micafungin
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.
Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.
Classification
echinocandin antibioticARO:3007496
- echinocandin
CHEBI:57248 - antibiotic antifungal drug
CHEBI:87113 - echinocandin antibiotic
ARO:3007496
Chemical structure
| Molecular formula | C56H71N9O23S |
|---|---|
| Charge | 0 |
| Average mass | 1270.291 Da |
| Monoisotopic mass | 1269.43835 Da |
| Source | ChEBI |
| InChIKey | PIEUQSKUWLMALL-YABMTYFHSA-N |
CCCCCOc1ccc(-c2cc(-c3ccc(C(=O)N[C@H]4C[C@@H](O)[C@@H](O)NC(=O)[C@@H]5[C@@H](O)[C@@H](C)CN5C(=O)[C@H]([C@H](O)CC(N)=O)NC(=O)[C@H]([C@H](O)[C@@H](O)c5ccc(O)c(OS(=O)(=O)O)c5)NC(=O)[C@@H]5C[C@@H](O)CN5C(=O)[C@H]([C@@H](C)O)NC4=O)cc3)no2)cc1
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
Also called
- 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}
- Mycamine
Cross-references
- micafungin
ARO:3007502 - beilstein:9610508
- cas:235114-32-6
- chembl:CHEMBL457547
- pubchem.compound:477468
Drug registries
Activity roles
- antifungal agent
CHEBI:35718 - antifungal drug
CHEBI:86327
Source concepts
| Source | Native ID | Label | Minted CURIE | Version |
|---|---|---|---|---|
| ARO | ARO:3007502 |
micafungin | antibioticmech:aro-f469649fb1 |
2026-08-30 |
| CHEBI | CHEBI:600520 |
micafungin | antibioticmech:chebi-755d23d56a |
2026-08-30 |
Mechanism summary
- Mode of action
- CELL_WALL_SYNTHESIS_INHIBITION microbial target
Resistance mechanisms
ANTIBIOTIC_TARGET_ALTERATION 13
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Candida albicans FKS1 with mutations conferring resistance to micafungin | ARO:3009418 | — | ||
| Candida auris FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin | ARO:3009421 | — | ||
| Candida dubliniensis FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin | ARO:3009593 | — | ||
| Candida glabrata FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin | ARO:3009232 | — | ||
| Candida glabrata FKS2 with mutations conferring resistance to micafungin | ARO:3007548 | — | ||
| Candida metapsilosis FKS1 beta-1,3-glucan with mutations conferring resistance to micafungin | ARO:3009596 | — | ||
| Candida parapsilosis Erg3 C-5 sterol desaturase with mutations conferring resistance to micafungin | ARO:3009248 | — | ||
| Candida parapsilosis FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin | ARO:3009599 | — | ||
| Candida tropicalis FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin | ARO:3009602 | — | ||
| Kluyveromyces marxianus FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin | ARO:3009606 | — | ||
| Pichia kudriavzevii Fks1 beta-1,3-glucan synthase with mutations associated with resistance to micafungin | ARO:3009608 | — | ||
| Saccharomyces cerevisiae FKS1 beta-1,3-D-glucan synthase with mutations conferring resistance to micafungin | ARO:3009610 | — | ||
| antifungal resistance-associated MSH | ARO:3009134 | — |
UNKNOWN 9
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| FKS1(F641S) (amino acid mutation) [Not assayed] associated with resistance to micafungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000575 |
— | |
| FKS1(L644F S645C) (amino acid mutation) [Not assayed] associated with resistance to micafungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000575 |
— | |
| FKS1(P647A) (amino acid mutation) [Not assayed] associated with resistance to micafungin |
— | Saccharomyces cerevisiae NCBITaxon:4932PHIPO:0000575 |
— | |
| FKS1(S645F) (amino acid mutation) [Not assayed] associated with resistance to micafungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000575 |
— | |
| FKS1(S645F) (amino acid mutation) [Not assayed] associated with resistance to micafungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000575 |
— | |
| FKS1(S645P) (amino acid mutation) [Not assayed] associated with resistance to micafungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000575 |
— | |
| FKS1(S645P) (amino acid mutation) [Not assayed] associated with resistance to micafungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000575 |
— | |
| FKS1(S645Y) (amino acid mutation) [Not assayed] associated with resistance to micafungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000575 |
— | |
| FKS1(S645Y) (amino acid mutation) [Not assayed] associated with resistance to micafungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000575 |
— |
Curation history
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SEEDED_FROM_SOURCES
Seeded from data/raw/ inventories (ARO, CHEBI)
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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REVIEWED_RESISTANCE_IDENTIFIER_SCOPE
Scoped eight PHI-base FKS1 associations to parent-background context, withheld reference protein/strain IDs as experimental-subject identifiers, and retained the explicit AF027295-to-UniProtKB:O13383 reference crosswalk. Alleles, phenotypes, species, and mechanism unchanged; no isolate MIC inferred.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Applied 1 pinned subject-context reviews, retaining reference-locus grounding while withholding unverified experimental protein/strain identifiers. Source alterations, phenotypes, species, genes, and existing activities unchanged. Refreshed provenance checksums on any previously reviewed claims. Resolved the FKS1 table's derivative label with its explicit numbering discrepancy.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after Eddouzi subject reviews; all biological fields and prior decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after Rybak reference-context reviews; all biological fields and previous decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after carboxin reference-context reviews; all biological fields, activities and previous decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after two additional carboxin identifier-scope corrections; all biological fields, activities and previous decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after eleven additional identifier-scope corrections; biological fields, activities and decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after seventeen additional identifier-scope corrections; biological fields, activities and decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after one yeast identity-scope correction; biological fields, activities and prior decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after twelve reference-scope corrections; biological fields, activities and prior decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after nine identifier-scope corrections; previous decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after six identifier-scope corrections; previous decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after eight subject-identity corrections; previous decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Darlington subject correction; prior review decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Nakayama reference-scope review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Duan reference-scope review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Piotrowska parent-reference review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Xu subject and species corrections; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Shima parent-reference review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Mehrabi parent-reference review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Huang parent-reference review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the HDF1 subject-reference review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Fouche parent-cohort review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_REFERENCE_CONTEXT
Refreshed shared PHI-base review checksum after the SDH8 reference-alias correction; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after the Posteraro subject-context review; previous decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_REFERENCE_CONTEXT
Refreshed the shared PHI-base review checksum after four reference-identifier scope corrections; previous decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after one Neurospora subject-context correction; previous decisions, biological fields and activities unchanged.