EUGENOL

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Synonyms
UNII 3T8H1794QW
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 RRAFCDWBNXTKKO-UHFFFAOYSA-N
Smiles COc1cc(CC=C)ccc1O
InChI
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H12O2
Molecular Weight 164.2
AlogP 2.58
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 29.46
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 12.0
Assay Description Organism Bioactivity Reference
Nematicidal activity against Meloidogyne incognita J2 (root-knot nematode) larvae immersed in compound solution for 24 hr assessed as reduction in larval motility Meloidogyne incognita 256.0 ug.mL-1
Nematicidal activity against Meloidogyne incognita J2 (root-knot nematode) larvae immersed in compound solution for 48 hr assessed as reduction in larval motility Meloidogyne incognita 192.0 ug.mL-1
Nematicidal activity against Meloidogyne incognita J2 (root-knot nematode) larvae immersed in compound solution for 96 hr assessed as reduction in larval motility Meloidogyne incognita 133.0 ug.mL-1
Selectivity index, ratio of LC50 for human U937 cells to EC50 for axenic amastigote stage of Leishmania panamensis MHOM/CO/87/UA140epir GFP None 0.7
Leishmanicidal activity against axenic amastigote stage of Leishmania panamensis MHOM/CO/87/UA140epir GFP assessed as parasite viability after 72 hr by MTT assay Leishmania panamensis 21.4 ug.mL-1
Cytotoxicity against Homo sapiens (human) U937 cells assessed as cell viability after 72 hr by MTT assay Homo sapiens 14.2 ug.mL-1
Fungicidal activity against Blumeria graminis infected barley assessed as reduction in powdery mildew disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Blumeria graminis 0.0 %
Fungicidal activity against Blumeria graminis infected barley assessed as reduction in powdery mildew disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Blumeria graminis 5.0 %
Fungicidal activity against Puccinia recondita infected wheat assessed as reduction in wheat leaf rust disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Puccinia recondita 0.0 %
Fungicidal activity against Puccinia recondita infected wheat assessed as reduction in wheat leaf rust disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Puccinia recondita 0.0 %
Fungicidal activity against Phytophthora infestans infected tomato assessed as reduction in tomato late blight disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Phytophthora infestans 0.0 %
Fungicidal activity against Phytophthora infestans infected tomato assessed as reduction in tomato late blight disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Phytophthora infestans 0.0 %
Fungicidal activity against Botryotinia fuckeliana infected cucumber assessed as reduction in cucumber gray mold disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Botryotinia fuckeliana 0.0 %
Fungicidal activity against Botryotinia fuckeliana infected cucumber assessed as reduction in cucumber gray mold disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Botryotinia fuckeliana 0.0 %
Fungicidal activity against Rhizoctonia solani infected rice assessed as reduction in rice sheath blight disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Rhizoctonia solani 0.0 %
Fungicidal activity against Rhizoctonia solani infected rice assessed as reduction in rice sheath blight disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Rhizoctonia solani 0.0 %
Fungicidal activity against Magnaporthe grisea infected rice assessed as reduction in rice blast disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Magnaporthe grisea 0.0 %
Fungicidal activity against Magnaporthe grisea infected rice assessed as reduction in rice blast disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Magnaporthe grisea 0.0 %
Antifungal activity against Aspergillus niger at 1% Aspergillus niger 100.0 %
Antifungal activity against Aspergillus flavus at 1% Aspergillus flavus 100.0 %
Antifungal activity against Fusarium verticillioides at 0.25% Fusarium verticillioides 100.0 %
Antifungal activity against Nigrospora sp. at 0.25% Nigrospora 50.04 %
Antifungal activity against Curvularia sp. at 0.25% Curvularia 50.04 %
Antifungal activity against Rhizoctonia solani at 0.25% Rhizoctonia solani 100.0 %
Antifungal activity against Alternaria solani at 1% Alternaria solani 100.0 %
Antifungal activity against Bipolaris oryzae at 0.25% Bipolaris oryzae 86.98 %
Antifungal activity against Aspergillus niger at 0.25% Aspergillus niger 70.58 %
Antifungal activity against Aspergillus flavus at 0.25% Aspergillus flavus 44.22 %
Antifungal activity against Alternaria solani at 0.25% Alternaria solani 100.0 %
Antifungal activity against Rhizoctonia solani assessed as inhibition of spore germination at 1% after 24 hr by compound microscopy Rhizoctonia solani 100.0 %
Antifungal activity against Curvularia sp. assessed as inhibition of spore germination at 1% after 24 hr by compound microscopy Curvularia 100.0 %
Antifungal activity against Fusarium verticillioides assessed as inhibition of spore germination at 1% after 24 hr by compound microscopy Fusarium verticillioides 100.0 %
Antifungal activity against Aspergillus niger assessed as inhibition of spore germination at 1% after 24 hr by compound microscopy Aspergillus niger 100.0 %
Antifungal activity against Aspergillus flavus assessed as inhibition of spore germination at 1% after 24 hr by compound microscopy Aspergillus flavus 100.0 %
Antifungal activity against Alternaria solani assessed as inhibition of spore germination at 1% after 24 hr by compound microscopy Alternaria solani 100.0 %
Antifungal activity against Rhizoctonia solani assessed as inhibition of spore germination at 0.5% after 24 hr by compound microscopy Rhizoctonia solani 100.0 %
Antifungal activity against Curvularia sp. assessed as inhibition of spore germination at 0.5% after 24 hr by compound microscopy Curvularia 100.0 %
Antifungal activity against Fusarium verticillioides assessed as inhibition of spore germination at 0.5% after 24 hr by compound microscopy Fusarium verticillioides 100.0 %
Antifungal activity against Aspergillus niger assessed as inhibition of spore germination at 0.5% after 24 hr by compound microscopy Aspergillus niger 100.0 %
Antifungal activity against Aspergillus flavus assessed as inhibition of spore germination at 0.5% after 24 hr by compound microscopy Aspergillus flavus 100.0 %
Antifungal activity against Alternaria solani assessed as inhibition of spore germination at 0.5% after 24 hr by compound microscopy Alternaria solani 65.68 %
Antifungal activity against Rhizoctonia solani assessed as inhibition of spore germination at 0.25% after 24 hr by compound microscopy Rhizoctonia solani 100.0 %
Antifungal activity against Curvularia sp. assessed as inhibition of spore germination at 0.25% after 24 hr by compound microscopy Curvularia 85.39 %
Antifungal activity against Fusarium verticillioides assessed as inhibition of spore germination at 0.25% after 24 hr by compound microscopy Fusarium verticillioides 74.11 %
Antifungal activity against Aspergillus niger assessed as inhibition of spore germination at 0.25% after 24 hr by compound microscopy Aspergillus niger 65.6 %
Antifungal activity against Aspergillus flavus assessed as inhibition of spore germination at 0.25% after 24 hr by compound microscopy Aspergillus flavus 65.6 %
Antifungal activity against Alternaria solani assessed as inhibition of spore germination at 0.25% after 24 hr by compound microscopy Alternaria solani 24.16 %
Antifungal activity against Rhizoctonia solani assessed as inhibition of spore germination at 0.10% after 24 hr by compound microscopy Rhizoctonia solani 93.53 %
Antifungal activity against Curvularia sp. assessed as inhibition of spore germination at 0.10% after 24 hr by compound microscopy Curvularia 44.94 %
Antifungal activity against Fusarium verticillioides assessed as inhibition of spore germination at 0.10% after 24 hr by compound microscopy Fusarium verticillioides 21.88 %
Antifungal activity against Aspergillus niger assessed as inhibition of spore germination at 0.10% after 24 hr by compound microscopy Aspergillus niger 37.59 %
Antifungal activity against Aspergillus flavus assessed as inhibition of spore germination at 0.10% after 24 hr by compound microscopy Aspergillus flavus 54.0 %
Antifungal activity against Alternaria solani assessed as inhibition of spore germination at 0.10% after 24 hr by compound microscopy Alternaria solani 14.41 %
Antifungal activity against Rhizoctonia solani at 1% Rhizoctonia solani 100.0 %
Antifungal activity against Colletotrichum sp. at 1% Colletotrichum 100.0 %
Antifungal activity against Fusarium verticillioides at 1% Fusarium verticillioides 100.0 %
Antifungal activity against Nigrospora sp. at 1% Nigrospora 98.23 %
Antifungal activity against Bipolaris oryzae at 1% Bipolaris oryzae 100.0 %
Antifungal activity against Curvularia sp. at 1% Curvularia 97.04 %
Antipyretic activity against yeast-induced hyperthermia in Rattus norvegicus (rat) assessed as change in body temperature at 1.5 mmol/kg after 6 hr Rattus norvegicus -1.21 degrees C
Antipyretic activity against yeast-induced hyperthermia in Rattus norvegicus (rat) assessed as change in body temperature at 1.5 mmol/kg after 2 hr Rattus norvegicus -0.94 degrees C
Antipyretic activity against yeast-induced hyperthermia in Rattus norvegicus (rat) assessed as change in body temperature at 1.5 mmol/kg after 4 hr Rattus norvegicus -1.11 degrees C
Analgesic activity in Mus musculus (mouse) assessed as pain threshold at 1.1 mmol/kg, ig after 120 min by hot plate test (Rvb = 19.06 +/- 4.55 sec) Mus musculus 24.86 s
Analgesic activity in Mus musculus (mouse) assessed as pain threshold at 1.1 mmol/kg, ig after 180 min by hot plate test (Rvb = 17.67 +/- 5.78 sec) Mus musculus 25.5 s
Analgesic activity in Mus musculus (mouse) assessed as pain threshold at 1.1 mmol/kg, ig after 60 min by hot plate test (Rvb = 21.28 +/- 3 sec) Mus musculus 28.01 s
Analgesic activity in Mus musculus (mouse) assessed as pain threshold at 1.1 mmol/kg, ig after 30 min by hot plate test (Rvb = 24.88 +/- 5.28 sec) Mus musculus 30.76 s
Toxicity in ig dosed Mus musculus (mouse) Mus musculus 3.0 g/Kg
Anti-inflammatory activity against xylene-induced ear swelling Mus musculus (mouse) model as suppression of ear swelling at 1.11 mmol/kg, ig measured 1 hr after xylene challenge Mus musculus 32.93 %
Insecticidal activity against Mechoris ursulus assessed as mortality at 1 mg/paper at 25 +/- 1 degC measured after 48 hr by filter paper diffusion method Mechoris ursulus 66.7 %
Insecticidal activity against Mechoris ursulus assessed as mortality at 2.5 mg/paper at 25 +/- 1 degC measured after 48 hr by filter paper diffusion method Mechoris ursulus 90.0 %
Insecticidal activity against Mechoris ursulus assessed as mortality at 5 mg/paper at 25 +/- 1 degC measured after 48 hr by filter paper diffusion method Mechoris ursulus 100.0 %
Acaricidal activity against Dermatophagoides pteronyssinus assessed as mortality at 25.5 ug/cm2 applied as fumes in open container after 24 hr by fabric disk assay relative to untreated control Dermatophagoides pteronyssinus 21.0 %
Acaricidal activity against Dermatophagoides pteronyssinus assessed as mortality at 25.5 ug/cm2 applied as fumes in closed container after 24 hr by fabric disk assay relative to untreated control Dermatophagoides pteronyssinus 100.0 %
Acaricidal activity against Dermatophagoides farinae assessed as mortality at 25.5 ug/cm2 applied as fumes in open container after 24 hr by fabric disk assay relative to untreated control Dermatophagoides farinae 11.0 %
Acaricidal activity against Dermatophagoides farinae assessed as mortality at 25.5 ug/cm2 applied as fumes in closed container after 24 hr by fabric disk assay relative to untreated control Dermatophagoides farinae 100.0 %
Acaricidal activity against Dermatophagoides pteronyssinus assessed as mortality at 6.4 to 8 ug/cm2 after 24 to 72 hr by fabric disk assay relative to untreated control Dermatophagoides pteronyssinus None
Acaricidal activity against Dermatophagoides farinae assessed as mortality at 6.4 ug/cm2 after 72 hr by fabric disk assay relative to untreated control Dermatophagoides farinae 50.0 %
Acaricidal activity against Dermatophagoides farinae assessed as mortality at 6.4 ug/cm2 after 48 hr by fabric disk assay relative to untreated control Dermatophagoides farinae 50.0 %
Acaricidal activity against Dermatophagoides farinae assessed as mortality at 8 ug/cm2 after 48 hr by fabric disk assay relative to untreated control Dermatophagoides farinae 85.0 %
Acaricidal activity against Dermatophagoides farinae assessed as mortality at 6.4 ug/cm2 after 24 hr by fabric disk assay relative to untreated control Dermatophagoides farinae 50.0 %
Acaricidal activity against Dermatophagoides farinae assessed as mortality at 8 ug/cm2 after 24 hr by fabric disk assay relative to untreated control Dermatophagoides farinae 85.0 %
Ratio of benzyl benzoate LD50 to compound LD50 for Dermatophagoides pteronyssinus Dermatophagoides pteronyssinus 1.8
Acaricidal activity against Dermatophagoides pteronyssinus after 24 hr by fabric disk assay Dermatophagoides pteronyssinus 3.71 microg/cm2
Ratio of benzyl benzoate LD50 to compound LD50 for Dermatophagoides farinae Dermatophagoides farinae 1.7
Acaricidal activity against Dermatophagoides farinae after 24 hr by fabric disk assay Dermatophagoides farinae 5.47 microg/cm2
Acaricidal activity against Dermatophagoides farinae assessed as mortality at 8 ug/cm2 after 72 hr by fabric disk assay relative to untreated control Dermatophagoides farinae 85.0 %
Toxicity against third-instar larval stage of Trichoplusia ni (cabbage looper) assessed as mortality at 0.25% after 24 hr by contact toxicity bioassay Trichoplusia ni 30.0 %
Oviposition deterrent activity against adult female Trichoplusia ni (cabbage looper) moths introduced along with male moths into oviposition cage containing compound pretreated cabbage leaves assessed as eggs laying on the leaf disks at 0.25% after 48 hr Trichoplusia ni None
Feeding deterrent activity against freshly molted third-instar larval stage of Trichoplusia ni (cabbage looper) in compound pretreated cabbage leaves after 3 to 5 hr by leaf disk choice bioassay Trichoplusia ni 56.0 microg/cm2
Feeding deterrent activity against freshly molted third-instar larval stage of Trichoplusia ni (cabbage looper) in compound pretreated cabbage leaves at 50 ug/cm2 after 3 to 5 hr by leaf disk choice bioassay Trichoplusia ni 44.0 %
Toxicity to Musca domestica (house fly) applied to pronotum assessed as compound level per fly causing insect mortality measured after 24 hr Musca domestica 46.4 ug
Displacement of [3H]TBOB binding to GABA receptor in Musca domestica (house fly) heads homogenates assessed as [3H]TBOB binding at 500 uM incubated for 90 min by scintillation counting method Musca domestica 88.0 %
Antimicrobial activity against Corticium sp. assessed as inhibition of mycelial growth on potato dextrose agar at 1000 ppm at 27 degC measured after 4 days Corticium 100.0 %
Antimicrobial activity against Corticium sp. assessed as inhibition of mycelial growth on potato dextrose agar at 100 ppm at 27 degC measured after 4 days Corticium 67.6 %
Antimicrobial activity against Pythium sp. assessed as inhibition of mycelial growth on potato dextrose agar at 1000 ppm at 27 degC measured after 4 days Pythium 100.0 %
Antimicrobial activity against Pythium sp. assessed as inhibition of mycelial growth on potato dextrose agar at 100 ppm at 27 degC measured after 4 days Pythium 92.7 %
Insecticidal activity against abamectin-resistant female Tetranychus urticae ART-53 (two-spotted spider mite) in kidney bean assessed as mortality in 3 cm disks measured after 24 hr exposure by vapour-phase mortality bioassay Tetranychus urticae 27.8 microg/cm3
Insecticidal activity against pyridaben-resistant female Tetranychus urticae PRT-53 (two-spotted spider mite) in kidney bean assessed as mortality in 3 cm disks measured after 24 hr exposure by vapour-phase mortality bioassay Tetranychus urticae 31.7 microg/cm3
Insecticidal activity against fenpropathrin-resistant female Tetranychus urticae FRT-53 (two-spotted spider mite) in kidney bean assessed as mortality in 3 cm disks measured after 24 hr exposure by vapour-phase mortality bioassay Tetranychus urticae 28.6 microg/cm3
Insecticidal activity against chlorfenapyr-resistant female Tetranychus urticae CRT-53 (two-spotted spider mite) in kidney bean assessed as mortality in 3 cm disks measured after 24 hr exposure by vapour-phase mortality bioassay Tetranychus urticae 25.9 microg/cm3
Insecticidal activity against acaricide-susceptible female Tetranychus urticae KST (two-spotted spider mite) in kidney bean assessed as mortality in 3 cm disks measured after 24 hr exposure by vapour-phase mortality bioassay Tetranychus urticae 24.6 microg/cm3
Fungicidal activity against Athelia rolfsii assessed as growth inhibition at 100 ppm after 5 days by agar dilution test Athelia rolfsii 67.6 %
Fungicidal activity against Athelia rolfsii assessed as growth inhibition at 10 ppm after 5 days by agar dilution test Athelia rolfsii 5.9 %
Fungicidal activity against Pythium sp. assessed as growth inhibition at 100 ppm after 5 days by agar dilution test Pythium 92.7 %
Fungicidal activity against Pythium sp. assessed as growth inhibition at 10 ppm after 5 days by agar dilution test Pythium 7.4 %

Cross References

Resources Reference
ChEMBL CHEMBL42710
FDA SRS 3T8H1794QW
PDB EOL
PubChem 3314
SureChEMBL SCHEMBL20361
ZINC ZINC00001411
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