Identification

PhytoHub ID
PHUB001435
Name
Dihydroferulic acid-4'-O-glucuronide
Systematic Name
3-(3'-methoxyphenyl)propanoic acid-4'-glucuronide
Synonyms
  • 3-(3-methoxyphenyl)propionic acid-4-glucuronide
  • 3-(3-Methoxyphenyl)propionic acid-4'-O-glucuronide
  • dihydroferulic acid-4-glucuronide
  • Dihydroferulic acid-4-O-glucuronide
CAS Number
Not Available
Average Mass
372.326
Monoisotopic Mass
372.105646844
Chemical Formula
C16H20O10
IUPAC Name
(2S,3S,4S,5R,6S)-6-[4-(2-carboxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI Key
KYERCTIKYSSKPA-JHZZJYKESA-N
InChI Identifier
InChI=1S/C16H20O10/c1-24-9-6-7(3-5-10(17)18)2-4-8(9)25-16-13(21)11(19)12(20)14(26-16)15(22)23/h2,4,6,11-14,16,19-21H,3,5H2,1H3,(H,17,18)(H,22,23)/t11-,12-,13+,14-,16+/m0/s1
SMILES
COC1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=CC(CCC(O)=O)=C1
Structure

Calculated Properties

Solubility (ALOGPS)
4.96e+00 g/l
LogS (ALOGPS)
-1.88
LogP (ALOGPS)
-0.24
Hydrogen Acceptors
10
Hydrogen Donors
5
Rotatable Bond Count
7
Polar Surface Area
162.98
Refractivity
82.4225
Polarizability
35.15537805790356
Formal Charge
0
Physiological Charge
-2
pKa (strongest basic)
-3.6868279760573377
pKa (strongest acidic)
3.045350255368854
Number of Rings
2
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

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

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Coffee hydroxycinnamatesPolyphenolsFlavonoidsHydroxycinnamic acidsShow Food Phytochemical
Caffeic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Black tea Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Coffee Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Yerba mate Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Ferulic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Organooxygen compounds
Super-class
Organic oxygen compounds
Sub-class
Carbohydrates and carbohydrate conjugates
Direct Parent Name
Phenolic glycosides
Alternative Parent Names
["Acetals", "Alkyl aryl ethers", "Anisoles", "Beta hydroxy acids and derivatives", "Carbonyl compounds", "Carboxylic acids", "Dicarboxylic acids and derivatives", "Hexoses", "Hydrocarbon derivatives", "Methoxybenzenes", "O-glucuronides", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Phenoxy compounds", "Phenylpropanoic acids", "Polyols", "Pyrans", "Secondary alcohols"]
External Descriptor Annotations
Not Available
Substituent Names
["1-o-glucuronide", "3-phenylpropanoic-acid", "Acetal", "Alcohol", "Alkyl aryl ether", "Anisole", "Aromatic heteromonocyclic compound", "Benzenoid", "Beta-hydroxy acid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Dicarboxylic acid or derivatives", "Ether", "Glucuronic acid or derivatives", "Hexose monosaccharide", "Hydrocarbon derivative", "Hydroxy acid", "Methoxybenzene", "Monocyclic benzene moiety", "Monosaccharide", "O-glucuronide", "O-glycosyl compound", "Organic oxide", "Organoheterocyclic compound", "Oxacycle", "Oxane", "Phenol ether", "Phenolic glycoside", "Phenoxy compound", "Polyol", "Pyran", "Secondary alcohol"]

Spectra from Online Resources

No spectra information available

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
Caffeic acidAmerican cranberryFruit, Berries PublicationsShow
Ferulic acidAmerican cranberryFruit, Berries PublicationsShow
Caffeic acidAppleFruit, Pomes PublicationsShow
Caffeic acidApple juiceBeverages, Non-alcoholic PublicationsShow
Ferulic acidApple juiceBeverages, Non-alcoholic PublicationsShow
Caffeic acidBeerBeverages, Alcoholic PublicationsShow
Ferulic acidBeerBeverages, Alcoholic PublicationsShow
Ferulic acidBilberryFruit, Berries PublicationsShow
Ferulic acidBlack mulberryFruit, Berries PublicationsShow
Caffeic acidBlackberryFruit, Berries PublicationsShow
Ferulic acidBlackberryFruit, Berries PublicationsShow
Caffeic acidBlueberryFruit, Berries PublicationsShow
Ferulic acidBlueberryFruit, Berries PublicationsShow
Caffeic acidBroccoliVegetables, Cabbages PublicationsShow
Ferulic acidBroccoliVegetables, Cabbages PublicationsShow
Caffeic acidCarrotVegetables, Root vegetables PublicationsShow
Caffeic acidCiderBeverages, Alcoholic PublicationsShow
Ferulic acidCocoa beanCocoa and cocoa products PublicationsShow
Caffeic acidCoffeeCoffee and coffee products PublicationsShow
Ferulic acidCoffeeCoffee and coffee products PublicationsShow
Ferulic acidCommon beanPulses and beans PublicationsShow
Ferulic acidCommon walnutNuts PublicationsShow
Caffeic acidCommon wheatCereals and cereal products PublicationsShow
Ferulic acidCommon wheatCereals and cereal products PublicationsShow
Ferulic acidCornCereals and cereal products PublicationsShow
Ferulic acidDateFruit, Other fruits PublicationsShow
Caffeic acidEggplantVegetables, Fruit vegetables PublicationsShow
Ferulic acidEggplantVegetables, Fruit vegetables PublicationsShow
Caffeic acidEuropean cranberryFruit, Berries PublicationsShow
Ferulic acidEuropean cranberryFruit, Berries PublicationsShow
Caffeic acidEuropean plumFruit, Drupes PublicationsShow
Ferulic acidFennelHerbs and Spices PublicationsShow
Ferulic acidGrapefruitFruit, Citrus PublicationsShow
Ferulic acidHard wheatCereals and cereal products PublicationsShow
Caffeic acidMateTeas and herbal teas PublicationsShow
Caffeic acidOlive, blackFruit, Drupes PublicationsShow
Ferulic acidOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, greenFruit, Drupes PublicationsShow
Ferulic acidOlive, greenFruit, Drupes PublicationsShow
Ferulic acidOrange juiceBeverages, Non-alcoholic PublicationsShow
Caffeic acidPearFruit, Pomes PublicationsShow
Ferulic acidRapeseedOilseed crops PublicationsShow
Ferulic acidRed raspberryFruit, Berries PublicationsShow
Ferulic acidRiceCereals and cereal products PublicationsShow
Ferulic acidRosemaryHerbs and Spices PublicationsShow
Ferulic acidRye breadCereals and cereal products PublicationsShow
Ferulic acidSpinachVegetables, Leaf vegetables PublicationsShow
Caffeic acidStrawberryFruit, Berries PublicationsShow
Ferulic acidStrawberryFruit, Berries PublicationsShow
Caffeic acidSweet cherryFruit, Drupes PublicationsShow
Ferulic acidSweet orangeFruit, Citrus PublicationsShow
Ferulic acidTarragonHerbs and Spices PublicationsShow
Caffeic acidTomatoVegetables, Fruit vegetables PublicationsShow
Ferulic acidTomatoVegetables, Fruit vegetables PublicationsShow
Ferulic acidWhite wineBeverages, Alcoholic PublicationsShow
Caffeic acidWhite wine grapeFruit, Berries PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Coffee hydroxycinnamates Dihydroferulic acid-4'-O-glucuronidehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC16H20O10372.105646844 Detailed Intervention Studies Publications
Caffeic acid Dihydroferulic acid-4'-O-glucuronidehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC16H20O10372.105646844 Publications
Orange flavanones Dihydroferulic acid-4'-O-glucuronidehumanplasmahost-gut microbiota co-metabolite5h-8h20-50 nmol/LNot AvailableC16H20O10372.105646844 Detailed Intervention Studies Publications
Black tea Flavan-3-ols Dihydroferulic acid-4'-O-glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available<1%C16H20O10372.105646844 Detailed Intervention Studies Publications
Coffee Chlorogenic acids Dihydroferulic acid-4'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite5h-8h50-200 nmol/L1-5%C16H20O10372.105646844 Detailed Intervention Studies Publications
Yerba mate Chlorogenic acids Dihydroferulic acid-4'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite5h-8h50-200 nmol/L<1%C16H20O10372.105646844 Detailed Intervention Studies Publications
Ferulic acid Dihydroferulic acid-4'-O-glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available1-5%C16H20O10372.105646844 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Coffee Chlorogenic acids Dihydroferulic acid-4'-O-glucuronideMicrobiotaEffect, clusters Publications
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