyruvate dehydrogenase complex and lactate dehydrogenase are targets for therapy of acute liver failure.
Journal of hepatology, Volume: 69, Issue: 2
2018
Hydrangenol inhibits lipopolysaccharide-induced nitric oxide production in BV2 microglial cells by suppressing the NF-κB pathway and activating the Nrf2-mediated HO-1 pathway.
International immunopharmacology, Volume: 35
2016
Hypervalent Iodine-Mediated Intramolecular trans-Aminocarboxylation and Oxoaminocarboxylation of Alkynes: Divergent Cascade Annulations of Isocoumarins under Metal-Free Conditions.
Organic letters, Nov-06, Volume: 17, Issue: 21
2015
1H-2-Benzopyran-1-one derivatives, microbial products with pharmacological activity. Conversion into orally active derivatives with antiinflammatory and antiulcer activities.
Journal of medicinal chemistry, Volume: 28, Issue: 1
1985
Ulcerogenic and antiulcerogenic effects of a new antiinflammatory drug, the gamma-lactone-N-ethyl derivative of 6-[1S-(3S,4-dihydro-8-hydroxy-1H-2-benzo- pyran-1-one-3-yl)-3-methylbutylamino]-4S,5S-dihydroxy-6-oxo-3S- ammoniohexanoate, on gastrointestinal
Arzneimittel-Forschung, Volume: 36, Issue: 9
1986
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Interactions (3)

ArticleYear
Constituents of Fagraea fragrans with Antimycobacterial Activity in Combination with Erythromycin.
Journal of natural products, Apr-22, Volume: 79, Issue: 4
2016
Effect of 2-(8-hydroxy-6-methoxy-1-oxo-1H-2-benzopyran-3-yl) propionic acid in combination with carboplatin on gastric carcinoma growth in vivo.
World journal of gastroenterology, Jan-28, Volume: 13, Issue: 4
2007
The angiogenesis inhibitor NM-3 is active against human NSCLC xenografts alone and in combination with docetaxel.
Cancer chemotherapy and pharmacology, Volume: 56, Issue: 6
2005
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Natural Sources (2)

ArticleYear
Acylphloroglucinolated Catechin and Phenylethyl Isocoumarin Derivatives from Agrimonia pilosa.
Journal of natural products, 09-23, Volume: 79, Issue: 9
2016
[Studies on metabolites from marine microorganism Aspergillus terreus collected from nature reserve region of mangrove].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, Volume: 36, Issue: 18
2011
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]