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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-02-04 11:53:19 UTC
Update Date2020-02-26 21:35:38 UTC
HMDB IDHMDB0011687
Secondary Accession Numbers
  • HMDB11687
Metabolite Identification
Common NamePhenylbutyrylglutamine
DescriptionPhenylbutyrylglutamine has been identified as a new metabolite of phenylbutyrate in human plasma and urine. Phenylbutyrate is used in humans for treating inborn errors of ureagenesis, certain forms of cancer, cystic fibrosis and thalassemia. After administration of phenylbutyrate to normal humans, the cumulative urinary excretion of phenylacetate, phenylbutyrate, phenylacetylglutamine and phenylbutyrylglutamine amounts to about half of the dose of phenylbutyrate.
Structure
Data?1582752938
Synonyms
ValueSource
2-[(1-Hydroxy-4-phenylbutylidene)amino]-4-(C-hydroxycarbonimidoyl)butanoateGenerator
PhenylbutyrylglutamineMeSH
Chemical FormulaC15H20N2O4
Average Molecular Weight292.3303
Monoisotopic Molecular Weight292.142307138
IUPAC Name4-carbamoyl-2-(4-phenylbutanamido)butanoic acid
Traditional Name4-carbamoyl-2-(4-phenylbutanamido)butanoic acid
CAS Registry NumberNot Available
SMILES
NC(=O)CCC(NC(=O)CCCC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C15H20N2O4/c16-13(18)10-9-12(15(20)21)17-14(19)8-4-7-11-5-2-1-3-6-11/h1-3,5-6,12H,4,7-10H2,(H2,16,18)(H,17,19)(H,20,21)
InChI KeyXKQKXKRCMAJADR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamine and derivatives
Alternative Parents
Substituents
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • 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 DescriptorsNot Available
Ontology
Disposition

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 Solubility0.082 g/LALOGPS
logP0.65ALOGPS
logP0.8ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)-0.56ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.49 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity76.48 m³·mol⁻¹ChemAxon
Polarizability30.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-5940000000-cb91536291a0d1d77c92Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-6491000000-d2d6f8a36651e178d805Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004m-0390000000-89244cc570d929f90b11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f9t-1950000000-5b217dec9038e8054d86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxv-9800000000-9be5e6834101a0ca124eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-d2b089cb2095eac1d76cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006y-3790000000-212bbc125f1e930cc334Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-ae977a37688dc57b66acSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028374
KNApSAcK IDNot Available
Chemspider ID8119529
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9943917
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available