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CHEBI:65570 - caminoside A

Default Structure
ChEBI IDCHEBI:65570
ChEBI Namecaminoside A
Stars
DefinitionA glycolipid with an unusual non-glycerol aglycone, 10-hydroxynonadecan-2-one that is glycosylated at the C10 hydroxy group by a branched tetrasaccharide residue. It is isolated from the marine sponge Caminus sphaeroconia and exhibits potent activity as an inhibitor of a type III bacterial secretory system.
Last Modified4 December 2012
DownloadsMolfile
FormulaC49H86O22
Net Charge0
Average Mass1027.205
Monoisotopic Mass1026.56107
SMILES[H][C@@]1(O[C@H]2[C@H](O[C@@]3([H])[C@H](O[C@H](CCCCCCCCC)CCCCCCCC(C)=O)O[C@H](CO)[C@@H](O)[C@@H]3O)O[C@H](CO[C@@H]3O[C@H](C)[C@H](O)[C@H](O)[C@@H]3O)[C@@H](OC(C)=O)[C@@H]2OC(=O)CCC)O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]1O
InChIInChI=1S/C49H86O22/c1-7-9-10-11-12-15-18-22-30(23-19-16-13-14-17-21-26(3)51)66-48-43(39(59)36(56)31(24-50)67-48)70-49-45(71-47-41(61)38(58)35(55)28(5)64-47)44(69-33(53)20-8-2)42(65-29(6)52)32(68-49)25-62-46-40(60)37(57)34(54)27(4)63-46/h27-28,30-32,34-50,54-61H,7-25H2,1-6H3/t27-,28+,30-,31-,32-,34+,35+,36-,37+,38-,39+,40+,41+,42-,43-,44+,45-,46-,47+,48-,49+/m1/s1
InChIKeyXTQWRNIJLVUYJY-ZFMPSFEPSA-N
Species of MetaboliteComponentSourceComments
Caminus sphaeroconia (WORMS:170055) - PubMed (12423093)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
ChEBI Ontology
Outgoing Relation(s)
caminoside A (CHEBI:65570) has role antibacterial agent (CHEBI:33282)
caminoside A (CHEBI:65570) has role metabolite (CHEBI:25212)
caminoside A (CHEBI:65570) is a acetate ester (CHEBI:47622)
caminoside A (CHEBI:65570) is a butyrate ester (CHEBI:50477)
caminoside A (CHEBI:65570) is a glycolipid (CHEBI:33563)
caminoside A (CHEBI:65570) is a methyl ketone (CHEBI:51867)
caminoside A (CHEBI:65570) is a tetrasaccharide derivative (CHEBI:63567)
caminoside A (CHEBI:65570) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(10R)-2-oxononadecan-10-yl 6-deoxy-α-L-glucopyranosyl-(1→2)-[6-deoxy-β-D-talopyranosyl-(1→6)]-4-O-acetyl-3-O-butyryl-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside
Registry NumbersSources
Reaxys:9985572Reaxys
Citations