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Substrate Report for: Cerulenin-hemiaminal

Name Class
Cerulenin-hemiaminalTypeEpoxide
Other_NameSCHEMBL12202400
Chemical_Nomenclature(1R,4R,5S)-4-hydroxy-4-[(3E,6E)-octa-3,6-dienyl]-6-oxa-3-azabicyclo[3.1.0]hexan-2-one
FormulaC12H17NO3
MW223.27
PaperCogan_2020_ACS.Chem.Biol_15_2783
CommentCerulenin is an epoxydodecadienamide isolated from several fungi species, including Acremonium, Acrocylindrum and Helicoceras Cephalosporium caerulens. It inhibits the biosynthesis of several lipids by interfering with enzyme function. It has a role as an antifungal agent, an antiinfective agent, an antilipemic drug, an antimetabolite, a fatty acid synthesis inhibitor and an antimicrobial agent. It is a monocarboxylic acid amide and an epoxide.In fatty acid synthesi inhibits b-keto-acyl-ACP synthase. In sterol synthesis, inhibits HMG-CoA synthetase activity. Interconversion of cerulenin from its linear to cyclic hemiaminal form,occurs in polar protic solvents. It is this hemiaminal form which is substrate of epoxide ring opening by NcmC
Gene_locus9pseu-NcmC
CID88892498
FamilyDieckmann_Cyclase
InChIKeyXYRMBRBAWFZQDU-NUBWZSAQSA-N
CanonicalSMILESCC=CCC=CCCC1(C2C(O2)C(=O)N1)O
InChIInChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-12(15)10-9(16-10)11(14)13-12/h2-3,5-6,9-10,15H,4,7-8H2,1H3,(H,13,14)/b3-2+,6-5+/t9-,10+,12-/m1/s1

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Mail to: Nicolas Lenfant, Thierry Hotelier, Yves Bourne, Pascale Marchot and Arnaud Chatonnet.
Please cite: Lenfant 2013 Nucleic.Acids.Res. or Marchot Chatonnet 2012 Prot.Pept Lett.
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