1X9

Cerulenin

Created:	2013-08-27
Last modified:	2020-06-05

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1 entries where 1X9 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	33
Chiral Atom Count	2
Bond Count	33
Aromatic Bond Count	0

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Chemical Component Summary
Name	Cerulenin
Synonyms	(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
Systematic Name (OpenEye OEToolkits)	(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
Formula	C₁₂ H₁₇ N O₃
Molecular Weight	223.268
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C(CC/C=C/C/C=C/C)C1OC1C(=O)N
SMILES	CACTVS	3.385	CC=CCC=CCCC(=O)[CH]1O[CH]1C(N)=O
SMILES	OpenEye OEToolkits	1.7.6	CC=CCC=CCCC(=O)C1C(O1)C(=O)N
Canonical SMILES	CACTVS	3.385	C\C=C\C/C=C/CCC(=O)[C@H]1O[C@H]1C(N)=O
Canonical SMILES	OpenEye OEToolkits	1.7.6	C/C=C/C/C=C/CCC(=O)[C@@H]1[C@@H](O1)C(=O)N
InChI	InChI	1.03	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+/t10-,11-/m1/s1
InChIKey	InChI	1.03	GVEZIHKRYBHEFX-NQQPLRFYSA-N

Drug Info: DrugBank

DrugBank ID	DB01034
Name	Cerulenin
Groups	experimental
Description	Cerulenin 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
Indication	For 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 Lipid Regulating Agents
CAS number	17397-89-6

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
3-oxoacyl-[acyl-carrier-protein] synthase 1	MKRAVITGLGIVSSIGNNQQEVLASLREGRSGITFSQELKDSGMRSHVWG...	unknown	inhibitor
3-oxoacyl-[acyl-carrier-protein] synthase 2	MSKRRVVVTGLGMLSPVGNTVESTWKALLAGQSGISLIDHFDTSAYATKF...	unknown	inhibitor
3-oxoacyl-[acyl-carrier-protein] synthase 3	MYTKIIGTGSYLPEQVRTNADLEKMVDTSDEWIVTRTGIRERHIAAPNET...	unknown	inhibitor
Fatty acid synthase	MEEVVIAGMSGKLPESENLQEFWDNLIGGVDMVTDDDRRWKAGLYGLPRR...	unknown	inhibitor

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