micafungin
CHEBI:600520
·resolve ·ANTIFUNGAL
·EXACT
SEEDED
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. — ChEBI
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
Strictly broader compounds or drug classes this molecule belongs to.
Chemical structure
Computed structure properties
| Molecular formula | C56H71N9O23S |
|---|
| Charge | 0 |
|---|
| Average mass | 1270.291 Da |
|---|
| Monoisotopic mass | 1269.43835 Da |
|---|
| Source | ChEBI |
|---|
| InChIKey | PIEUQSKUWLMALL-YABMTYFHSA-N |
|---|
SMILES
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
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 (EXACT_SYNONYM)— chebi
- 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} (EXACT_SYNONYM)— chebi
- Mycamine (EXACT_SYNONYM)— chebi
Cross-references
Equivalent identifiers for this same structure in other resources.
Activity roles
Every antimicrobial role a source asserts for this compound — the
unreduced evidence behind its antimicrobial_class.
Source concepts
Every upstream concept that resolved to this record. The merge is
the product: this is what shows ChEBI and CARD are describing the same structure.
Upstream concepts merged into this record
| 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 — Assigned from ChEBI role CHEBI:230471 (EC 2.4.1.34 (1,3-β-glucan synthase) inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.
Resistance mechanisms
22 known routes by which microbes
resist this compound, grounded in ARO where CARD models them. Grouped by mechanism
type — expand a group to see its determinants.
ANTIBIOTIC_TARGET_ALTERATION 13
ANTIBIOTIC_TARGET_ALTERATION
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|
| Candida albicans FKS1 with mutations conferring resistance to micafungin |
ARO:3009418 |
not organism-specific |
— |
- ARO:3009418 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| Candida auris FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin |
ARO:3009421 |
not organism-specific |
— |
- ARO:3009421 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| Candida dubliniensis FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin |
ARO:3009593 |
not organism-specific |
— |
- ARO:3009593 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| Candida glabrata FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin |
ARO:3009232 |
not organism-specific |
— |
- ARO:3009232 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| Candida glabrata FKS2 with mutations conferring resistance to micafungin |
ARO:3007548 |
not organism-specific |
— |
- ARO:3007548 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| Candida metapsilosis FKS1 beta-1,3-glucan with mutations conferring resistance to micafungin |
ARO:3009596 |
not organism-specific |
— |
- ARO:3009596 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| Candida parapsilosis Erg3 C-5 sterol desaturase with mutations conferring resistance to micafungin |
ARO:3009248 |
not organism-specific |
— |
- ARO:3009248 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| Candida parapsilosis FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin |
ARO:3009599 |
not organism-specific |
— |
- ARO:3009599 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| Candida tropicalis FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin |
ARO:3009602 |
not organism-specific |
— |
- ARO:3009602 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| Kluyveromyces marxianus FKS1 beta-1,3-glucan synthase with mutations conferring resistance to micafungin |
ARO:3009606 |
not organism-specific |
— |
- ARO:3009606 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| Pichia kudriavzevii Fks1 beta-1,3-glucan synthase with mutations associated with resistance to micafungin |
ARO:3009608 |
not organism-specific |
— |
- ARO:3009608 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| Saccharomyces cerevisiae FKS1 beta-1,3-D-glucan synthase with mutations conferring resistance to micafungin |
ARO:3009610 |
not organism-specific |
— |
- ARO:3009610 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
| antifungal resistance-associated MSH |
ARO:3009134 |
not organism-specific |
— |
- ARO:3009134 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007502 (micafungin); database assertion, not a primary citation.)
|
UNKNOWN 9
UNKNOWN
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|
FKS1(F641S) (amino acid mutation) [Not assayed] associated with resistance to micafungin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. |
— |
Candida albicans NCBITaxon:5476
strain M70 NCBITaxon:237561
UniProtKB:A0A1D8PCT0
PHIPO:0000575 |
— |
- PMID:16723566 (PHI-base primary-literature antimicrobial interaction PHIG:1428; joined to this record by exact ChEBI identifier.)
Cell growth assay |
FKS1(L644F S645C) (amino acid mutation) [Not assayed] associated with resistance to micafungin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. |
— |
Candida albicans NCBITaxon:5476
strain M70 NCBITaxon:237561
UniProtKB:A0A1D8PCT0
PHIPO:0000575 |
— |
- PMID:16723566 (PHI-base primary-literature antimicrobial interaction PHIG:1428; joined to this record by exact ChEBI identifier.)
Cell growth assay |
FKS1(P647A) (amino acid mutation) [Not assayed] associated with resistance to micafungin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. |
— |
Saccharomyces cerevisiae NCBITaxon:4932
strain BY4742 NCBITaxon:559292
UniProtKB:P38631 YLR342W_mRNA
PHIPO:0000575 |
— |
- PMID:18443110 (PHI-base primary-literature antimicrobial interaction PHIG:2386; joined to this record by exact ChEBI identifier.)
Cell growth assay |
FKS1(S645F) (amino acid mutation) [Not assayed] associated with resistance to micafungin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. |
— |
Candida albicans NCBITaxon:5476
strain M70 NCBITaxon:237561
UniProtKB:A0A1D8PCT0
PHIPO:0000575 |
— |
- PMID:16723566 (PHI-base primary-literature antimicrobial interaction PHIG:1428; joined to this record by exact ChEBI identifier.)
Cell growth assay |
FKS1(S645F) (amino acid mutation) [Not assayed] associated with resistance to micafungin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. |
— |
Candida albicans NCBITaxon:5476
strain SC5314 NCBITaxon:237561
UniProtKB:A0A1D8PCT0
PHIPO:0000575 |
— |
- PMID:16723566 (PHI-base primary-literature antimicrobial interaction PHIG:1428; joined to this record by exact ChEBI identifier.)
Cell growth assay |
FKS1(S645P) (amino acid mutation) [Not assayed] associated with resistance to micafungin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. |
— |
Candida albicans NCBITaxon:5476
strain M70 NCBITaxon:237561
UniProtKB:A0A1D8PCT0
PHIPO:0000575 |
— |
- PMID:16723566 (PHI-base primary-literature antimicrobial interaction PHIG:1428; joined to this record by exact ChEBI identifier.)
Cell growth assay |
FKS1(S645P) (amino acid mutation) [Not assayed] associated with resistance to micafungin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. |
— |
Candida albicans NCBITaxon:5476
strain SC5314 NCBITaxon:237561
UniProtKB:A0A1D8PCT0
PHIPO:0000575 |
— |
- PMID:16723566 (PHI-base primary-literature antimicrobial interaction PHIG:1428; joined to this record by exact ChEBI identifier.)
Cell growth assay |
FKS1(S645Y) (amino acid mutation) [Not assayed] associated with resistance to micafungin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. |
— |
Candida albicans NCBITaxon:5476
strain M70 NCBITaxon:237561
UniProtKB:A0A1D8PCT0
PHIPO:0000575 |
— |
- PMID:16723566 (PHI-base primary-literature antimicrobial interaction PHIG:1428; joined to this record by exact ChEBI identifier.)
Cell growth assay |
FKS1(S645Y) (amino acid mutation) [Not assayed] associated with resistance to micafungin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. |
— |
Candida albicans NCBITaxon:5476
strain SC5314 NCBITaxon:237561
UniProtKB:A0A1D8PCT0
PHIPO:0000575 |
— |
- PMID:16723566 (PHI-base primary-literature antimicrobial interaction PHIG:1428; joined to this record by exact ChEBI identifier.)
Cell growth assay |
Curation history
-
SEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
-
RESEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
2026-09-02 · seed_from_sources
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
2026-09-02 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
2026-09-03 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
2026-09-03 · seed_from_sources
Re-seeded from updated data/raw/ inventories
Provenance
Seeded by scripts/seed_from_sources.py from the committed
inventories in data/raw/.
View the record.