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Amphotericin B

CAT: 0013-GTR19177802-02Size: 5 gDry Ice: NoHazardous: No
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CAT#:0013-GTR19177802-02Size:5 g
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Description
Amphotericin B is a broad-spectrum polyene antifungal that acts by irreversibly binding to ergosterol, thereby disrupting fungal membrane integrity. It is widely used in both in vitro susceptibility testing and in vivo models of systemic fungal infections such as aspergillosis and candidiasis.
CAS Number
1397-89-3
Product Name Alternative
NSC 527017
Field of Research
Infectious Disease & Virology, Pharmacology & Drug Discovery
Purity
>90%
Bioactivity
Antifungal agent
Form
Powder
Solubility
Soluble in DMSO (up to 18 mg/ml)
Smiles
[H][C@]12C[C@@H] (O[C@@H]3O[C@H] (C) [C@@H] (O) [C@H] (N) [C@@H]3O) \C=C\C=C\C=C/C=C/C=C/C=C/C=C/[C@H] (C) [C@@H] (O) [C@@H] (C) [C@H] (C) OC (=O) C[C@H] (O) C[C@H] (O) CC[C@@H] (O) [C@H] (O) C[C@H] (O) C[C@] (O) (C[C@H] (O) [C@H]1C (O) =O) O2
Molecular Formula
C47H73NO17
Molecular Weight
924.1
Storage Conditions
-20°C / protect from light
Notes
For research use only.

Chemical Information

Amphotericin B

Amphotericin B is a macrolide antibiotic used to treat potentially life-threatening fungal infections. It has a role as an antiamoebic agent, an antiprotozoal drug and a bacterial metabolite. It is a macrolide antibiotic, a polyene antibiotic and an antibiotic antifungal drug.

CAS Number1397-89-3
PubChem CID5280965
IUPAC Name(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,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
Molecular FormulaC47H73NO17
Molecular Weight924.1
XLogP0
Topological Polar Surface Area320
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count18
Rotatable Bond Count3
Heavy Atom Count65
Formal Charge0
Complexity1670
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]3[C@H]([C@H]([C@@H]([C@H](O3)C)O)N)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-INPOYWNPSA-N
Chemical Structure
2D Structure
2D structure of Amphotericin B
CAS: 1397-89-3
CID: 5280965
Formula: C47H73NO17
MW: 924.1
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight924.1
XLogP30
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count18
Rotatable Bond Count3
Exact Mass923.48784986
Monoisotopic Mass923.48784986
Topological Polar Surface Area320 Ų
Heavy Atom Count65
Formal Charge0
Complexity1670
Isotope Atom Count0
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count7
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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HY-125682Amphotericin A
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