CHEBI:600520 - micafungin

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ChEBI Name micafungin
ChEBI ID CHEBI:600520
Definition A cyclic hexapeptide echinocandin antibiotic which exerts its effect by inhibiting the synthesis of 1,3-β-D-glucan, an integral component of the fungal cell wall. It is used as the sodium salt for the treatment of invasive candidiasis, and of aspergillosis in patients who are intolerant of other therapy.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:533643, CHEBI:533785, CHEBI:473847, CHEBI:530001
Supplier Information
Download Molfile XML SDF
Formula C56H71N9O23S
Net Charge 0
Average Mass 1270.27400
Monoisotopic Mass 1269.438
InChI InChI=1S/C56H71N9O23S/c1-4-5-6-17-86-32-14-11-28(12-15-32)39-21-33(63-87-39)27-7-9-29(10-8-27)49(75)58-34-20-38(70)52(78)62-54(80)45-46(72)25(2)23-65(45)56(82)43(37(69)22-41(57)71)60-53(79)44(48(74)47(73)30-13-16-36(68)40(18-30)88-89(83,84)85)61-51(77)35-19-31(67)24-64(35)55(81)42(26(3)66)59-50(34)76/h7-16,18,21,25-26,31,34-35,37-38,42-48,52,66-70,72-74,78H,4-6,17,19-20,22-24H2,1-3H3,(H2,57,71)(H,58,75)(H,59,76)(H,60,79)(H,61,77)(H,62,80)(H,83,84,85)/t25-,26+,31+,34-,35-,37+,38+,42-,43-,44-,45-,46-,47-,48-,52+/m0/s1
InChIKey PIEUQSKUWLMALL-YABMTYFHSA-N
SMILES CCCCCOc1ccc(cc1)-c1cc(no1)-c1ccc(cc1)C(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@@H](C)CN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC1=O)[C@@H](C)O)[C@H](O)[C@@H](O)c1ccc(O)c(OS(O)(=O)=O)c1)[C@H](O)CC(N)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via antibiotic antifungal agent )
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via antibiotic antifungal drug )
Application(s): antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
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 micafungin (CHEBI:600520) has role antiinfective agent (CHEBI:35441)
micafungin (CHEBI:600520) is a antibiotic antifungal drug (CHEBI:87113)
micafungin (CHEBI:600520) is a echinocandin (CHEBI:57248)
IUPAC Names
5-[(1S,2S)-2-{(2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-20-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-2,11,12,15-tetrahydroxy-6-[(1R)-1-hydroxyethyl]-16-methyl-5,8,14,19,22,25-hexaoxo-9-[(4-{5-[4-(pentyloxy)phenyl]isoxazol-3-yl}benzoyl)amino]tetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-23-yl}-1,2-dihydroxyethyl]-2-hydroxyphenyl hydrogen sulfate
5.1:6-anhydro{(4R,5R)-4,5-dihydroxy-N2-(4-{5-[4-(pentyloxy)phenyl]isoxazol-3-yl}benzoyl)-L-ornithyl-L-threonyl-(4R)-4-hydroxy-L-prolyl-(4S)-4-hydroxy-4-[4-hydroxy-3-(sulfooxy)phenyl]-L-threonyl-(3R)-3-hydroxy-L-glutaminyl-(3S,4S)-3-hydroxy-4-methyl-L-proline}
INNs Sources
micafungin ChemIDplus
micafungin KEGG DRUG
Synonym Source
Mycamine ChemIDplus
Manual Xrefs Databases
D08218 KEGG DRUG
DB01141 DrugBank
View more database links
Registry Numbers Types Sources
235114-32-6 CAS Registry Number ChemIDplus
235114-32-6 CAS Registry Number KEGG DRUG
9610508 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
17194830 PubMed citation ChEMBL
17307974 PubMed citation ChEMBL
17325217 PubMed citation ChEMBL
17325225 PubMed citation ChEMBL
17420211 PubMed citation ChEMBL
17785512 PubMed citation ChEMBL
Last Modified
22 February 2017