Showing Compound Card for 3-O-p-Coumaroylquinic acid (CDB005277)

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Record Information
Version1.0
Created at2020-04-17 19:27:04 UTC
Updated at2020-11-18 16:39:39 UTC
CannabisDB IDCDB005277
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-O-p-Coumaroylquinic acid
Description3-O-p-Coumaroylquinic acid 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. 3-p-coumaroylquinic acid can be found in a number of food items such as redcurrant, highbush blueberry, sweet cherry, and blackcurrant, which makes 3-p-coumaroylquinic acid a potential biomarker for the consumption of these food products. 3-O-p-Coumaroylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-O-p-Coumaroylquinic acid is found, on average, in the highest concentration within apples. 3-O-p-Coumaroylquinic acid has also been detected, but not quantified in, wild celeries. This could make 3-O-p-coumaroylquinic acid a potential biomarker for the consumption of these foods. 3-p-coumaroylquinic 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-p-coumaroylquinic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 3-O-p-Coumaroylquinic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-O-p-CoumaroylquinateGenerator
1,4,5-Trihydroxy-3-[[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]cyclohexanecarboxylic acid, 9ciHMDB
O-Coumaroylquinic acidHMDB
p-Coumaroyl quinic acidHMDB
trans-5-O-(4-Coumaroyl)-D-quinateHMDB
trans-5-O-(4-Coumaroyl)-D-quinic acidHMDB
2-Coumaroylquinic acidHMDB
Chemical FormulaC16H18O8
Average Molecular Weight338.31
Monoisotopic Molecular Weight338.1002
IUPAC Name(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid
Traditional Name(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H]1O)C(O)=O
InChI Identifier
InChI=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-QHAYPTCMSA-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
  • 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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point247 - 248 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability32.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-O-p-Coumaroylquinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9532000000-2dc7a87d77bc1c19a7a3Spectrum
Predicted GC-MS3-O-p-Coumaroylquinic acid, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-1240039000-8da17192a2ee13617f1fSpectrum
Predicted GC-MS3-O-p-Coumaroylquinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Negativesplash10-03di-0900000000-390db558397074a906252017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 30V, positivesplash10-0002-0900000000-fed2504c458f496f61182020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 15V, positivesplash10-0002-0900000000-ef57912ebc34156df3932020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-0002-0900000000-d3046051cdf55c7ab0382020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-0292-0914000000-8b2bc1f2847f25917bd02020-07-21View Spectrum
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-d78957a03558e557100f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-46e6cf4cf6a54ee606702021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-4910000000-7fff648cbfff88afe1592021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0902000000-600959b32de7a00f052c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xu-1900000000-89f3229591976d1bdbf92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3900000000-6b20c10637eed157aca22021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029681
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000240
KNApSAcK IDC00052747
Chemspider ID8121397
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9945785
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available