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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:35 UTC
HMDB IDHMDB0000764
Secondary Accession Numbers
  • HMDB00764
Metabolite Identification
Common NameHydrocinnamic acid
DescriptionHydrocinnamic acid, also known as phenylpropanoate or dihydrocinnamate, 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. Hydrocinnamic acid is a drug. Hydrocinnamic acid is a weakly acidic compound (based on its pKa). Hydrocinnamic acid exists in all living organisms, ranging from bacteria to humans. Phenylpropanoic acid can be prepared from cinnamic acid by hydrogenation. Hydrocinnamic acid is a sweet, balsamic, and cinnamon tasting compound. Outside of the human body, hydrocinnamic acid has been detected, but not quantified in, several different foods, such as macadamia nuts, watercress, bamboo shoots, lupines, and ohelo berries. This could make hydrocinnamic acid a potential biomarker for the consumption of these foods. This compound is used frequently in cosmetic products such as perfumes, bath gels, detergent powders, liquid detergents, fabric softeners, and soaps as it gives off a floral scent. A characteristic reaction of phenylpropanoic acid is its cyclization to indanones. Phenylpropanoic acid is used in the food industry to preserve and maintain the original aroma quality of frozen foods. Phenylpropanoic acid is also added to food for technological purposes in a wide variety including manufacturing, processing, preparation, treatment, packaging, transportation or storage, and food additives. This compound is used as a sweetener as well to sweeten food and can be found in table top sweeteners. It is a white, crystalline solid with a sweet, floral scent at room temperature.
Structure
Data?1582752155
Synonyms
ValueSource
3-Phenyl-propionic acidChEBI
3-Phenylpropanoic acidChEBI
3-PhenylpropionsaeureChEBI
3PPChEBI
Benzenepropanoic acidChEBI
Benzenepropionic acidChEBI
Benzylacetic acidChEBI
beta-Phenylpropionic acidChEBI
Dihydrocinnamic acidChEBI
HydrozimtsaeureChEBI
PhenylpropanoateChEBI
3-Phenylpropionic acidKegg
3-Phenyl-propionateGenerator
3-PhenylpropanoateGenerator
BenzenepropanoateGenerator
BenzenepropionateGenerator
BenzylacetateGenerator
b-PhenylpropionateGenerator
b-Phenylpropionic acidGenerator
beta-PhenylpropionateGenerator
Β-phenylpropionateGenerator
Β-phenylpropionic acidGenerator
DihydrocinnamateGenerator
Phenylpropanoic acidGenerator
3-PhenylpropionateGenerator
HydrocinnamateGenerator
3-Phenyl-N-propionateHMDB
3-Phenyl-N-propionic acidHMDB
Omega-phenylpropanoateHMDB
Omega-phenylpropanoic acidHMDB
W-PhenylpropanoateHMDB
W-Phenylpropanoic acidHMDB
3-Phenylpropionic acid, sodium saltHMDB
3-Phenyl propionic acidHMDB
HYDROCINNAMIC ACIDChEBI
Phenylpropionic acidHMDB
beta-Phenylpropanoic acidHMDB
β-Phenylpropanoic acidHMDB
ω-Phenylpropanoic acidHMDB
Chemical FormulaC9H10O2
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
IUPAC Name3-phenylpropanoic acid
Traditional Name3-phenylpropionic acid
CAS Registry Number501-52-0
SMILES
OC(=O)CCC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)
InChI KeyXMIIGOLPHOKFCH-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
  • 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:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point45 - 48 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.9 mg/mLNot Available
LogP1.84HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.7 g/LALOGPS
logP1.84ALOGPS
logP2.06ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.73ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.97 m³·mol⁻¹ChemAxon
Polarizability15.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-1920000000-829ee511cbcb511eaa0dSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-6910000000-1df0ef2a35aedd93b1f0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udl-9600000000-685b73e7f17a8be64f76Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9400000000-6b08d11fe7d8828ea0b4Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0900000000-271b64525610b577f87cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udl-9300000000-faf8506e70502be88599Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6x-9800000000-6d3e3634b1663556c431Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-1940000000-4bdbde45f0dac2b3ec59Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1920000000-829ee511cbcb511eaa0dSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-6910000000-1df0ef2a35aedd93b1f0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-2910000000-b14f8ca2c631d87eb834Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-8900000000-bbfe334bf7c6f8fab3edSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0596-9510000000-32f6cb9988fbfb2c022eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-60af9a7ac23f78383156Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-9009f92e094d3f88cea0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9000000000-1009c57a9a26d3fd03a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0udl-9600000000-f55343cc6dbf913455ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-300) , Positivesplash10-0006-9400000000-6b08d11fe7d8828ea0b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - CI-B (JEOL JMS-D-300) , Positivesplash10-0udi-0900000000-271b64525610b577f87cSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0udl-9300000000-0b08772b626dd7c66febSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-56bd4f79b41d2e676de8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0900000000-7cb5eea800e6e65e5ea1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052b-2900000000-b4b013241fad936a6040Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9100000000-21973848f978136e5896Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00dj-0229210000-3bd038d0275527aaf06eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00dj-0229210000-3bd038d0275527aaf06eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-270ffc8363f873d177bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1900000000-add76f4d7844f97853a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9700000000-96205e3f347617fff0efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-270ffc8363f873d177bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1900000000-add76f4d7844f97853a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9700000000-96205e3f347617fff0efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd537546837259692Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd537546837259692Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.553 +/- 0.109 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.938 +/- 0.429 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.057 +/- 0.424 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified44.348 +/- 43.85 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.58 +/- 0.121 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.504 +/- 0.062 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.54 +/- 0.108 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.111 +/- 1.705 uMAdult (>18 years old)Male
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 975 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified199.768 +/- 141.169 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)Both
Normal
details
FecesDetected and Quantified200.433 +/- 195.772 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected and Quantified415.517 +/- 423.507 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified543.368 +/- 417.514 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)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified514.735 +/- 219.611 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not AvailableNormal 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 Quantified76.977 (44.868-308.974) nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified284.336 +/- 246.380 nmol/g wet fecesNot SpecifiedNot Specified
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)BothNormal 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 and Quantified2.34 +/- 2.49 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified2.40 +/- 3.87 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified44.28 +/- 23.39 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified3.54 +/- 2.71 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified4.07 +/- 3.99 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 975 details
UrineDetected and Quantified0.142 +/- 0.06 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.181 +/- 0.038 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.176 +/- 0.075 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
details
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)Both
Crohn disease
details
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)Both
Ulcerative colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal 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)MaleProsthesis/Missing teeth details
SalivaDetected but not Quantified Adult (>18 years old)MaleSupragingival Plaque details
SalivaDetected but not Quantified Adult (>18 years old)MaleTooth Decay details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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 ]
  2. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
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 ]
Crohn's disease
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
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 ]
Prosthesis/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 ]
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 ]
Tooth Decay
  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 IDDB02024
Phenol Explorer Compound IDNot Available
FooDB IDFDB008271
KNApSAcK IDNot Available
Chemspider ID10181339
KEGG Compound IDC05629
BioCyc ID3-PHENYLPROPIONATE
BiGG IDNot Available
Wikipedia LinkPhenylpropanoic_acid
METLIN ID4153
PubChem Compound107
PDB IDNot Available
ChEBI ID28631
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceMuller, August John; Bowers, Joseph Stanton, Jr.; Eubanks, John Robert Ira; Geiger, Carey Cecil; Santobianco, John Gabriel. Process for preparing hydrocinnamic acid from cinnamaldehyde. PCT Int. Appl. (1999), 18 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Allen MC, Stafford CG, Nocerini MR: Quantitation of 4-cyclohexyl-2-hydroxy-3-(3-methylsulfanyl-2- [2-[(morpholine-4-carbonyl)amino]-3-phenylpropionylamino]propi onylamino ) butyric acid isopropyl ester (CP-80,794), a renin inhibitor, and its hydrolytic cleavage metabolite 2-[(morpholine-4-carbonyl)amino]-3-phenylpropionic acid (CP-84,364) in dog and human plasma by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1997 Aug 29;696(2):243-51. [PubMed:9323544 ]
  2. Iyer RA, Malhotra B, Khan S, Mitroka J, Bonacorsi S Jr, Waller SC, Rinehart JK, Kripalani K: Comparative biotransformation of radiolabeled [(14)C]omapatrilat and stable-labeled [(13)C(2)]omapatrilat after oral administration to rats, dogs, and humans. Drug Metab Dispos. 2003 Jan;31(1):67-75. [PubMed:12485955 ]
  3. Iyer RA, Mitroka J, Malhotra B, Bonacorsi S Jr, Waller SC, Rinehart JK, Roongta VA, Kripalani K: Metabolism of [(14)C]omapatrilat, a sulfhydryl-containing vasopeptidase inhibitor in humans. Drug Metab Dispos. 2001 Jan;29(1):60-9. [PubMed:11124231 ]
  4. 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 ]
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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
Hydrocinnamic acid → 3,4,5-trihydroxy-6-[(3-phenylpropanoyl)oxy]oxane-2-carboxylic aciddetails