CHEBI:72611 - papulacandin A

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ChEBI Name papulacandin A
ChEBI ID CHEBI:72611
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C47H66O16
Net Charge 0
Average Mass 887.01730
Monoisotopic Mass 886.43509
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
InChIKey DPVWBQZOSHCQTG-NVTMJBNDSA-N
SMILES CCCCC\C=C\C=C\C(=O)OC[C@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@]3(OCc4cc(O)cc(O)c34)[C@H](O)[C@H]2OC(=O)\C=C\C=C\C[C@H](O)C(\C)=C\C=C\CC[C@@H](C)CC)[C@H](O)[C@@H](O)[C@H]1O
Roles Classification
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via carbohydrate-containing antibiotic )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing papulacandin A (CHEBI:72611) has functional parent α-lactose (CHEBI:36219)
papulacandin A (CHEBI:72611) has functional parent (2E,4E)-deca-2,4-dienoic acid (CHEBI:72614)
papulacandin A (CHEBI:72611) has role antifungal agent (CHEBI:35718)
papulacandin A (CHEBI:72611) has role metabolite (CHEBI:25212)
papulacandin A (CHEBI:72611) is a disaccharide derivative (CHEBI:63353)
papulacandin A (CHEBI:72611) is a organic heterotricyclic compound (CHEBI:26979)
papulacandin A (CHEBI:72611) is a papulacandin (CHEBI:72596)
IUPAC Name
(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
Synonyms Sources
A-32283-A ChemIDplus
papulacandin-A ChEBI
Registry Numbers Types Sources
61036-46-2 CAS Registry Number ChemIDplus
6444369 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20711516 PubMed citation Europe PMC
7440418 PubMed citation Europe PMC
Last Modified
27 February 2013