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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-02-26 19:01:51 UTC
Update Date2022-03-07 03:17:35 UTC
HMDB IDHMDB0059747
Secondary Accession Numbers
  • HMDB59747
Metabolite Identification
Common Name4-Hydroxy-3-methoxy-cinnamoylglycine
Description4-Hydroxy-3-methoxy-cinnamoylglycine 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. 4-Hydroxy-3-methoxy-cinnamoylglycine is an extremely weak basic (essentially neutral) compound (based on its pKa). These are organic compounds containing a glycine residue with the N-atom attached to another moiety through an N-ester bond.
Structure
Data?1563865970
Synonyms
ValueSource
N-[3-(4-Hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]glycineKegg
Chemical FormulaC12H13NO5
Average Molecular Weight251.2353
Monoisotopic Molecular Weight251.079372531
IUPAC Name2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]acetic acid
Traditional NameN-feruloylglycine
CAS Registry NumberNot Available
SMILES
COC1=CC(\C=C\C(=O)NCC(O)=O)=CC=C1O
InChI Identifier
InChI=1S/C12H13NO5/c1-18-10-6-8(2-4-9(10)14)3-5-11(15)13-7-12(16)17/h2-6,14H,7H2,1H3,(H,13,15)(H,16,17)/b5-3+
InChI KeyCLGNQAIRBLDHIN-HWKANZROSA-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
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility0.43 g/LALOGPS
logP1.59ALOGPS
logP0.57ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)0.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.86 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.31 m³·mol⁻¹ChemAxon
Polarizability25.09 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]+158.19430932474
DeepCCS[M-H]-155.83630932474
DeepCCS[M-2H]-188.91630932474
DeepCCS[M+Na]+164.28730932474
AllCCS[M+H]+156.132859911
AllCCS[M+H-H2O]+152.432859911
AllCCS[M+NH4]+159.432859911
AllCCS[M+Na]+160.432859911
AllCCS[M-H]-156.732859911
AllCCS[M+Na-2H]-156.932859911
AllCCS[M+HCOO]-157.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-3-methoxy-cinnamoylglycineCOC1=CC(\C=C\C(=O)NCC(O)=O)=CC=C1O4172.0Standard polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycineCOC1=CC(\C=C\C(=O)NCC(O)=O)=CC=C1O2374.5Standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycineCOC1=CC(\C=C\C(=O)NCC(O)=O)=CC=C1O2662.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-3-methoxy-cinnamoylglycine,1TMS,isomer #1COC1=CC(/C=C/C(=O)NCC(=O)O[Si](C)(C)C)=CC=C1O2611.0Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,1TMS,isomer #2COC1=CC(/C=C/C(=O)NCC(=O)O)=CC=C1O[Si](C)(C)C2622.6Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,1TMS,isomer #3COC1=CC(/C=C/C(=O)N(CC(=O)O)[Si](C)(C)C)=CC=C1O2593.0Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TMS,isomer #1COC1=CC(/C=C/C(=O)NCC(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2665.8Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TMS,isomer #2COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O2553.4Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TMS,isomer #3COC1=CC(/C=C/C(=O)N(CC(=O)O)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2627.8Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TMS,isomer #1COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2610.7Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TMS,isomer #1COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2573.0Standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TMS,isomer #1COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2833.6Standard polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,1TBDMS,isomer #1COC1=CC(/C=C/C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O2895.8Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,1TBDMS,isomer #2COC1=CC(/C=C/C(=O)NCC(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C2902.2Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,1TBDMS,isomer #3COC1=CC(/C=C/C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O2843.8Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TBDMS,isomer #1COC1=CC(/C=C/C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3195.6Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TBDMS,isomer #2COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O3047.4Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TBDMS,isomer #3COC1=CC(/C=C/C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3143.1Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TBDMS,isomer #1COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3315.6Semi standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TBDMS,isomer #1COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3223.3Standard non polar33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TBDMS,isomer #1COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3079.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2940000000-68fbe21644bff52199f52017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine GC-MS (2 TMS) - 70eV, Positivesplash10-00gi-9047000000-45f1efb450d6ad5562842017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 10V, Positive-QTOFsplash10-0fk9-9160000000-744298d87bf18ec4b6a22017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 20V, Positive-QTOFsplash10-00fr-9210000000-bbf4a1d1d2d84d84d8562017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 40V, Positive-QTOFsplash10-00fr-9200000000-da8639fc4456a4a8c5832017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 10V, Negative-QTOFsplash10-0udi-0190000000-88aa56e4cca7e999df412017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 20V, Negative-QTOFsplash10-0ue9-3590000000-c2a725902a93090b41ba2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 40V, Negative-QTOFsplash10-00di-9500000000-1171a97ac3b7e5d279492017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 10V, Negative-QTOFsplash10-0pba-1490000000-0d82c19a854d2bdc8f212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 20V, Negative-QTOFsplash10-001i-2900000000-f762ab31918e815cf3222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 40V, Negative-QTOFsplash10-001r-1900000000-1dcba79c43f68112702f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 10V, Positive-QTOFsplash10-0fb9-0890000000-866638cae32d314727ff2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 20V, Positive-QTOFsplash10-002b-1910000000-e3ec4df22d23ae6158c02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 40V, Positive-QTOFsplash10-004j-6900000000-3032f20b6908622bbdb02021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444158
KEGG Compound IDC02564
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280527
PDB IDNot Available
ChEBI ID17691
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 ReferencesNot Available