COUMARIC ACID

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Synonyms
Molecule Category Free-form
UNII IBS9D1EU3J
Source Gaulton A, Kale N, van Westen GJ, Bellis LJ, Bento AP, Davies M, Hersey A, Papadatos G, Forster M, Wege P, Overington JP. A large-scale crop protection bioassay data set. Sci Data. 2015 Jul 7;2:150032. Read more ...

Structure

InChI Key NGSWKAQJJWESNS-ZZXKWVIFSA-N
Smiles OC(=O)\C=C\c1ccc(O)cc1
InChI
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H8O3
Molecular Weight 164.16
AlogP 1.69
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 57.53
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 12.0
Assay Description Organism Bioactivity Reference
Drug recovery in leaf of Lolium perenne (perennial ryegrass) at 50 ng/g by LC-MS analysis Lolium perenne 81.0 %
Drug recovery in leaf of Lolium perenne (perennial ryegrass) at 5 ng/g by LC-MS analysis Lolium perenne 79.0 %
Nematotoxic activity against freshly hatched Meloidogyne incognita J2 (root-knot nematode) isolated from tomato roots assessed as induction of nematode paralysis measured 24 hr after immersion in compound test solutions Meloidogyne incognita 840.0 ug.mL-1
Antifungal activity against Diplodia seriata BoF98-1 assessed as growth inhibition measured after 1 to 10 days Diplodia seriata 24.0 %
Antifungal activity against Diplodia seriata BoF99-1 assessed as growth inhibition measured after 1 to 10 days Diplodia seriata 24.0 %
Antifungal activity against Diplodia seriata LAT28 assessed as growth inhibition measured after 1 to 10 days Diplodia seriata 24.0 %
Antifungal activity against Lasiodiplodia theobromae CBS116460 assessed as growth inhibition measured after 1 to 10 days Lasiodiplodia theobromae 24.0 %
Antifungal activity against Diplodia seriata PLU03 assessed as growth inhibition measured after 1 to 10 days Diplodia seriata 24.0 %
Antifungal activity against Diplodia mutila BRA08 assessed as growth inhibition measured after 1 to 10 days Diplodia mutila 24.0 %
Antifungal activity against Neofusicoccum luteum CBS110299 assessed as growth inhibition measured after 1 to 10 days Neofusicoccum luteum 14.0 %
Antifungal activity against Neofusicoccum parvum PER20 assessed as growth inhibition measured after 1 to 10 days Neofusicoccum parvum 14.0 %
Antifungal activity against Neofusicoccum parvum Bp0014 assessed as growth inhibition measured after 1 to 10 days Neofusicoccum parvum 14.0 %
Antifungal activity against Botryosphaeria dothidea OGE14 assessed as growth inhibition measured after 1 to 10 days relative to control Botryosphaeria dothidea 14.0 %
Antifungal activity against Togninia minima SO21 assessed as susceptibility at 500 uM measured after 1 to 10 days Togninia minima None
Increase in quinate content in Pisum sativum (pea) leaves at 1 mM added to nutrient medium measured 5 to 15 days post onset of compound treatment by ion chromatography Pisum sativum None
Induction of ADH protein enzyme expression in Pisum sativum (pea) roots at 1 mM added to nutrient medium measured 5 to 15 days post onset of compound treatment by immunoblot Pisum sativum None
Induction of PDC protein expression in Pisum sativum (pea) roots at 1 mM added to nutrient medium measured 5 to 15 days post onset of compound treatment by immunoblot Pisum sativum None
Increase in starch content in Pisum sativum (pea) leaves at 1 mM added to nutrient medium measured 5 to 15 days post onset of compound treatment by capillary electrophoresis method Pisum sativum None
Increase in soluble sugars content in Pisum sativum (pea) leaves at 1 mM added to nutrient medium measured 5 to 15 days post onset of compound treatment by capillary electrophoresis method Pisum sativum None
Effect on starch content in Pisum sativum (pea) roots at 1 mM added to nutrient medium measured 5 to 15 days post onset of compound treatment by capillary electrophoresis method Pisum sativum None
Effect on sucrose content in Pisum sativum (pea) roots at 1 mM added to nutrient medium measured 5 to 15 days post onset of compound treatment by capillary electrophoresis method Pisum sativum None
Growth inhibition in Pisum sativum (pea) assessed as shoot growth arrest at 1 mM added to nutrient medium measured within 10 days post onset of compound treatment Pisum sativum None
Growth inhibition in Pisum sativum (pea) assessed as root elongation arrest at 1 mM added to nutrient medium measured within 1 day post onset of compound treatment Pisum sativum None
Drug level in Pisum sativum (pea) leaves at 1 mM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method Pisum sativum None
Drug level in Pisum sativum (pea) roots at 1 mM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method Pisum sativum None
Inhibition of yeast alpha-glucosidase using p-nitrophenyl-alpha-D-glucopyranoside as substrate preincubated at 300 uM for 10 min before substrate addition and measured after 10 min by spectrophotometry Saccharomyces cerevisiae 4.9 %
Inhibition of yeast alpha-glucosidase using p-nitrophenyl-alpha-D-glucopyranoside as substrate preincubated for 10 min before substrate addition and measured after 10 min by spectrophotometry Saccharomyces cerevisiae 300000.0 nM
Antioxidant activity assessed as DPPH scavenging activity after 30 min by UV-vis spectroscopy None 200000.0 nM
Inhibition of baker's yeast alpha-glucosidase using p-nitrophenyl-alpha-D-glucopyranoside as substrate by spectrophotometry Saccharomyces cerevisiae 2.3
Herbicidal activity against Raphanus sativus var.Japanese White (radish) assessed as inhibition of seed germination at 200 ppm at 25 degC measured after 5 days Raphanus sativus 100.0 %
Herbicidal activity against Raphanus sativus var.Japanese White (radish) assessed as inhibition of seed germination at 100 ppm at 25 degC measured after 5 days Raphanus sativus 73.33 %
Herbicidal activity against Raphanus sativus var.Japanese White (radish) assessed as inhibition of seed germination at 50 ppm at 25 degC measured after 5 days Raphanus sativus 53.33 %
Antifungal activity against Verticillium dahliae assessed as inhibition of mycelial radial growth measured after 350 hr Verticillium dahliae 1470.0 ug.mL-1
Inhibition of aldose reductase (unknown origin) Homo sapiens 140.0 nM
Antimicrobial activity against Athelia rolfsii assessed as growth inhibition at 100 ppm by agar dilution method Athelia rolfsii 46.0 %
Antimicrobial activity against Pythium sp. assessed as growth inhibition at 100 ppm by agar dilution method Pythium 10.0 %
Antibacterial activity against Ralstonia solanacearum grown on potato semi-synthetic agar medium at 5 umol/disk by paper disk method Ralstonia solanacearum 11.0 mm
Antibacterial activity against Ralstonia solanacearum grown on potato semi-synthetic agar medium at 0.5 umol/disk by paper disk method Ralstonia solanacearum None
Decrease in Botryosphaeria dothidea ligninolytic enzyme production assessed as pectinase activity using pectin as substrate at 1 mM measured at 28 degC after 4 days Botryosphaeria dothidea None
Decrease in Neofusicoccum ribis ligninolytic enzyme production assessed as pectinase activity using pectin as substrate measured at 28 degC after 4 days Neofusicoccum ribis None
Decrease in Lasiodiplodia theobromae ligninolytic enzyme production assessed as pectinase activity using pectin as substrate at 25 mM measured at 28 degC after 4 days Lasiodiplodia theobromae 57.0 %
Decrease in Botryosphaeria dothidea ligninolytic enzyme production assessed as laccase activity using ABTS as substrate measured at 28 degC after 4 days Botryosphaeria dothidea None
Decrease in Lasiodiplodia theobromae ligninolytic enzyme production assessed as laccase activity using ABTS as substrate at 1 mM measured at 28 degC after 4 days Lasiodiplodia theobromae 71.0 %
Decrease in Neofusicoccum ribis ligninolytic enzyme production assessed as laccase activity using ABTS as substrate at 1 mM measured at 28 degC after 4 days Neofusicoccum ribis 71.0 %
Decrease in Diplodia seriata (Schwein.) Shoemaker ligninolytic enzyme production assessed as laccase activity using ABTS as substrate at 1 mM measured at 28 degC after 4 days Diplodia seriata 71.0 %
Decrease in Botryosphaeria dothidea ligninolytic enzyme production assessed as laccase activity using ABTS as substrate at 1 mM measured at 28 degC after 4 days Botryosphaeria dothidea 71.0 %
Decrease in Lasiodiplodia theobromae mycelium biomass production measured at 28 degC after 4 days by gravimetric analysis Lasiodiplodia theobromae 58.0 %
Decrease in Diplodia seriata (Schwein.) Shoemaker mycelium biomass production measured at 28 degC after 4 days by gravimetric analysis Diplodia seriata 58.0 %
Inhibition of Diplodia seriata (Schwein.) Shoemaker mycelium growth at 10 mM measured at 28 degC after 4 days Diplodia seriata None
Inhibition of Botryosphaeria dothidea mycelium growth at 10 mM measured at 28 degC after 4 days Botryosphaeria dothidea None
Inhibition of Neofusicoccum ribis mycelium growth at 25 mM measured at 28 degC after 4 days Neofusicoccum ribis 81.0 %
Inhibition of Lasiodiplodia theobromae mycelium growth at 25 mM measured at 28 degC after 4 days Lasiodiplodia theobromae 100.0 %
Inhibition of Lasiodiplodia theobromae mycelium growth measured at 28 degC after 4 days Lasiodiplodia theobromae 5000000.0 nM
Inhibition of Neofusicoccum ribis mycelium growth measured at 28 degC after 4 days Neofusicoccum ribis 5000000.0 nM
Inhibition of Diplodia seriata (Schwein.) Shoemaker mycelium growth measured at 28 degC after 4 days Diplodia seriata 5000000.0 nM
Inhibition of Botryosphaeria dothidea mycelium growth measured at 28 degC after 4 days Botryosphaeria dothidea 5000000.0 nM
Inhibition of autoxidation of pure triacylglycerols of sunflower oil at 1 mM by iodometric analysis None None
Antioxidant activity assessed as DPPH radical scavenging activity at 3.6 mM after 20 min None 6.1 %
Antioxidant activity assessed as DPPH radical scavenging activity at 3.6 mM after 10 min None 4.5 %
Antioxidant activity assessed as DPPH radical scavenging activity at 1.8 mM after 20 min None 4.7 %
Antioxidant activity assessed as DPPH radical scavenging activity at 0.9 mM after 20 min None 2.9 %
Antioxidant activity assessed as DPPH radical scavenging activity at 1.8 mM after 10 min None 3.7 %
Antioxidant activity assessed as DPPH radical scavenging activity at 0.9 mM after 10 min None 2.1 %
Inhibition of monophenolase activity of mushroom tyrosinase using L-tyrosine as substrate after 30 min by dopachrome method Agaricus bisporus None

Cross References

Resources Reference
ChEMBL CHEMBL66879
FDA SRS IBS9D1EU3J
PDB HC4
PubChem 637542
SureChEMBL SCHEMBL39106
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