(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19Z,21Z,23Z,25Z,27Z,29Z,31Z,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid

• ChemBase ID: 132590
• Molecular Formular: C47H73NO17
• Molecular Mass: 924.07902
• Monoisotopic Mass: 923.48784988
• SMILES: C[C@H]1/C=C\C=C/C=C\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[C@H]([C@@H](CC[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@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/C=C\C=C/C=C\[C@@H]([C@H]([C@H]([C@@H](OC(=O)C[C@@H](C1)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/C47H73NO17/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)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5-,9-7-,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: APKFDSVGJQXUKY-ZNVUZQDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19Z,21Z,23Z,25Z,27Z,29Z,31Z,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
• IUPAC Traditional name: amphotericin B
• Synonyms: Amphotericin B solution; Fungizone; Amphotericin B solubilized; 两性霉素 B 溶液

Database IDs

• CAS Number: 1397-89-3
• EC Number: 231-791-2
• MDL Number: MFCD00877763
• Beilstein Number: 78342
• PubChem SID: 24890711; 162226867; 24891468
• PubChem CID: 14956

CALCULATED PROPERTIES

• Acid pKa: 3.5797393
• H Acceptors: 17
• H Donor: 12
• LogD (pH = 5.5): -2.3028812
• LogD (pH = 7.4): -2.3064086
• Log P: -2.3001616
• Molar Refractivity: 244.6705 cm^3
• Polarizability: 94.662575 Å^3
• Polar Surface Area: 319.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: sterile water: soluble20 mg/mL (as a stock solution. Stock solutions should be stored at -20 °C. Stable at 37 °C for 3 days.)
• Apperance: powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C; 2-8°C

Product Information

• Concentration: 250 μg/mL in deionized water
• Suitability: suitable for cell culture
• Sterility: sterile-filtered; γ-irradiated
• Quality Level: PREMIUM
• Shipped in: dry ice

DETAILS

Sigma Aldrich - A2942

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Recommended for use in cell culture applications at 10 ml/L.
Biochem/physiol Actions
Mode of action: Interferes with fungal membrane permeability by forming channels in the membranes and causing small molecules to leak out.Antimicrobial spectrum: Yeasts and molds.
Caution
Stable at 37 °C for 3 days.
Preparation Note
Prepared from A 9528.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - A9528

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Recommended for use in cell culture applications at 5.6 mg (solid)/L. It is used to study the formation of ion-permeable channels in fungal cell membranes
Biochem/physiol Actions
Mode of Action: Interferes with fungal membrane permeability by forming channels in the membranes and causing small molecules to leak out.
Polyene antifungal antibiotic from Streptomyces. Affinity for sterols, primarily ergosterols, of fungal cell membranes. Forms channels in the membranes, causing small molecules to leak out. Antimicrobial spectrum: fungi and yeast.
包装
Package size based on amphotericin B
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information