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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2009-01-29 16:36:31 UTC
Update Date2019-07-23 05:56:10 UTC
HMDB IDHMDB0011621
Secondary Accession Numbers
  • HMDB11621
Metabolite Identification
Common NameCinnamoylglycine
DescriptionCinnamoylglycine is known as a urinary metabolite in man (PMID 649712 ) although whether it is formed de novo from plant cinnamate or is a plant product excreted. unchanged has not been conclusively demonstrated. When cinnamoylglycine occurs naturally it is probably a food constituent excreted unchanged. It is not found when small quantities (0.5-6 g) of cinnamic acid are fed to man, but by analogy with animal experiments may be produced when much larger quantities are given. (PMID 6743769 ).
Structure
Data?1563861370
Synonyms
ValueSource
N-(1-oxo-3-Phenyl-2-propenyl)-glycineChEBI
N-CinnamylglycineChEBI
N-(1-oxo-3-Phenyl-2-propen-1-yl)-glycineHMDB
N-Cinnamoyl-glycineHMDB
N-CinnamoylglycineHMDB
Chemical FormulaC11H11NO3
Average Molecular Weight205.2099
Monoisotopic Molecular Weight205.073893223
IUPAC Name2-[(2E)-3-phenylprop-2-enamido]acetic acid
Traditional Name[(2E)-3-phenylprop-2-enamido]acetic acid
CAS Registry Number16534-24-0
SMILES
OC(=O)CNC(=O)\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H11NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-7H,8H2,(H,12,13)(H,14,15)/b7-6+
InChI KeyYAADMLWHGMUGQL-VOTSOKGWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Cinnamic acid amide
  • Cinnamic acid or derivatives
  • Styrene
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

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 Solubility0.24 g/LALOGPS
logP1.42ALOGPS
logP1.03ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.9ChemAxon
pKa (Strongest Basic)-0.71ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.86 m³·mol⁻¹ChemAxon
Polarizability21.16 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-1910000000-7b0490fa51a377269e9dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0f89-2910000000-16c2b17bb853369ad245JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1910000000-7b0490fa51a377269e9dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f89-2910000000-16c2b17bb853369ad245JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2900000000-2a02e57572e92e42f09bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9720000000-16dc0e03c0e019315f45JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0900000000-9d2464a406e5dd831998JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0900000000-5279a0674a2cf7a0cae3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0900000000-02398618d42e8fcb08b0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-5406a752964d808bc261JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-6dd52db5d562fa3bf1d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-e6e6c83e592b714e4e33JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-ad00be066d9fa571526aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-052b-9680000000-5c522e402b24b9a95d49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-052b-9780000000-085070e5f5be5445ca47JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-4970000000-d8ec4cda1b0df3564ea4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-9700000000-d9761862670d5f40657dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-9500000000-b566a112d1ac6cf8c790JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0390000000-f5226ad4335bb382cd9cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-6970000000-4573208136664eb993fbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kmi-9300000000-a18fe23acd114627f210JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Not Available
Colectomy patients.
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028325
KNApSAcK IDNot Available
Chemspider ID618829
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound709625
PDB IDNot Available
ChEBI ID68616
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Brown GK, Stokke O, Jellum E: Chromatographic profile of high boiling point organic acids in human urine. J Chromatogr. 1978 Mar 1;145(2):177-84. [PubMed:649712 ]
  2. Hoskins JA, Holliday SB, Greenway AM: The metabolism of cinnamic acid by healthy and phenylketonuric adults: a kinetic study. Biomed Mass Spectrom. 1984 Jun;11(6):296-300. [PubMed:6743769 ]