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amphotericin B (CHEBI:2682)

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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
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Formula Source
C47H73NO17 ChEBI
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.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. Antifungal agents differ from industrial fungicides in that they defend against fungi present in human or animal tissues.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
antibiotic
A substance that is biostatic or biocidal at low concentrations towards bacteria, yeasts, moulds, or other form of life, especially pathogenic or noxious organisms. Although the term was originally restricted to substances produced by microorganisms, its use was later expanded to include derivatives of such substances and it is now commonly used to include entirely synthetic compounds.
(via macrolide antibiotic )
(via polyene antibiotic )
Application(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. Antifungal agents differ from industrial fungicides in that they defend against fungi present in human or animal tissues.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
antibiotic
A substance that is biostatic or biocidal at low concentrations towards bacteria, yeasts, moulds, or other form of life, especially pathogenic or noxious organisms. Although the term was originally restricted to substances produced by microorganisms, its use was later expanded to include derivatives of such substances and it is now commonly used to include entirely synthetic compounds.
(via macrolide antibiotic )
(via polyene antibiotic )
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing amphotericin B (CHEBI:2682) has role antifungal agent (CHEBI:35718)
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 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 ChemIDplus
1397-89-3 CAS Registry Number DrugBank
1397-89-3 CAS Registry Number KEGG DRUG
4645978 Reaxys Registry Number Reaxys
4645978 Beilstein Registry Number Beilstein
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
06 août 2014

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