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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2020-06-04 21:44:49 UTC
Update Date2022-09-22 18:34:33 UTC
HMDB IDHMDB0240661
Secondary Accession NumbersNone
Metabolite Identification
Common NameIndole-3-acetylglycine
DescriptionIndole-3-acetylglycine also known as N-(3-indolylacetyl)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. Indole-3-acetylglycine has been identified in urine (PMID: 31396400 ).
Structure
Data?1591307251
Synonyms
ValueSource
N-(1H-indol-3-Ylacetyl)glycineChEBI
N-IndoleacetylglycineChEBI
2-[2-(1H-Indol-3-yl)acetamido]acetic acidHMDB
2-[[2-(1H-Indol-3-yl)acetyl]amino]acetic acidHMDB
Indole-3-acetylglycineHMDB
IndoleacetylglycineHMDB
N-(3-Indolylacetyl)glycineHMDB
N-[2-(1H-Indol-3-yl)acetyl]glycineHMDB
Chemical FormulaC12H12N2O3
Average Molecular Weight232.2353
Monoisotopic Molecular Weight232.08479226
IUPAC Name2-[2-(1H-indol-3-yl)acetamido]acetic acid
Traditional Name[2-(1H-indol-3-yl)acetamido]acetic acid
CAS Registry Number13113-08-1
SMILES
OC(=O)CNC(=O)CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C12H12N2O3/c15-11(14-7-12(16)17)5-8-6-13-10-4-2-1-3-9(8)10/h1-4,6,13H,5,7H2,(H,14,15)(H,16,17)
InChI KeyYDXXLJMIHMIOIF-UHFFFAOYSA-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
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP1.15ALOGPS
logP0.6ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.19 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity61.26 m³·mol⁻¹ChemAxon
Polarizability23.22 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+H]+145.49530932474
DeepCCS[M-H]-143.1130932474
DeepCCS[M-2H]-176.98530932474
DeepCCS[M+Na]+151.77230932474
AllCCS[M+H]+151.432859911
AllCCS[M+H-H2O]+147.632859911
AllCCS[M+NH4]+154.932859911
AllCCS[M+Na]+155.932859911
AllCCS[M-H]-154.032859911
AllCCS[M+Na-2H]-153.932859911
AllCCS[M+HCOO]-154.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Indole-3-acetylglycineOC(=O)CNC(=O)CC1=CNC2=C1C=CC=C23912.8Standard polar33892256
Indole-3-acetylglycineOC(=O)CNC(=O)CC1=CNC2=C1C=CC=C22052.7Standard non polar33892256
Indole-3-acetylglycineOC(=O)CNC(=O)CC1=CNC2=C1C=CC=C22575.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indole-3-acetylglycine,1TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)CC1=C[NH]C2=CC=CC=C122508.9Semi standard non polar33892256
Indole-3-acetylglycine,1TMS,isomer #2C[Si](C)(C)N(CC(=O)O)C(=O)CC1=C[NH]C2=CC=CC=C122512.8Semi standard non polar33892256
Indole-3-acetylglycine,1TMS,isomer #3C[Si](C)(C)N1C=C(CC(=O)NCC(=O)O)C2=CC=CC=C212528.0Semi standard non polar33892256
Indole-3-acetylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C2492.7Semi standard non polar33892256
Indole-3-acetylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C2448.2Standard non polar33892256
Indole-3-acetylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C2930.1Standard polar33892256
Indole-3-acetylglycine,2TMS,isomer #2C[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122488.1Semi standard non polar33892256
Indole-3-acetylglycine,2TMS,isomer #2C[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122392.9Standard non polar33892256
Indole-3-acetylglycine,2TMS,isomer #2C[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122883.4Standard polar33892256
Indole-3-acetylglycine,2TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122505.8Semi standard non polar33892256
Indole-3-acetylglycine,2TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122485.7Standard non polar33892256
Indole-3-acetylglycine,2TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122962.4Standard polar33892256
Indole-3-acetylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C2481.9Semi standard non polar33892256
Indole-3-acetylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C2497.3Standard non polar33892256
Indole-3-acetylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C2714.2Standard polar33892256
Indole-3-acetylglycine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=C[NH]C2=CC=CC=C122793.8Semi standard non polar33892256
Indole-3-acetylglycine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CC1=C[NH]C2=CC=CC=C122779.5Semi standard non polar33892256
Indole-3-acetylglycine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=C(CC(=O)NCC(=O)O)C2=CC=CC=C212767.0Semi standard non polar33892256
Indole-3-acetylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2986.4Semi standard non polar33892256
Indole-3-acetylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2877.0Standard non polar33892256
Indole-3-acetylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C3063.3Standard polar33892256
Indole-3-acetylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122959.7Semi standard non polar33892256
Indole-3-acetylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122819.9Standard non polar33892256
Indole-3-acetylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C123017.2Standard polar33892256
Indole-3-acetylglycine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122955.8Semi standard non polar33892256
Indole-3-acetylglycine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122884.2Standard non polar33892256
Indole-3-acetylglycine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C123080.9Standard polar33892256
Indole-3-acetylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C3118.5Semi standard non polar33892256
Indole-3-acetylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C3090.0Standard non polar33892256
Indole-3-acetylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2980.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-acetylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4940000000-2c6689ca8c94fce67cdf2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-acetylglycine 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 - Indole-3-acetylglycine 10V, Positive-QTOFsplash10-00e9-9350000000-adc6e0e4dbb74ff02a0f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetylglycine 20V, Positive-QTOFsplash10-00fr-9300000000-b89a0e374f736ec1d22f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetylglycine 40V, Positive-QTOFsplash10-00c0-9300000000-4d6a52fe9ef347ccb2642017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetylglycine 10V, Negative-QTOFsplash10-001i-0390000000-5fc9d4f087b67215ec802017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetylglycine 20V, Negative-QTOFsplash10-001i-4960000000-7d65845431b48c7f6bea2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetylglycine 40V, Negative-QTOFsplash10-01b9-8900000000-70f20f051ef685593fdf2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetylglycine 10V, Negative-QTOFsplash10-05o0-1930000000-5ed1994e6ff7c3c90cc02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetylglycine 20V, Negative-QTOFsplash10-014i-1900000000-9983c157c88aaee17d702021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetylglycine 40V, Negative-QTOFsplash10-066r-8900000000-53c9fadbd6a8af3a5c8d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetylglycine 10V, Positive-QTOFsplash10-001i-0940000000-fd52f2371126f6f58f582021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetylglycine 20V, Positive-QTOFsplash10-001i-0900000000-f80374c87cd6ea03aea32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetylglycine 40V, Positive-QTOFsplash10-001i-0900000000-0d13c78e93faa52ddc5a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID393944
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID90332
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. Zarei I, Oppel RC, Borresen EC, Brown RJ, Ryan EP: Modulation of plasma and urine metabolome in colorectal cancer survivors consuming rice bran. Integr Food Nutr Metab. 2019 May;6(3). doi: 10.15761/IFNM.1000252. Epub 2019 Apr 5. [PubMed:31396400 ]