(1S,3R,4R,7R,9R,11R,15S,16S,17R,18S,19Z,21Z,25Z,27Z,29Z,31Z,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic acid

• ChemBase ID: 131813
• Molecular Formular: C47H75NO17
• Molecular Mass: 926.0949
• Monoisotopic Mass: 925.50349995
• SMILES: C[C@H]1/C=C\C=C/CC/C=C\C=C/C=C\C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H]([C@@H](CC[C@H](C[C@H](C[C@H](CC(=O)O[C@H]([C@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)C)O)N)O
• Canonical SMILES: O[C@@H]1CC[C@@H](O)[C@H](O)C[C@]2(O)C[C@H](O)[C@H]([C@@H](O2)C[C@H](/C=C\C=C/C=C\C=C/CC/C=C\C=C/[C@@H]([C@H]([C@@H]([C@@H](OC(=O)C[C@@H](C[C@@H](C1)O)O)C)C)O)C)O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)N)O)C(=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
• InChIKey: VQOXZBDYSJBXMA-HBQQHZFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,4R,7R,9R,11R,15S,16S,17R,18S,19Z,21Z,25Z,27Z,29Z,31Z,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic acid
• IUPAC Traditional name: (1S,3R,4R,7R,9R,11R,15S,16S,17R,18S,19Z,21Z,25Z,27Z,29Z,31Z,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic acid
• Synonyms: Fungicidin; Mycostatin; Nystatin; Nystatin Suspension

Database IDs

• CAS Number: 1400-61-9
• EC Number: 215-749-0
• PubChem SID: 162226090; 24897511; 24897647
• PubChem CID: 71308475

CALCULATED PROPERTIES

• Acid pKa: 3.611593
• H Acceptors: 17
• H Donor: 12
• LogD (pH = 5.5): -1.9412671
• LogD (pH = 7.4): -1.9444739
• Log P: -1.9383262
• Molar Refractivity: 243.5539 cm^3
• Polarizability: 94.91027 Å^3
• Polar Surface Area: 319.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: yellow suspension

Safety Information

• RTECS: RF5950000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Concentration: 10,000 unit/mL in DPBS
• Suitability: suitable for cell culture
• Impurities: endotoxin, tested
• Sterility: aseptically processed
• Quality Level: PREMIUM
• Shipped in: dry ice

DETAILS

Sigma Aldrich - N3503

Biochem/physiol Actions
Mode of Action: Increases the permeability of the cell membrane of sensitive fungi by binding to sterols.Antimicrobial spectrum: Yeasts and molds.
Nystatin binds to ergosterol in fungal cell membranes which causes the formation of pores in the membrane. Potassium and other cellular constituents leak from the pores causing cell death. Antimicrobial spectrum: Yeasts and molds.
Application
Product N3503 is ≥4,400 USP units/mg. Nystatin is a polyene, antifungal antibiotic with potent proinflammatory properties. It has many applications such as preventing cell culture contamination and inducing interleukin (IL)-, IL-8, and tumor necrosis factor α s secretion in TLR2-expressing THP1 cells 1. It is used as a fungal membrane (ergosterol binding) pore forming agent and to create nystatin/ergosterol based ion channels in lipid bilayers.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - N1638

Application
Recommended for use in cell culture applications at 24 ml/L. Used as a fungal membrane (ergosterol binding) pore forming agent and to create nystatin/ergosterol based ion channels in lipid bilayers and as a lipid raft-inhibiting reagent and membrane associated cholesterol aggregator.
Biochem/physiol Actions
Mode of Action: Increases the permeability of the cell membrane of sensitive fungi by binding to sterols.Antimicrobial spectrum: Yeasts and molds.
Caution
Stable at 37 °C for 3 days.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information