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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-01-29 16:36:31 UTC
Update Date2023-02-21 17:17:30 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?1676999850
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
CinnamoylglycineMeSH
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
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+142.52930932474
DeepCCS[M-H]-140.13330932474
DeepCCS[M-2H]-173.93430932474
DeepCCS[M+Na]+148.59430932474
AllCCS[M+H]+144.432859911
AllCCS[M+H-H2O]+140.432859911
AllCCS[M+NH4]+148.132859911
AllCCS[M+Na]+149.232859911
AllCCS[M-H]-146.332859911
AllCCS[M+Na-2H]-146.732859911
AllCCS[M+HCOO]-147.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CinnamoylglycineOC(=O)CNC(=O)\C=C\C1=CC=CC=C13317.0Standard polar33892256
CinnamoylglycineOC(=O)CNC(=O)\C=C\C1=CC=CC=C11808.4Standard non polar33892256
CinnamoylglycineOC(=O)CNC(=O)\C=C\C1=CC=CC=C12189.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cinnamoylglycine,1TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)/C=C/C1=CC=CC=C12152.4Semi standard non polar33892256
Cinnamoylglycine,1TMS,isomer #2C[Si](C)(C)N(CC(=O)O)C(=O)/C=C/C1=CC=CC=C12157.0Semi standard non polar33892256
Cinnamoylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)/C=C/C1=CC=CC=C1)[Si](C)(C)C2126.3Semi standard non polar33892256
Cinnamoylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)/C=C/C1=CC=CC=C1)[Si](C)(C)C2117.2Standard non polar33892256
Cinnamoylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)/C=C/C1=CC=CC=C1)[Si](C)(C)C2475.4Standard polar33892256
Cinnamoylglycine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)/C=C/C1=CC=CC=C12412.7Semi standard non polar33892256
Cinnamoylglycine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)/C=C/C1=CC=CC=C12387.1Semi standard non polar33892256
Cinnamoylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)/C=C/C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2589.7Semi standard non polar33892256
Cinnamoylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)/C=C/C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2533.9Standard non polar33892256
Cinnamoylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)/C=C/C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2676.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Cinnamoylglycine GC-MS (2 TMS)splash10-001i-1910000000-7b0490fa51a377269e9d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cinnamoylglycine GC-MS (1 TMS)splash10-0f89-2910000000-16c2b17bb853369ad2452014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cinnamoylglycine GC-MS (Non-derivatized)splash10-001i-1910000000-7b0490fa51a377269e9d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cinnamoylglycine GC-MS (Non-derivatized)splash10-0f89-2910000000-16c2b17bb853369ad2452017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamoylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2900000000-2a02e57572e92e42f09b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamoylglycine GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9720000000-16dc0e03c0e019315f452017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamoylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamoylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine Linear Ion Trap , negative-QTOFsplash10-03di-0900000000-9d2464a406e5dd8319982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine Linear Ion Trap , negative-QTOFsplash10-03di-0900000000-5279a0674a2cf7a0cae32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine Linear Ion Trap , negative-QTOFsplash10-03di-0900000000-02398618d42e8fcb08b02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine Linear Ion Trap , positive-QTOFsplash10-001i-0900000000-5406a752964d808bc2612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine Linear Ion Trap , positive-QTOFsplash10-001i-0900000000-6dd52db5d562fa3bf1d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine Linear Ion Trap , positive-QTOFsplash10-001i-0900000000-e6e6c83e592b714e4e332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine Linear Ion Trap , positive-QTOFsplash10-001i-0900000000-ad00be066d9fa571526a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine Linear Ion Trap , positive-QTOFsplash10-052b-9680000000-5c522e402b24b9a95d492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine Linear Ion Trap , positive-QTOFsplash10-052b-9780000000-085070e5f5be5445ca472017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine 10V, Negative-QTOFsplash10-0w29-1920000000-aaea2b41d7eb51e127152021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine 20V, Negative-QTOFsplash10-0udi-4900000000-60a27ed96b70d796d8cc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine 20V, Positive-QTOFsplash10-0f89-0900000000-64951a0d5fe4498693f22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine 10V, Negative-QTOFsplash10-0il0-1900000000-1dab32dc7e5a173d57ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine 40V, Negative-QTOFsplash10-0fb9-9200000000-86fa47a6317f07190d892021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine 10V, Positive-QTOFsplash10-001i-0900000000-37e671e90343bf321c662021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine 35V, Negative-QTOFsplash10-0udi-1900000000-693e3661882f7c68795d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine 40V, Negative-QTOFsplash10-0fbc-9000000000-49f940bc8e977d1340cc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine 30V, Negative-QTOFsplash10-0ufr-9300000000-e43c6766895cc1a9e89a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamoylglycine 40V, Positive-QTOFsplash10-0fb9-9800000000-9cd1c962edde3e7df0852021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamoylglycine 10V, Positive-QTOFsplash10-0a4i-4970000000-d8ec4cda1b0df3564ea42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamoylglycine 20V, Positive-QTOFsplash10-0a7i-9700000000-d9761862670d5f40657d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamoylglycine 40V, Positive-QTOFsplash10-0zi0-9500000000-b566a112d1ac6cf8c7902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamoylglycine 10V, Negative-QTOFsplash10-0udi-0390000000-f5226ad4335bb382cd9c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamoylglycine 20V, Negative-QTOFsplash10-0uk9-6970000000-4573208136664eb993fb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamoylglycine 40V, Negative-QTOFsplash10-0kmi-9300000000-a18fe23acd114627f2102017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]