CHEBI:69136 - latrunculin A

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ChEBI Name latrunculin A
ChEBI ID CHEBI:69136
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43626
Supplier Information
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Formula C22H31NO5S
Net Charge 0
Average Mass 421.55000
Monoisotopic Mass 421.192
InChI InChI=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
InChIKey DDVBPZROPPMBLW-IZGXTMSKSA-N
SMILES [H][C@]1(CSC(=O)N1)[C@@]1(O)C[C@H]2C[C@@H](CC[C@H](C)\C=C/C=C/CC\C(C)=C/C(=O)O2)O1
Metabolite of Species Details
Cacospongia mycofijiensis (NCBI:txid1162744) See: PubMed
Roles Classification
Biological Role(s): 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.
actin polymerisation inhibitor
Any substance that inhibits the polymerisation of the protein actin.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(+)-latrunculin A ChEBI
(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 PDBeChem
LAT-A ChemIDplus
LatA ChEBI
LATRUNCULIN A PDBeChem
NSC 613011 ChemIDplus
Manual Xref Database
LAR PDBeChem
View more database links
Registry Numbers Types Sources
4239363 Reaxys Registry Number Reaxys
76343-93-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10859320 PubMed citation Europe PMC
12087066 PubMed citation Europe PMC
17897856 PubMed citation Europe PMC
19528469 PubMed citation Europe PMC
20677927 PubMed citation Europe PMC
22492972 PubMed citation Europe PMC
22498812 PubMed citation Europe PMC
3200109 PubMed citation Europe PMC
3556584 PubMed citation Europe PMC
9250716 PubMed citation Europe PMC
Last Modified
23 November 2012