3-O-Feruloylquinic acid (CHEM024684)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:51:31 UTC
Update Date2016-11-09 01:17:56 UTC
Accession NumberCHEM024684
Identification
Common Name3-O-Feruloylquinic acid
ClassSmall Molecule
DescriptionConstituent of coffee beansand is also from tomato (Lycopersicon esculentum) and sunflower (Helianthus annuus). 3-O-Feruloylquinic acid is found in many foods, some of which are chicory, fats and oils, garden tomato (variety), and coffee and coffee products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-O-FeruloylquinateGenerator
3-Ferulylquinic acidHMDB
1,3,4-Trihydroxy-5-{[(2Z)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylateGenerator
Chemical FormulaC17H20O9
Average Molecular Mass368.335 g/mol
Monoisotopic Mass368.111 g/mol
CAS Registry Number62929-69-5
IUPAC Name1,3,4-trihydroxy-5-{[(2Z)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid
Traditional Name1,3,4-trihydroxy-5-{[(2Z)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid
SMILESCOC1=C(O)C=C(\C=C/C(=O)OC2CC(O)(CC(O)C2O)C(O)=O)C=C1
InChI IdentifierInChI=1S/C17H20O9/c1-25-12-4-2-9(6-10(12)18)3-5-14(20)26-13-8-17(24,16(22)23)7-11(19)15(13)21/h2-6,11,13,15,18-19,21,24H,7-8H2,1H3,(H,22,23)/b5-3-
InChI KeyZHBZPCLRULAFBL-HYXAFXHYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentQuinic acids and derivatives
Alternative Parents
Substituents
  • Quinic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Cyclohexanol
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Alpha,beta-unsaturated carboxylic ester
  • Tertiary alcohol
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Ether
  • Polyol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility3.16 g/LALOGPS
logP0.25ALOGPS
logP-0.12ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.75 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity87.72 m³·mol⁻¹ChemAxon
Polarizability35.39 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-0kbf-9504000000-7b003edf091d7ea04f44Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0006-2433069000-2c7542e62edf662c5931Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0709000000-3de3c4ebaca3b614e329Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0903000000-a937e1d694bbafede385Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-0900000000-7325179a4374e6cdb6b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01bc-0409000000-146dee01557264d7ae08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0597-1915000000-85267775f64763c96225Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-0900000000-7e462285977809a9fd62Spectrum
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 IDHMDB0030669
FooDB IDFDB002583
Phenol Explorer IDNot Available
KNApSAcK IDC00035939
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131751068
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.