(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,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: 153350
• 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)/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1
• InChIKey: APKFDSVGJQXUKY-KKGHZKTASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,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: Fungizone; Amphotericin B from Streptomyces sp.; 两性霉素 B 来源于链霉菌 属

Database IDs

• CAS Number: 1397-89-3
• EC Number: 215-742-2
• MDL Number: MFCD00877763
• Beilstein Number: 78342
• PubChem SID: 24890749; 162247489; 24890655
• PubChem CID: 71311649

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: DMF: 1 M HCl (3:1): soluble, clear to slightly hazy; DMF: 1 M HCl (3:1): soluble50 mg/mL, clear to slightly turbid, orange to very deep red; DMF: soluble2-4 mg/mL; DMSO: soluble30-40 mg/mL; H2O: insoluble; H2O: slightly soluble
• Apperance: powder

Safety Information

• RTECS: BU2625000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ~80% (HPLC)
• Suitability: plant cell culture tested; suitable for cell culture
• Quality Level: PREMIUM
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C47H73NO17

DETAILS

Sigma Aldrich - A6804

Application
Recommended for antifungal use in cell culture media at 2.5 mg/L. Stable at 37 °C for 3 days.
Biochem/physiol Actions
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.
Amphotericin B Streptomyces sp. Is a polyene antifungal antibiotic that forms membrane channels.

Sigma Aldrich - A2411

Application
Recommended for antifungal use in cell culture media at 2.5 mg/L. Stable at 37 °C for 3 days.
Recommended for antifungal use in cell culture media at 2.5 mg/L. Stable at 37 °C for 3 days.
Biochem/physiol Actions
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.
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.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - A4888

Biochem/physiol Actions
Amphotericin B is a polyene antifungal antibiotic from Streptomyces. It has an affinity for sterols, primarily ergosterols, of fungal cell membranes. It forms channels in the membranes, causing small molecules to leak out which contributes to cell death. Antimicrobial spectrum: fungi and yeast.
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.
Application
Amphotericin B is used to study the affects of the influx of calcium on antifungal activity, 1 and to study the binding and kinetics of Amphotericin B to sterols in monolayers, aqueous solutions, and phospholipid bilayers 2,3. It is also commonly used in tissue culture as an antifungal supplement.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 10042

Biochem/physiol Actions
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.