4-p-Coumaroyl-1,5-quinolactone (CHEM022993)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:46:21 UTC
Update Date2016-11-09 01:17:37 UTC
Accession NumberCHEM022993
Identification
Common Name4-p-Coumaroyl-1,5-quinolactone
ClassSmall Molecule
Description4-p-Coumaroyl-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-Coumaroyl-1,5-lactoneHMDB
4-Coumaroyl-1,5-quinideHMDB
4-Coumaroylquinic acid lactoneHMDB
(1S,3R,4R,5R)-1,3-Dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acidHMDB
Chemical FormulaC16H16O7
Average Molecular Mass320.294 g/mol
Monoisotopic Mass320.090 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-hydroxyphenyl)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-hydroxyphenyl)prop-2-enoate
SMILESO[C@@H]1C[C@]2(O)C[C@@H](OC2=O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C16H16O7/c17-10-4-1-9(2-5-10)3-6-13(19)23-14-11(18)7-16(21)8-12(14)22-15(16)20/h1-6,11-12,14,17-18,21H,7-8H2/b6-3+/t11-,12-,14-,16+/m1/s1
InChI KeyPZLNXMHSYFPCAE-OTCYKTEZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acid esters
Alternative Parents
Substituents
  • Coumaric acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Caprolactone
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Oxepane
  • Phenol
  • Fatty acyl
  • Monocyclic benzene moiety
  • Benzenoid
  • Gamma butyrolactone
  • Dicarboxylic acid or derivatives
  • Enoate ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • 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 Solubility3.2 g/LALOGPS
logP0.47ALOGPS
logP0.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.76 m³·mol⁻¹ChemAxon
Polarizability30.96 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, Positivesplash10-00kf-7971000000-fd7c74a3df4f2e2bb737Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01di-3723930000-40c0cac7181ece45fb81Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dj-0917000000-29f8e654f5e402e60cfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0911000000-3bda04e9ba873e16092aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-2900000000-28d413349b1ff61021b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0829000000-254f67f0cb401c58d11fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0cka-0901000000-18f1a13c04cd5cf771dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-2900000000-ebb30e782f67f1355e8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0309000000-402b82c9e011f3ec9e39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06dj-1923000000-dc510a9fdd2119041712Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2910000000-c794038a60a20ffa3af0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0109000000-604a00d22dcf9e4907b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0923000000-42f196a9d03aece69cf0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-4920000000-cd99365e33d26b341bcbSpectrum
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 IDHMDB0029293
FooDB IDFDB000297
Phenol Explorer ID548
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776764
ChEBI ID175083
PubChem Compound ID102210473
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.