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5-p-Coumaroylquinic acid (FDB000236)

Record Information
Version1.0
Creation date2010-04-08 22:04:29 UTC
Update date2019-11-26 02:54:35 UTC
Primary IDFDB000236
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-p-Coumaroylquinic acid
Description5-p-coumaroylquinic acid, also known as trans-5-O-(4-coumaroyl)-D-quinate or P-coumaroyl quinate, 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. 5-p-coumaroylquinic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 5-p-coumaroylquinic acid can be found in a number of food items such as wild leek, brussel sprouts, ucuhuba, and lemon grass, which makes 5-p-coumaroylquinic acid a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.92 g/LALOGPS
logP0.13ALOGPS
logP0.035ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.36ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity81.25 m³·mol⁻¹ChemAxon
Polarizability32.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H18O8
IUPAC name(1S,3R,4R,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid
InChI IdentifierInChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14-,16+/m1/s1
InChI KeyBMRSEYFENKXDIS-OTCYKTEZSA-N
Isomeric SMILESO[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@@H]1O)C(O)=O
Average Molecular Weight338.3093
Monoisotopic Molecular Weight338.100167552
Classification
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
  • Coumaric acid ester
  • Quinic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Styrene
  • Phenol
  • Fatty acid ester
  • Cyclohexanol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acyl
  • Benzenoid
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Enoate ester
  • Tertiary alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
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
EI-MSMass Spectrum (Electron Ionization)Not Available2022-08-06View Spectrum
Predicted GC-MS5-p-Coumaroylquinic acid, TMS_4_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-009m-0936000000-4575bb1f18835ad1f7c52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0911000000-5088a3a2e259bc6b88012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-1900000000-5bb81d1e3b6075572c1d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-0988000000-68ceb4befe110f98609f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002e-1931000000-4f0bf43a1a7bcf541c7a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0900000000-debf809729d9088ae7a72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0946000000-d78957a03558e557100f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-46e6cf4cf6a54ee606702021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-4910000000-7fff648cbfff88afe1592021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0902000000-600959b32de7a00f052c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xu-1900000000-89f3229591976d1bdbf92021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3900000000-19ac9d611ec33e3333d12021-10-21View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID455
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID5-O-COUMARYLQUINIC-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 ID455
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).