CHEBI:49703 - latrunculin B

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ChEBI Name latrunculin B
ChEBI ID CHEBI:49703
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H29NO5S
Net Charge 0
Average Mass 395.51300
Monoisotopic Mass 395.177
InChI InChI=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
InChIKey NSHPHXHGRHSMIK-JRIKCGFMSA-N
SMILES [H][C@]1(CSC(=O)N1)[C@@]1(O)C[C@H]2C[C@@H](CC[C@H](C)\C=C/CC\C(C)=C/C(=O)O2)O1
Roles Classification
Biological Role(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
(+)-latrunculin B ChEBI
Lat B ChEBI
LAT-B ChemIDplus
LATRUNCULIN B PDBeChem
Manual Xref Database
LAB PDBeChem
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Registry Numbers Types Sources
5456050 Reaxys Registry Number Reaxys
76343-94-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14613176 PubMed citation Europe PMC
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Last Modified
06 June 2014