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CHEBI:69136 - latrunculin A

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:
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.
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
LATRUNCULIN APDBeChem
(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
(+)-latrunculin AChEBI
NSC 613011ChemIDplus
LAT-AChemIDplus
LatAChEBI
Manual XrefsDatabases
LARPDBeChem
Registry NumbersSources
Reaxys:4239363Reaxys
CAS:76343-93-6ChemIDplus
Citations