CHEBI:156434 - 5-[[3-(1-phenylethoxy)-4-(2-phenylethoxy)phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid

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ChEBI Name 5-[[3-(1-phenylethoxy)-4-(2-phenylethoxy)phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid
ChEBI ID CHEBI:156434
Definition A member of the class of thiazolidinones that is 2-sulfanylidene-1,3-thiazolidin-4-one in which the hydrogens at positions 3 and 5 are replaced by carboxymethyl and 3-(1-phenylethoxy)-4-(2-phenylethoxy)benzylidene groups, respectively. It is an inhibitor of protein mannosyl transferase 1 (PMT1) and blocks protein O-mannosylation.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Rob Nash
Supplier Information
Download Molfile XML SDF
Formula C28H25NO5S2
Net Charge 0
Average Mass 519.630
Monoisotopic Mass 519.11742
InChI InChI=1S/C28H25NO5S2/c1-19(22-10-6-3-7-11-22)34-24-16-21(17-25-27(32)29(18-26(30)31)28(35)36-25)12-13-23(24)33-15-14-20-8-4-2-5-9-20/h2-13,16-17,19H,14-15,18H2,1H3,(H,30,31)/b25-17-
InChIKey FFYJVTLTZYPAAB-UQQQWYQISA-N
SMILES CC(OC1=CC(\C=C2/SC(=S)N(CC(O)=O)C2=O)=CC=C1OCCC1=CC=CC=C1)C1=CC=CC=C1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
EC 2.4.1.109 (dolichyl-phosphate-mannose-protein mannosyltransferase) inhibitor
An EC 2.4.1.* (hexosyltransferase) inhibitor that interferes with the action of dolichyl-phosphate-mannose-protein mannosyltransferase (EC 2.4.1.109).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 5-[[3-(1-phenylethoxy)-4-(2-phenylethoxy)phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid (CHEBI:156434) has role antifungal agent (CHEBI:35718)
5-[[3-(1-phenylethoxy)-4-(2-phenylethoxy)phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid (CHEBI:156434) has role EC 2.4.1.109 (dolichyl-phosphate-mannose-protein mannosyltransferase) inhibitor (CHEBI:156527)
5-[[3-(1-phenylethoxy)-4-(2-phenylethoxy)phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid (CHEBI:156434) is a aromatic ether (CHEBI:35618)
5-[[3-(1-phenylethoxy)-4-(2-phenylethoxy)phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid (CHEBI:156434) is a monocarboxylic acid (CHEBI:25384)
5-[[3-(1-phenylethoxy)-4-(2-phenylethoxy)phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid (CHEBI:156434) is a thiazolidinone (CHEBI:48891)
IUPAC Name
{(5Z)-4-oxo-5-[3-(1-phenylethoxy)-4-(2-phenylethoxy)benzylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl}acetic acid
Synonyms Sources
[(5Z)-4-oxo-5-{[3-(1-phenylethoxy)-4-(2-phenylethoxy)phenyl]methylidene}-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid IUPAC
OGT2468 SUBMITTER
R3A-5a SUBMITTER
Citations Waiting for Citations Types Sources
15225710 PubMed citation SUBMITTER
21231968 PubMed citation SUBMITTER
24297939 PubMed citation SUBMITTER
28598353 PubMed citation SUBMITTER
Last Modified
21 September 2020