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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:06 UTC
HMDB IDHMDB0000375
Secondary Accession Numbers
  • HMDB00375
Metabolite Identification
Common Name3-(3-Hydroxyphenyl)propanoic acid
Description3-(3-Hydroxyphenyl)propanoic (hMPP) acid is one of the major metabolites of ingested caffeic acid (PMID: 15479001 ) and of the phenolic degradation products of proanthocyanidins (the most abundant polyphenol present in chocolate) by the microflora in the colon (PMID: 12663291 ). mHPP is suspected to have antioxidants properties and is actively absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers (PMID: 15479001 , 12663291 ). hMPP has been found to be a metabolite of Clostridium, Escherichia, and Eubacterium (PMID: 28393285 , 19520845 ). 3-(3-Hydroxyphenyl)propanoic acid is a flavonoid metabolite. 3-(3-Hydroxyphenyl)propanoic acid is a phenolic acid metabolite formed by the gut microflora detected after the consumption of whole grain.
Structure
Data?1563860646
Synonyms
ValueSource
3-(3-Hydroxy-phenyl)-propanoic acidChEBI
3-(3-Hydroxyphenyl)propionic acidChEBI
3-(m-Hydroxyphenyl)propionic acidChEBI
beta-(m-Hydroxyphenyl)propionic acidChEBI
Dihydro-3-coumaric acidChEBI
3-HydroxyphenylpropanoateKegg
3-(3-Hydroxyphenyl)propanoateKegg
3-(3-Hydroxy-phenyl)-propanoateGenerator
3-(3-Hydroxyphenyl)propionateGenerator
3-(m-Hydroxyphenyl)propionateGenerator
b-(m-Hydroxyphenyl)propionateGenerator
b-(m-Hydroxyphenyl)propionic acidGenerator
beta-(m-Hydroxyphenyl)propionateGenerator
Β-(m-hydroxyphenyl)propionateGenerator
Β-(m-hydroxyphenyl)propionic acidGenerator
Dihydro-3-coumarateGenerator
3-Hydroxyphenylpropanoic acidGenerator
3-(3-Hydroxy-phenyl)-propionic acidHMDB
3-HydroxybenzenepropanoateHMDB
3-Hydroxybenzenepropanoic acidHMDB
3-HydroxydihydrocinnamateHMDB
3-Hydroxydihydrocinnamic acidHMDB
3-Hydroxyhydrocinnamic acidHMDB
3-HydroxyphenylpropionateHMDB
3-Hydroxyphenylpropionic acidHMDB
b-(3-Hydroxyphenyl)propionateHMDB
b-(3-Hydroxyphenyl)propionic acidHMDB
beta-(3-Hydroxyphenyl)propionateHMDB
beta-(3-Hydroxyphenyl)propionic acidHMDB
Dihydro-m-coumarateHMDB
Dihydro-m-coumaric acidHMDB
m-Hydrocoumaric acidHMDB
m-Hydroxy-hydrocinnamateHMDB
m-Hydroxy-hydrocinnamic acidHMDB
m-HydroxyphenylpropionateHMDB
m-Hydroxyphenylpropionic acidHMDB
Dihydro-3-coumaric acid, monosodium saltHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name3-(3-hydroxyphenyl)propanoic acid
Traditional Name3-hydroxyphenylpropionic acid
CAS Registry Number621-54-5
SMILES
OC(=O)CCC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)
InChI KeyQVWAEZJXDYOKEH-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
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.8 g/LALOGPS
logP1.14ALOGPS
logP1.75ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.95 m³·mol⁻¹ChemAxon
Polarizability16.92 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-1900000000-77779ae60312f591e17eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-0930000000-cb674deffe8e93afca7eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-1900000000-77779ae60312f591e17eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-0930000000-cb674deffe8e93afca7eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-3900000000-df46f44d343adb6bf4beJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9660000000-4030a1092b3837900ee3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-4a45085593200cc6c7d3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-1900000000-ac287061b5cdcc1f846bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-9400000000-1e275b3ba45b8048aa13JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-ec17e3f1692cb9469bebJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0900000000-4407c82bb7a72d9feb58JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r5-4900000000-2b7cd80f8f959113fe79JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    BloodDetected and Quantified0.056 +/- 0.015 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.035 +/- 0.008 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.086 +/- 0.021 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.084 +/- 0.022 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.04 +/- 0.008 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.039 +/- 0.012 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.034 +/- 0.01 uMAdult (>18 years old)Male
    Normal
    details
    BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 details
    BloodDetected and Quantified0.775 +/- 0.747 uMAdult (>18 years old)Male
    Normal
    details
    BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified74.0188 +/- 139.0110 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified105.913 +/- 182.941 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified288.854 +/- 717.321 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified290.659 +/- 834.0660 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified9.0508 (0.0722-110.366) nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)BothNormal details
    FecesDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
    UrineDetected and Quantified0.32 (0.2 - 0.5) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
    UrineDetected and Quantified1.5 +/- 0.46 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 details
    UrineDetected and Quantified0.043 +/- 0.006 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Irritable bowel syndrome
    details
    FecesDetected but not Quantified Adult (>18 years old)Not Specifiedasymptomatic diverticulosis details
    FecesDetected but not Quantified Adult (>18 years old)Not Specifiedsymptomatic uncomplicated diverticular disease details
    UrineDetected and Quantified2.292 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified1.325 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Gastroesophageal reflux disease
      • Mordechai, Hien, ...
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    Associated Disorders and Diseases
    Disease References
    Irritable bowel syndrome
    1. Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
    Colorectal cancer
    1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
    Diverticular disease
    1. Tursi A, Mastromarino P, Capobianco D, Elisei W, Miccheli A, Capuani G, Tomassini A, Campagna G, Picchio M, Giorgetti G, Fabiocchi F, Brandimarte G: Assessment of Fecal Microbiota and Fecal Metabolome in Symptomatic Uncomplicated Diverticular Disease of the Colon. J Clin Gastroenterol. 2016 Oct;50 Suppl 1:S9-S12. doi: 10.1097/MCG.0000000000000626. [PubMed:27622378 ]
    Eosinophilic esophagitis
    1. (). Mordechai, Hien, and David S. Wishart. .
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB021993
    KNApSAcK IDNot Available
    Chemspider ID89
    KEGG Compound IDC11457
    BioCyc ID3-HYDROXYPHENYL-PROPIONATE
    BiGG IDNot Available
    Wikipedia LinkM-Coumaric acid
    METLIN ID5364
    PubChem Compound91
    PDB IDNot Available
    ChEBI ID1427
    References
    Synthesis ReferenceDombrow, M.; Linnell, W. H. Preparation of m-hydroxyphenylpropionic acid. Journal of Pharmacy and Pharmacology (1952), 4 118-19.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. [PubMed:10706426 ]
    2. Duran M, Wanders RJ, de Jager JP, Dorland L, Bruinvis L, Ketting D, Ijlst L, van Sprang FJ: 3-Hydroxydicarboxylic aciduria due to long-chain 3-hydroxyacyl-coenzyme A dehydrogenase deficiency associated with sudden neonatal death: protective effect of medium-chain triglyceride treatment. Eur J Pediatr. 1991 Jan;150(3):190-5. [PubMed:2044590 ]
    3. Konishi Y, Kobayashi S: Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. J Agric Food Chem. 2004 Oct 20;52(21):6418-24. [PubMed:15479001 ]
    4. Rios LY, Gonthier MP, Remesy C, Mila I, Lapierre C, Lazarus SA, Williamson G, Scalbert A: Chocolate intake increases urinary excretion of polyphenol-derived phenolic acids in healthy human subjects. Am J Clin Nutr. 2003 Apr;77(4):912-8. [PubMed:12663291 ]
    5. Rowland I, Gibson G, Heinken A, Scott K, Swann J, Thiele I, Tuohy K: Gut microbiota functions: metabolism of nutrients and other food components. Eur J Nutr. 2018 Feb;57(1):1-24. doi: 10.1007/s00394-017-1445-8. Epub 2017 Apr 9. [PubMed:28393285 ]
    6. Manso I, Torres B, Andreu JM, Menendez M, Rivas G, Alfonso C, Diaz E, Garcia JL, Galan B: 3-Hydroxyphenylpropionate and phenylpropionate are synergistic activators of the MhpR transcriptional regulator from Escherichia coli. J Biol Chem. 2009 Aug 7;284(32):21218-28. doi: 10.1074/jbc.M109.008243. Epub 2009 Jun 11. [PubMed:19520845 ]
    7. Upadhyaya S, Banerjee G: Type 2 diabetes and gut microbiome: at the intersection of known and unknown. Gut Microbes. 2015;6(2):85-92. doi: 10.1080/19490976.2015.1024918. [PubMed:25901889 ]
    8. 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-(3-Hydroxyphenyl)propanoic acid → 6-[3-(2-carboxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
    3-(3-Hydroxyphenyl)propanoic acid → 3,4,5-trihydroxy-6-{[3-(3-hydroxyphenyl)propanoyl]oxy}oxane-2-carboxylic aciddetails
    General function:
    sulfotransferase activity
    Specific function:
    Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
    Gene Name:
    SULT1A3
    Uniprot ID:
    P0DMM9
    Molecular weight:
    34195.96
    Reactions
    3-(3-Hydroxyphenyl)propanoic acid → 3-[3-(Sulfooxy)phenyl]propanoic aciddetails