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Record Information
StatusExpected but not Quantified
Creation Date2007-04-12 20:13:16 UTC
Update Date2020-02-26 21:26:10 UTC
Secondary Accession Numbers
  • HMDB06005
Metabolite Identification
Common NameIndolylacryloylglycine
DescriptionIndolylacryloylglycine, also known as IAG or indoleacrylic glycine, 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. Indolylacryloylglycine (IAG) is a compound that is derived, in the same way as many other indole compounds, from tryptophan or indole compounds in the diet. Indolylacryloylglycine is a moderately basic compound (based on its pKa). Outside of the human body, Indolylacryloylglycine has been detected, but not quantified in, milk (cow). This could make indolylacryloylglycine a potential biomarker for the consumption of these foods. Indolylacryloylglycine is elevated in the urine of autistic children with gastrointestinal disturbances. It is likely a product of gut metabolism although the exact source is still unclear.
Indoleacrylic glycineHMDB
Indolyl acryloylglycineHMDB
Indolylacryloylglycine, (e)-isomerHMDB
Chemical FormulaC13H12N2O3
Average Molecular Weight244.246
Monoisotopic Molecular Weight244.08479226
IUPAC Name2-{[(2E)-1-hydroxy-3-(1H-indol-3-yl)prop-2-en-1-ylidene]amino}acetic acid
Traditional Name{[(2E)-1-hydroxy-3-(1H-indol-3-yl)prop-2-en-1-ylidene]amino}acetic acid
CAS Registry Number3475-68-1
InChI Identifier
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
  • N-acyl-alpha-amino acid
  • Indole
  • Indole or derivatives
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available


Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.076 g/LALOGPS
pKa (Strongest Acidic)4.03ChemAxon
pKa (Strongest Basic)2.37ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area85.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.47 m³·mol⁻¹ChemAxon
Polarizability25.58 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1910000000-af9421f979b84f7c1d21Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-5920000000-34a6af95e2fa1e07e867Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-4590000000-bfd50d5180c6bd14c6cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9710000000-8b4ac64ee5199a960b5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056u-7900000000-12988d991d4fb8d3f60cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-4a969f2be20f7b81f7fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-6890000000-d7bb4b025f6e9caddfc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9400000000-0ac0d883ab78f58631e6Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 IDFDB023799
KNApSAcK IDNot Available
Chemspider ID4521424
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5370648
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bull G, Shattock P, Whiteley P, Anderson R, Groundwater PW, Lough JW, Lees G: Indolyl-3-acryloylglycine (IAG) is a putative diagnostic urinary marker for autism spectrum disorders. Med Sci Monit. 2003 Oct;9(10):CR422-5. [PubMed:14523330 ]
  2. Wright B, Brzozowski AM, Calvert E, Farnworth H, Goodall DM, Holbrook I, Imrie G, Jordan J, Kelly A, Miles J, Smith R, Town J: Is the presence of urinary indolyl-3-acryloylglycine associated with autism spectrum disorder? Dev Med Child Neurol. 2005 Mar;47(3):190-2. [PubMed:15739724 ]
  3. Anderson RJ, Bendell DJ, Garnett I, Groundwater PW, Lough WJ, Mills MJ, Savery D, Shattock PE: Identification of indolyl-3-acryloylglycine in the urine of people with autism. J Pharm Pharmacol. 2002 Feb;54(2):295-8. [PubMed:11858215 ]