Indolyl-3-acryloylglycine

Last updated
Indolyl-3-acryloylglycine
Indolylacryloylglycine.svg
Names
Preferred IUPAC name
[(2E)-3-(1H-Indol-3-yl)prop-2-enamido]acetic acid
Other names
indoleacrylic glycine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • 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+
    Key: DUIFVCFSAWHIOD-AATRIKPKSA-N
  • C1=CC=C2C(=C1)C(=CN2)C=CC(=O)NCC(=O)O
Properties
C13H12N2O3
Molar mass 244.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Indolyl-3-acryloylglycine, also known as trans-indolyl-3-acryloylglycine, or IAG for short, is a compound consisting of an indole group attached to an acrylic acid moiety, which is in turn attached to a glycine molecule. This compound has been shown to isomerize when exposed to light. [1] It is likely a metabolic intermediate in the biosynthesis of tryptophan, [2] and is synthesized from tryptophan via indolepropionic acid and indoleacrylicacid (IAcrA). It is also likely that IAcrA is converted into IAG in the gut wall. [3] It may also be produced by certain elements of the mammalian gut microbiota by phenylalanine ammonia-lyase. [4] Identifiable in the urine by high-performance liquid chromatography, it may be a biomarker for autism spectrum disorders, as demonstrated by the research of Paul Shattock [5] [6] [7] and other researchers from Australia. [8] These researchers have reported that urinary levels of IAG are much higher in autistic children than in controls; however, other researchers have found no association between IAG concentrations in the urine and autism. [9] Its excretion in the urine may also be changed in Hartnup disease and celiac disease, [10] as well as photodermatosis, muscular dystrophy, and liver cirrhosis. [11]

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Phenylalanine is an essential α-amino acid with the formula C
9
H
11
NO
2
. It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino acid is classified as neutral, and nonpolar because of the inert and hydrophobic nature of the benzyl side chain. The L-isomer is used to biochemically form proteins coded for by DNA. Phenylalanine is a precursor for tyrosine, the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), and the biological pigment melanin. It is encoded by the messenger RNA codons UUU and UUC.

A gluten-free casein-free diet, also known as a gluten-free dairy-free diet, is a diet that does not include gluten, and casein. Despite an absence of scientific evidence, there have been advocates for the use of this diet as a treatment for autism and related conditions.

<span class="mw-page-title-main">Tryptamine</span> Metabolite of the amino acid tryptophan

Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon. The structure of tryptamine is a shared feature of certain aminergic neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others.

<span class="mw-page-title-main">Alkylresorcinol</span> Class of chemical compounds

Alkylresorcinols (ARs), also known as resorcinolic lipids, are amphiphilic phenolic lipids characterised by a non-polar odd-numbered alkyl side chain with up to 27 carbon atoms attached to a polar resorcinol (1,3-dihydroxybenzene) ring.

<span class="mw-page-title-main">Hartnup disease</span> Metabolic disorder

Hartnup disease is an autosomal recessive metabolic disorder affecting the absorption of nonpolar amino acids. Niacin is a precursor to nicotinamide, a necessary component of NAD+.

<span class="mw-page-title-main">5-Hydroxyindoleacetic acid</span> Chemical compound

5-Hydroxyindoleacetic acid (5-HIAA) is the main metabolite of serotonin. The metabolic intermediate 5-hydroxyindoleacetaldehyde (5-HIAL) is formed from serotonin by monoamine oxidase (MAO) and then 5-HIAA is formed from 5-HIAL via aldehyde dehydrogenase (ALDH). In chemical analysis of urine samples, 5-HIAA is used to determine serotonin levels in the body.

<span class="mw-page-title-main">Trace amine</span> Amine receptors in the mammalian brain

Trace amines are an endogenous group of trace amine-associated receptor 1 (TAAR1) agonists – and hence, monoaminergic neuromodulators – that are structurally and metabolically related to classical monoamine neurotransmitters. Compared to the classical monoamines, they are present in trace concentrations. They are distributed heterogeneously throughout the mammalian brain and peripheral nervous tissues and exhibit high rates of metabolism. Although they can be synthesized within parent monoamine neurotransmitter systems, there is evidence that suggests that some of them may comprise their own independent neurotransmitter systems.

<span class="mw-page-title-main">Tryptophan hydroxylase</span> Class of enzymes

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<span class="mw-page-title-main">Aromatic amino acid</span> Amino acid having an aromatic ring

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<span class="mw-page-title-main">Phenylacetylglutamine</span> Chemical compound

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3,5-Dihydroxybenzoic acid is a dihydroxybenzoic acid. It is a colorless solid.

<span class="mw-page-title-main">3,5-Dihydroxyphenylpropionoic acid</span> Chemical compound

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<span class="mw-page-title-main">Auto-brewery syndrome</span> Medical condition

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<span class="mw-page-title-main">Urolithin A</span> Chemical compound

Urolithin A is a metabolite compound resulting from the transformation of ellagitannins by the gut bacteria. It belongs to the class of organic compounds known as benzo-coumarins or dibenzo-α-pyrones. Its precursors – ellagic acids and ellagitannins – are ubiquitous in nature, including edible plants, such as pomegranates, strawberries, raspberries, walnuts, and others.

<span class="mw-page-title-main">3-Indolepropionic acid</span> Chemical compound

3-Indolepropionic acid (IPA), or indole-3-propionic acid, has been studied for its therapeutic value in the treatment of Alzheimer's disease. As of 2022 IPA shows potential in the treatment of this disease, though the therapeutic effect of IPA depends on dose and time of therapy initiation.

<i>N</i>-Acetyltaurine Chemical compound

N-Acetyltaurine (NAcT) is an endogenous metabolite. Biochemically, N-acetyltaurine is formed as a result of an acetylation of taurine. The main substrate for this reaction is acetate. An increase of endogenous N-acetyltaurine concentrations was observed after the consumption of alcohol and after extended physical activity (ketoacidosis).

References

  1. Mills, M. J.; Savery, D.; Shattock, P. E. (1998). "Rapid analysis of low levels of indolyl-3-acryloylglycine in human urine by high-performance liquid chromatography". Journal of Chromatography B. 712 (1–2): 51–58. doi:10.1016/S0378-4347(98)00153-4. PMID   9698228.
  2. Marklová, E. (1999). "Where does indolylacrylic acid come from". Amino Acids. 17 (4): 401–413. doi:10.1007/BF01361665. PMID   10707769.
  3. Shattock, Paul. "The Role of Tryptophan in Autism and Related Disorders" (PDF). The Nutrition Practitioner (Summer 2006).
  4. Clayton, T. A. (2012). "Metabolic differences underlying two distinct rat urinary phenotypes, a suggested role for gut microbial metabolism of phenylalanine and a possible connection to autism". FEBS Letters. 586 (7): 956–961. Bibcode:2012FEBSL.586..956C. doi: 10.1016/j.febslet.2012.01.049 . PMID   22306194.
  5. Anderson, R. J.; Bendell, D. J.; Garnett, I.; Groundwater, P. W.; Lough, W. J.; Mills, M. J.; Savery, D.; Shattock, P. E. G. (2002). "Identification of indolyl-3-acryloylglycine in the urine of people with autism". Journal of Pharmacy and Pharmacology. 54 (2): 295–298. doi: 10.1211/0022357021778349 . PMID   11858215.
  6. Bull, G.; Shattock, P.; Whiteley, P.; Anderson, R.; Groundwater, P. W.; Lough, J. W.; Lees, G. (2003). "Indolyl-3-acryloylglycine (IAG) is a putative diagnostic urinary marker for autism spectrum disorders". Medical Science Monitor. 9 (10): CR422 –CR425. PMID   14523330.
  7. Whiteley, P.; Mrpharms, P. S. (2003). "What Makes Trans-indolyl-3-acryloylglycine Identified by High-performance Liquid Chromatography Relevant to Pervasive Developmental Disorders?". Journal of Nutritional and Environmental Medicine. 13 (4): 231. doi:10.1080/13590840310001641996.
  8. Wang, L.; Angley, M. T.; Gerber, J. P.; Young, R. L.; Abarno, D. V.; McKinnon, R. A.; Sorich, M. J. (2009). "Is urinary indolyl-3-acryloylglycine a biomarker for autism with gastrointestinal symptoms?". Biomarkers. 14 (8): 596–603. doi:10.3109/13547500903183962. PMID   19697973.
  9. Wright, B.; Brzozowski, A. M.; Calvert, E.; Farnworth, H.; Goodall, D. M.; Holbrook, I.; Imrie, G.; Jordan, J.; Kelly, A.; Miles, J.; Smith, R.; Town, J. (2005). "Is the presence of urinary indolyl-3-acryloylglycine associated with autism spectrum disorder?". Developmental Medicine & Child Neurology. 47 (3): 190–192. doi:10.1017/S0012162205000344 (inactive 16 January 2025). PMID   15739724.{{cite journal}}: CS1 maint: DOI inactive as of January 2025 (link)
  10. Keszthelyi, D.; Troost, F. J.; Masclee, A. A. M. (2009). "Understanding the role of tryptophan and serotonin metabolism in gastrointestinal function". Neurogastroenterology & Motility. 21 (12): 1239–1249. doi:10.1111/j.1365-2982.2009.01370.x. PMID   19650771.
  11. Marklová, E.; Fojtásková, A. (1996). "High-performance liquid chromatographic profiling of indolylacryloylglycine and its possible precursors in body fluids". Journal of Chromatography A. 730 (1–2): 133–137. doi:10.1016/0021-9673(95)00943-4. PMID   8680585.