Structure Database (LMSD)
Common Name
Amphotericin B
Systematic Name
Synonyms
3D model of Amphotericin B
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Amphotericin B is a classic antifungal polyene macrolide that has been used in the treatment of systemic fungal infections, primarily caused by C. albicans, A. fumigatus, and parasitic L. protozoans, as well as in tissue culture to prevent fungi from contaminating cell cultures.1,2,3 Amphotericin B binds with ergosterol, the main component of fungal cell membranes, forming a transmembrane channel that results in altered plasma membrane permeability and leakage of vital cytoplasmic components, such as K+, ultimately inducing cell death.4 Because prolonged use of amphotericin B is associated with infusion-related events and nephrotoxicity, lipid-based formulations have been devised for more favorable clinical relevance.1,2
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
APKFDSVGJQXUKY-INPOYWNPSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@]12([H])C[C@H](C=CC=CC=CC=CC=CC=CC=C[C@@H]([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@@](C[C@H](O)[C@H]1C(=O)O)(O)O2)C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](N)[C@@H]1O)C
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
65
Rings
3
Aromatic Rings
0
Rotatable Bonds
3
Van der Waals Molecular Volume
921.25
Topological Polar Surface Area
325.82
Hydrogen Bond Donors
12
Hydrogen Bond Acceptors
17
logP
5.29
Molar Refractivity
245.18
Admin
Created at
-
Updated at
-