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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-08-17 21:43:49 UTC
HMDB IDHMDB00764
Secondary Accession NumbersNone
Metabolite Identification
Common NameHydrocinnamic acid
DescriptionHydrocinnamic acid is an analogue of phenylalanine. It is a substrate of the enzyme oxidoreductases [EC 1.14.12.-] in the pathway phenylalanine metabolism (KEGG).
Structure
Thumb
Synonyms
ValueSource
3-Phenyl-propionic acidKegg
3-Phenylpropanoic acidKegg
3-Phenylpropionic acidKegg
3-Phenyl-propionateGenerator
HydrocinnamateGenerator
3-PhenylpropanoateGenerator
3-PhenylpropionateGenerator
3-Phenyl-N-propionateHMDB
3-Phenyl-N-propionic acidHMDB
b-PhenylpropionateHMDB
b-Phenylpropionic acidHMDB
BenzenepropionateHMDB
Benzenepropionic acidHMDB
BenzylacetateHMDB
Benzylacetic acidHMDB
beta-PhenylpropionateHMDB
beta-Phenylpropionic acidHMDB
DihydrocinnamateHMDB
Dihydrocinnamic acidHMDB
Omega-phenylpropanoateHMDB
Omega-phenylpropanoic acidHMDB
W-PhenylpropanoateHMDB
W-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 KeyInChIKey=XMIIGOLPHOKFCH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Microbial
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 mg/mLALOGPS
logP1.84ALOGPS
logP2.06ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.73ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.97 m3·mol-1ChemAxon
Polarizability15.94 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-1920000000-829ee511cbcb511eaa0dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-6910000000-1df0ef2a35aedd93b1f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-60af9a7ac23f78383156View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-9009f92e094d3f88cea0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9000000000-1009c57a9a26d3fd03a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0udl-9600000000-f55343cc6dbf913455ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-300) , Positivesplash10-0006-9400000000-6b08d11fe7d8828ea0b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (JEOL JMS-D-300) , Positivesplash10-0udi-0900000000-271b64525610b577f87cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0udl-9300000000-0b08772b626dd7c66febView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-56bd4f79b41d2e676de8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0900000000-7cb5eea800e6e65e5ea1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052b-2900000000-b4b013241fad936a6040View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9100000000-21973848f978136e5896View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-270ffc8363f873d177bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1900000000-add76f4d7844f97853a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9700000000-96205e3f347617fff0efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-270ffc8363f873d177bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1900000000-add76f4d7844f97853a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9700000000-96205e3f347617fff0efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd537546837259692View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd537546837259692View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 975
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified199.768 +/- 141.169 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected and Quantified200.433 +/- 195.772 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected and Quantified415.517 +/- 423.507 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified543.368 +/- 417.514 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified514.735 +/- 219.611 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified284.336 +/- 246.380 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 975
  • Not Applicable
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Irritable bowel syndrome
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. [19212411 ]
Associated OMIM IDs
DrugBank IDDB02024
DrugBank Metabolite IDDBMET00510
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID975
FoodDB IDFDB008271
KNApSAcK IDNot Available
Chemspider ID10181339
KEGG Compound IDC05629
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00764
Metagene LinkHMDB00764
METLIN ID4153
PubChem Compound107
PDB IDHCI
ChEBI ID28631
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. [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. [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. [11124231 ]