3-Caffeoyl-1,5-quinolactone (CHEM022987)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:46:08 UTC
Update Date2016-11-09 01:17:37 UTC
Accession NumberCHEM022987
Identification
Common Name3-Caffeoyl-1,5-quinolactone
ClassSmall Molecule
Description3-Caffeoyl-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-Caffeoyl-1,5-quinideHMDB
3-Caffeoylquinic acid lactoneHMDB
3-Caffeoylquinic-1,5-lactoneHMDB
(1R,3R,4R,5R)-1,4-Dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acidHMDB
Chemical FormulaC16H16O8
Average Molecular Mass336.293 g/mol
Monoisotopic Mass336.085 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-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Name(1R,3R,4R,5R)-1,4-dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
SMILESO[C@H]1[C@H]2C[C@@](O)(C[C@H]1OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(=O)O2
InChI IdentifierInChI=1S/C16H16O8/c17-9-3-1-8(5-10(9)18)2-4-13(19)23-11-6-16(22)7-12(14(11)20)24-15(16)21/h1-5,11-12,14,17-18,20,22H,6-7H2/b4-2+/t11-,12-,14-,16+/m1/s1
InChI KeyFXXATDNXMJKMSF-JUHZACGLSA-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
  • Caprolactone
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Oxepane
  • Phenol
  • Fatty acyl
  • Benzenoid
  • Gamma butyrolactone
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Enoate ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • 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 Solubility2.75 g/LALOGPS
logP0.19ALOGPS
logP0.4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity79.74 m³·mol⁻¹ChemAxon
Polarizability31.79 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, Positivesplash10-052f-9564000000-4ebd26696043fd0b80e5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-06di-3223092000-fb73f16b4e38efeba9dcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-0916000000-23db13c059bd2061e052Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08i0-0901000000-7f5306433134388a22e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-1900000000-3b1c80b3cae9d02994e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0819000000-6340e3cfe0515285e4c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-022i-0912000000-bb5ba72511f07d818715Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-1900000000-964826950a8990433c39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0309000000-50aaf8079ae6e4dad8ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-0933000000-87fd3f40b410596b3de8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ds-1910000000-d4507f49bb1a9fedfb13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-0809000000-d4d3bf38c852acabc2e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0901000000-929e813aafd78aab8c9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ar-2900000000-74a316d9089eaa186db5Spectrum
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 IDHMDB0029287
FooDB IDFDB000291
Phenol Explorer ID541
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776761
ChEBI ID175265
PubChem Compound ID102210472
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.