Identification

PhytoHub ID
PHUB001177
Name
4-Hydroxyphenylpropionic acid
Systematic Name
3-(4'-Hydroxyphenyl)propanoic acid
Synonyms
  • 3-(4-Hydroxyphenyl)propanoic acid
  • 3-(4-Hydroxyphenyl)propionic acid
  • Desaminotyrosine
  • Dihydrocoumaric acid
  • Hydroxyphenylpropionate
  • Phloretic acid
CAS Number
501-97-3
Average Mass
166.176
Monoisotopic Mass
166.062994182
Chemical Formula
C9H10O3
IUPAC Name
3-(4-hydroxyphenyl)propanoic acid
InChI Key
NMHMNPHRMNGLLB-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)
SMILES
OC(=O)CCC1=CC=C(O)C=C1
Structure

Calculated Properties

Solubility (ALOGPS)
2.71e+00 g/l
LogS (ALOGPS)
-1.79
LogP (ALOGPS)
1.15
Hydrogen Acceptors
3
Hydrogen Donors
2
Rotatable Bond Count
3
Polar Surface Area
57.53
Refractivity
43.947500000000005
Polarizability
16.972150949657607
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-5.958297991799354
pKa (strongest acidic)
4.214213970870649
Number of Rings
1
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
Caffeic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Coffee Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Yerba mate Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Phenylpropanoic acids
Super-class
Phenylpropanoids and polyketides
Sub-class
Not Available
Direct Parent Name
Phenylpropanoic acids
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "Benzene and substituted derivatives", "Carbonyl compounds", "Carboxylic acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides"]
External Descriptor Annotations
["hydroxy monocarboxylic acid"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "3-phenylpropanoic-acid", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Hydrocarbon derivative", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol"]

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 4-Hydroxyphenylpropionic acidratplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Orange flavanones 4-Hydroxyphenylpropionic acidhumanplasmagut microbiota metabolite5h-8h20-50 nmol/LNot AvailableC9H10O3166.062994182 Detailed Intervention Studies Publications
Coffee Chlorogenic acids 4-Hydroxyphenylpropionic acidhumanurinegut microbiota metaboliteNot AvailableNot Available<1%C9H10O3166.062994182 Detailed Intervention Studies Publications
Yerba mate Chlorogenic acids 4-Hydroxyphenylpropionic acidhumanurinegut microbiota metaboliteNot AvailableNot Available<1%C9H10O3166.062994182 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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