CHEBI:2682 - amphotericin B

Main ChEBI Ontology Automatic Xrefs
ChEBI Name amphotericin B
ChEBI ID CHEBI:2682
Definition A macrolide antibiotic used to treat potentially life-threatening fungal infections.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:106303, CHEBI:566395
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Formula C47H73NO17
Net Charge 0
Average Mass 924.07900
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
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
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via polyene antibiotic )
(via macrolide antibiotic )
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via antibiotic antifungal drug )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via antibiotic antifungal agent )
Application(s): antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via antibiotic antifungal drug )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing amphotericin B (CHEBI:2682) has role antiprotozoal drug (CHEBI:35820)
amphotericin B (CHEBI:2682) has role bacterial metabolite (CHEBI:76969)
amphotericin B (CHEBI:2682) is a antibiotic antifungal drug (CHEBI:87113)
amphotericin B (CHEBI:2682) is a macrolide antibiotic (CHEBI:25105)
amphotericin B (CHEBI:2682) is a polyene antibiotic (CHEBI:26177)
Incoming amphotericin B methyl ester (CHEBI:277842) has functional parent amphotericin B (CHEBI:2682)
IUPAC Name
(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(3-amino-3,6-dideoxy-β-D-mannopyranosyl)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
INNs Sources
amfotericina B ChemIDplus
amphotericin B KEGG DRUG
amphotericine B ChemIDplus
amphotericinum B ChemIDplus
Synonyms Sources
AMPH-B DrugBank
Amphotericine B DrugBank
Liposomal Amphotericin B DrugBank
Database Links Databases
Amphotericin_B Wikipedia
C06573 KEGG COMPOUND
D00203 KEGG DRUG
DB00681 DrugBank
LMPK06000002 LIPID MAPS
US2908611 Patent
View more database links
Registry Numbers Types Sources
1397-89-3 CAS Registry Number KEGG DRUG
1397-89-3 CAS Registry Number DrugBank
1397-89-3 CAS Registry Number ChemIDplus
4645978 Beilstein Registry Number Beilstein
4645978 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11429202 PubMed citation CiteXplore
16120633 PubMed citation CiteXplore
16793999 PubMed citation CiteXplore
1732516 PubMed citation ChEMBL
17507115 PubMed citation ChEMBL
Last Modified
23 July 2015