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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2019-07-29 19:20:59 UTC
HMDB IDHMDB0002199
Secondary Accession Numbers
  • HMDB0061145
  • HMDB02199
  • HMDB61145
Metabolite Identification
Common NameDesaminotyrosine
DescriptionDesaminotyrosine, also known as 4-hydroxyphenylpropionic acid, is a normal constituent of human urine. It is a product of tyrosine metabolism; its concentration in urine increases in patients with gastrointestinal diseases (Dictionary of Organic Compounds). Desaminotyrosine is a major phenolic acid breakdown product of proanthocyanidin metabolism (PMID: 15315398 ). Urinary desaminotyrosine is produced by Clostridium sporogenes and C. botulinum (PMID: 29168502 ). Desaminotyrosine is also found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas, and Staphylococcus (PMID: 29168502 , 28393285 , 19961416 ) (https://www.gutmicrobiotaforhealth.com/en/dietary-compound-gut-microbe-team-flu-prevention/). Desaminotyrosine is a phenolic acid metabolite formed by the gut microflora detected after the consumption of whole grain.
Structure
Data?1563860723
Synonyms
ValueSource
3-(4-Hydroxyphenyl)propionic acidChEBI
3-(p-Hydroxyphenyl)propionic acidChEBI
4-Hydroxyphenylpropionic acidChEBI
beta-(p-Hydroxyphenyl)propionic acidChEBI
Dihydro-p-coumaric acidChEBI
HYDROXYPHENYL propionIC ACIDChEBI
p-Hydroxyhydrocinnamic acidChEBI
p-Hydroxyphenylpropionic acidChEBI
Phloretinic acidChEBI
Phloretic acidKegg
3-(4-Hydroxyphenyl)propionateGenerator
3-(p-Hydroxyphenyl)propionateGenerator
4-HydroxyphenylpropionateGenerator
b-(p-Hydroxyphenyl)propionateGenerator
b-(p-Hydroxyphenyl)propionic acidGenerator
beta-(p-Hydroxyphenyl)propionateGenerator
Β-(p-hydroxyphenyl)propionateGenerator
Β-(p-hydroxyphenyl)propionic acidGenerator
Dihydro-p-coumarateGenerator
HYDROXYPHENYL propionateGenerator
p-HydroxyhydrocinnamateGenerator
p-HydroxyphenylpropionateGenerator
PhloretinateGenerator
PhloretateGenerator
3-(4'-Hydroxyphenyl)-propionateHMDB
3-(4'-Hydroxyphenyl)-propionic acidHMDB
3-(4'-Hydroxyphenyl)propionic acidHMDB
3-(4-Hydroxy-phenyl)-propionateHMDB
3-(4-Hydroxy-phenyl)-propionic acidHMDB
3-(4-Hydroxyphenyl)-propionateHMDB
3-(4-Hydroxyphenyl)-propionic acidHMDB
3-(4-Hydroxyphenyl)propanoateHMDB
3-(4-Hydroxyphenyl)propanoic acidHMDB
3-(Para-hydroxyphenyl)propionateHMDB
3-(Para-hydroxyphenyl)propionic acidHMDB
4'-Hydroxyphenylpropionic acidHMDB
4-(4-HydroxyphenylpropanoateHMDB
4-(4-Hydroxyphenylpropanoic acidHMDB
4-Hydroxy-(9ci)benzenepropanoateHMDB
4-Hydroxy-(9ci)benzenepropanoic acidHMDB
4-Hydroxy-benzenepropanoateHMDB
4-Hydroxy-benzenepropanoic acidHMDB
4-HydroxybenzenepropanoateHMDB
4-Hydroxybenzenepropanoic acidHMDB
Hydro-p-coumarateHMDB
Hydro-p-coumaric acidHMDB
Hydroxy-hydrocinnamic acidHMDB
N-Hydroxysuccinimide esterHMDB
p-Hydroxy-benzene propionateHMDB
p-Hydroxy-benzene propionic acidHMDB
p-Hydroxy-hydrocinnamateHMDB
p-Hydroxy-hydrocinnamic acidHMDB
4-Hydroxyhydrocinnamic acidHMDB
DesaminotyrosineChEBI
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name3-(4-hydroxyphenyl)propanoic acid
Traditional Namehydroxyphenyl propionic acid
CAS Registry Number501-97-3
SMILES
OC(=O)CCC1=CC=C(O)C=C1
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)
InChI KeyNMHMNPHRMNGLLB-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-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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.16HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.71 g/LALOGPS
logP1.15ALOGPS
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
Polarizability16.97 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)splash10-066r-9800000000-44e113d8fc2602ffba88JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004l-0900000000-5ae3f727b5218398aa83JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066r-9800000000-44e113d8fc2602ffba88JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004l-0900000000-5ae3f727b5218398aa83JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-3900000000-424e95de0b8037c4aa20JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9660000000-261dcfd72b0dbd1c03dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kv-5900000000-db98339dadc21116c7aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052r-9400000000-7d2340d4f6981ee8aecbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00bi-9100000000-cac6ca239c2cbe36238dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-e131522c5a7352167afbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-3900000000-5c5920f4693d31baa640JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9500000000-49bd07916272cdc49e68JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a6u-9100000000-683b03c9384a9a750863JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-9000000000-d4af6cba1b370fd620edJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-514be816ed648e5588b7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-3900000000-5c5920f4693d31baa640JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9500000000-49bd07916272cdc49e68JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a6u-9100000000-683b03c9384a9a750863JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-d4af6cba1b370fd620edJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-3603746465916eaf1e98JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0601-1900000000-a85683e512fff2c291ddJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdi-9500000000-dbb0fa659379ccf4eb26JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-17bb794e8bbfe1aad6b3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-9708817125183e0214a3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-d9a164ed2938481885d9JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry details
BloodDetected and Quantified0.664 +/- 0.089 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.628 +/- 0.075 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.712 +/- 0.088 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.705 +/- 0.1 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.701 +/- 0.071 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.69 +/- 0.099 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.574 +/- 0.078 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.189 +/- 2.633 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not Quantified Not AvailableNot Available
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 Quantified76.426 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified131.790 +/- 93.878 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified143.825 +/- 106.515 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified184.746 +/- 169.702 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)BothNormal details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Not Specified
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedBoth
    Normal
    details
    FecesDetected and Quantified16.128 +/- 15.165 nmol/g wet fecesNot SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified84.249 (62.465-111.931) nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified25.877 +/- 30.0890 nmol/g wet fecesNot SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Infant (0-1 year old)Both
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
    SalivaDetected and Quantified1.03 +/- 1.26 uMAdult (>18 years old)Not Specified
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified1.32 +/- 2.81 uMAdult (>18 years old)Both
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected and Quantified1.59 +/- 2.05 uMAdult (>18 years old)Not Specified
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified1.64 +/- 1.89 uMAdult (>18 years old)Female
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified2.02 +/- 2.48 uMAdult (>18 years old)Not Specified
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified3.11 +/- 5.21 uMAdult (>18 years old)Not Specified
    Normal
      • Sugimoto et al. (...
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry details
    UrineDetected and Quantified0.089 +/- 0.016 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    UrineDetected and Quantified0.2 +/- 0.041 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    UrineDetected and Quantified0.078 +/- 0.009 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    UrineDetected but not Quantified Not AvailableNot AvailableNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Irritable bowel syndrome
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Ulcerative colitis
    details
    FecesDetected but not Quantified Adult (>18 years old)BothIleal Crohn's disease details
    FecesDetected but not Quantified Adult (>18 years old)BothCCD details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Irritable bowel syndrome
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    SalivaDetected but not Quantified Adult (>18 years old)MaleAttachment loss  details
    SalivaDetected but not Quantified Adult (>18 years old)MaleMissing teeth details
    SalivaDetected but not Quantified Adult (>18 years old)MalePeriodontal Probing Depth details
    SalivaDetected but not Quantified Adult (>18 years old)MaleSupragingival Plaque 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 ]
    2. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
    Ulcerative colitis
    1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
    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 ]
    2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
    3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    Attachment loss
    1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
    Missing teeth
    1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
    Periodontal Probing Depth
    1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
    Supragingival Plaque
    1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
    Associated OMIM IDs
    DrugBank IDDB03897
    Phenol Explorer Compound ID578
    FoodDB IDFDB000849
    KNApSAcK IDC00029471
    Chemspider ID9965
    KEGG Compound IDC01744
    BioCyc ID2-3-DIHYDROXYPHENYL-PROPIONATE
    BiGG IDNot Available
    Wikipedia LinkPhloretic acid
    METLIN ID4148
    PubChem Compound10394
    PDB IDNot Available
    ChEBI ID32980
    References
    Synthesis ReferenceJin, Enqing. Preparation of 4-hydroxyphenylpropionic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (1998), 5 pp.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Herr JC, Woodward MP: An enzyme-linked immunosorbent assay (ELISA) for human semen identification based on a biotinylated monoclonal antibody to a seminal vesicle-specific antigen. J Forensic Sci. 1987 Mar;32(2):346-56. [PubMed:3572333 ]
    2. Ward NC, Croft KD, Puddey IB, Hodgson JM: Supplementation with grape seed polyphenols results in increased urinary excretion of 3-hydroxyphenylpropionic Acid, an important metabolite of proanthocyanidins in humans. J Agric Food Chem. 2004 Aug 25;52(17):5545-9. [PubMed:15315398 ]
    3. Neurath AR, Strick N, Szmuness W, Stevens CE, Harley EJ: Radioimmunoassay of hepatitis B e-antigen (HBeAg): identification of HBeAg not associated with immunoglobulins. J Gen Virol. 1979 Mar;42(3):493-504. [PubMed:107272 ]
    4. Fargeas C, Hommel M, Maingon R, Dourado C, Monsigny M, Mayer R: Synthetic peptide-based enzyme-linked immunosorbent assay for serodiagnosis of visceral leishmaniasis. J Clin Microbiol. 1996 Feb;34(2):241-8. [PubMed:8788994 ]
    5. Vickers S, Stuart EK, Hucker HB: Further studies on the metabolism of carbidopa, (minus)-L-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid monohydrate, in the human, Rhesus monkey, dog, and rat. J Med Chem. 1975 Feb;18(2):134-8. [PubMed:804550 ]
    6. Mel'nikova YaI, Kravchuk ZI, Preygerzon VA, Martsev SP: Functional activation of antibodies on modification with Pd(II) coproporphyrin I N-Hydroxysuccinimide ester. Biochemistry (Mosc). 1997 Aug;62(8):924-7. [PubMed:9360305 ]
    7. Dodd D, Spitzer MH, Van Treuren W, Merrill BD, Hryckowian AJ, Higginbottom SK, Le A, Cowan TM, Nolan GP, Fischbach MA, Sonnenburg JL: A gut bacterial pathway metabolizes aromatic amino acids into nine circulating metabolites. Nature. 2017 Nov 30;551(7682):648-652. doi: 10.1038/nature24661. Epub 2017 Nov 22. [PubMed:29168502 ]
    8. 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 ]
    9. Beloborodova NV, Khodakova AS, Bairamov IT, Olenin AY: Microbial origin of phenylcarboxylic acids in the human body. Biochemistry (Mosc). 2009 Dec;74(12):1350-5. [PubMed:19961416 ]
    10. 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
    Desaminotyrosine → 6-[4-(2-carboxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
    Desaminotyrosine → 3,4,5-trihydroxy-6-{[3-(4-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
    Desaminotyrosine → 3-[4-(sulfooxy)phenyl]propanoic aciddetails