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CHEBI:49703 - latrunculin B

ChEBI IDCHEBI:49703
ChEBI Namelatrunculin B
Stars
DefinitionA macrolide consisting of a 14-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge Latrunculia magnifica.
Last Modified6 June 2014
DownloadsMolfile
FormulaC20H29NO5S
Net Charge0
Average Mass395.521
Monoisotopic Mass395.17664
SMILES[H][C@@]1([C@@]2(O)C[C@H]3C[C@@H](CC[C@H](C)/C=C\CC/C(C)=C\C(=O)O3)O2)CSC(=O)N1
InChIInChI=1S/C20H29NO5S/c1-13-5-3-4-6-14(2)9-18(22)25-16-10-15(8-7-13)26-20(24,11-16)17-12-27-19(23)21-17/h3,5,9,13,15-17,24H,4,6-8,10-12H2,1-2H3,(H,21,23)/b5-3-,14-9-/t13-,15-,16-,17+,20-/m1/s1
InChIKeyNSHPHXHGRHSMIK-JRIKCGFMSA-N
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.
actin polymerisation inhibitor  Any substance that inhibits the polymerisation of the protein actin.
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
ChEBI Ontology
Outgoing Relation(s)
latrunculin B (CHEBI:49703) has role actin polymerisation inhibitor (CHEBI:70728)
latrunculin B (CHEBI:49703) has role metabolite (CHEBI:25212)
latrunculin B (CHEBI:49703) has role toxin (CHEBI:27026)
latrunculin B (CHEBI:49703) is a cyclic hemiketal (CHEBI:59780)
latrunculin B (CHEBI:49703) is a macrolide (CHEBI:25106)
latrunculin B (CHEBI:49703) is a oxabicycloalkane (CHEBI:46733)
latrunculin B (CHEBI:49703) is a thiazolidinone (CHEBI:48891)
IUPAC Name 
(4R)-4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one
Synonyms  Source
LATRUNCULIN BPDBeChem
LAT-BChemIDplus
Lat BChEBI
(+)-latrunculin BChEBI
Manual XrefsDatabases
LABPDBeChem
Registry NumbersSources
Reaxys:5456050Reaxys
CAS:76343-94-7ChemIDplus
Citations