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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2009-11-30 15:51:32 UTC
Update Date2020-02-26 21:38:24 UTC
HMDB IDHMDB0013240
Secondary Accession Numbers
  • HMDB13240
Metabolite Identification
Common NameIndoleacetyl glutamine
DescriptionIndoleacetyl glutamine is indolic derivative of tryptophan. It is generated from indoleacetic acid. Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan. Indoleacetyl glutamine frequently occurs at low levels in urine and has been found in elevated levels in the urine of patients with hartnup disease, the characteristic symptoms of the disease are mental retardation and pellagra like skin rash.
Structure
Data?1582753104
Synonyms
ValueSource
3-IAA glutamineChEBI
Indole-3-acetyl-glutamineChEBI
N-IndoleacetylglutamineChEBI
(1H-indol-3-yl)-Acetate glutamineHMDB
(1H-indol-3-yl)-Acetic acid glutamineHMDB
1H-indol-3-Ylacetate glutamineHMDB
1H-indol-3-Ylacetic acid glutamineHMDB
1H-Indole-3-acetate glutamineHMDB
1H-Indole-3-acetic acid glutamineHMDB
2-(1H-indol-3-yl)Acetate glutamineHMDB
2-(1H-indol-3-yl)Acetic acid glutamineHMDB
2-(3-Indolyl)acetate glutamineHMDB
2-(3-Indolyl)acetic acid glutamineHMDB
3-(Carboxymethyl)indole glutamineHMDB
3-Indole-acetic acid glutamineHMDB
3-Indoleacetate glutamineHMDB
3-Indoleacetic acid glutamineHMDB
3-Indolylacetate glutamineHMDB
3-Indolylacetic acid glutamineHMDB
b-Indoleacetate glutamineHMDB
b-Indoleacetic acid glutamineHMDB
b-Indolylacetate glutamineHMDB
b-Indolylacetic acid glutamineHMDB
beta-Indole-3-acetic acid glutamineHMDB
beta-Indoleacetate glutamineHMDB
beta-Indoleacetic acid glutamineHMDB
beta-Indolylacetate glutamineHMDB
beta-Indolylacetic acid glutamineHMDB
Heteroauxin glutamineHMDB
indol-3-Ylacetate glutamineHMDB
indol-3-Ylacetic acid glutamineHMDB
Indole-3-acetate glutamineHMDB
Indole-3-acetic acid glutamineHMDB
Indole-3-acetic-acid-O-glutamineHMDB
Indoleacetate glutamineHMDB
Indoleacetic acid glutamineHMDB
Indolyl-3-acetate glutamineHMDB
Indolyl-3-acetic acid glutamineHMDB
Indolylacetate glutamineHMDB
Indolylacetic acid glutamineHMDB
Kyselina 3-indolyloctova glutamineHMDB
Chemical FormulaC15H17N3O4
Average Molecular Weight303.3132
Monoisotopic Molecular Weight303.121906047
IUPAC Name4-carbamoyl-2-[2-(1H-indol-3-yl)acetamido]butanoic acid
Traditional Name4-carbamoyl-2-[2-(1H-indol-3-yl)acetamido]butanoic acid
CAS Registry Number6899-04-3
SMILES
NC(=O)CCC(NC(=O)CC1=CNC2=CC=CC=C12)C(O)=O
InChI Identifier
InChI=1S/C15H17N3O4/c16-13(19)6-5-12(15(21)22)18-14(20)7-9-8-17-11-4-2-1-3-10(9)11/h1-4,8,12,17H,5-7H2,(H2,16,19)(H,18,20)(H,21,22)
InChI KeyDVJIJAYHBZALOJ-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
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Fatty amide
  • Fatty acyl
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Carboxamide group
  • Primary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.32 g/LALOGPS
logP0.42ALOGPS
logP0.013ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-0.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.28 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity78.36 m³·mol⁻¹ChemAxon
Polarizability30.55 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-0a59-2920000000-f18722a0b27a4bc97d23Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-5793000000-19ad6f43825c469d8d49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9b-1893000000-db080e06058fd150bd19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0532-2940000000-37c6d9c2f3f2ece2f9b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f8a-4900000000-ff49a344ebc12e8637b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0469000000-a125ff4b561ededca93dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc3-3962000000-dcd757d07193eaae74c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-566fd336bfec8705c5edSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029352
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25200879
PDB IDNot Available
ChEBI ID70811
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]