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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:31:28 UTC
Update Date2023-02-21 17:24:49 UTC
HMDB IDHMDB0035514
Secondary Accession Numbers
  • HMDB35514
Metabolite Identification
Common Namexi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid
Descriptionxi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid, also known as 2-oxindol-3-yl-acetic acid or oxindole-3-acetate, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid has been detected, but not quantified in, several different foods, such as brassicas, breakfast cereal, cereals and cereal products, fats and oils, and fruits. This could make XI-2,3-dihydro-2-oxo-1H-indole-3-acetic acid a potential biomarker for the consumption of these foods. xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid.
Structure
Data?1677000289
Synonyms
ValueSource
2-Oxindol-3-yl-acetic acidChEBI
Oxindole-3-acetic acidChEBI
2-Oxindol-3-yl-acetateGenerator
Oxindole-3-acetateGenerator
XI-2,3-dihydro-2-oxo-1H-indole-3-acetateGenerator
2-(2-oxo-3-Indolinyl)acetic acidHMDB
2-Hydroxy-1H-indole-3-acetic acidHMDB
2-Oxindole-3-acetateGenerator
2-Oxindole-3-acetic acidMeSH
Chemical FormulaC10H9NO3
Average Molecular Weight191.1834
Monoisotopic Molecular Weight191.058243159
IUPAC Name2-(2-hydroxy-3H-indol-3-yl)acetic acid
Traditional Name(2-hydroxy-3H-indol-3-yl)acetic acid
CAS Registry Number2971-31-5
SMILES
OC(=O)CC1C(O)=NC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H9NO3/c12-9(13)5-7-6-3-1-2-4-8(6)11-10(7)14/h1-4,7H,5H2,(H,11,14)(H,12,13)
InChI KeyILGMGHZPXRDCCS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • Indole
  • Dihydroindole
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point146 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11880 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.66 g/LALOGPS
logP0.43ALOGPS
logP1.47ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)0.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.89 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.18 m³·mol⁻¹ChemAxon
Polarizability18.77 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
DarkChem[M+H]+142.21431661259
DarkChem[M-H]-139.43731661259
DarkChem[M+H]+142.21431661259
DarkChem[M-H]-139.43731661259
DeepCCS[M+H]+137.97530932474
DeepCCS[M-H]-135.51630932474
DeepCCS[M-2H]-170.95630932474
DeepCCS[M+Na]+146.1730932474
AllCCS[M+H]+140.932859911
AllCCS[M+H-H2O]+136.632859911
AllCCS[M+NH4]+144.932859911
AllCCS[M+Na]+146.132859911
AllCCS[M-H]-140.432859911
AllCCS[M+Na-2H]-140.632859911
AllCCS[M+HCOO]-140.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acidOC(=O)CC1C(O)=NC2=C1C=CC=C23188.1Standard polar33892256
xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acidOC(=O)CC1C(O)=NC2=C1C=CC=C21881.1Standard non polar33892256
xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acidOC(=O)CC1C(O)=NC2=C1C=CC=C21890.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CC1C(O)=NC2=CC=CC=C211870.2Semi standard non polar33892256
xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid,1TMS,isomer #2C[Si](C)(C)OC1=NC2=CC=CC=C2C1CC(=O)O1922.3Semi standard non polar33892256
xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CC1C(O[Si](C)(C)C)=NC2=CC=CC=C211906.7Semi standard non polar33892256
xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1C(O)=NC2=CC=CC=C212139.3Semi standard non polar33892256
xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC2=CC=CC=C2C1CC(=O)O2184.3Semi standard non polar33892256
xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1C(O[Si](C)(C)C(C)(C)C)=NC2=CC=CC=C212353.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000w-1900000000-e5a212fef915b5bbb8af2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-7091000000-9a678e4207c2b4a641782017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 35V, Negative-QTOFsplash10-0002-0900000000-d4feef136caeaca471172021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 35V, Positive-QTOFsplash10-004j-0900000000-6f63eb22bb20305d468a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 10V, Positive-QTOFsplash10-006x-0900000000-61b1ae7ba4cc295dfebc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 20V, Positive-QTOFsplash10-0005-2900000000-df96872eeeeda61461a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 40V, Positive-QTOFsplash10-0f6y-4900000000-cfdd72592cdd31791a7a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 10V, Negative-QTOFsplash10-0007-0900000000-64cbb94b04cb529faf962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 20V, Negative-QTOFsplash10-0007-1900000000-a9a300173b2b5995f6d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 40V, Negative-QTOFsplash10-000x-8900000000-26716a18ea0f2ee82b562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 10V, Negative-QTOFsplash10-0007-0900000000-8c68ddb4684f01e96ee12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 20V, Negative-QTOFsplash10-0005-0900000000-204d9d33f962e6d224ee2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 40V, Negative-QTOFsplash10-0006-2900000000-8843562bb7e3099125642021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 10V, Negative-QTOFsplash10-0002-0900000000-d599528bc7be47190d162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 20V, Negative-QTOFsplash10-0002-0900000000-bbf70df619332b0d40202021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 40V, Negative-QTOFsplash10-0006-9800000000-c243d8b2c91bace472d92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 10V, Positive-QTOFsplash10-0002-0900000000-0e5a500057afafba6fe92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 20V, Positive-QTOFsplash10-000w-0900000000-5b222475c4515a318a992021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 40V, Positive-QTOFsplash10-0gb9-4900000000-0ff12fbb89d952a763192021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 10V, Positive-QTOFsplash10-00ec-0900000000-91006a9414082b768b7c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 20V, Positive-QTOFsplash10-000y-0900000000-ba344dc68d97e927e1232021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid 40V, Positive-QTOFsplash10-0gb9-4900000000-5d3e07b5f34b93b1724c2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014206
KNApSAcK IDC00054677
Chemspider ID2338343
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3080590
PDB IDNot Available
ChEBI ID133221
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1850381
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .