echinocandin B

CHEBI:315018 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A cyclic hexapeptide echinocandin antibiotic isolated from Aspergillus nidulans var. echinulatus with specific anti-yeast activity. — 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

Strictly broader compounds or drug classes this molecule belongs to.

echinocandin CHEBI:57248

Chemical structure

Computed structure properties
Molecular formula	C52H81N7O16
Charge	0
Average mass	1060.253 Da
Monoisotopic mass	1059.57398 Da
Source	ChEBI
InChIKey	FAUOJMHVEYMQQG-HVYQDZECSA-N

SMILES

CCCCC/C=C\C/C=C\CCCCCCCC(=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]([C@@H](C)O)NC(=O)[C@H]([C@H](O)[C@@H](O)c2ccc(O)cc2)NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@H]([C@@H](C)O)NC1=O

InChI

InChI=1S/C52H81N7O16/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-38(65)53-35-26-37(64)48(71)57-50(73)42-43(66)29(2)27-59(42)52(75)40(31(4)61)55-49(72)41(45(68)44(67)32-21-23-33(62)24-22-32)56-47(70)36-25-34(63)28-58(36)51(74)39(30(3)60)54-46(35)69/h9-10,12-13,21-24,29-31,34-37,39-45,48,60-64,66-68,71H,5-8,11,14-20,25-28H2,1-4H3,(H,53,65)(H,54,69)(H,55,72)(H,56,70)(H,57,73)/b10-9-,13-12-/t29-,30+,31+,34+,35-,36-,37+,39-,40-,41-,42-,43-,44-,45-,48+/m0/s1

Also called

(9Z,12Z)-N-{(2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6,20-bis[(1R)-1-hydroxyethyl]-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}octadeca-9,12-dienamide (EXACT_SYNONYM)— chebi
5.1:6-anhydro{(4R,5R)-4,5-dihydroxy-N2-[(9Z,12Z)-octadeca-9,12-dienoyl]-L-ornithyl-L-threonyl-(4R)-4-hydroxy-L-prolyl-(4S)-4-hydroxy-4-(4-hydroxyphenyl)-L-threonyl-L-threonyl-(3S,4S)-3-hydroxy-4-methyl-L-proline} (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

beilstein:5474543
cas:54651-05-7

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antifungal agent CHEBI:35718

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
CHEBI	`CHEBI:315018`	echinocandin B	`antibioticmech:chebi-d06791dc9f`	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

4 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

UNKNOWN 4

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
Historical ACR1-associated laboratory echinocandin B resistance Historical unmapped locus in laboratory derivatives; not a species-wide phenotype. Molecular route, experimental protein and genome remain unresolved.	—	Saccharomyces cerevisiae `NCBITaxon:4932` ACR1	—	PMID:1839761 (Results, native Tables 1-2 and Discussion; DOI:10.1128/aac.35.12.2596. Biochemical and surface observations do not establish a molecular route.) https://wiki.yeastgenome.org/index.php?title=Genetic_Loci&oldid=406670 (ACR1 in the unmapped-locus table, revision 406670; inspected 2026-10-13. Modern alias matches are not accepted protein crosswalks.) Comparative growth susceptibility
Historical ACR2-associated laboratory echinocandin B resistance Historical unmapped locus in laboratory derivatives; not a species-wide phenotype. Molecular route, experimental protein and genome remain unresolved.	—	Saccharomyces cerevisiae `NCBITaxon:4932` ACR2	—	PMID:1839761 (Results, native Tables 1-2 and Discussion; DOI:10.1128/aac.35.12.2596. Biochemical and surface observations do not establish a molecular route.) https://wiki.yeastgenome.org/index.php?title=Genetic_Loci&oldid=406670 (ACR2 in the unmapped-locus table, revision 406670; inspected 2026-10-13. Modern alias matches are not accepted protein crosswalks.) Comparative growth susceptibility
Historical ACR3-associated laboratory echinocandin B resistance Historical unmapped locus in laboratory derivatives; not a species-wide phenotype. Molecular route, experimental protein and genome remain unresolved.	—	Saccharomyces cerevisiae `NCBITaxon:4932` ACR3	—	PMID:1839761 (Results, native Tables 1-2 and Discussion; DOI:10.1128/aac.35.12.2596. Biochemical and surface observations do not establish a molecular route.) https://wiki.yeastgenome.org/index.php?title=Genetic_Loci&oldid=406670 (ACR3 in the unmapped-locus table, revision 406670; inspected 2026-10-13. Modern alias matches are not accepted protein crosswalks.) Comparative growth susceptibility
Historical ACR4-associated laboratory echinocandin B resistance Historical unmapped locus in laboratory derivatives; not a species-wide phenotype. Molecular route, experimental protein and genome remain unresolved.	—	Saccharomyces cerevisiae `NCBITaxon:4932` ACR4	—	PMID:1839761 (Results, native Tables 1-2 and Discussion; DOI:10.1128/aac.35.12.2596. Biochemical and surface observations do not establish a molecular route.) https://wiki.yeastgenome.org/index.php?title=Genetic_Loci&oldid=406670 (ACR4 in the unmapped-locus table, revision 406670; inspected 2026-10-13. Modern alias matches are not accepted protein crosswalks.) Comparative growth susceptibility

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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
CURATED_RESISTANCE_EVIDENCE 2026-10-13 · codex · LLM-assisted
Added compound-specific historical ACR locus associations from primary results. Kept the molecular route unknown, rejected unsupported modern alias/protein joins, and retained species-only taxonomy. Existing claims are unchanged; no allele, genome or numerical AST assigned. Whole-record review remains open.

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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