CHEBI:569624 - papulacandin B

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ChEBI Name papulacandin B
ChEBI ID CHEBI:569624
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C47H64O17
Net Charge 0
Average Mass 901.00090
Monoisotopic Mass 900.41435
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
InChIKey UJLFRJFJTPPIOK-RZGJRGQUSA-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@@]2(OCc3cc(O)cc(O)c23)O[C@H](CO)[C@H]1O[C@@H]1O[C@H](COC(=O)\C=C\C=C/C=C/C(O)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 B (CHEBI:569624) has functional parent α-lactose (CHEBI:36219)
papulacandin B (CHEBI:569624) has role antifungal agent (CHEBI:35718)
papulacandin B (CHEBI:569624) has role metabolite (CHEBI:25212)
papulacandin B (CHEBI:569624) is a disaccharide derivative (CHEBI:63353)
papulacandin B (CHEBI:569624) is a organic heterotricyclic compound (CHEBI:26979)
papulacandin B (CHEBI:569624) is a papulacandin (CHEBI:72596)
IUPAC Name
(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
Synonym Source
papulacandin-B ChEBI
Manual Xref Database
Papulacandin_B Wikipedia
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Registry Numbers Types Sources
61032-80-2 CAS Registry Number ChemIDplus
7682569 Beilstein Registry Number Beilstein
7682569 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20711516 PubMed citation Europe PMC
3735029 PubMed citation Europe PMC
380990 PubMed citation Europe PMC
6396177 PubMed citation Europe PMC
7440418 PubMed citation Europe PMC
852996 PubMed citation Europe PMC
Last Modified
27 February 2013