caspofungin
A semisynthetic 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.
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
-
CHEBI:24613 - echinocandin
CHEBI:57248 -
CHEBI:72588 - antibiotic antifungal drug
CHEBI:87113 - echinocandin antibiotic
ARO:3007496
Chemical structure
| Molecular formula | C52H88N10O15 |
|---|---|
| Charge | 0 |
| Average mass | 1093.331 Da |
| Monoisotopic mass | 1092.64306 Da |
| Source | ChEBI |
| InChIKey | JYIKNQVWKBUSNH-WVDDFWQHSA-N |
[H][C@@]12C[C@@H](O)CN1C(=O)[C@H]([C@@H](C)O)NC(=O)[C@@]([H])(NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)C[C@@H](O)[C@@H](NCCN)NC(=O)[C@@H]1[C@@H](O)CCN1C(=O)[C@H]([C@H](O)CCN)NC(=O)[C@H]([C@H](O)[C@@H](O)c1ccc(O)cc1)NC2=O
InChI=1S/C52H88N10O15/c1-5-28(2)24-29(3)12-10-8-6-7-9-11-13-39(69)56-34-26-38(68)46(55-22-21-54)60-50(75)43-37(67)19-23-61(43)52(77)41(36(66)18-20-53)58-49(74)42(45(71)44(70)31-14-16-32(64)17-15-31)59-48(73)35-25-33(65)27-62(35)51(76)40(30(4)63)57-47(34)72/h14-17,28-30,33-38,40-46,55,63-68,70-71H,5-13,18-27,53-54H2,1-4H3,(H,56,69)(H,57,72)(H,58,74)(H,59,73)(H,60,75)/t28-,29+,30+,33+,34-,35-,36+,37-,38+,40-,41-,42-,43-,44-,45-,46-/m0/s1
Also called
- (10R,12S)-N-{(2R,6S,9S,11R,12S,14aS,15S,20S,23S,25aS)-12-[(2-aminoethyl)amino]-20-[(1R)-3-amino-1-hydroxypropyl]-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,15-trihydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}-10,12-dimethyltetradecanamide
- (4R,5S)-5-((2-aminoethyl)amino)-N2-(10,12-dimethyltetradecanoyl)-4-hydroxy-L-ornithyl-L-threonyl-trans-4-hydroxy-L-prolyl-(S)-4-hydroxy-4-(p-hydroxyphenyl)-L-threonyl-threo-3-hydroxy-L-ornithyl-trans-3-hydroxy-L-proline cyclic (6-1)-peptide
- 1-[(4R,5S)-5-[(2-aminoethyl)amino]-N2-(10,12-dimethyl-1-oxotetradecyl)-4-hydroxy-L-ornithine]-5-[(3R)-3-hydroxy-L-ornithine]-pneumocandin B0
- Caspofungin
Cross-references
- caspofungin
ARO:3007501 - beilstein:8471798
- cas:162808-62-0
- chembl:CHEMBL1630575
- pubchem.compound:3035406
Drug registries
Patents and articles
Activity roles
- antifungal agent
CHEBI:35718 - antifungal drug
CHEBI:86327
Source concepts
| Source | Native ID | Label | Minted CURIE | Version |
|---|---|---|---|---|
| ARO | ARO:3007501 |
caspofungin | antibioticmech:aro-ef25488e10 |
2026-08-30 |
| CHEBI | CHEBI:474180 |
caspofungin | antibioticmech:chebi-0abd2ece56 |
2026-08-30 |
Mechanism summary
- Mode of action
- CELL_WALL_SYNTHESIS_INHIBITION microbial target
Resistance mechanisms
ANTIBIOTIC_TARGET_ALTERATION 18
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Aspergillus fumigatus Cyp51A with mutations conferring resistance to caspofungin | ARO:3009557 | — | ||
| Candida albicans FKS1 with mutations conferring resistance to caspofungin | ARO:3009416 | — | ||
| Candida auris ADE17 with mutations conferring resistance to caspofungin | ARO:3009329 | — | ||
| Candida auris ERG11 lanosterol 14-alpha-demethylase with mutations conferring resistance against caspofungin | ARO:3009395 | — | ||
| Candida auris FKS1 beta-1,3-glucan synthase with mutations conferring resistance to caspofungin | ARO:3009420 | — | ||
| Candida dubliniensis FKS1 beta-1,3-glucan synthase with mutations conferring resistance to caspofungin | ARO:3009592 | — | ||
| Candida glabrata FKS1 beta-1,3-glucan with mutations conferring resistance to caspofungin | ARO:3009231 | — | ||
| Candida glabrata FKS2 with mutations conferring resistance to caspofungin | ARO:3009208 | — | ||
| Candida metapsilosis FKS1 beta-1,3-glucan with mutations conferring resistance to caspofungin | ARO:3009595 | — | ||
| Candida parapsilosis FSK1 beta-1,3-D-glucan synthase with mutations associated with resistance to caspofungin | ARO:3009598 | — | ||
| Candida tropicalis FKS1 beta-1,3-glucan synthase with mutations conferring resistance to caspofungin | ARO:3009601 | — | ||
| Clavispora lusitaniae FKS1 beta-1,3-glucan synthase with mutations conferring resistance to caspofungin | ARO:3009603 | — | ||
| Kluyveromyces marxianus FKS1 beta-1,3-glucan synthase with mutations conferring resistance to caspofungin | ARO:3009605 | — | ||
| Nakaseomyces glabratus Cdc6 with mutations conferring resistance against caspofungin | ARO:3009390 | — | ||
| Nakaseomyces glabratus MRPL11 mutations with resistance to caspofungin | ARO:3009372 | — | ||
| Pichia kudriavzevii Fks1 beta-1,3-glucan synthase with mutations associated with resistance to caspofungin | ARO:3009607 | — | ||
| Saccharomyces cerevisiae FKS1 beta-1,3-D-glucan synthase with mutations conferring resistance to caspofungin | ARO:3009609 | — | ||
| antifungal resistance-associated MSH | ARO:3009134 | — |
UNKNOWN 14
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Candida albicans AIF1 with mutations conferring resistance against caspofungin | ARO:3009378 | — | ||
| Candida spp. High Osmolarity Glycerol 1 conferring resistance to caspofungin via absence | ARO:3007664 | — | ||
| FKS1 transformant(CAI4-R1-FKS1(S645P)) (transformant) [Not assayed] associated with resistance to caspofungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000686 |
— | |
| FKS1(F641S) (amino acid mutation) [Not assayed] associated with resistance to caspofungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000686 |
— | |
| FKS1(L644F S645C) (amino acid mutation) [Not assayed] associated with resistance to caspofungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000686 |
— | |
| FKS1(P647A) (amino acid mutation) [Not assayed] associated with resistance to caspofungin |
— | Saccharomyces cerevisiae NCBITaxon:4932PHIPO:0000686 |
— | |
| FKS1(S645F) (amino acid mutation) [Not assayed] associated with resistance to caspofungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000686 |
— | |
| FKS1(S645F) (amino acid mutation) [Not assayed] associated with resistance to caspofungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000686 |
— | |
| FKS1(S645P) (amino acid mutation) [Not assayed] associated with resistance to caspofungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000686 |
— | |
| FKS1(S645P) (amino acid mutation) [Not assayed] associated with resistance to caspofungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000686 |
— | |
| FKS1(S645Y) (amino acid mutation) [Not assayed] associated with resistance to caspofungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000686 |
— | |
| FKS1(S645Y) (amino acid mutation) [Not assayed] associated with resistance to caspofungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000686 |
— | |
| FKS1-S645P(S645P) (amino acid mutation) [Not assayed] associated with resistance to caspofungin |
— | Candida albicans NCBITaxon:5476PHIPO:0000686 |
— | |
| Saccharomyces cerevasiae AIF1 with mutations conferring resistance against caspofungin | ARO:3009380 | — |
ANTIBIOTIC_EFFLUX 1
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Candida albicans CDR2 with mutations conferring resistance to caspofungin | ARO:3009445 | — |
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
Scoped source protein and reference-strain identifiers to provenance, not exact experimental subjects, after primary-paper review. Parent labels and source biological fields preserved; no new allele, measurement or genome inferred.
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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.