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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-04-12 20:13:16 UTC
Update Date2022-09-22 18:35:07 UTC
HMDB IDHMDB0006005
Secondary Accession Numbers
  • HMDB06005
Metabolite Identification
Common NameIndolylacryloylglycine
DescriptionIndolylacryloylglycine, also known as Indolyl-3-acrylogylglycine or IAG, 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 is synthesized from tryptophan via indoleacrylic acid (IAcrA) through the conjugation of glycine to IAcrA via endogenous enzymes such as glycine N-acyltransferase (PMID: 10707769 ). The IAcrA must be first conjugated to CoA for this reaction to occur. The indoleacrylic acid is typically produced via microbially derived commensal Peptostreptococcus species (PMID: 28704649 ). IAG is also directly produced by L-tryptophan via certain mammalian gut microbes containing the enzyme tryptophan ammonia lyase (PMID: 25961404 ). Tryptophan ammonia lyase (EC 4.3.1.31) catalyzes the reaction of L-tryptophan to directly produce indole-3-acrylic acid and ammonia. This enzyme was initially characterized from the bacterium Rubrivivax benzoatilyticus JA2 (PMID: 25961404 ). It requires no cofactors and acts on L-phenylalanine and L-glutamate with about 60% of the activity of L-tryptophan, and on L-tyrosine, glycine, and L-alanine with about 30% of the activity (PMID: 25961404 ). Overall, IAG is both a microbial-host co-metabolite and a pure microbial metabolite. IAG may be a biomarker for autism spectrum disorders (PMID: 11858215 , PMID: 14523330 , PMID: 19697973 ). It has been reported that urinary levels of IAG are much higher in autistic children than in controls. However, these findings are controversial and have not been reproduced consistently (PMID: 27569540 , PMID: 27879968 ). Elevated urinary Indolylacryloylglycine may also be a marker for gastroinstestinal dysfunction (PMID: 19697973 ). Urinary Indolylacryloylglycine has also been reported as a potential biomarker to distinguish high-grade bladder cancer from low-grade bladder cancer (PMID: 29451296 ). Indolylacryloylglycine has been detected, but not quantified in, several different foods, such as chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make indolylacryloylglycine a potential biomarker for the consumption of these foods.
Structure
Data?1582752370
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, HMDB
Indolyl-3-acryloylglycineMeSH, HMDB
2-{[(2E)-1-hydroxy-3-(1H-indol-3-yl)prop-2-en-1-ylidene]amino}acetateGenerator, HMDB
IndolylacryloylglycineMeSH
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
SMILES
[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)C(O)=NCC(O)=O
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
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
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.076 g/LALOGPS
logP1.75ALOGPS
logP1.8ChemAxon
logS-3.2ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-186.85930932474
DeepCCS[M+Na]+162.28330932474
AllCCS[M+H]+154.632859911
AllCCS[M+H-H2O]+150.832859911
AllCCS[M+NH4]+158.132859911
AllCCS[M+Na]+159.132859911
AllCCS[M-H]-157.332859911
AllCCS[M+Na-2H]-157.132859911
AllCCS[M+HCOO]-157.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Indolylacryloylglycine[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)C(O)=NCC(O)=O3872.4Standard polar33892256
Indolylacryloylglycine[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)C(O)=NCC(O)=O2400.7Standard non polar33892256
Indolylacryloylglycine[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)C(O)=NCC(O)=O2569.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indolylacryloylglycine,1TMS,isomer #1C[Si](C)(C)OC(/C=C/C1=C[NH]C2=CC=CC=C12)=NCC(=O)O2746.8Semi standard non polar33892256
Indolylacryloylglycine,1TMS,isomer #2C[Si](C)(C)OC(=O)CN=C(O)/C=C/C1=C[NH]C2=CC=CC=C122717.7Semi standard non polar33892256
Indolylacryloylglycine,1TMS,isomer #3C[Si](C)(C)N1C=C(/C=C/C(O)=NCC(=O)O)C2=CC=CC=C212864.9Semi standard non polar33892256
Indolylacryloylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN=C(/C=C/C1=C[NH]C2=CC=CC=C12)O[Si](C)(C)C2718.9Semi standard non polar33892256
Indolylacryloylglycine,2TMS,isomer #2C[Si](C)(C)OC(/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12)=NCC(=O)O2845.2Semi standard non polar33892256
Indolylacryloylglycine,2TMS,isomer #3C[Si](C)(C)OC(=O)CN=C(O)/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C122812.4Semi standard non polar33892256
Indolylacryloylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C2786.2Semi standard non polar33892256
Indolylacryloylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C2591.7Standard non polar33892256
Indolylacryloylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C2956.5Standard polar33892256
Indolylacryloylglycine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(/C=C/C1=C[NH]C2=CC=CC=C12)=NCC(=O)O3007.9Semi standard non polar33892256
Indolylacryloylglycine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CN=C(O)/C=C/C1=C[NH]C2=CC=CC=C122992.6Semi standard non polar33892256
Indolylacryloylglycine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=C(/C=C/C(O)=NCC(=O)O)C2=CC=CC=C213079.6Semi standard non polar33892256
Indolylacryloylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN=C(/C=C/C1=C[NH]C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C3216.9Semi standard non polar33892256
Indolylacryloylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)=NCC(=O)O3274.4Semi standard non polar33892256
Indolylacryloylglycine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CN=C(O)/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C123252.4Semi standard non polar33892256
Indolylacryloylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C3395.8Semi standard non polar33892256
Indolylacryloylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C3171.8Standard non polar33892256
Indolylacryloylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C3154.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Indolylacryloylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1910000000-af9421f979b84f7c1d212017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indolylacryloylglycine GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-5920000000-34a6af95e2fa1e07e8672017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indolylacryloylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 10V, Positive-QTOFsplash10-002b-4590000000-bfd50d5180c6bd14c6cd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 20V, Positive-QTOFsplash10-056r-9710000000-8b4ac64ee5199a960b5e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 40V, Positive-QTOFsplash10-056u-7900000000-12988d991d4fb8d3f60c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 10V, Negative-QTOFsplash10-0006-0190000000-4a969f2be20f7b81f7fb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 20V, Negative-QTOFsplash10-006x-6890000000-d7bb4b025f6e9caddfc72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 40V, Negative-QTOFsplash10-05fu-9400000000-0ac0d883ab78f58631e62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 10V, Negative-QTOFsplash10-006x-0960000000-27152d1fd1bb75d521172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 20V, Negative-QTOFsplash10-006x-2920000000-95b20ae472699500646a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 40V, Negative-QTOFsplash10-0006-0900000000-e1ada5cb92852f0445602021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 10V, Positive-QTOFsplash10-002b-0190000000-d2eeedccf34de3bbcbb52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 20V, Positive-QTOFsplash10-006x-0910000000-19365eb3817e6e25ff6f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolylacryloylglycine 40V, Positive-QTOFsplash10-0006-0900000000-e7f97c6d0f9554f2ee7a2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
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 ID145761
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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 ]
  4. Marklova E: Where does indolylacrylic acid come from? Amino Acids. 1999;17(4):401-13. [PubMed:10707769 ]
  5. Wlodarska M, Luo C, Kolde R, d'Hennezel E, Annand JW, Heim CE, Krastel P, Schmitt EK, Omar AS, Creasey EA, Garner AL, Mohammadi S, O'Connell DJ, Abubucker S, Arthur TD, Franzosa EA, Huttenhower C, Murphy LO, Haiser HJ, Vlamakis H, Porter JA, Xavier RJ: Indoleacrylic Acid Produced by Commensal Peptostreptococcus Species Suppresses Inflammation. Cell Host Microbe. 2017 Jul 12;22(1):25-37.e6. doi: 10.1016/j.chom.2017.06.007. [PubMed:28704649 ]
  6. Kumavath RN, Ramana ChV, Sasikala Ch, Barh D, Kumar AP, Azevedo V: Isolation and Characterization of L-Tryptophan Ammonia Lyase from Rubrivivax benzoatilyticus Strain JA2. Curr Protein Pept Sci. 2015;16(8):775-81. doi: 10.2174/1389203716666150505235929. [PubMed:25961404 ]
  7. Wang L, Angley MT, Gerber JP, Young RL, Abarno DV, McKinnon RA, Sorich MJ: Is urinary indolyl-3-acryloylglycine a biomarker for autism with gastrointestinal symptoms? Biomarkers. 2009 Dec;14(8):596-603. doi: 10.3109/13547500903183962. [PubMed:19697973 ]
  8. Dalton NR, Chandler S, Turner C, Charman T, Pickles A, Simonoff E, Baird G: Measurement of urine indolylacroylglycine is not useful in the diagnosis or dietary management of autism. Autism Res. 2017 Mar;10(3):408-413. doi: 10.1002/aur.1688. Epub 2016 Aug 29. [PubMed:27569540 ]
  9. Wilson J, Wright B, Jost S, Smith R, Pearce H, Richardson S: Can urinary indolylacroylglycine levels be used to determine whether children with autism will benefit from dietary intervention? Pediatr Res. 2017 Apr;81(4):672-679. doi: 10.1038/pr.2016.256. Epub 2016 Nov 23. [PubMed:27879968 ]
  10. Liu X, Cheng X, Liu X, He L, Zhang W, Wang Y, Sun W, Ji Z: Investigation of the urinary metabolic variations and the application in bladder cancer biomarker discovery. Int J Cancer. 2018 Jul 15;143(2):408-418. doi: 10.1002/ijc.31323. Epub 2018 Mar 2. [PubMed:29451296 ]