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> Main
CHEBI:49703 - latrunculin B
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ChEBI Ontology
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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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Molfile
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Formula
C20H29NO5S
Net Charge
0
Average Mass
395.51300
Monoisotopic Mass
395.17664
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.
View more via ChEBI Ontology
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
(4
R
)-
4-
[(1
R
,4
Z
,8
Z
,10
S
,13
R
,15
R
)-
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
View more database links
Registry Numbers
Types
Sources
5456050
Reaxys Registry Number
Reaxys
76343-94-7
CAS Registry Number
ChemIDplus
Citations
Types
Sources
14613176
PubMed citation
Europe PMC
16499319
PubMed citation
Europe PMC
18342638
PubMed citation
Europe PMC
21831923
PubMed citation
Europe PMC
22138731
PubMed citation
Europe PMC
22175603
PubMed citation
Europe PMC
22247475
PubMed citation
Europe PMC
23341780
PubMed citation
Europe PMC
23483897
PubMed citation
Europe PMC
23541521
PubMed citation
Europe PMC
23727052
PubMed citation
Europe PMC
23935614
PubMed citation
Europe PMC
Last Modified
06 June 2014