Record Information
Version1.0
Creation date2010-04-08 22:04:30 UTC
Update date2019-11-26 02:54:36 UTC
Primary IDFDB000249
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Feruloylquinic acid
Description3-feruloylquinic acid belongs to quinic acids and derivatives class of compounds. Those 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. 3-feruloylquinic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 3-feruloylquinic acid can be found in a number of food items such as carrot, peach (variety), apricot, and pear, which makes 3-feruloylquinic acid a potential biomarker for the consumption of these food products. .
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
5-FeruloylquinateGenerator
5-FQAHMDB
5-Ferulylquinic acidHMDB
5-O-(e)-Feruloylquinic acidHMDB
5-O-Feruloylquinic acidHMDB
Feruloylquinic acidHMDB
trans-5-O-Feruloyl quinic acidHMDB
trans-5-O-Feruloylquinic acidHMDB
5-Feruloylquinic acidHMDB
Predicted Properties
PropertyValueSource
Water Solubility3.04 g/LALOGPS
logP0.23ALOGPS
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
Polarizability35.22 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H20O9
IUPAC name(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid
InChI IdentifierInChI=1S/C17H20O9/c1-25-12-6-9(2-4-10(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+/t11-,13-,15+,17-/m1/s1
InChI KeyRAGZUCNPTLULOL-KQJPBSFVSA-N
Isomeric SMILESCOC1=CC(\C=C\C(=O)O[C@@H]2C[C@](O)(C[C@@H](O)[C@@H]2O)C(O)=O)=CC=C1O
Average Molecular Weight368.3353
Monoisotopic Molecular Weight368.110732238
Classification
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • O-glycosyl compound
  • Phenoxy compound
  • Phenol ether
  • Beta-hydroxy acid
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Gamma butyrolactone
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Tetrahydrofuran
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Foods

Fruits and vegetables:

Beverages:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-Feruloylquinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0809000000-a0b4fb39e484c9e4a447Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0902000000-5525ad317bd5829829f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-0900000000-221021777b5b7d1f9789Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01bc-0409000000-3b8c4a4ee437bcbf77a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0597-1914000000-c155906736b9ca46cf18Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-0900000000-577d3a9635ca7d022279Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fvj-0906000000-2a9bfdc3b69bee915a97Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fs-0900000000-105e141794d45a08050cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-3910000000-02a23fb45109b3e09d7aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0902000000-c482dab26a32aaf99ad7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0077-2900000000-3e8bef53f4b479cfb5c0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ry-3902000000-d77d9f2de22831344beeSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID480
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID3-FERULOYLQUINIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID480
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).