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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-09-13 02:14:49 UTC
Update Date2023-02-21 17:31:31 UTC
HMDB IDHMDB0125533
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,5-Dihydroxyphenylpropionic acid
Description3,5-Dihydroxyphenylpropionic acid (3,5-DHPPA) is an alkylresorcinol metabolite. It is a potential urinary biomarker of whole grain intake (PMID: 15282102 ). BioTransformer predicts that 3,5-DHPPA is a product of 3,5-dihydroxycinnamic acid metabolism via a reduction-of-alpha-beta-unsaturated-compounds-pattern1 reaction occurring in human gut microbiota and catalyzed by the abkar1 enzyme (PMID: 30612223 ).
Structure
Thumb
Synonyms
ValueSource
3,5-DihydroxyphenylpropionateGenerator
3-(3,5-Dihydroxyphenyl)propanoateGenerator
3,5-DHPPAHMDB
3,5-Dihydroxybenzenepropionic acidHMDB
3,5-Dihydroxyphenylpropanoic acidHMDB
3,5-Dihydroxyphenylpropionic acidHMDB
3-(3,5-Dihydroxyphenyl)-1-propanoic acidHMDB
3-(3,5-Dihydroxyphenyl)-1-propionic acidHMDB
3-(3',5'-Dihydroxyphenyl)propanoic acidHMDB
3-(3,5-Dihydroxyphenyl)propanoic acidHMDB
3-(3,5-Dihydroxyphenyl)propanoic acid;HMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.175
Monoisotopic Molecular Weight182.057908802
IUPAC Name3-(3,5-dihydroxyphenyl)propanoic acid
Traditional Name3-(3,5-dihydroxyphenyl)propanoic acid
CAS Registry Number26539-01-5
SMILES
OC(=O)CCC1=CC(O)=CC(O)=C1
InChI Identifier
InChI=1S/C9H10O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h3-5,10-11H,1-2H2,(H,12,13)
InChI KeyITPFIKQWNDGDLG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB084412
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound161525
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ross AB, Aman P, Kamal-Eldin A: Identification of cereal alkylresorcinol metabolites in human urine-potential biomarkers of wholegrain wheat and rye intake. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Sep 25;809(1):125-30. doi: 10.1016/j.jchromb.2004.06.015. [PubMed:15282102 ]
  2. Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]
  3. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3,5-Dihydroxyphenylpropionic acid → 6-[3-(2-carboxyethyl)-5-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,5-Dihydroxyphenylpropionic acid → 6-{[3-(3,5-dihydroxyphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails