Identification

PhytoHub ID
PHUB001916
Name
caffeic acid-3'-O-glucuronide
Systematic Name
4′-Hydroxycinnamic acid-3′-glucuronide
Synonyms
Not Available
CAS Number
Not Available
Average Mass
356.283
Monoisotopic Mass
356.074346715
Chemical Formula
C15H16O10
IUPAC Name
6-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI Key
BSOMSDFTZKNUHY-DUXPYHPUSA-N
InChI Identifier
InChI=1S/C15H16O10/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/h1-5,10-13,15-16,19-21H,(H,17,18)(H,22,23)/b4-2+
SMILES
OC1C(OC2=C(O)C=CC(\C=C\C(O)=O)=C2)OC(C(O)C1O)C(O)=O
Structure

Calculated Properties

Solubility (ALOGPS)
6.29e+00 g/l
LogS (ALOGPS)
-1.75
LogP (ALOGPS)
0.69
Hydrogen Acceptors
10
Hydrogen Donors
6
Rotatable Bond Count
5
Polar Surface Area
173.98
Refractivity
79.03349999999999
Polarizability
32.404161214709006
Formal Charge
0
Physiological Charge
-2
pKa (strongest basic)
-3.6868279771414696
pKa (strongest acidic)
2.8794562240175425
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
Cinnamic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Caffeic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Cranberry (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Coffee Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Globe artichoke (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical

Spectra from Online Resources

No spectra information available

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Caffeic acid caffeic acid-3'-O-glucuronideratNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H16O10356.074346715 Publications
Orange flavanones caffeic acid-3'-O-glucuronideNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H16O10356.074346715 Detailed Intervention Studies
Cranberry (Poly)phenols caffeic acid-3'-O-glucuronidehumanplasma, urinehost metabolism1h-3h20-50 nmol/L<1%C15H16O10356.074346715 Detailed Intervention Studies Publications
Coffee Chlorogenic acids caffeic acid-3'-O-glucuronidehumanplasma, urinehost metabolism1h-3h20-50 nmol/L<1%C15H16O10356.074346715 Detailed Intervention Studies Publications
Globe artichoke (Poly)phenols caffeic acid-3'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite5h-8h<20 nmol/L<1%C15H16O10356.074346715 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Coffee Chlorogenic acids caffeic acid-3'-O-glucuronideMicrobiotaEffect, clusters Publications
Globe artichoke (Poly)phenols caffeic acid-3'-O-glucuronideMicrobiotaEffect, clusters Publications
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