You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:29:26 UTC
Update Date2017-12-07 02:56:40 UTC
HMDB IDHMDB0029287
Secondary Accession Numbers
  • HMDB29287
Metabolite Identification
Common Name3-Caffeoyl-1,5-quinolactone
Description3-Caffeoyl-1,5-quinolactone, also known as 3-caffeoylquinic acid lactone, 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. 3-Caffeoyl-1,5-quinolactone is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Within the cell, 3-caffeoyl-1,5-quinolactone is primarily located in the cytoplasm.
Structure
Thumb
Synonyms
ValueSource
3-Caffeoyl-1,5-quinideHMDB
3-Caffeoylquinic acid lactoneHMDB
3-Caffeoylquinic-1,5-lactoneHMDB
Chemical FormulaC16H16O8
Average Molecular Weight336.2934
Monoisotopic Molecular Weight336.084517488
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
CAS Registry NumberNot Available
SMILES
O[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 Identifier
InChI=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
DescriptionThis compound 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
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9564000000-4ebd26696043fd0b80e5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-06di-3223092000-fb73f16b4e38efeba9dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-0916000000-23db13c059bd2061e052View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08i0-0901000000-7f5306433134388a22e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-1900000000-3b1c80b3cae9d02994e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0819000000-6340e3cfe0515285e4c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-022i-0912000000-bb5ba72511f07d818715View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-1900000000-964826950a8990433c39View in MoNA
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 ID541
FoodDB IDFDB000291
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102210472
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:20428313 ]