Showing metabocard for Alpha-N-Phenylacetyl-L-glutamine (BMDB0006344)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:21:41 UTC
Update Date2020-05-21 16:28:34 UTC
BMDB IDBMDB0006344
Secondary Accession Numbers
  • BMDB06344
Metabolite Identification
Common NameAlpha-N-Phenylacetyl-L-glutamine
DescriptionPhenylacetylglutamine 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. Phenylacetylglutamine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylacetylglutamine can be biosynthesized from L-glutamine through the action of the enzyme glycine N-acyltransferase. In cattle, phenylacetylglutamine is involved in the metabolic pathway called the phenylacetate metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
alpha-N-Phenylacetyl-L-glutamineChEBI
Phenylacetyl-L-glutamineChEBI
N2-(2-Phenylacetyl)-L-glutamineKegg
a-N-Phenylacetyl-L-glutamineGenerator
Α-N-phenylacetyl-L-glutamineGenerator
PhenylacetylglutamineChEBI
N(2)-(Phenylacetyl)-L-glutamineHMDB
N(2)-(2-Phenylacetyl)-L-glutamineGenerator, HMDB
N-PhenylacetylglutamineHMDB
N2-(Phenylacetyl)-L-glutamineHMDB
α-N-PhenylacetylglutamineHMDB
alpha-N-PhenylacetylglutamineGenerator, HMDB
Chemical FormulaC13H16N2O4
Average Molecular Weight264.2771
Monoisotopic Molecular Weight264.11100701
IUPAC Name(2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid
Traditional Namephenylacetylglutamine
CAS Registry Number28047-15-6
SMILES
NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)/t10-/m0/s1
InChI KeyJFLIEFSWGNOPJJ-JTQLQIEISA-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
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.35ALOGPS
logP-0.086ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.9ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.49 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity67.28 m³·mol⁻¹ChemAxon
Polarizability26.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9520000000-5d0fcec2811fdda6e493View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9210000000-b1470e0601bcb76fcddaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0900000000-16da6849ac342b179bb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0190000000-0e5d477fb2aa8bfecabaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001l-0090000000-b74aefa0573c8e2d497cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-9300000000-309b6dbe599b4262ff80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0019-1790000000-34a22833325f47aff746View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-3900000000-2056d9abb5c0fdd85256View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-014r-0090000000-9a963271774da671d529View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001r-2950000000-506c649376dd55c452c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-014i-0090000000-3cd0e6901a93d015f159View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001l-9200000000-25c13edfa9d657619b43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-1910000000-7f99e9784ad6de2851d8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-5900000000-a9229c68d62fec012834View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001l-9000000000-0f312f25ec486fde9a50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-002b-0900000000-fc88effe954753003aa1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-3900000000-cd91c7242291d95e088eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0910000000-c889b0e15c63f54c93e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0002-0900000000-be097e5cfb29710afc22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-054o-9500000000-09820d1b2dd8e5f5d551View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0910000000-bd099f1990927d0cc710View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-1590000000-43b5b1154ff8c459a8e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-5950000000-d9a6090fc4170f3cbec0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-74c33c21f286a44eb712View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0290000000-c95723e9e5991b3a938fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02td-5980000000-c54142cded19fc0b1975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-744617f4104fc833e5d6View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Placenta
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0006344
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023896
KNApSAcK IDC00052383
Chemspider ID83292
KEGG Compound IDC04148
BioCyc IDCPD-1097
BiGG ID43248
Wikipedia LinkPhenylacetylglutamine
METLIN IDNot Available
PubChem Compound92258
PDB IDNot Available
ChEBI ID17884
References
Synthesis ReferenceSuyama, Tadashi; Toyoda, Takeshi; Kanao, Seizo. N-Phenylacetyl amino acids and their homologs. I. N-Acylamino acids. Yakugaku Zasshi (1965), 85(4), 279-83. CODEN: YKKZAJ ISSN:0031-6903. CAN 63:39385 AN 1965:439385
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Glycine N-acyltransferase
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate a multitude of substrates to form a variety of N-acylglycines, thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q2KIR7
Molecular weight:
33907.0
Reactions
Phenylacetyl-CoA + L-Glutamine → Alpha-N-Phenylacetyl-L-glutamine + Coenzyme Adetails