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Cerulenin


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Chemical Component Summary

NameCerulenin
Synonyms(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
Identifiers(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
FormulaC12 H17 N O3
Molecular Weight223.268
TypeNON-POLYMER
Isomeric SMILESC/C=C/C/C=C/CCC(=O)[C@@H]1[C@@H](O1)C(=O)N
InChIInChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1
InChIKeyGVEZIHKRYBHEFX-NQQPLRFYSA-N

Chemical Details

Formal Charge0
Atom Count33
Chiral Atom Count2
Bond Count33
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB01034 
NameCerulenin
Groups experimental
DescriptionCerulenin is an antifungal agent whose activity interferes with or otherwise acts to prevent the formation of fatty acids and sterols. In fatty acid synthesis, reported to bind in equimolar ratio to b-keto-acyl-ACP synthase. In sterol synthesis, inhibits HMG-CoA synthetase activity. It is also shown to inhibit feeding and induce dramatic weight loss in mice. It is found naturally in the Cephalosporium caerulensfungus.
Synonyms
  • (2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)-oxirane-2-carboxylic acid amide
  • Cerulenin
  • (2R,3S)-3-((4E,7E)-nona-4,7-dienoyl)oxirane-2-carboxamide
IndicationFor use as a biochemical tool, Cerulenin is shown to cause dramatic weight loss in animals
Categories
  • Amides
  • Anti-Infective Agents
  • Antifungal Agents
  • Fatty Acid Synthesis Inhibitors
  • Hypolipidemic Agents
CAS number17397-89-6

Drug Targets

NameTarget SequencePharmacological ActionActions
3-oxoacyl-[acyl-carrier-protein] synthase 1MKRAVITGLGIVSSIGNNQQEVLASLREGRSGITFSQELKDSGMRSHVWG...unknowninhibitor
3-oxoacyl-[acyl-carrier-protein] synthase 2MSKRRVVVTGLGMLSPVGNTVESTWKALLAGQSGISLIDHFDTSAYATKF...unknowninhibitor
3-oxoacyl-[acyl-carrier-protein] synthase 3MYTKIIGTGSYLPEQVRTNADLEKMVDTSDEWIVTRTGIRERHIAAPNET...unknowninhibitor
Fatty acid synthaseMEEVVIAGMSGKLPESENLQEFWDNLIGGVDMVTDDDRRWKAGLYGLPRR...unknowninhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5282054
ChEMBL CHEMBL45627
ChEBI CHEBI:171741, CHEBI:94649