precursor

Showing entry for 5-O-Caffeoylquinic acid

Identification

PhytoHub ID
PHUB000585
Name
5-O-Caffeoylquinic acid
Systematic Name
5-Caffeoylquinic acid
Synonyms
  • 5-(3,4-Dihydroxycinnamoyl)quinic acid
  • 5-Caffeoylquinic acid
  • Chlorogenic acid
  • Neochlorogenic acid
CAS Number
906-33-2
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

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks

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
MateTeas and herbal teas 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

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
5-O-Caffeoylquinic acid 3-Hydroxybenzoic acidraturinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC7H6O3138.031694053
5-O-Caffeoylquinic acid Benzoic acidNot AvailableNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC7H6O2122.036779433
5-O-Caffeoylquinic acid Caffeic acidraturinehost metabolismNot AvailableNot AvailableNot AvailableC9H8O4180.042258738 Publications
5-O-Caffeoylquinic acid 5-O-Caffeoylquinic acidhumanplasma, urineunchanged1h-3h<20 nmol/L<1%C16H18O9354.09508216 Detailed Intervention Studies Publications
5-O-Caffeoylquinic acid Dihydrocaffeic acidraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O4182.057908802 Publications
5-O-Caffeoylquinic acid Ferulic acidratplasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC10H10O4194.057908802 Publications
5-O-Caffeoylquinic acid Isoferulic acidraturinehost metabolismNot AvailableNot AvailableNot AvailableC10H10O4194.057908802
5-O-Caffeoylquinic acid 3-(3'-Hydroxyphenyl)propionic acidratplasma, urinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
5-O-Caffeoylquinic acid 3-Hydroxyhippuric acidraturinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC9H9NO4195.053157774 Publications
5-O-Caffeoylquinic acid Hippuric acidratplasma, urinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC9H9NO3179.058243154 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
5-O-Caffeoylquinic acid 5-O-Caffeoylquinic acidMicrobiotaEffect, clusters Publications
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