Identification

PhytoHub ID
PHUB000585
Name
5-O-Caffeoylquinic acid
Systematic Name
Not Available
Synonyms
  • 5-Caffeoylquinic acid
  • Chlorogenic acid
CAS Number
Not Available
Average Mass
354.311
Monoisotopic Mass
354.09508216
Chemical Formula
C16H18O9
IUPAC Name
chlorogenic acid
InChI Key
CWVRJTMFETXNAD-DUXPYHPUNA-N
InChI Identifier
InChI=1/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

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

Family
Polyphenols
Class
Phenolic acids
Sub-class
Hydroxycinnamic acids

Spectra

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
PS063601ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS063602ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS063603ReSpectN/A Spectrum - 30, [M+H]+View Spectra
PS063604ReSpectN/A Spectrum - 40, [M+H]+View Spectra
PS063605ReSpectN/A Spectrum - 50, [M+H]+View Spectra
PS063607ReSpectN/A Spectrum - 10, [M-H]-View Spectra
PS063608ReSpectN/A Spectrum - 20, [M-H]-View Spectra
PS063609ReSpectN/A Spectrum - 30, [M-H]-View Spectra
PS063610ReSpectN/A Spectrum - 40, [M-H]-View Spectra
PS063611ReSpectN/A Spectrum - 50, [M-H]-View Spectra

Food Sources

NameGroup
AppleFruit, Pomes PublicationsShow
Apple ciderBeverages, Alcoholic PublicationsShow
Apple juiceBeverages, Non-alcoholic PublicationsShow
ApricotFruit, Drupes PublicationsShow
BlackberryFruit, Berries PublicationsShow
BlackcurrantFruit, Berries PublicationsShow
BlueberryFruit, Berries PublicationsShow
BroccoliVegetables, Cabbages PublicationsShow
CarrotVegetables, Root vegetables PublicationsShow
Cherry tomatoVegetables, Fruit vegetables PublicationsShow
CiderBeverages, Alcoholic PublicationsShow
CoffeeCoffee and coffee products PublicationsShow
EggplantVegetables, Fruit vegetables PublicationsShow
European cranberryFruit, Berries PublicationsShow
European plumFruit, Drupes PublicationsShow
Globe artichokeVegetables, Other vegetables PublicationsShow
Green teaTeas and herbal teas PublicationsShow
LettuceVegetables, Leaf vegetables PublicationsShow
MateBeverages, Non-alcoholic PublicationsShow
Olive, blackFruit, Drupes PublicationsShow
PeachFruit, Drupes PublicationsShow
PearFruit, Pomes PublicationsShow
PotatoVegetables, Tubers PublicationsShow
Roasted coffeeCoffee and coffee products PublicationsShow
StrawberryFruit, Berries PublicationsShow
Sweet cherryFruit, Drupes PublicationsShow
TomatoVegetables, Fruit vegetables PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginFormulaMonoisotopic mass
5-O-Caffeoylquinic acid 3-Hydroxybenzoic acidraturinehost-gut microbiota co-metaboliteC7H6O3138.031694053
5-O-Caffeoylquinic acid Benzoic acidNot AvailableNot Availablegut microbiota metaboliteC7H6O2122.036779433
5-O-Caffeoylquinic acid Caffeic acidraturinehost metabolismC9H8O4180.042258738 Publications
5-O-Caffeoylquinic acid Coumaric acid (m-)ratplasma, urinegut microbiota metaboliteC9H8O3164.047344118 Publications
5-O-Caffeoylquinic acid Dihydrocaffeic acidraturinegut microbiota metaboliteC9H10O4182.057908802 Publications
5-O-Caffeoylquinic acid Ferulic acidratplasma, urinehost metabolismC10H10O4194.057908802 Publications
5-O-Caffeoylquinic acid Isoferulic acidraturinehost metabolismC10H10O4194.057908802
5-O-Caffeoylquinic acid 3-(3'-Hydroxyphenyl)propionic acidratplasma, urinegut microbiota metaboliteC9H10O3166.062994182 Publications
5-O-Caffeoylquinic acid 3-Hydroxyhippuric acidraturinehost-gut microbiota co-metaboliteC9H9NO4195.053157774 Publications
5-O-Caffeoylquinic acid Hippuric acidratplasma, urinehost-gut microbiota co-metaboliteC9H9NO3179.058243154 Publications
Back