Cerulenin (CHEM002327)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (30)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:13 UTC
Update Date2026-05-14 16:56:22 UTC
Accession NumberCHEM002327
Identification
Common NameCerulenin
ClassSmall Molecule
DescriptionCerulenin is a solid exogenous compound with the formula C12H17NO3 and an average molecular weight of 223.27 g/mol. Cerulenin belongs to the oxirane carboxylic acids and derivatives, a subclass of epoxides within the organic compounds. It is classified as an organoheterocyclic compound. This compound serves as an antibiotic, antifungal agent, antiinfective agent, and antilipemic drug. Biologically, it acts as an antimetabolite and a fatty acid synthesis inhibitor. Its recorded sources include electrical and electronic equipment, such as magnets and relays, as well as food, food processing and cookware, specifically brew kettles and the preparation of wine or sparkling wine. Cerulenin targets four proteins, specifically acting as an inhibitor of Beta-ketoacyl-[acyl-carrier-protein] synthase III (fabH), 3-oxoacyl-[acyl-carrier-protein] synthase 1 (fabB), and 3-oxoacyl-[acyl-carrier-protein] synthase 2 (fabF). It irreversibly binds to fatty acid synthase (FASN), specifically the b-ketoacyl-acyl carrier protein synthase condensation enzymes FabH, FabB, and FabF. Because a number of tumor cells and cell lines have been observed to have highly upregulated expression and activity of fatty acid synthase (FAS), the inhibition of FAS by cerulenin leads to apoptosis and cytotoxicity in human cancer cell lines. This effect is believed to be mediated by the accumulation of malonyl-coenzyme A in cells with an upregulated FAS pathway.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Antibiotic, Antifungal
  • Antifungal Agent
  • Drug
  • Ether
  • Fatty Acid Synthesis Inhibitor
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)-oxirane-2-carboxylic acid amideChEBI
(2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)oxirane-2-carboxamideChEBI
(2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)-oxirane-2-carboxylate amideGenerator
CeruleninMeSH
2,3-Epoxy-4-oxo-7,10-dodecadienoylamideMeSH
Chemical FormulaC12H17NO3
Average Molecular Mass223.272 g/mol
Monoisotopic Mass223.121 g/mol
CAS Registry Number17397-89-6
IUPAC Name(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboximidic acid
Traditional Namecerulenin
SMILES[H]\C(C)=C(\[H])C\C([H])=C(/[H])CCC(=O)[C@@]1([H])O[C@@]1([H])C(O)=N
InChI IdentifierInChI=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
InChI KeyGVEZIHKRYBHEFX-NQQPLRFYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oxirane carboxylic acids and derivatives. Oxirane carboxylic acids and derivatives are compounds containing an oxirane ring bearing a carboxylic acid group (or a derivative thereof).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassEpoxides
Sub ClassOxirane carboxylic acids and derivatives
Direct ParentOxirane carboxylic acids and derivatives
Alternative Parents
Substituents
  • Oxirane carboxylic acid or derivatives
  • Monosaccharide
  • Carboxamide group
  • Ketone
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point93.5°C
Boiling PointNot Available
SolubilitySlightly soluble
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP1.83ALOGPS
logP-0.33ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)-3.4ChemAxon
pKa (Strongest Basic)12.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area73.68 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity73.48 m³·mol⁻¹ChemAxon
Polarizability23.62 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-1290000000-202e41a2408ad9df3f62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-8950000000-c0265c2ede42a8a7b944Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frf-9100000000-c8d70361d98f08b9775aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-4490000000-130e0abcad17614007d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0570-9830000000-b6afbfbbfa11b458c4baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-289b3846b10b0578e10fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityIrreversibly binds to fatty acid synthase, specifically b-ketoacyl-acyl carrier protein synthase (FabH, FabB and FabF condensation enzymes). A number of tumor cells and cell lines have been observed to have highly upregulated expression and activity of fatty acid synthase (FAS). Inhibition of FAS by cerulenin leads to cytotoxicity and apoptosis in human cancer cell lines, an effect believed to be mediated by the accumulation of malonyl-coenzyme A in cells with an upregulated FAS pathway.
MetabolismNot Available
Toxicity ValuesLD50: 547 mg/kg (Oral, Mouse) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor use as a biochemical tool, Cerulenin is shown to cause dramatic weight loss in animals
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overexposure include moderate to severe erythema (redness) and moderate edema (raised skin), nausea, vomiting, and headache.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00018711
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCerulenin
Chemspider IDNot Available
ChEBI ID171741
PubChem Compound ID5282054
Kegg Compound IDC12058
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Garfield P. Royer, Craig A. Townsend, “Cerulenin compounds for fatty acid synthesis inhibition.” U.S. Patent US5539132, issued July, 1975.

MSDSLink
General ReferencesNot Available