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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:20:23 UTC
Update Date2021-10-13 06:33:58 UTC
HMDB IDHMDB0033594
Secondary Accession Numbers
  • HMDB33594
Metabolite Identification
Common NameCuelure
DescriptionCuelure belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Cuelure is a berry, blueberry, and jam tasting compound. Based on a literature review a small amount of articles have been published on Cuelure.
Structure
Data?1563862430
Synonyms
ValueSource
1-Hexadecanesulfonyl fluorideHMDB
1-HEXADECYLsulfonyl fluorideHMDB
2-Butanone, 4-(P-hydroxyphenyl)-, acetateHMDB
4-(3-Oxobutyl)phenyl acetateHMDB
4-(4-Acetoxyphenyl)-2-butanoneHMDB
4-(P-ACETOXYPHENYL)-2-butanoneHMDB, MeSH
4-(P-Hydroxyphenyl)-2-butanone, acetateHMDB
4-[4-(Acetyloxy)phenyl]-2-butanoneHMDB
Acetate OF 4-(hydroxyphenyl)-2-butanoneHMDB
Cue-lureHMDB, MeSH
FEMA 3652HMDB
HDSFHMDB
P-(3-Oxobutyl)phenyl acetateHMDB
Para-(2-acetylethyl)phenyl acetateHMDB
Pherocon QFFHMDB
Q-LureHMDB
4-(3-Oxobutyl)phenyl acetic acidGenerator
Chemical FormulaC12H14O3
Average Molecular Weight206.2378
Monoisotopic Molecular Weight206.094294314
IUPAC Name4-(3-oxobutyl)phenyl acetate
Traditional Name4-(3-oxobutyl)phenyl acetate
CAS Registry Number3572-06-3
SMILES
CC(=O)CCC1=CC=C(OC(C)=O)C=C1
InChI Identifier
InChI=1S/C12H14O3/c1-9(13)3-4-11-5-7-12(8-6-11)15-10(2)14/h5-8H,3-4H2,1-2H3
InChI KeyUMIKWXDGXDJQJK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol esters
Sub ClassNot Available
Direct ParentPhenol esters
Alternative Parents
Substituents
  • Phenol ester
  • Phenoxy compound
  • Monocyclic benzene moiety
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point123.00 to 124.00 °C. @ 0.20 mm HgThe Good Scents Company Information System
Water Solubility1888 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.323 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.084 g/LALOGPS
logP10(1.91) g/LALOGPS
logP10(1.99) g/LChemAxon
logS10(-3.4) g/LALOGPS
pKa (Strongest Acidic)19.59ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity56.65 m³·mol⁻¹ChemAxon
Polarizability22.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.23731661259
DarkChem[M-H]-147.56731661259
DeepCCS[M+H]+145.16130932474
DeepCCS[M-H]-142.76630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CuelureCC(=O)CCC1=CC=C(OC(C)=O)C=C12559.8Standard polar33892256
CuelureCC(=O)CCC1=CC=C(OC(C)=O)C=C11608.2Standard non polar33892256
CuelureCC(=O)CCC1=CC=C(OC(C)=O)C=C11630.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cuelure,1TMS,isomer #1CC(=O)OC1=CC=C(CC=C(C)O[Si](C)(C)C)C=C11844.8Semi standard non polar33892256
Cuelure,1TMS,isomer #1CC(=O)OC1=CC=C(CC=C(C)O[Si](C)(C)C)C=C11796.6Standard non polar33892256
Cuelure,1TMS,isomer #2C=C(CCC1=CC=C(OC(C)=O)C=C1)O[Si](C)(C)C1765.9Semi standard non polar33892256
Cuelure,1TMS,isomer #2C=C(CCC1=CC=C(OC(C)=O)C=C1)O[Si](C)(C)C1735.8Standard non polar33892256
Cuelure,1TBDMS,isomer #1CC(=O)OC1=CC=C(CC=C(C)O[Si](C)(C)C(C)(C)C)C=C12097.8Semi standard non polar33892256
Cuelure,1TBDMS,isomer #1CC(=O)OC1=CC=C(CC=C(C)O[Si](C)(C)C(C)(C)C)C=C12022.5Standard non polar33892256
Cuelure,1TBDMS,isomer #2C=C(CCC1=CC=C(OC(C)=O)C=C1)O[Si](C)(C)C(C)(C)C2020.0Semi standard non polar33892256
Cuelure,1TBDMS,isomer #2C=C(CCC1=CC=C(OC(C)=O)C=C1)O[Si](C)(C)C(C)(C)C1956.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cuelure GC-MS (Non-derivatized) - 70eV, Positivesplash10-01oy-4900000000-6e739f42486a3851df662017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cuelure GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cuelure GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 10V, Positive-QTOFsplash10-0a4r-0940000000-10d011f5ac46a90eab562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 20V, Positive-QTOFsplash10-00mt-1900000000-e6c32f7b26073aa86e472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 40V, Positive-QTOFsplash10-0kbb-2900000000-9cab2b651bd9f2a77bc82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 10V, Negative-QTOFsplash10-0bt9-0790000000-304b4b3f6b8fa377a7112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 20V, Negative-QTOFsplash10-08fr-3930000000-274cfd7faa069a09a9112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 40V, Negative-QTOFsplash10-0a4j-7900000000-a19b8daa91338cb9837e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 10V, Positive-QTOFsplash10-000i-0930000000-8ff016f749893216bd322021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 20V, Positive-QTOFsplash10-000i-1900000000-41f6db6079c0a3bc5c422021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 40V, Positive-QTOFsplash10-004i-3900000000-9cc8a3d70ae56feaac432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 10V, Negative-QTOFsplash10-0a4i-5590000000-c73c6639ad8c73999bce2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 20V, Negative-QTOFsplash10-0a4i-5940000000-1d8ba9f0756d9ba85c9d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuelure 40V, Negative-QTOFsplash10-0aou-9700000000-1d60825f91ec17262e092021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011678
KNApSAcK IDNot Available
Chemspider ID18057
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound19137
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1037262
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chang CL, Cho IK, Li QX: Insecticidal activity of basil oil, trans-anethole, estragole, and linalool to adult fruit flies of Ceratitis capitata, Bactrocera dorsalis, and Bactrocera cucurbitae. J Econ Entomol. 2009 Feb;102(1):203-9. [PubMed:19253638 ]
  2. Jang EB, Casana-Giner V, Oliver JE: Field captures of wild melon fly (Diptera: Tephritidae) with an improved male attractant, raspberry ketone formate. J Econ Entomol. 2007 Aug;100(4):1124-8. [PubMed:17849860 ]
  3. Suckling DM, Jang EB, Carvalho LA, Nagata JT, Schneider EL, El-Sayed AM: Can menage-a-trois be used for controlling insects? J Chem Ecol. 2007 Aug;33(8):1494-504. Epub 2007 Jul 6. [PubMed:17619106 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .