4-Feruloyl-1,5-quinolactone (CHEM022990)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:46:14 UTC
Update Date2016-11-09 01:17:37 UTC
Accession NumberCHEM022990
Identification
Common Name4-Feruloyl-1,5-quinolactone
ClassSmall Molecule
Description4-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
4-Feruloyl-1,5-quinideHMDB
4-Feruloylquinic acid lactoneHMDB
4-Feruloylquinic-1,5-lactoneHMDB
(1S,3R,4R,5R)-1,3-Dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-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(1S,3R,4R,5R)-1,3-dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Traditional Name(1S,3R,4R,5R)-1,3-dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
SMILESCOC1=C(O)C=CC(\C=C\C(=O)O[C@H]2[C@H]3C[C@@](O)(C[C@H]2O)C(=O)O3)=C1
InChI IdentifierInChI=1S/C17H18O8/c1-23-12-6-9(2-4-10(12)18)3-5-14(20)25-15-11(19)7-17(22)8-13(15)24-16(17)21/h2-6,11,13,15,18-19,22H,7-8H2,1H3/b5-3+/t11-,13-,15-,17+/m1/s1
InChI KeyOIGFDFULTVHQNZ-KJJWLSQTSA-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 Solubility1.65 g/LALOGPS
logP0.4ALOGPS
logP0.54ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.87ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity84.22 m³·mol⁻¹ChemAxon
Polarizability34 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, Positivesplash10-00fu-9545000000-0303d57bae0646e49d74Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0kmi-4230190000-60e8188bce90d949afe5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufr-0908000000-40f4ea992b72ff083291Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0902000000-67276e3d9f8f50531683Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0570-1900000000-5548178aae24fda427a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0609000000-5806f9862b836fe8c815Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05dl-0901000000-440d75611781741269d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-ce27a3ea0fbb00d09c3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0209000000-830c8f28ada915714326Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-055b-0904000000-1a54578b0c8ddec03431Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-1902000000-2b318fd3f67f3326ca63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-181c336dcc303c9f0ca2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fr2-0915000000-29603648f2913a984f42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05bk-1900000000-719c00b549ed6d25c3fcSpectrum
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 IDHMDB0029290
FooDB IDFDB000294
Phenol Explorer ID545
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776760
ChEBI ID175471
PubChem Compound ID102210475
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.