GRISEOFULVIN

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC D01AA08 D01BA01
UNII 32HRV3E3D5
EPA CompTox DTXSID8020674

Structure

InChI Key DDUHZTYCFQRHIY-RBHXEPJQSA-N
Smiles COC1=CC(=O)C[C@@H](C)[C@]12Oc1c(Cl)c(OC)cc(OC)c1C2=O
InChI
InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H17ClO6
Molecular Weight 352.77
AlogP 2.81
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 71.06
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 24.0

Bioactivity

Mechanism of Action Action Reference
Tubulin inhibitor INHIBITOR ISBN PubMed PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 51 Cytochrome P450 family 51A Cytochrome P450 51A1
- 50000 - - -
Enzyme Hydrolase
- - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 66
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 7300 - - -
Assay Description Organism Bioactivity Reference
Antibacterial activity against Escherichia coli at 100 ug/mL after 48 hrs by cup-plate method Escherichia coli 100.0 %
Antibacterial activity against Escherichia coli at 50 ug/mL after 48 hrs by cup-plate method Escherichia coli 220.0 %
Antibacterial activity against Escherichia coli at 25 ug/mL after 48 hrs by cup-plate method Escherichia coli 100.0 %
Antibacterial activity against Bacillus cirrhosis at 100 ug/mL after 48 hrs by cup-plate method Bacillus 100.0 %
Antibacterial activity against Bacillus cirrhosis at 50 ug/mL after 48 hrs by cup-plate method Bacillus 100.0 %
Antibacterial activity against Bacillus cirrhosis at 25 ug/mL after 48 hrs by cup-plate method Bacillus 100.0 %
Antifungal activity against Aspergillus niger at 100 ug/mL after 48 hrs by cup-plate method Aspergillus niger 100.0 %
Antifungal activity against Aspergillus niger at 50 ug/mL after 48 hrs by cup-plate method Aspergillus niger 100.0 %
Antifungal activity against Aspergillus niger at 25 ug/mL after 48 hrs by cup-plate method Aspergillus niger 100.0 %
Antifungal activity against Rhizoctonia bataticola at 100 ug/mL after 48 hrs by cup-plate method Rhizoctonia bataticola 100.0 %
Antifungal activity against Rhizoctonia bataticola at 50 ug/mL after 48 hrs by cup-plate method Rhizoctonia bataticola 100.0 %
Antifungal activity against Rhizoctonia bataticola at 25 ug/mL after 48 hrs by cup-plate method Rhizoctonia bataticola 100.0 %
Antifungal activity against Pyricularia grisea assessed as inhibition of germ-tube development by microdilution method Magnaporthe grisea 4.0 ug.mL-1
Antifungal activity against Trichophyton mentagrophytes IBT 2724 after 7 days by micro broth dilution method Trichophyton mentagrophytes 58.0 nM
Antifungal activity against Trichophyton rubrum IBT 29284 after 7 days by micro broth dilution method Trichophyton rubrum 380.0 nM
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method Electrophorus electricus -8.73 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method Equus caballus -4.49 %
Fungitoxicity against Fusarium oxysporum assessed as inhibition of mycelia growth at 28 +/- 1 degC at 1000 ug/mL for 96 hr by poisoned food technique Fusarium oxysporum 100.0 %
Fungitoxicity against Fusarium oxysporum assessed as inhibition of mycelia growth at 28 +/- 1 degC at 100 ug/mL for 96 hr by poisoned food technique Fusarium oxysporum 95.0 %
Fungitoxicity against Fusarium oxysporum assessed as inhibition of mycelia growth at 28 +/- 1 degC at 10 ug/mL for 96 hr by poisoned food technique Fusarium oxysporum 91.0 %
Fungitoxicity against Penicillium citrinum assessed as inhibition of mycelia growth at 28 +/- 1 degC at 1000 ug/mL for 96 hr by poisoned food technique Penicillium citrinum 100.0 %
Fungitoxicity against Penicillium citrinum assessed as inhibition of mycelia growth at 28 +/- 1 degC at 100 ug/mL for 96 hr by poisoned food technique Penicillium citrinum 94.0 %
Fungitoxicity against Penicillium citrinum assessed as inhibition of mycelia growth at 28 +/- 1 degC at 10 ug/mL for 96 hr by poisoned food technique Penicillium citrinum 90.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 65.59 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 97.62 %
Antiproliferative activity against exponentially growing adherent human HCC1937 cells assessed as inhibition of cell proliferation at 10 uM after 72 hrs by luminescence detection based ATPlite assay Homo sapiens 0.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 7.83 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 2.08 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 11.08 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 21.48 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 27.35 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.42 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -0.94 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 23.47 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 9.326 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.13 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.13 %

Environmental Exposure

Environmental Exposure Map
Countries
Vietnam

Cross References

Resources Reference
ChEBI 27779
ChEMBL CHEMBL562
DrugBank DB00400
DrugCentral 1331
FDA SRS 32HRV3E3D5
Human Metabolome Database HMDB0014544
KEGG C06686
PharmGKB PA449814
PubChem 441140
SureChEMBL SCHEMBL21988
ZINC ZINC000000622123
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