Page last updated: 2024-12-05

3-hydroxy-1-benzopyran-2-one

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Description

3-Hydroxy-1-benzopyran-2-one, also known as coumarin, is a naturally occurring compound found in a variety of plants. Coumarin is a colorless crystalline compound with a sweet, fragrant odor. It is used in perfumes, flavorings, and pharmaceuticals. Coumarin is synthesized through various methods, including the Perkin reaction and the Knoevenagel condensation. It exhibits various biological effects, including anticoagulant, anti-inflammatory, and antioxidant activities. Coumarin is studied extensively due to its potential applications in medicine, particularly as an anticoagulant and anti-cancer agent. Research is ongoing to explore its therapeutic potential and to understand its mechanisms of action.'

3-hydroxycoumarin: Photoprotective from sea urchin gametes and embryonic cells; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

hydroxycoumarin : Any coumarin carrying at least one hydroxy substituent. [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 CID13650
CHEMBL ID150372
CHEBI ID113542
SCHEMBL ID76090

Synonyms (67)

Synonym
rqx0cmd9pn ,
unii-rqx0cmd9pn
5-18-01-00376 (beilstein handbook reference)
BRD-K92019075-001-02-0
3-hydroxy-2h-chromen-2-one
AN-829/40355682
DIVK1C_006956
SDCCGMLS-0066523.P001
einecs 213-355-3
nsc 74691
2h-1-benzopyran-2-one, 3-hydroxy-
coumarin, 3-hydroxy-
3-hydroxy-2h-1-benzopyran-2-one
brn 0128032
3-hydroxy-2-benzopyrone
SPECTRUM_000476
SPECTRUM4_001576
NCGC00178445-01
nsc74691
939-19-5
nsc-74691
BSPBIO_002834
3-hydroxycoumarin
SPECTRUM5_000232
NCGC00095536-01
KBIO2_000956
KBIO2_003524
KBIOGR_002132
KBIO2_006092
KBIO1_001900
KBIO3_002334
KBIOSS_000956
SPBIO_000669
SPECPLUS_000860
SPECTRUM3_001267
SPECTRUM2_000805
SPECTRUM211538
CHEBI:113542
CHEMBL150372 ,
3-hydroxychromen-2-one
3-hydroxy-chromen-2-one
bdbm50206007
NCGC00095536-02
43070-85-5
CCG-39664
FT-0633159
AKOS015916452
3-coumarinol
3 hydroxycoumarin
SCHEMBL76090
hydroxy-2h-chromen-2-one
hydroxycoumarin
MJKVTPMWOKAVMS-UHFFFAOYSA-N
H1585
mfcd00017490
Q27194434
2h-1-benzopyran-2-one,3-hydroxy-
DTXSID50239863
o-hydroxyphenylpyruvic acid lactone
3-hydroxy-coumarin
HY-127170
AMY202100133
CS-0094421
3-hydroxychromenone
T73087
MS-22894
PD002122
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
hydroxycoumarinAny coumarin carrying at least one hydroxy substituent.
[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 (18)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency17.78280.001815.663839.8107AID894
[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)
Neuronal acetylcholine receptor subunit alpha-4Rattus norvegicus (Norway rat)Ki0.26500.00000.12345.5000AID726215
Neuronal acetylcholine receptor subunit beta-2Rattus norvegicus (Norway rat)Ki0.26500.00000.10825.5000AID726215
TyrosinaseHomo sapiens (human)Ki3.40001.70004.73339.1000AID1717734
D-amino-acid oxidaseHomo sapiens (human)IC50 (µMol)0.47260.00401.119910.0000AID726221; AID726222; AID745648
D-amino-acid oxidaseHomo sapiens (human)Ki1.03100.01302.13868.1600AID726213; AID726214; AID726215; AID745647
Aldo-keto reductase family 1 member B1Homo sapiens (human)IC50 (µMol)62.00000.00101.191310.0000AID516862
Xanthine dehydrogenase/oxidaseHomo sapiens (human)IC50 (µMol)131.00000.00132.81389.8200AID294445
Sorbitol dehydrogenaseHomo sapiens (human)IC50 (µMol)106.00000.24000.49531.0000AID516864
D-aspartate oxidaseHomo sapiens (human)IC50 (µMol)7,579.00000.00400.39370.8550AID726223
[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)
D-amino-acid oxidaseRattus norvegicus (Norway rat)Kd5.60005.60005.60005.6000AID745618
D-amino-acid oxidaseSus scrofa (pig)Kd6.30000.15002.81006.3000AID745649
D-amino-acid oxidaseHomo sapiens (human)Kd5.30000.00311.72789.0000AID745618; AID745619; AID745649
[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)
Carbonic anhydrase 12Homo sapiens (human)Kinact9.60000.00300.66749.6000AID493457
Carbonic anhydrase 1Homo sapiens (human)Kinact79.40000.01000.93878.6000AID493454
Carbonic anhydrase 2Homo sapiens (human)Kinact100.00000.00300.794610.0000AID493455
Substance-P receptorCavia porcellus (domestic guinea pig)CD1.50000.90004.50009.8000AID144377
Quinone oxidoreductaseMus musculus (house mouse)CD1.50000.20002.74219.8000AID144377
Carbonic anhydrase 9Homo sapiens (human)Kinact0.50800.00500.31976.6700AID493456
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (96)

Processvia Protein(s)Taxonomy
estrous cycleCarbonic anhydrase 12Homo sapiens (human)
chloride ion homeostasisCarbonic anhydrase 12Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 12Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
melanin biosynthetic process from tyrosineTyrosinaseHomo sapiens (human)
eye pigment biosynthetic processTyrosinaseHomo sapiens (human)
visual perceptionTyrosinaseHomo sapiens (human)
cell population proliferationTyrosinaseHomo sapiens (human)
response to UVTyrosinaseHomo sapiens (human)
response to blue lightTyrosinaseHomo sapiens (human)
response to vitamin DTyrosinaseHomo sapiens (human)
melanin biosynthetic processTyrosinaseHomo sapiens (human)
thymus developmentTyrosinaseHomo sapiens (human)
response to cAMPTyrosinaseHomo sapiens (human)
pigmentationTyrosinaseHomo sapiens (human)
proline catabolic processD-amino-acid oxidaseHomo sapiens (human)
digestionD-amino-acid oxidaseHomo sapiens (human)
D-amino acid catabolic processD-amino-acid oxidaseHomo sapiens (human)
D-serine catabolic processD-amino-acid oxidaseHomo sapiens (human)
dopamine biosynthetic processD-amino-acid oxidaseHomo sapiens (human)
D-alanine catabolic processD-amino-acid oxidaseHomo sapiens (human)
D-serine metabolic processD-amino-acid oxidaseHomo sapiens (human)
neutrophil-mediated killing of gram-negative bacteriumD-amino-acid oxidaseHomo sapiens (human)
retinoid metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
epithelial cell maturationAldo-keto reductase family 1 member B1Homo sapiens (human)
renal water homeostasisAldo-keto reductase family 1 member B1Homo sapiens (human)
carbohydrate metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
prostaglandin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
C21-steroid hormone biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
L-ascorbic acid biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
regulation of urine volumeAldo-keto reductase family 1 member B1Homo sapiens (human)
retinol metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
negative regulation of apoptotic processAldo-keto reductase family 1 member B1Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
fructose biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
cellular hyperosmotic salinity responseAldo-keto reductase family 1 member B1Homo sapiens (human)
metanephric collecting duct developmentAldo-keto reductase family 1 member B1Homo sapiens (human)
allantoin metabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of protein phosphorylationXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of endothelial cell proliferationXanthine dehydrogenase/oxidaseHomo sapiens (human)
guanine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
inosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyinosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
adenosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyadenosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyguanosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
AMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
IMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
lactationXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
xanthine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of gene expressionXanthine dehydrogenase/oxidaseHomo sapiens (human)
iron-sulfur cluster assemblyXanthine dehydrogenase/oxidaseHomo sapiens (human)
amide catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of endothelial cell differentiationXanthine dehydrogenase/oxidaseHomo sapiens (human)
GMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
dGMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
dAMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionXanthine dehydrogenase/oxidaseHomo sapiens (human)
positive regulation of p38MAPK cascadeXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of vascular endothelial growth factor signaling pathwayXanthine dehydrogenase/oxidaseHomo sapiens (human)
positive regulation of reactive oxygen species metabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of vasculogenesisXanthine dehydrogenase/oxidaseHomo sapiens (human)
glucose metabolic processSorbitol dehydrogenaseHomo sapiens (human)
sorbitol catabolic processSorbitol dehydrogenaseHomo sapiens (human)
glucuronate catabolic process to xylulose 5-phosphateSorbitol dehydrogenaseHomo sapiens (human)
flagellated sperm motilitySorbitol dehydrogenaseHomo sapiens (human)
fructose biosynthetic processSorbitol dehydrogenaseHomo sapiens (human)
L-xylitol catabolic processSorbitol dehydrogenaseHomo sapiens (human)
L-xylitol metabolic processSorbitol dehydrogenaseHomo sapiens (human)
response to hypoxiaCarbonic anhydrase 9Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 9Homo sapiens (human)
response to xenobiotic stimulusCarbonic anhydrase 9Homo sapiens (human)
response to testosteroneCarbonic anhydrase 9Homo sapiens (human)
secretionCarbonic anhydrase 9Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 9Homo sapiens (human)
inseminationD-aspartate oxidaseHomo sapiens (human)
grooming behaviorD-aspartate oxidaseHomo sapiens (human)
regulation of cell communicationD-aspartate oxidaseHomo sapiens (human)
D-amino acid catabolic processD-aspartate oxidaseHomo sapiens (human)
hormone metabolic processD-aspartate oxidaseHomo sapiens (human)
nervous system processD-aspartate oxidaseHomo sapiens (human)
aspartate catabolic processD-aspartate oxidaseHomo sapiens (human)
L-serine metabolic processSerine racemaseHomo sapiens (human)
serine family amino acid metabolic processSerine racemaseHomo sapiens (human)
response to xenobiotic stimulusSerine racemaseHomo sapiens (human)
response to organic cyclic compoundSerine racemaseHomo sapiens (human)
response to lipopolysaccharideSerine racemaseHomo sapiens (human)
pyruvate biosynthetic processSerine racemaseHomo sapiens (human)
D-serine metabolic processSerine racemaseHomo sapiens (human)
D-serine biosynthetic processSerine racemaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (49)

Processvia Protein(s)Taxonomy
zinc ion bindingCarbonic anhydrase 12Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 12Homo sapiens (human)
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
tyrosinase activityTyrosinaseHomo sapiens (human)
copper ion bindingTyrosinaseHomo sapiens (human)
protein bindingTyrosinaseHomo sapiens (human)
identical protein bindingTyrosinaseHomo sapiens (human)
protein homodimerization activityTyrosinaseHomo sapiens (human)
D-amino-acid oxidase activityD-amino-acid oxidaseHomo sapiens (human)
protein bindingD-amino-acid oxidaseHomo sapiens (human)
identical protein bindingD-amino-acid oxidaseHomo sapiens (human)
FAD bindingD-amino-acid oxidaseHomo sapiens (human)
retinal dehydrogenase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member B1Homo sapiens (human)
protein bindingAldo-keto reductase family 1 member B1Homo sapiens (human)
electron transfer activityAldo-keto reductase family 1 member B1Homo sapiens (human)
prostaglandin H2 endoperoxidase reductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
glyceraldehyde oxidoreductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
allyl-alcohol dehydrogenase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
L-glucuronate reductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
glycerol dehydrogenase [NADP+] activityAldo-keto reductase family 1 member B1Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member B1Homo sapiens (human)
xanthine dehydrogenase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
xanthine oxidase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
iron ion bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
protein bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
protein homodimerization activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
molybdopterin cofactor bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
flavin adenine dinucleotide bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
2 iron, 2 sulfur cluster bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine dehydrogenase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine oxidase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
FAD bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
(R,R)-butanediol dehydrogenase activitySorbitol dehydrogenaseHomo sapiens (human)
L-iditol 2-dehydrogenase activitySorbitol dehydrogenaseHomo sapiens (human)
zinc ion bindingSorbitol dehydrogenaseHomo sapiens (human)
carbohydrate bindingSorbitol dehydrogenaseHomo sapiens (human)
identical protein bindingSorbitol dehydrogenaseHomo sapiens (human)
D-xylulose reductase activitySorbitol dehydrogenaseHomo sapiens (human)
D-sorbitol dehydrogenase (acceptor) activitySorbitol dehydrogenaseHomo sapiens (human)
ribitol 2-dehydrogenase activitySorbitol dehydrogenaseHomo sapiens (human)
NAD bindingSorbitol dehydrogenaseHomo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 9Homo sapiens (human)
protein bindingCarbonic anhydrase 9Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 9Homo sapiens (human)
molecular function activator activityCarbonic anhydrase 9Homo sapiens (human)
protein bindingD-aspartate oxidaseHomo sapiens (human)
D-aspartate oxidase activityD-aspartate oxidaseHomo sapiens (human)
D-glutamate oxidase activityD-aspartate oxidaseHomo sapiens (human)
FAD bindingD-aspartate oxidaseHomo sapiens (human)
magnesium ion bindingSerine racemaseHomo sapiens (human)
L-serine ammonia-lyase activitySerine racemaseHomo sapiens (human)
calcium ion bindingSerine racemaseHomo sapiens (human)
protein bindingSerine racemaseHomo sapiens (human)
ATP bindingSerine racemaseHomo sapiens (human)
D-serine ammonia-lyase activitySerine racemaseHomo sapiens (human)
glycine bindingSerine racemaseHomo sapiens (human)
threonine racemase activitySerine racemaseHomo sapiens (human)
PDZ domain bindingSerine racemaseHomo sapiens (human)
pyridoxal phosphate bindingSerine racemaseHomo sapiens (human)
serine racemase activitySerine racemaseHomo sapiens (human)
identical protein bindingSerine racemaseHomo sapiens (human)
protein homodimerization activitySerine racemaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (29)

Processvia Protein(s)Taxonomy
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
membraneCarbonic anhydrase 12Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 12Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 12Homo sapiens (human)
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
cytoplasmTyrosinaseHomo sapiens (human)
lysosomeTyrosinaseHomo sapiens (human)
Golgi-associated vesicleTyrosinaseHomo sapiens (human)
melanosome membraneTyrosinaseHomo sapiens (human)
melanosomeTyrosinaseHomo sapiens (human)
intracellular membrane-bounded organelleTyrosinaseHomo sapiens (human)
perinuclear region of cytoplasmTyrosinaseHomo sapiens (human)
mitochondrial outer membraneD-amino-acid oxidaseHomo sapiens (human)
extracellular regionD-amino-acid oxidaseHomo sapiens (human)
cytoplasmD-amino-acid oxidaseHomo sapiens (human)
peroxisomal matrixD-amino-acid oxidaseHomo sapiens (human)
cytosolD-amino-acid oxidaseHomo sapiens (human)
cell projectionD-amino-acid oxidaseHomo sapiens (human)
presynaptic active zoneD-amino-acid oxidaseHomo sapiens (human)
cytoplasmD-amino-acid oxidaseHomo sapiens (human)
extracellular spaceAldo-keto reductase family 1 member B1Homo sapiens (human)
nucleoplasmAldo-keto reductase family 1 member B1Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B1Homo sapiens (human)
extracellular exosomeAldo-keto reductase family 1 member B1Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B1Homo sapiens (human)
cytosolXanthine dehydrogenase/oxidaseHomo sapiens (human)
extracellular spaceXanthine dehydrogenase/oxidaseHomo sapiens (human)
peroxisomeXanthine dehydrogenase/oxidaseHomo sapiens (human)
cytosolXanthine dehydrogenase/oxidaseHomo sapiens (human)
sarcoplasmic reticulumXanthine dehydrogenase/oxidaseHomo sapiens (human)
extracellular spaceXanthine dehydrogenase/oxidaseHomo sapiens (human)
extracellular spaceSorbitol dehydrogenaseHomo sapiens (human)
cytosolSorbitol dehydrogenaseHomo sapiens (human)
membraneSorbitol dehydrogenaseHomo sapiens (human)
motile ciliumSorbitol dehydrogenaseHomo sapiens (human)
mitochondrial membraneSorbitol dehydrogenaseHomo sapiens (human)
extracellular exosomeSorbitol dehydrogenaseHomo sapiens (human)
nucleolusCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
membraneCarbonic anhydrase 9Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 9Homo sapiens (human)
microvillus membraneCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
peroxisomeD-aspartate oxidaseHomo sapiens (human)
peroxisomeD-aspartate oxidaseHomo sapiens (human)
peroxisomal matrixD-aspartate oxidaseHomo sapiens (human)
cytosolD-aspartate oxidaseHomo sapiens (human)
cytoplasmD-aspartate oxidaseHomo sapiens (human)
cytoplasmSerine racemaseHomo sapiens (human)
cytosolSerine racemaseHomo sapiens (human)
neuronal cell bodySerine racemaseHomo sapiens (human)
apical part of cellSerine racemaseHomo sapiens (human)
cytoplasmSerine racemaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (58)

Assay IDTitleYearJournalArticle
AID1163510Cytotoxicity against human PANC1 cells under nutrient-deprived condition after 24 hrs by WST8 dye based assay2014Bioorganic & medicinal chemistry letters, Oct-01, Volume: 24, Issue:19
Synthesis and biological evaluation of isoprenylated coumarins as potential anti-pancreatic cancer agents.
AID726205Inhibition of human recombinant DAO expressed in G418-resistant HEK293/NEO cells assessed as effect on D-alanine level at 83 uM incubated for 30 mins prior to D-alanine addition measured after 24 hrs by HPLC analysis relative to vehicle-treated control2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID726214Inhibition of human recombinant N-terminal His-tagged DAO Y224A mutant expressed in Escherichia coli BL21(DE3) using D-alanine as substrate after 10 mins by Lineweaver-Burk plot analysis2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID541494Inhibition of beta-glucosidase using salicin substrate2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Hydroxycoumarin derivatives: novel and potent α-glucosidase inhibitors.
AID315168Induction of apoptosis in human U937 cells at 250 uM after 24 hrs2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells.
AID593513Binding affinity to corpus collosum myelin in central nervous system of mouse at 100 uM after 20 mins by fluorescent microscopy2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Design, synthesis, and evaluation of coumarin-based molecular probes for imaging of myelination.
AID726222Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) using D-serine as substrate by colorimetric assay2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID1171397Drug metabolism in mouse liver microsomes assessed as glucuronidation of compound measured as compound remaining after 30 mins by LC/MS analysis2014ACS medicinal chemistry letters, Nov-13, Volume: 5, Issue:11
Structure-Metabolism Relationships in the Glucuronidation of d-Amino Acid Oxidase Inhibitors.
AID144377Ability to induce NAD(P)H quinone reductase activity in cultured Hepa 1c1c7 murine hepatoma cells.1998Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26
Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones, and related Michael reaction acceptors: correlation of potencies as phase 2 enzyme inducers and radical scavengers.
AID745618Binding affinity to human recombinant DAAO at 496 nm spectral modification by spectrophotometric analysis in presence of FAD2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Structural, kinetic, and pharmacodynamic mechanisms of D-amino acid oxidase inhibition by small molecules.
AID1105456Antifungal activity against Aspergillus flavus ATCC 16013 after 72 hr by broth microdilution method2013International journal of molecular sciences, Jan-10, Volume: 14, Issue:1
Synthesis, structure-activity relationships (SAR) and in silico studies of coumarin derivatives with antifungal activity.
AID726215Inhibition of human recombinant N-terminal His-tagged DAO Y224F mutant expressed in Escherichia coli BL21(DE3) using D-alanine as substrate after 10 mins by Lineweaver-Burk plot analysis2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID516863Inhibition kidney aldose reductase 2 by spectrophotometric analysis2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
6,7-Dihydroxy-4-phenylcoumarin as inhibitor of aldose reductase 2.
AID1105460Antifungal activity against Aspergillus fumigatus IPP 210 after 72 hr by broth microdilution method2013International journal of molecular sciences, Jan-10, Volume: 14, Issue:1
Synthesis, structure-activity relationships (SAR) and in silico studies of coumarin derivatives with antifungal activity.
AID745647Competitive inhibition of human recombinant DAAO by Michaelis-Menten plot analysis in presence of D-serine2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Structural, kinetic, and pharmacodynamic mechanisms of D-amino acid oxidase inhibition by small molecules.
AID1163511Cytotoxicity against human PANC1 cells under nutrient-rich condition after 24 hrs by WST8 dye based assay2014Bioorganic & medicinal chemistry letters, Oct-01, Volume: 24, Issue:19
Synthesis and biological evaluation of isoprenylated coumarins as potential anti-pancreatic cancer agents.
AID726223Inhibition of human recombinant N-terminal His-tagged DDO expressed in Escherichia coli BL21(DE3) using D-aspartate as substrate by colorimetric assay2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID1105457Antifungal activity against Aspergillus flavus LM 247 after 72 hr by broth microdilution method2013International journal of molecular sciences, Jan-10, Volume: 14, Issue:1
Synthesis, structure-activity relationships (SAR) and in silico studies of coumarin derivatives with antifungal activity.
AID493454Inhibition of human CA1 by CO2 hydration assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II.
AID294445Inhibition of xanthine oxidase2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Relationship between quantum-chemical descriptors of proton dissociation and experimental acidity constants of various hydroxylated coumarins. Identification of the biologically active species for xanthine oxidase inhibition.
AID1265003Antioxidant activity assessed as DPPH radical scavenging activity2015European journal of medicinal chemistry, Dec-01, Volume: 106Novel oxime-bearing coumarin derivatives act as potent Nrf2/ARE activators in vitro and in mouse model.
AID1105459Antifungal activity against Aspergillus fumigatus ATCC 46913 after 72 hr by broth microdilution method2013International journal of molecular sciences, Jan-10, Volume: 14, Issue:1
Synthesis, structure-activity relationships (SAR) and in silico studies of coumarin derivatives with antifungal activity.
AID726220Inhibition of human recombinant N-terminal His-tagged serine racemase expressed in Escherichia coli BL21(DE3) using L-serine as substrate after 10 mins by fluorescence assay2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID726206Effect on L-alanine level in G418-resistant HEK293 cells at 17 uM by HPLC analysis relative to vehicle-treated control2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID726207Effect on L-alanine level in G418-resistant HEK293/NEO cells at 17 uM by HPLC analysis relative to vehicle-treated control2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID745649Binding affinity to human recombinant DAAO by stopped flow spectrophotometric analysis in presence of FAD2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Structural, kinetic, and pharmacodynamic mechanisms of D-amino acid oxidase inhibition by small molecules.
AID493457Inhibition of human CA12 by CO2 hydration assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II.
AID516864Inhibition sorbitol dehydrogenase by spectrophotometric analysis2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
6,7-Dihydroxy-4-phenylcoumarin as inhibitor of aldose reductase 2.
AID726221Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) using D-alanine as substrate by colorimetric assay2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID726212Inhibition of N-terminal HA-tagged human recombinant DAO overexpressed in G418-resistant HEK293 cells assessed as increase in D-alanine levels at 83 uM incubated for 30 mins prior to D-alanine addition measured after 24 hrs by HPLC analysis relative to ve2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID315164Cytotoxicity against human U937 cells by trypan blue assay after 48 hrs2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells.
AID1717734Inhibition of human tyrosinase expressed in Escherichia coli2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Advances in the Design of Genuine Human Tyrosinase Inhibitors for Targeting Melanogenesis and Related Pigmentations.
AID726218Binding affinity to human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) at 40 uM after 2 to 30 mins by absorption spectra analysis2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID541341Inhibition of Aspergillus oryzae Beta-galactosidase2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Hydroxycoumarin derivatives: novel and potent α-glucosidase inhibitors.
AID1171400Drug metabolism in mouse liver microsomes assessed as glucuronidation of compound measured as compound remaining after 60 mins by LC/MS analysis2014ACS medicinal chemistry letters, Nov-13, Volume: 5, Issue:11
Structure-Metabolism Relationships in the Glucuronidation of d-Amino Acid Oxidase Inhibitors.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID493456Inhibition of human CA9 by CO2 hydration assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II.
AID493455Inhibition of human CA2 by CO2 hydration assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II.
AID745619Binding affinity to human recombinant DAAO at 443 nm spectral modification by spectrophotometric analysis in presence of FAD2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Structural, kinetic, and pharmacodynamic mechanisms of D-amino acid oxidase inhibition by small molecules.
AID541342Inhibition of Aspergillus oryzae Beta-galactosidase at 400 uM2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Hydroxycoumarin derivatives: novel and potent α-glucosidase inhibitors.
AID516862Inhibition human recombinant aldose reductase 1 by spectrophotometric analysis2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
6,7-Dihydroxy-4-phenylcoumarin as inhibitor of aldose reductase 2.
AID1105454Antifungal activity against Aspergillus flavus LM 26 after 72 hr by broth microdilution method2013International journal of molecular sciences, Jan-10, Volume: 14, Issue:1
Synthesis, structure-activity relationships (SAR) and in silico studies of coumarin derivatives with antifungal activity.
AID1105461Antifungal activity against Aspergillus fumigatus ATCC 16913 after 72 hr by broth microdilution method2013International journal of molecular sciences, Jan-10, Volume: 14, Issue:1
Synthesis, structure-activity relationships (SAR) and in silico studies of coumarin derivatives with antifungal activity.
AID726213Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) using D-serine as substrate by Lineweaver-Burk plot analysis2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID315165Growth inhibition of human U937 cells by [3H]thymidine incorporation assay2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells.
AID726211Effect on L-alanine level in G418-resistant HEK293/NEO cells at 83 uM by HPLC analysis relative to vehicle-treated control2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID745648Competitive inhibition of human recombinant DAAO after 1 hr by coupled enzyme assay in presence of D-serine2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Structural, kinetic, and pharmacodynamic mechanisms of D-amino acid oxidase inhibition by small molecules.
AID726216Competitive inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) using D-alanine as substrate by Lineweaver-Burk plot analysis2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID1105455Antifungal activity against Aspergillus flavus LM 210 after 72 hr by broth microdilution method2013International journal of molecular sciences, Jan-10, Volume: 14, Issue:1
Synthesis, structure-activity relationships (SAR) and in silico studies of coumarin derivatives with antifungal activity.
AID726210Effect on L-alanine level in G418-resistant HEK293 cells at 83 uM by HPLC analysis relative to vehicle-treated control2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID1105458Antifungal activity against Aspergillus fumigatus ATCC 40640 after 72 hr by broth microdilution method2013International journal of molecular sciences, Jan-10, Volume: 14, Issue:1
Synthesis, structure-activity relationships (SAR) and in silico studies of coumarin derivatives with antifungal activity.
AID516866Selectivity index, ratio of IC50 for human recombinant aldose reductase 1 to IC50 for kidney aldose reductase 22010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
6,7-Dihydroxy-4-phenylcoumarin as inhibitor of aldose reductase 2.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID516865Selectivity index, ratio of IC50 for sorbitol dehydrogenase to IC50 for kidney aldose reductase 22010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
6,7-Dihydroxy-4-phenylcoumarin as inhibitor of aldose reductase 2.
AID541338Inhibition of alpha-glucosidase using para-nitrophenyl substrate2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Hydroxycoumarin derivatives: novel and potent α-glucosidase inhibitors.
AID1265014Activation of Nrf2 in human HSC3-ARE9 cells assessed as increase of ARE-mediated luciferase expression at 50 uM after 24 hrs relative to control2015European journal of medicinal chemistry, Dec-01, Volume: 106Novel oxime-bearing coumarin derivatives act as potent Nrf2/ARE activators in vitro and in mouse model.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (5.00)18.2507
2000's2 (10.00)29.6817
2010's16 (80.00)24.3611
2020's1 (5.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.22

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 Index12.22 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index5.27 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.22)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (10.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other18 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]