Drug General Information
Drug ID
D03ZFG
Former ID
DAP000659
Drug Name
Cerulenin
Synonyms
Helicocerin; Cerulenin, Cephalosporium caerulens; Oxiranecarboxamide, 3-(1-oxo-4,7-nonadienyl)-, (2R-(2-alpha,3-alpha(4E,7E)))-(9CI); (2R,3S)-2,3-Epoxy-4-oxo-7E,10E-dodecadienamide; (2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)-oxirane-2-carboxylic acid amide; (2R,3S)-3-((4E,7E)-nona-4,7-dienoyl)oxirane-2-carboxamide; (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide; (2R,3S)-3-nona-4,7-dienoyloxirane-2-carboxamide; (2R,3S,E,E)-2,3-Epoxy-4-oxo-7,10-dodecadienamide; (2R-(2alpha,3alpha(4E,7E)))-3-(1-Oxonona-4,7-dienyl)oxirane-2-carboxamide; (2S)(3R)-2,3-Epoxy-4-oxo-7,10-dodecadienoylamide; (2S,3R)-2,3-epoxy-4-oxy-7,10-dodecadienoylamide; (2r,3s)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide; 2,3-Epoxy-4-oxo-7,10-dodecadienamide; 2,3-Epoxy-4-oxo-7,10-dodecadienoylamide; 3-(1-Oxo-4,7-nonadienyl)oxiranecarboxamide; 3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide; 3-nona-4,7-dienoyloxirane-2-carboxamide
Drug Type
Small molecular drug
Indication Dramatic weight loss [ICD9: 783.21; ICD10:R63.4] Approved [536472]
Therapeutic Class
Antiinfective Agents
Structure
Download
2D MOL

3D MOL

Formula
C12H17NO3
Canonical SMILES
CC=CCC=CCCC(=O)C1C(O1)C(=O)N
InChI
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+
InChIKey
GVEZIHKRYBHEFX-ZIMISOLQSA-N
CAS Number
CAS 17397-89-6
PubChem Compound ID
PubChem Substance ID
Target and Pathway
Target(s) Fatty acid synthase Target Info Inhibitor [535387], [537249], [537888]
BioCyc Pathway Fatty acid biosynthesis initiation
Fatty acid elongation -- saturated
Palmitate biosynthesis
KEGG Pathway Fatty acid biosynthesis
Metabolic pathways
Fatty acid metabolism
AMPK signaling pathway
Insulin signaling pathway
Pathway Interaction Database p73 transcription factor network
Validated transcriptional targets of deltaNp63 isoforms
PathWhiz Pathway Fatty Acid Biosynthesis
Reactome ChREBP activates metabolic gene expression
Activation of gene expression by SREBF (SREBP)
Fatty Acyl-CoA Biosynthesis
WikiPathways Fatty Acid Biosynthesis
Nuclear Receptors Meta-Pathway
Liver X Receptor Pathway
Activation of Gene Expression by SREBP (SREBF)
SREBF and miR33 in cholesterol and lipid homeostasis
SREBP signalling
Metabolism of water-soluble vitamins and cofactors
Integration of energy metabolism
Fatty acid, triacylglycerol, and ketone body metabolism
AMPK Signaling
References
Ref 536472Novel agents in the management of Mycobacterium tuberculosis disease. Curr Med Chem. 2007;14(18):2000-8.
Ref 535387Proliferation inhibition and apoptosis induction of K562 cells by fatty acid synthase inhibitor--cerulenin. Zhonghua Xue Ye Xue Za Zhi. 2000 May;21(5):244-6.
Ref 537249Inhibition of Fatty Acid Biosynthesis Prevents Adipocyte Lipotoxicity on Human Osteoblasts In Vitro. J Cell Mol Med. 2009 Mar 27.
Ref 537888The antibiotic cerulenin, a novel tool for biochemistry as an inhibitor of fatty acid synthesis. Bacteriol Rev. 1976 Sep;40(3):681-97.

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