Identification

PhytoHub ID
PHUB001204
Name
Dihydrocaffeic acid-3'-O-glucuronide
Systematic Name
3-(4'-hydroxyphenyl)propanoic acid-3'-glucuronide
Synonyms
  • 3-(4-hydroxyphenyl)propanoic acid-3-glucuronide
  • 3-(4-hydroxyphenyl)propionic acid-3-glucuronide
  • 3-(4'-Hydroxyphenyl)propionic acid-3'-O-glucuronide
  • dihydrocaffeic acid-3-glucuronide
CAS Number
Not Available
Average Mass
358.299
Monoisotopic Mass
358.08999678
Chemical Formula
C15H18O10
IUPAC Name
(2R,3R,4R,5S,6R)-6-[5-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI Key
AELQNMHOLDHBFA-VVSAWPALSA-N
InChI Identifier
InChI=1S/C15H18O10/c16-7-3-1-6(2-4-9(17)18)5-8(7)24-15-12(21)10(19)11(20)13(25-15)14(22)23/h1,3,5,10-13,15-16,19-21H,2,4H2,(H,17,18)(H,22,23)/t10-,11-,12+,13-,15+/m1/s1
SMILES
O[[email protected]]1[[email protected]](O)[[email protected]@H](OC2=C(O)C=CC(CCC(O)=O)=C2)O[[email protected]]([[email protected]@H]1O)C(O)=O
Structure

Calculated Properties

Solubility (ALOGPS)
8.41e+00 g/l
LogS (ALOGPS)
-1.63
LogP (ALOGPS)
-0.09
Hydrogen Acceptors
10
Hydrogen Donors
6
Rotatable Bond Count
6
Polar Surface Area
173.98
Refractivity
77.9402
Polarizability
32.98813207252531
Formal Charge
0
Physiological Charge
-2
pKa (strongest basic)
-3.6868279761517333
pKa (strongest acidic)
3.0131597965048678
Number of Rings
2
Rule of Five
No
Bioavailability
Yes
Ghose Filter
No
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 Precursor(s)

PrecursorFamilyClassSub-class
Dihydrocaffeic acid(Poly)phenol metabolitesPhenolic acid metabolitesPhenylpropanoic acidsShow Precursor
Caffeic acid(Poly)phenol metabolitesPhenolic acid metabolitesCinnamic acidsShow Precursor
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Precursor

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
["1-hydroxy-2-unsubstituted benzenoids", "Acetals", "Beta hydroxy acids and derivatives", "Carbonyl compounds", "Carboxylic acids", "Dicarboxylic acids and derivatives", "Hexoses", "Hydrocarbon derivatives", "O-glucuronides", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Phenol ethers", "Phenoxy compounds", "Phenylpropanoic acids", "Polyols", "Pyrans", "Secondary alcohols"]
External Descriptor Annotations
Not Available
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "1-o-glucuronide", "3-phenylpropanoic-acid", "Acetal", "Alcohol", "Aromatic heteromonocyclic compound", "Benzenoid", "Beta-hydroxy acid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Dicarboxylic acid or derivatives", "Glucuronic acid or derivatives", "Hexose monosaccharide", "Hydrocarbon derivative", "Hydroxy acid", "Monocyclic benzene moiety", "Monosaccharide", "O-glucuronide", "O-glycosyl compound", "Organic oxide", "Organoheterocyclic compound", "Oxacycle", "Oxane", "Phenol", "Phenol ether", "Phenolic glycoside", "Phenoxy compound", "Polyol", "Pyran", "Secondary alcohol"]

Spectra

No spectra information available

Food Sources

PrecursorFood SourceFood Source Group
Caffeic acidAmerican cranberryFruit, Berries PublicationsShow
Caffeic acidAppleFruit, Pomes PublicationsShow
Caffeic acidApple juiceBeverages, Non-alcoholic PublicationsShow
Caffeic acidBlackberryFruit, Berries PublicationsShow
Dihydrocaffeic acidBlueberryFruit, BerriesShow
Caffeic acidBlueberryFruit, Berries PublicationsShow
Dihydrocaffeic acidBroccoliVegetables, CabbagesShow
Caffeic acidBroccoliVegetables, Cabbages PublicationsShow
Caffeic acidCarrotVegetables, Root vegetables PublicationsShow
Dihydrocaffeic acidCiderBeverages, AlcoholicShow
Caffeic acidCiderBeverages, Alcoholic PublicationsShow
Dihydrocaffeic acidCoffeeCoffee and coffee productsShow
Caffeic acidCoffeeCoffee and coffee products PublicationsShow
Dihydrocaffeic acidCommon wheatCereals and cereal productsShow
Caffeic acidCommon wheatCereals and cereal products PublicationsShow
Dihydrocaffeic acidCornCereals and cereal productsShow
Caffeic acidEggplantVegetables, Fruit vegetables PublicationsShow
Caffeic acidEuropean cranberryFruit, Berries PublicationsShow
Caffeic acidEuropean plumFruit, Drupes PublicationsShow
Dihydrocaffeic acidGrapesFruit, BerriesShow
Dihydrocaffeic acidLemonFruit, CitrusShow
Dihydrocaffeic acidLettuceVegetables, Leaf vegetablesShow
Dihydrocaffeic acidLimeFruit, CitrusShow
Caffeic acidMateBeverages, Non-alcoholic PublicationsShow
Dihydrocaffeic acidOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, blackFruit, Drupes PublicationsShow
Dihydrocaffeic acidOlive, greenFruit, Drupes PublicationsShow
Caffeic acidOlive, greenFruit, Drupes PublicationsShow
Caffeic acidPearFruit, Pomes PublicationsShow
Dihydrocaffeic acidSpinachVegetables, Leaf vegetablesShow
Caffeic acidStrawberryFruit, Berries PublicationsShow
Caffeic acidSweet cherryFruit, Drupes PublicationsShow
Caffeic acidTomatoVegetables, Fruit vegetables PublicationsShow
Dihydrocaffeic acidWheat breadCereals and cereal productsShow
Caffeic acidWhite wine grapeFruit, Berries PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Dihydrocaffeic acid Dihydrocaffeic acid-3'-O-glucuronideraturineNot AvailableNot AvailableNot AvailableC15H18O10358.08999678 Publications
Caffeic acid Dihydrocaffeic acid-3'-O-glucuronidehumanplasmahost metabolismNot AvailableNot AvailableC15H18O10358.08999678 Publications
Orange flavanones Dihydrocaffeic acid-3'-O-glucuronideNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H18O10358.08999678 Detailed Intervention Studies

Inter-Individual Variations Metabolism

No inter-individual variations available

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