precursor metabolite

Showing entry for 3-O-Caffeoylquinic acid

Identification

PhytoHub ID
PHUB000530
Name
3-O-Caffeoylquinic acid
Systematic Name
3-Caffeoylquinic acid
Synonyms
  • 3-(3,4-Dihydroxycinnamoyl)quinic acid
  • 3-Caffeoylquinic acid
  • chlorogenic acid
  • Neochlorogenic acid
CAS Number
327-97-9
Average Mass
354.311
Monoisotopic Mass
354.09508216
Chemical Formula
C16H18O9
IUPAC Name
3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
InChI Key
CWVRJTMFETXNAD-DUXPYHPUSA-N
InChI Identifier
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+
SMILES
[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)OC1CC(O)(CC(O)C1O)C(O)=O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
3.44e+00 g/l
LogS (ALOGPS)
-2.01
LogP (ALOGPS)
0.17
Hydrogen Acceptors
8
Hydrogen Donors
6
Rotatable Bond Count
5
Polar Surface Area
164.74999999999997
Refractivity
83.23469999999999
Polarizability
33.92029446068079
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-3.2318239809154075
pKa (strongest acidic)
3.3338531471838464
Number of Rings
2
Rule of Five
No
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Phenolic acids
Sub-class
Hydroxycinnamic acids

Taxonomy as Metabolite

Metabolite Family
(Poly)phenol metabolites
Metabolite Class
Phenolic acid metabolites
Metabolite Sub-class
Cinnamic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
3-O-Caffeoylquinic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical

Spectra from Online Resources

Record IDSourceDescriptionView
FIO00618MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00619MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00620MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00621MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00622MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
FIO00623MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00624MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00625MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00626MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00627MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
KO000466MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO000467MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO000468MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO000469MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO000470MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
KO002577MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO002578MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO002579MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO002580MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO002581MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
KO008922MassBankLC-ESI-IT Spectrum - 0.80, unspecifiedView Spectra
KO008923MassBankLC-ESI-IT Spectrum - 0.80/0.50, unspecifiedView Spectra
OUF00135MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
OUF00136MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PB005541MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
PB006181MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB006182MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
3-O-Caffeoylquinic acid 3-O-Caffeoylquinic acidhumanplasma, serum, urineunchanged1h-3h<20 nmol/L<1%C16H18O9354.09508216 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
3-O-Caffeoylquinic acid 3-O-Caffeoylquinic acidMicrobiotaEffect, clusters Publications
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