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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2019-10-08 18:28:26 UTC
Update Date2019-11-13 17:27:56 UTC
HMDB IDHMDB0240478
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Feruloylquinic acid
Description5-Feruloylquinic acid (5-FQA) (CAS: 40242-06-6) 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. Coffee, especially green or raw coffee, is a major source of chlorogenic acids (CGA). CGAs have been associated with a range of health benefits including a reduction in the risk of cardiovascular disease, diabetes type 2, and Alzheimer's disease. Major CGAs in coffee include 3-, 4-, and 5-feruloylquinic acids (PMID: 19022950 ). 5-FQA has been detected in the plasma and urine of humans who have ingested coffee (PMID: 19460943 ).
Structure
Data?1573666076
Synonyms
ValueSource
5-FQAHMDB
5-FeruloylquinateHMDB
5-Feruloylquinic acidHMDB
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
Chemical FormulaC17H20O9
Average Molecular Weight368.3353
Monoisotopic Molecular Weight368.110732238
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
Traditional Name(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid
CAS Registry Number87099-72-7
SMILES
COC1=CC(\C=C\C(=O)O[C@@H]2C[C@](O)(C[C@@H](O)[C@@H]2O)C(O)=O)=CC=C1O
InChI Identifier
InChI=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
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
  • Phenoxy compound
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexanol
  • Fatty acid ester
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Polyol
  • Carboxylic acid
  • Ether
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
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
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0809000000-a0b4fb39e484c9e4a447Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0902000000-5525ad317bd5829829f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-0900000000-221021777b5b7d1f9789Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01bc-0409000000-3b8c4a4ee437bcbf77a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0597-1914000000-c155906736b9ca46cf18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-0900000000-577d3a9635ca7d022279Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000247
KNApSAcK IDNot Available
Chemspider ID8309124
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10133609
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Farah A, Monteiro M, Donangelo CM, Lafay S: Chlorogenic acids from green coffee extract are highly bioavailable in humans. J Nutr. 2008 Dec;138(12):2309-15. doi: 10.3945/jn.108.095554. [PubMed:19022950 ]
  2. Stalmach A, Mullen W, Barron D, Uchida K, Yokota T, Cavin C, Steiling H, Williamson G, Crozier A: Metabolite profiling of hydroxycinnamate derivatives in plasma and urine after the ingestion of coffee by humans: identification of biomarkers of coffee consumption. Drug Metab Dispos. 2009 Aug;37(8):1749-58. doi: 10.1124/dmd.109.028019. Epub 2009 May 21. [PubMed:19460943 ]