NYSTATIN

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC A07AA02 D01AA01 G01AA01
UNII W1LX4T91WI
EPA CompTox DTXSID80872323

Structure

InChI Key VQOXZBDYSJBXMA-NQTDYLQESA-N
Smiles C[C@@H]1[C@H](O)[C@@H](C)/C=C/C=C/CC/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)C[C@@H]2O[C@](O)(C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)C[C@@H](O)CC(=O)O[C@H]1C)C[C@H](O)[C@H]2C(=O)O
InChI
InChI=1S/C47H75NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-36(53)35(52)20-19-31(49)21-32(50)22-33(51)23-39(55)62-29(3)28(2)42(27)56/h5-6,8,10-18,27-38,40-44,46,49-54,56-58,61H,7,9,19-26,48H2,1-4H3,(H,59,60)/b6-5+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33+,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C47H75NO17
Molecular Weight 926.11
AlogP 0.94
Hydrogen Bond Acceptor 17.0
Hydrogen Bond Donor 12.0
Number of Rotational Bond 3.0
Polar Surface Area 319.61
Molecular species ZWITTERION
Aromatic Rings 0.0
Heavy Atoms 65.0

Pharmacology

Mechanism of Action Action Reference
Ergosterol sequestering agent SEQUESTERING AGENT FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 49-69
Assay Description Organism Bioactivity Reference
Antifungal activity against Aspergillus niger was determined by twofold Micro-broth dilution assay Aspergillus niger 2.5 ug.mL-1
Antifungal activity against Aspergillus flavus was determined by twofold Micro-broth dilution assay Aspergillus flavus 2.5 ug.mL-1
Antifungal activity against Candida albicans was determined by twofold Micro-broth dilution assay Candida albicans 0.25 ug.mL-1
Antifungal activity against Microsporum gypseum was determined by twofold Micro-broth dilution assay Arthroderma gypseum 3.125 ug.mL-1
Antifungal activity against Sporothrix schenck ii was determined by twofold Micro-broth dilution assay Sporothrix schenckii 3.125 ug.mL-1
Antifungal activity against Trichophyton rubrum was determined by twofold Micro-broth dilution assay Trichophyton rubrum 2.5 ug.mL-1
Antifungal activity against Aspergillus flavus NRRL 6541 Aspergillus flavus 5.0 ug.mL-1
Antifungal activity against Fusarium verticillioides NRRL 25457 Gibberella moniliformis 3.0 ug.mL-1
Inhibition of synthetic amyloid beta-42 fibrillation by ThT fluorescence analysis relative to control None 275.0 %
Inhibition of synthetic amyloid beta-42 fibrillation by light scattering analysis relative to control None -9.2 %
Antifungal activity against Gibberella moniliformis NRRL 25457 by agar disk diffusion assay Gibberella moniliformis 3.0 ug.mL-1
Antifungal activity against Aspergillus flavus NRRL 6541 by agar disk diffusion assay Aspergillus flavus 5.0 ug.mL-1
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 69.3 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 74.9 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 23.4 %
Antifungal activity against Fusarium oxysporum assessed as inhibition of fungal spore germination after 24 hr by compound microscopic analysis relative to control Fusarium oxysporum 100.0 %
Antifungal activity against Curvularia lunata assessed as inhibition of fungal spore germination after 24 hr by compound microscopic analysis relative to control Curvularia lunata 100.0 %
Antifungal activity against Alternaria alternata assessed as inhibition of fungal spore germination after 24 hr by compound microscopic analysis relative to control Alternaria alternata 100.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 49.23 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 76.2 %
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 -4.11 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 13.27 %
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 0.08 % 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 0.08 %
Antibiofilm activity against Candida albicans ATCC 10231 assessed as reduction in mature biofilm at 125 ug/ml incubated for 48 hrs by crystal violet staining based spectrophotometric analysis relative to control Candida albicans 25.0 %

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL450895
DrugCentral 1977
FDA SRS W1LX4T91WI
KEGG C12155
SureChEMBL SCHEMBL18633553
ZINC ZINC000253387941
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