CHEBI:2682 - amphotericin B

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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
Supplier Information ChemicalBook:CB5437014, eMolecules:518345, ZINC000013512210
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4-Methylcatechol is an organic compound with the formula CH3C6H3(OH)2 A white solid, it is one of the isomers of methylbenzenediol.
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Formula C47H73NO17
Net Charge 0
Average Mass 924.07900
Monoisotopic Mass 923.48785
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): antiamoebic agent
An antiparasitic agent which is effective against amoeba, a genus of single-celled amoeboids in the family Amoebidae.
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 antiamoebic agent (CHEBI:171664)
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
Manual Xrefs Databases
197 DrugCentral
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 Reaxys Registry Number Reaxys
Citations Types Sources
11429202 PubMed citation Europe PMC
11930683 PubMed citation Europe PMC
15793154 PubMed citation Europe PMC
16120633 PubMed citation Europe PMC
16793999 PubMed citation Europe PMC
1732516 PubMed citation ChEMBL
17507115 PubMed citation ChEMBL
33846129 PubMed citation Europe PMC
Last Modified
28 April 2021