precursor metabolite

Showing entry for Caffeic acid

Identification

PhytoHub ID
PHUB000574
Name
Caffeic acid
Systematic Name
3',4'-dihydroxycinnamic acid
Synonyms
  • 3-(3,4-dihydroxyphenyl)acrylic acid
  • 3,4-Dihydroxycinnamic acid
  • 3,4-Dihydroxyphenylpropenic acid
  • trans-caffeic acid
CAS Number
331-39-5
Average Mass
180.159
Monoisotopic Mass
180.042258738
Chemical Formula
C9H8O4
IUPAC Name
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
InChI Key
QAIPRVGONGVQAS-DUXPYHPUSA-N
InChI Identifier
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
SMILES
OC(=O)\C=C\C1=CC(O)=C(O)C=C1
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
1.61e+00 g/l
LogS (ALOGPS)
-2.05
LogP (ALOGPS)
1.67
Hydrogen Acceptors
4
Hydrogen Donors
3
Rotatable Bond Count
2
Polar Surface Area
77.76
Refractivity
47.021699999999996
Polarizability
17.3100815082372
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-6.283746523508148
pKa (strongest acidic)
3.4517963199924626
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Precursor

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 Precursor(s)

PrecursorFamilyClassSub-class
Cyanidin 3-O-glucosidePolyphenolsFlavonoidsAnthocyaninsShow Precursor
5-O-Caffeoylquinic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Precursor
Rosmarinic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Precursor

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Cinnamic acids and derivatives
Super-class
Phenylpropanoids and polyketides
Sub-class
Hydroxycinnamic acids and derivatives
Direct Parent Name
Hydroxycinnamic acids
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Catechols", "Cinnamic acids", "Coumaric acids and derivatives", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Styrenes"]
External Descriptor Annotations
["Caffeate derivatives", "caffeic acid"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Catechol", "Cinnamic acid", "Coumaric acid or derivatives", "Hydrocarbon derivative", "Hydroxycinnamic acid", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Styrene"]

Spectra from Online Resources

Record IDSourceDescriptionView
BML00722MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00729MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML80856MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
JP004107MassBankEI-B Spectrum - -, [M]+*View Spectra
JP007237MassBankEI-B Spectrum - -, [M]+*View Spectra
KO000510MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO000511MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO000512MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO000513MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO000514MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
OUF00132MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PR010139MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PR010140MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PR040210MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, [M-H]-View Spectra
PR040211MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, [M-H-CO2]-View Spectra
PR040212MassBankLC-ESI-QTOF Spectrum - 30 V, [M-H]-View Spectra
PR040213MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, [M+H]+View Spectra
PR040214MassBankLC-ESI-QTOF Spectrum - 30 V, [M+H]+View Spectra
PR100110MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100533MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PS017701ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS017702ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS017707ReSpectN/A Spectrum - 10, [M-H]-View Spectra
PS017708ReSpectN/A Spectrum - 20, [M-H]-View Spectra
PS017709ReSpectN/A Spectrum - 30, [M-H]-View Spectra
PS044601ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS044602ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS044607ReSpectN/A Spectrum - 10, [M-H]-View Spectra
PS044608ReSpectN/A Spectrum - 20, [M-H]-View Spectra
PS044609ReSpectN/A Spectrum - 30, [M-H]-View Spectra

Food Sources

NameGroup
American cranberryFruit, Berries PublicationsShow
AppleFruit, Pomes PublicationsShow
Apple juiceBeverages, Non-alcoholic PublicationsShow
BeerBeverages, Alcoholic PublicationsShow
BlackberryFruit, Berries PublicationsShow
BlueberryFruit, Berries PublicationsShow
BroccoliVegetables, Cabbages PublicationsShow
CarrotVegetables, Root vegetables PublicationsShow
CiderBeverages, Alcoholic PublicationsShow
CoffeeCoffee and coffee products PublicationsShow
Common wheatCereals and cereal products PublicationsShow
EggplantVegetables, Fruit vegetables PublicationsShow
European cranberryFruit, Berries PublicationsShow
European plumFruit, Drupes PublicationsShow
MateTeas and herbal teas PublicationsShow
Olive, blackFruit, Drupes PublicationsShow
Olive, greenFruit, Drupes PublicationsShow
PearFruit, Pomes PublicationsShow
StrawberryFruit, Berries PublicationsShow
Sweet cherryFruit, Drupes PublicationsShow
TomatoVegetables, Fruit vegetables PublicationsShow
White wine grapeFruit, Berries PublicationsShow

Food Sources of its Precursor(s)

PrecursorFood SourceFood Source Group
5-O-Caffeoylquinic acidAppleFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidApple ciderBeverages, Alcoholic PublicationsShow
5-O-Caffeoylquinic acidApple juiceBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidApricotFruit, Drupes PublicationsShow
Cyanidin 3-O-glucosideBlackberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidBlackberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidBlackcurrantFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidBlueberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidBroccoliVegetables, Cabbages PublicationsShow
5-O-Caffeoylquinic acidCarrotVegetables, Root vegetables PublicationsShow
5-O-Caffeoylquinic acidCherry tomatoVegetables, Fruit vegetables PublicationsShow
5-O-Caffeoylquinic acidCiderBeverages, Alcoholic PublicationsShow
5-O-Caffeoylquinic acidCoffeeCoffee and coffee products PublicationsShow
Rosmarinic acidCommon oreganoHerbs and Spices PublicationsShow
Rosmarinic acidCommon sageHerbs and Spices PublicationsShow
Rosmarinic acidCommon thymeHerbs and Spices PublicationsShow
5-O-Caffeoylquinic acidEggplantVegetables, Fruit vegetables PublicationsShow
5-O-Caffeoylquinic acidEuropean cranberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideEuropean plumFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidEuropean plumFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidGlobe artichokeVegetables, Other vegetables PublicationsShow
5-O-Caffeoylquinic acidGreen teaTeas and herbal teas PublicationsShow
Cyanidin 3-O-glucosideLettuceVegetables, Leaf vegetables PublicationsShow
5-O-Caffeoylquinic acidLettuceVegetables, Leaf vegetables PublicationsShow
5-O-Caffeoylquinic acidMateTeas and herbal teas PublicationsShow
Rosmarinic acidMintHerbs and Spices PublicationsShow
Cyanidin 3-O-glucosideOlive, blackFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidOlive, blackFruit, Drupes PublicationsShow
Cyanidin 3-O-glucosidePeachFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidPeachFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidPearFruit, Pomes PublicationsShow
Rosmarinic acidPeppermintHerbs and Spices PublicationsShow
Cyanidin 3-O-glucosidePomegranate juiceBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidPotatoVegetables, Tubers PublicationsShow
5-O-Caffeoylquinic acidRoasted coffeeCoffee and coffee products PublicationsShow
Rosmarinic acidRosemaryHerbs and Spices PublicationsShow
Cyanidin 3-O-glucosideStrawberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidStrawberryFruit, Berries PublicationsShow
Rosmarinic acidSweet basilHerbs and Spices PublicationsShow
Cyanidin 3-O-glucosideSweet cherryFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidSweet cherryFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidTomatoVegetables, Fruit vegetables PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Caffeic acid 3-Hydroxybenzoic acidhuman in vitro (human) ratfaeces, urinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC7H6O3138.031694053 Publications
Caffeic acid p-Hydroxybenzoic acidhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC7H6O3138.031694053 Publications
Caffeic acid Benzoic acidhumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC7H6O2122.036779433 Publications
Caffeic acid Protocatechuic acidhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC7H6O4154.026608673 Publications
Caffeic acid Vanillic acidhumanurinehost metabolismNot AvailableNot AvailableNot AvailableC8H8O4168.042258738 Publications
Caffeic acid 3',4'-Dihydroxyphenylacetic acidhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC8H8O4168.042258738 Publications
Caffeic acid 4'-Hydroxyphenylacetic acidhumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Publications
Caffeic acid CatecholhumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC6H6O2110.036779433 Publications
Caffeic acid Coumaric acid (m-)raturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H8O3164.047344118 Publications
Caffeic acid Dihydrocaffeic acidraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O4182.057908802 Publications
Caffeic acid Phloretic acidhumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Caffeic acid Ferulic acidhuman ratplasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC10H10O4194.057908802 Publications
Caffeic acid Isoferulic acidhuman ratfaeces, plasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC10H10O4194.057908802 Publications
Caffeic acid 3-(3',4'-Dihydroxyphenyl)propionic acidhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC9H10O4182.057908802 Publications
Caffeic acid 3-(3'-Hydroxyphenyl)propionic acidratplasma, urinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Caffeic acid 3'-Hydroxyphenylacetic acidhumanNot Availablehost metabolismNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Publications
Caffeic acid Phenylacetic acidhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC8H8O2136.052429498 Publications
Caffeic acid 3-Phenylpropionic acidhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC9H10O2150.068079562 Publications
Caffeic acid 3-Hydroxyhippuric acidraturinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC9H9NO4195.053157774 Publications
Caffeic acid Caffeic acid sulfoglucuronideratplasmaNot AvailableNot AvailableNot AvailableNot AvailableC15H16O13S436.3485242 Publications
Caffeic acid Dihydroferulic acidhumanurineNot AvailableNot AvailableNot AvailableNot AvailableC10H12O4196.073558866 Publications
Caffeic acid Ferulic acid-4'-O-glucuronideratplasmaNot AvailableNot AvailableNot AvailableNot AvailableC16H18O10370.08999678 Publications
Caffeic acid Ferulic acid-4'-sulfateratplasmaNot AvailableNot AvailableNot AvailableNot AvailableC10H10O7S274.014723836 Publications
Caffeic acid Ferulic acid sulfoglucuronideratplasmaNot AvailableNot AvailableNot AvailableNot AvailableC16H18O13S450.375513 Publications
Caffeic acid FeruloylglycinehumanurineNot AvailableNot AvailableNot AvailableNot AvailableC12H13NO5251.079372523 Publications
Caffeic acid Hippuric acidratplasma, urinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC9H9NO3179.058243154 Publications
Caffeic acid Hydroxybenzoic acidraturineNot AvailableNot AvailableNot AvailableNot AvailableC7H6O3138.1230293 Publications
Caffeic acid α-hydroxyhippuric acidraturineNot AvailableNot AvailableNot AvailableNot AvailableC9H9NO4195.053157774 Publications
Caffeic acid 4-Hydroxyphenylpropionic acidratplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Caffeic acid Vanilloyl-glycinehumanurineNot AvailableNot AvailableNot AvailableNot AvailableC10H11NO5225.063722458 Publications
Caffeic acid Dihydrocaffeic acid-3'-O-glucuronidehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC15H18O10358.08999678 Publications
Caffeic acid Isoferulic acid-3'-sulfatehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC10H10O7S274.014723836 Publications
Caffeic acid 4-Hydroxyhippuric acidhumanNot Availablehost metabolismNot AvailableNot AvailableNot AvailableC9H9NO4195.053157774 Publications
Caffeic acid Isoferulic acid-3'-O-glucuronidehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC16H18O10370.08999678 Publications
Caffeic acid Dihydroisoferulic acidhumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC10H12O4196.073558866 Publications
Caffeic acid Dihydroisoferulic acid-3'-glucuronidehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC16H20O9356.110732224 Publications
Caffeic acid Dihydroferulic acid-4'-O-glucuronidehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC16H20O10372.105646844 Publications
Caffeic acid Dihydroferulic acid-4'-sulfatehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC10H12O7S276.0303739 Publications
Caffeic acid 4-Hydroxymandelic acidhumanNot Availablehost metabolismNot AvailableNot AvailableNot AvailableC8H8O4168.042258738 Publications
Caffeic acid Dihydrocaffeic acid-3-sulfatehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC9H10O7S262.014723836 Publications
Caffeic acid Caffeic acid 3'-sulfatehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC9H8O7S259.999073772 Publications
Caffeic acid 4-Hydroxybenzoic acid -3-sulfatehumanNot Availablehost metabolismNot AvailableNot AvailableNot AvailableC7H5O7S232.976147255 Publications
Caffeic acid 3-(4'-Hydroxyphenyl)propionic acid-3'-sulfatehumanNot Availablehost metabolismNot AvailableNot AvailableNot AvailableC9H9O7S261.007447384 Publications
Caffeic acid caffeic acid-3'-O-glucuronideratNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H16O10356.074346715 Publications
Caffeic acid caffeic acid-4'-O-glucuronideratNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H16O10356.074346715 Publications
Caffeic acid caffeic acid-4-O-sulfatehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC9H8O7S259.999073772 Publications
Caffeic acid 3'-Methoxy-4'-hydroxyphenylacetic acidhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC9H10O4182.057908802 Publications
Caffeic acid 3-Hydroxybenzoic acid-4-sulfatehumanNot Availablehost metabolismNot AvailableNot AvailableNot AvailableC8H8O7S247.999073772 Publications
Cyanidin 3-O-glucoside Caffeic acidhumanfaecesNot AvailableNot AvailableNot AvailableNot AvailableC9H8O4180.042258738 Publications
5-O-Caffeoylquinic acid Caffeic acidraturinehost metabolismNot AvailableNot AvailableNot AvailableC9H8O4180.042258738 Publications
Rosmarinic acid Caffeic acidraturineNot AvailableNot AvailableNot AvailableNot AvailableC9H8O4180.042258738 Publications

Inter-Individual Variations Metabolism

No data on inter-individual variations available

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