CHEBI:68236 - platensimycin

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ChEBI Name platensimycin
ChEBI ID CHEBI:68236
Definition A monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-amino-2,4-dihydroxybenzoic acid with the carboxy group of the oxatetracyclic cage component. It is an antibiotic isolated from Streptomyces platensis and exhibits inhibitory activity against fatty acid synthase.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H27NO7
Net Charge 0
Average Mass 441.47370
Monoisotopic Mass 441.179
InChI InChI=1S/C24H27NO7/c1-22(7-6-17(28)25-18-14(26)4-3-13(19(18)29)21(30)31)16(27)5-8-24-10-12-9-15(20(22)24)32-23(12,2)11-24/h3-5,8,12,15,20,26,29H,6-7,9-11H2,1-2H3,(H,25,28)(H,30,31)/t12-,15+,20+,22-,23+,24+/m1/s1
InChIKey CSOMAHTTWTVBFL-OFBLZTNGSA-N
SMILES [H][C@]12C[C@@H]3O[C@@]1(C)C[C@@]1(C2)C=CC(=O)[C@@](C)(CCC(=O)Nc2c(O)ccc(C(O)=O)c2O)[C@]31[H]
Metabolite of Species Details
Streptomyces platensis (NCBI:58346) of strain MA7327 See: PubMed
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): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
EC 2.3.1.85 (fatty acid synthase) inhibitor
An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of fatty acid synthase (EC 2.3.1.85), a multi-enzyme protein involved in fatty acid synthesis.
antibacterial agent
A substance that kills or slows the growth of bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing platensimycin (CHEBI:68236) has role antibacterial agent (CHEBI:33282)
platensimycin (CHEBI:68236) has role antimicrobial agent (CHEBI:33281)
platensimycin (CHEBI:68236) has role bacterial metabolite (CHEBI:76969)
platensimycin (CHEBI:68236) has role EC 2.3.1.85 (fatty acid synthase) inhibitor (CHEBI:71476)
platensimycin (CHEBI:68236) is a aromatic amide (CHEBI:62733)
platensimycin (CHEBI:68236) is a cyclic ether (CHEBI:37407)
platensimycin (CHEBI:68236) is a cyclic ketone (CHEBI:3992)
platensimycin (CHEBI:68236) is a dihydroxybenzoic acid (CHEBI:23778)
platensimycin (CHEBI:68236) is a monocarboxylic acid amide (CHEBI:29347)
platensimycin (CHEBI:68236) is a polycyclic cage (CHEBI:33640)
Incoming platensimycin A2 methyl ester (CHEBI:68261) has functional parent platensimycin (CHEBI:68236)
platensimycin A3 methyl ester (CHEBI:68262) has functional parent platensimycin (CHEBI:68236)
platensimycin A4 methyl ester (CHEBI:68263) has functional parent platensimycin (CHEBI:68236)
platensimycin A5 methyl ester (CHEBI:68264) has functional parent platensimycin (CHEBI:68236)
platensimycin A1 (CHEBI:68242) has functional parent platensimycin (CHEBI:68236)
platensimycin B1 (CHEBI:68238) has functional parent platensimycin (CHEBI:68236)
platensimycin B2 (CHEBI:68244) has functional parent platensimycin (CHEBI:68236)
platensimycin B3 (CHEBI:68245) has functional parent platensimycin (CHEBI:68236)
platensimycin B4 (CHEBI:68239) has functional parent platensimycin (CHEBI:68236)
platensimycin methyl ester (CHEBI:68237) has functional parent platensimycin (CHEBI:68236)
IUPAC Name
3-({3-[(1S,4aS,6S,7S,9S,9aR)-1,6-dimethyl-2-oxo-1,2,5,6,7,8,9,9a-octahydro-6,9-epoxy-4a,7-methanobenzo[7]annulen-1-yl]propanoyl}amino)-2,4-dihydroxybenzoic acid
Synonym Source
(−)-platensimycin KEGG COMPOUND
Database Links Databases
C20132 KEGG COMPOUND
CA2770486 Patent
DB08407 DrugBank
Platensimycin Wikipedia
PMN PDBeChem
US2009081673 Patent
View more database links
Registry Numbers Types Sources
10740321 Reaxys Registry Number Reaxys
835876-32-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
20158476 PubMed citation Europe PMC
21214253 PubMed citation Europe PMC
21808805 PubMed citation Europe PMC
21915133 PubMed citation Europe PMC
23373732 PubMed citation Europe PMC
Last Modified
06 March 2014