papulacandin B

CHEBI:569624 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A papulacandin that is papulacandin A in which the (2E,4E)-deca-2,4-dienoyl chain at the O-(6') position is replaced by a (2E,4Z,6E)-8-hydroxydeca-2,4,6-trienoyl chain. It is the major carbohydrate-containing antibiotic from the deuteromycetous fungus Papularia sphaerosperma which shows potent antifungal activity against Candida albicans. — 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.

Label unavailable CHEBI:26979
Label unavailable CHEBI:63353
papulacandin CHEBI:72596

Chemical structure

Computed structure properties
Molecular formula	C47H64O17
Charge	0
Average mass	901.012 Da
Monoisotopic mass	900.41435 Da
Source	ChEBI
InChIKey	UJLFRJFJTPPIOK-RZGJRGQUSA-N

SMILES

CCC(O)/C=C/C=C\C=C\C(=O)OC[C@H]1O[C@@H](O[C@H]2[C@H](OC(=O)/C=C/C=C/C[C@H](O)/C(C)=C/C=C/CC[C@@H](C)CC)[C@@H](O)[C@@]3(OCc4cc(O)cc(O)c43)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O

InChI

InChI=1S/C47H64O17/c1-5-28(3)17-11-9-12-18-29(4)33(51)20-14-10-16-22-38(54)62-44-43(35(25-48)64-47(45(44)58)39-30(26-60-47)23-32(50)24-34(39)52)63-46-42(57)41(56)40(55)36(61-46)27-59-37(53)21-15-8-7-13-19-31(49)6-2/h7-10,12-16,18-19,21-24,28,31,33,35-36,40-46,48-52,55-58H,5-6,11,17,20,25-27H2,1-4H3/b8-7-,12-9+,14-10+,19-13+,21-15+,22-16+,29-18+/t28-,31?,33-,35+,36+,40-,41-,42+,43+,44-,45+,46-,47-/m0/s1

Also called

(1S,3'R,4'R,5'R,6'R)-3',5,7-trihydroxy-5'-({6-O-[(2E,4Z,6E)-8-hydroxydeca-2,4,6-trienoyl]-β-D-galactopyranosyl}oxy)-6'-(hydroxymethyl)-3',4',5',6'-tetrahydro-3H-spiro[2-benzofuran-1,2'-pyran]-4'-yl (2E,4E,7S,8E,10E,14S)-7-hydroxy-8,14-dimethylhexadeca-2,4,8,10-tetraenoate (EXACT_SYNONYM)— chebi
papulacandin-B (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.

cas:61032-80-2
reaxys:7682569

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Papulacandin_B

Activity roles

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

antimicrobial agent CHEBI:33281
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:569624`	papulacandin B	`antibioticmech:chebi-836fd9781f`	2026-08-30

Resistance mechanisms

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

UNKNOWN 3

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
Historical ACR1-associated laboratory papulacandin B resistance Historical unmapped locus in laboratory derivatives; not a species-wide phenotype. Molecular route, experimental protein and genome remain unresolved. Compound-specific, background-dependent association; not transferred to ACR2.	—	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 ACR3-associated laboratory papulacandin B resistance Historical unmapped locus in laboratory derivatives; not a species-wide phenotype. Molecular route, experimental protein and genome remain unresolved. Compound-specific, background-dependent association; not transferred to ACR2.	—	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 papulacandin B resistance Historical unmapped locus in laboratory derivatives; not a species-wide phenotype. Molecular route, experimental protein and genome remain unresolved. Compound-specific, background-dependent association; not transferred to ACR2.	—	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

OTHER 2

OTHER
Determinant	ARO ID	Organism	Gene families	Evidence
PBR1-associated papulacandin B resistance in Saccharomyces cerevisiae Laboratory derivatives in the X2180-1A background, not resistance inferred from gene presence or assigned to the parent or species. Reference-only mapping: UniProtKB:P38631 (FKS1, YLR342W; NCBITaxon:559292), not a tested allele or protein assignment. Figures were not independently reanalyzed; no numeric AST or clinical category is inferred. The paper also reports a non-resistant comparison at this locus.	—	Saccharomyces cerevisiae `NCBITaxon:4932` PBR1	FKS1	PMID:7592316 (Primary Results, physiological characterization; Methods identify the tested compounds. Qualitative PDF-text review, not independent image or numeric reanalysis.) UniProtKB:P38631 (Reference locus only; UniProtKB 2026_03, entry version 209, sequence version 2.) Growth susceptibility comparisons
pbr1-associated papulacandin B resistance in Schizosaccharomyces pombe Laboratory derivatives in the 972 background, not resistance inferred from gene presence or assigned to the parent or species. Reference-only mapping: UniProtKB:O74475 (bgs4, SPCC1840.02c; NCBITaxon:284812), not a tested allele or protein assignment. Figures were not independently reanalyzed; no numeric AST or clinical category is inferred. PomBase explicitly aliases pbr1 to bgs4; the inspected UniProt synonym list omits pbr1.	—	Schizosaccharomyces pombe `NCBITaxon:4896` pbr1	bgs4	PMID:7592316 (Primary Results, physiological characterization; Methods identify the tested compounds. Qualitative PDF-text review, not independent image or numeric reanalysis.) UniProtKB:O74475 (Reference locus only; UniProtKB 2026_03, entry version 158, sequence version 1.) https://www.pombase.org/gene/SPCC1840.02c (Reference-name alias and UniProt cross-reference only; official gene page inspected 2026-10-09, release date 2026-09-15.) Growth susceptibility comparisons

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
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANCE_EVIDENCE 2026-10-09 · codex · LLM-assisted
Added primary author-reported qualitative gene associations with species grounding and reference-only UniProt provenance. Kept experimental allele, strain and genome assignments unresolved; no quantitative AST added; figure review remains pending.
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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