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Record Information
Version4.0
Creation Date2007-04-12 20:13:16 UTC
Update Date2017-09-27 08:24:40 UTC
HMDB IDHMDB0006005
Secondary Accession Numbers
  • HMDB06005
Metabolite Identification
Common NameIndolylacryloylglycine
DescriptionIndolylacryloylglycine (IAG) is a compound that is derived, in the same way as many other indole compounds, from tryptophan or indole compounds in the diet. It is likely a product of gut metabolism although the exact source is still unclear. IAG is elevated in the urine of autistic children with gastrointestinal disturbances.
Structure
Thumb
Synonyms
ValueSource
IAGHMDB
Indole-3-acryloyl-glycineHMDB
Indoleacrylic glycineHMDB
Indolyl acryloylglycineHMDB
N-(3-(1-indol-3-yl)-1-oxo-2-Propenyl)glycineHMDB
Indolylacryloylglycine, (e)-isomerMeSH
Indolyl-3-acryloylglycineMeSH
Chemical FormulaC13H12N2O3
Average Molecular Weight244.246
Monoisotopic Molecular Weight244.08479226
IUPAC Name2-[(2E)-3-(1H-indol-3-yl)prop-2-enamido]acetic acid
Traditional Name[(2E)-3-(1H-indol-3-yl)prop-2-enamido]acetic acid
CAS Registry Number3475-68-1
SMILES
OC(=O)CNC(=O)\C=C\C1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C13H12N2O3/c16-12(15-8-13(17)18)6-5-9-7-14-11-4-2-1-3-10(9)11/h1-7,14H,8H2,(H,15,16)(H,17,18)/b6-5+
InChI KeyDUIFVCFSAWHIOD-AATRIKPKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • 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
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 Solubility0.076 g/LALOGPS
logP1.62ALOGPS
logP1.13ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.95ChemAxon
pKa (Strongest Basic)0.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.19 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity66.95 m³·mol⁻¹ChemAxon
Polarizability25.37 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-00di-1910000000-af9421f979b84f7c1d21View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-5920000000-34a6af95e2fa1e07e867View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-4590000000-bfd50d5180c6bd14c6cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9710000000-8b4ac64ee5199a960b5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056u-7900000000-12988d991d4fb8d3f60cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-4a969f2be20f7b81f7fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-6890000000-d7bb4b025f6e9caddfc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9400000000-0ac0d883ab78f58631e6View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
References
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 ]