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CHEBI:69136 - latrunculin A

Default Structure
ChEBI IDCHEBI:69136
ChEBI Namelatrunculin A
Stars
DefinitionA bicyclic macrolide natural product consisting of a 16-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge Latrunculia magnifica and from the Fiji Islands sponge Cacospongia mycofijiensis. Latrunculin A inhibits actin polymerisation, microfilament organsation and microfilament-mediated processes.
Secondary ChEBI IDCHEBI:43626
Last Modified23 November 2012
DownloadsMolfile
FormulaC22H31NO5S
Net Charge0
Average Mass421.559
Monoisotopic Mass421.19229
SMILES[H][C@@]1([C@@]2(O)C[C@H]3C[C@@H](CC[C@H](C)/C=C\C=C\CC/C(C)=C\C(=O)O3)O2)CSC(=O)N1
InChIInChI=1S/C22H31NO5S/c1-15-7-5-3-4-6-8-16(2)11-20(24)27-18-12-17(10-9-15)28-22(26,13-18)19-14-29-21(25)23-19/h3-5,7,11,15,17-19,26H,6,8-10,12-14H2,1-2H3,(H,23,25)/b4-3+,7-5-,16-11-/t15-,17-,18-,19+,22-/m1/s1
InChIKeyDDVBPZROPPMBLW-IZGXTMSKSA-N
Species of MetaboliteComponentSourceComments
Cacospongia mycofijiensis (ncbitaxon:1162744) - PubMed (22129061)
Roles Classification
Biological Roles:
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
actin polymerisation inhibitor  Any substance that inhibits the polymerisation of the protein actin.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
latrunculin A (CHEBI:69136) has role actin polymerisation inhibitor (CHEBI:70728)
latrunculin A (CHEBI:69136) has role metabolite (CHEBI:25212)
latrunculin A (CHEBI:69136) has role toxin (CHEBI:27026)
latrunculin A (CHEBI:69136) is a cyclic hemiketal (CHEBI:59780)
latrunculin A (CHEBI:69136) is a macrolide (CHEBI:25106)
latrunculin A (CHEBI:69136) is a oxabicycloalkane (CHEBI:46733)
latrunculin A (CHEBI:69136) is a thiazolidinone (CHEBI:48891)
IUPAC Name 
(4R)-4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one
Synonyms  Source
(4R)-4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-onePDBeChem
LatAChEBI
LAT-AChemIDplus
(+)-latrunculin AChEBI
LATRUNCULIN APDBeChem
NSC 613011ChemIDplus
Manual XrefsDatabases
LARPDBeChem
Registry NumbersSources
Reaxys:4239363Reaxys
CAS:76343-93-6ChemIDplus
Citations