metabolite

Showing entry for Isoferulic acid-3'-O-glucuronide

Identification

PhytoHub ID
PHUB001432
Name
Isoferulic acid-3'-O-glucuronide
Systematic Name
4’-methoxycinnamic acid-3'-glucuronide
Synonyms
  • 4-methoxycinnamic acid-3-glucuronide
  • isoferulic acid-3-glucuronide
  • isoferulic acid-3'-glucuronide
CAS Number
1065272-10-7
Average Mass
370.31
Monoisotopic Mass
370.08999678
Chemical Formula
C16H18O10
IUPAC Name
(2S,3S,4S,5R,6S)-6-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI Key
SHJZLGVIOYFHCB-MBAOVNHDSA-N
InChI Identifier
InChI=1S/C16H18O10/c1-24-8-4-2-7(3-5-10(17)18)6-9(8)25-16-13(21)11(19)12(20)14(26-16)15(22)23/h2-6,11-14,16,19-21H,1H3,(H,17,18)(H,22,23)/b5-3+/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=C(\C=C\C(O)=O)C=C1
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
4.18e+00 g/l
LogS (ALOGPS)
-1.95
LogP (ALOGPS)
-0.23
Hydrogen Acceptors
10
Hydrogen Donors
5
Rotatable Bond Count
6
Polar Surface Area
162.98000000000002
Refractivity
83.5158
Polarizability
34.13116906602628
Formal Charge
0
Physiological Charge
-2
pKa (strongest basic)
-3.686827977923865
pKa (strongest acidic)
2.963519929853911
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
Cinnamic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Coffee hydroxycinnamatesPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Caffeic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Hazelnut Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Cranberry (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Coffee Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Red Raspberries AnthocyaninsPolyphenolsFlavonoidsAnthocyaninsShow Food Phytochemical
Rosemary tea (poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Globe artichoke (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Yerba mate Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Grape (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Orange (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Oat (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Coffee hydroxycinnamates Isoferulic acid-3'-O-glucuronidehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC16H18O10370.08999678 Detailed Intervention Studies Publications
Caffeic acid Isoferulic acid-3'-O-glucuronidehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC16H18O10370.08999678 Publications
Orange flavanones Isoferulic acid-3'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite5h-8h<20 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Hazelnut Flavan-3-ols Isoferulic acid-3'-O-glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Cranberry (Poly)phenols Isoferulic acid-3'-O-glucuronidehumanplasma, urinehost metabolism1h-3h200-500 nmol/L1-5%C16H18O10370.08999678 Detailed Intervention Studies Publications
Coffee Chlorogenic acids Isoferulic acid-3'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite3h-5h50-200 nmol/L1-5%C16H18O10370.08999678 Detailed Intervention Studies Publications
Red Raspberries Anthocyanins Isoferulic acid-3'-O-glucuronidehumanplasma, urinehost metabolism1h-3h<20 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Rosemary tea (poly)phenols Isoferulic acid-3'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite8h-12h200-500 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Globe artichoke (Poly)phenols Isoferulic acid-3'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite5h-8h50-200 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Yerba mate Chlorogenic acids Isoferulic acid-3'-O-glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Grape (Poly)phenols Isoferulic acid-3'-O-glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Orange (Poly)phenols Isoferulic acid-3'-O-glucuronideNot AvailableNot Availablehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC16H18O10370.08999678 Detailed Intervention Studies Publications
Oat (Poly)phenols Isoferulic acid-3'-O-glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available<1%C16H18O10370.08999678 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

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