3-Feruloyl-1,5-quinolactone (CHEM022989)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:46:11 UTC
Update Date2016-11-09 01:17:37 UTC
Accession NumberCHEM022989
Identification
Common Name3-Feruloyl-1,5-quinolactone
ClassSmall Molecule
Description3-Feruloyl-1,5-quinolactone is a polyphenol compound found in foods of plant origin (PMID: 20428313)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-Feruloyl-1,5-lactoneHMDB
3-Feruloyl-1,5-quinideHMDB
3-Feruloylquinic acid lactoneHMDB
(1R,3R,4R,5R)-1,4-Dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acidHMDB
Chemical FormulaC17H18O8
Average Molecular Mass350.320 g/mol
Monoisotopic Mass350.100 g/mol
CAS Registry NumberNot Available
IUPAC Name(1R,3R,4R,5R)-1,4-dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Traditional Name(1R,3R,4R,5R)-1,4-dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
SMILESCOC1=C(O)C=CC(\C=C\C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2O)=C1
InChI IdentifierInChI=1S/C17H18O8/c1-23-11-6-9(2-4-10(11)18)3-5-14(19)24-12-7-17(22)8-13(15(12)20)25-16(17)21/h2-6,12-13,15,18,20,22H,7-8H2,1H3/b5-3+/t12-,13-,15-,17+/m1/s1
InChI KeyKFVJGWDDYWUTHM-AWOKGZDASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Methoxyphenol
  • Anisole
  • Caprolactone
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Alkyl aryl ether
  • Phenol
  • Oxepane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.63 g/LALOGPS
logP0.4ALOGPS
logP0.54ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.87ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity84.22 m³·mol⁻¹ChemAxon
Polarizability33.81 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9523000000-c0e26d44c264d09a784fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-5231190000-e832b1719d0c623dc24fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufr-0907000000-3a50d15344844119dc8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0901000000-e0cd2fa74d69ebf7502aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-1900000000-511a23220d0038d449f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0709000000-91470a394b4ed3c2dd96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i0-0902000000-1864caad4d28bcf7a918Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-41e3fa516cfa36d0425dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0902000000-de5cde31b78169166170Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0901000000-944ad5db00b310d0be94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-1903000000-be76a87397666ad6d2ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0309000000-03e64a36ba0a98b4212cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0902000000-257092d95b68ede4d495Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-1900000000-0e16c6c8dded3f2faaa8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029289
FooDB IDFDB000293
Phenol Explorer ID544
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776759
ChEBI ID175470
PubChem Compound ID102210470
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.