papulacandin A

CHEBI:72611 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A papulacandin substituted by a (2E,4E)-deca-2,4-dienoyl chain at the O-(6') position and a (2E,4E,7S,8E,10E,14S)-7-hydroxy-8,14-dimethylhexadeca-2,4,8,10-tetraenoyl chain at the O-(3) position. It is a 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.

CHEBI:26979 CHEBI:26979
CHEBI:63353 CHEBI:63353
CHEBI:72596 CHEBI:72596

Chemical structure

Computed structure properties
Molecular formula	C47H66O16
Charge	0
Average mass	887.029 Da
Monoisotopic mass	886.43509 Da
Source	ChEBI
InChIKey	DPVWBQZOSHCQTG-NVTMJBNDSA-N

SMILES

CCCCC/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/C47H66O16/c1-5-7-8-9-10-11-17-22-37(52)58-28-36-40(54)41(55)42(56)46(60-36)62-43-35(26-48)63-47(39-31(27-59-47)24-32(49)25-34(39)51)45(57)44(43)61-38(53)23-18-13-16-21-33(50)30(4)20-15-12-14-19-29(3)6-2/h10-13,15-18,20,22-25,29,33,35-36,40-46,48-51,54-57H,5-9,14,19,21,26-28H2,1-4H3/b11-10+,15-12+,16-13+,22-17+,23-18+,30-20+/t29-,33-,35+,36+,40-,41-,42+,43+,44-,45+,46-,47-/m0/s1

Also called

(1S,3'R,4'R,5'R,6'R)-5'-({6-O-[(2E,4E)-deca-2,4-dienoyl]-β-D-galactopyranosyl}oxy)-3',5,7-trihydroxy-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
A-32283-A (EXACT_SYNONYM)— chebi
papulacandin-A (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:61036-46-2
reaxys:6444369

Activity roles

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

CHEBI:33281 CHEBI:33281
CHEBI:35718 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:72611`	papulacandin A	`antibioticmech:chebi-c65db1785b`	2026-08-30

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

Provenance

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