CHEBI:72630 - papulacandin D

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ChEBI Name papulacandin D
ChEBI ID CHEBI:72630
Definition A papulacandin that is papulacandin A in which the 6-O-acylgalactosyl group is replaced by a hydrogen. 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 C31H42O10
Net Charge 0
Average Mass 574.65920
Monoisotopic Mass 574.27780
InChI InChI=1S/C31H42O10/c1-4-19(2)11-7-5-8-12-20(3)23(34)13-9-6-10-14-26(36)40-29-28(37)25(17-32)41-31(30(29)38)27-21(18-39-31)15-22(33)16-24(27)35/h5-6,8-10,12,14-16,19,23,25,28-30,32-35,37-38H,4,7,11,13,17-18H2,1-3H3/b8-5+,9-6+,14-10+,20-12+/t19-,23-,25+,28+,29-,30+,31-/m0/s1
InChIKey XKSZJTQIZHUMGA-HPZFVNCBSA-N
SMILES CC[C@H](C)CC\C=C\C=C(/C)[C@@H](O)C\C=C\C=C\C(=O)O[C@H]1[C@H](O)[C@@H](CO)O[C@]2(OCc3cc(O)cc(O)c23)[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 D (CHEBI:72630) has role antifungal agent (CHEBI:35718)
papulacandin D (CHEBI:72630) has role metabolite (CHEBI:25212)
papulacandin D (CHEBI:72630) is a monosaccharide derivative (CHEBI:63367)
papulacandin D (CHEBI:72630) is a organic heterotricyclic compound (CHEBI:26979)
papulacandin D (CHEBI:72630) is a papulacandin (CHEBI:72596)
IUPAC Name
(1S,3'R,4'S,5'R,6'R)-3',5,5',7-tetrahydroxy-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
(+)-papulacandin D ChEBI
(+)-papulacandin-D ChEBI
papulacandin-D ChEBI
Registry Numbers Types Sources
61036-49-5 CAS Registry Number ChemIDplus
7239678 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17305346 PubMed citation Europe PMC
20711516 PubMed citation Europe PMC
7440418 PubMed citation Europe PMC
Last Modified
27 February 2013
General Comment
2013-02-27 See also Anthony G. M. Barrett, Michael Pena and J. Adam Willardsen, 'Total synthesis and structural elucidation of the antifungal agent papulacandin D.' J. Org. Chem., 1996, 61 (3), pp 1082-1100. DOI: 10.1021/jo951895e