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Human Metabolome Database Version 3.5

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Showing metabocard for Indolylacryloylglycine (HMDB06005)

Record Information
Version 3.5
Creation Date 2007-04-12 14:13:16 -0600
Update Date 2013-02-08 17:14:27 -0700
HMDB ID HMDB06005
Secondary Accession Numbers None
Metabolite Identification
Common Name Indolylacryloylglycine
Description 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. 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. IAG
  2. Indole-3-acryloyl-glycine
  3. Indoleacrylic glycine
  4. Indolyl acryloylglycine
  5. N-(3-(1-Indol-3-yl)-1-oxo-2-propenyl)glycine
Chemical Formula C13H12N2O3
Average Molecular Weight 244.246
Monoisotopic Molecular Weight 244.08479226
IUPAC Name 2-[(2E)-3-(1H-indol-3-yl)prop-2-enamido]acetic acid
Traditional IUPAC Name [(2E)-3-(1H-indol-3-yl)prop-2-enamido]acetic acid
CAS Registry Number 3475-68-1
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 Key DUIFVCFSAWHIOD-AATRIKPKSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Alpha Amino Acids and Derivatives
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Carboxamide Group
  • Carboxylic Acid
  • Enone
  • Indole
  • Pyrrole
  • Secondary Carboxylic Acid Amide
Direct Parent Acyl Glycines
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.076 g/L ALOGPS
LogP 1.62 ALOGPS
LogP 1.13 ChemAxon
LogS -3.51 ALOGPS
pKa (strongest acidic) 3.95 ChemAxon
pKa (strongest basic) 0.52 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 82.19 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 66.95 ChemAxon
Polarizability 25.37 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023799
KNApSAcK ID Not Available
Chemspider ID 4521424 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06005 Link_out
Metagene Link HMDB06005 Link_out
METLIN ID Not Available
PubChem Compound 5370648 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out