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CHEBI:72611 - papulacandin A

ChEBI IDCHEBI:72611
ChEBI Namepapulacandin A
Stars
DefinitionA 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.
Last Modified27 February 2013
SubmitterGareth Owen
DownloadsMolfile
FormulaC47H66O16
Net Charge0
Average Mass887.029
Monoisotopic Mass886.43509
SMILESCCCCC/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
InChIInChI=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
InChIKeyDPVWBQZOSHCQTG-NVTMJBNDSA-N
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
papulacandin A (CHEBI:72611) has functional parent (2E,4E)-deca-2,4-dienoic acid (CHEBI:72614)
papulacandin A (CHEBI:72611) has functional parent α-lactose (CHEBI:36219)
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  Source
A-32283-AChemIDplus
papulacandin-AChEBI
Registry NumbersSources
Reaxys:6444369Reaxys
CAS:61036-46-2ChemIDplus
Citations