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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:17:26 UTC
Update Date2022-03-07 02:56:00 UTC
HMDB IDHMDB0038942
Secondary Accession Numbers
  • HMDB38942
Metabolite Identification
Common NameMethyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid
DescriptionMethyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid, also known as methyl 2-(2,3,5-trihydroxy-3H-indol-3-yl)acetic acid, 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. Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid.
Structure
Data?1563863285
Synonyms
ValueSource
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetateGenerator
Methyl 2-(2,3,5-trihydroxy-3H-indol-3-yl)acetic acidHMDB
Chemical FormulaC11H11NO5
Average Molecular Weight237.2087
Monoisotopic Molecular Weight237.063722467
IUPAC Namemethyl 2-(3,5-dihydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate
Traditional Namemethyl 2-(3,5-dihydroxy-2-oxo-1H-indol-3-yl)acetate
CAS Registry Number57061-18-4
SMILES
COC(=O)CC1(O)C(=O)NC2=C1C=C(O)C=C2
InChI Identifier
InChI=1S/C11H11NO5/c1-17-9(14)5-11(16)7-4-6(13)2-3-8(7)12-10(11)15/h2-4,13,16H,5H2,1H3,(H,12,15)
InChI KeyYPPHXVJCTQPTBV-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
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Methyl ester
  • Tertiary alcohol
  • Carboxamide group
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point78 - 80 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.1 g/LALOGPS
logP0.54ALOGPS
logP-0.0098ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)9.25ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.86 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity58.42 m³·mol⁻¹ChemAxon
Polarizability22.52 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]+156.82831661259
DarkChem[M-H]-152.83631661259
DeepCCS[M+H]+157.19630932474
DeepCCS[M-H]-154.83830932474
DeepCCS[M-2H]-187.76430932474
DeepCCS[M+Na]+163.28930932474
AllCCS[M+H]+151.732859911
AllCCS[M+H-H2O]+147.832859911
AllCCS[M+NH4]+155.332859911
AllCCS[M+Na]+156.432859911
AllCCS[M-H]-151.732859911
AllCCS[M+Na-2H]-151.732859911
AllCCS[M+HCOO]-151.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acidCOC(=O)CC1(O)C(=O)NC2=C1C=C(O)C=C23729.3Standard polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acidCOC(=O)CC1(O)C(=O)NC2=C1C=C(O)C=C21883.1Standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acidCOC(=O)CC1(O)C(=O)NC2=C1C=C(O)C=C22359.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TMS,isomer #1COC(=O)CC1(O[Si](C)(C)C)C(=O)NC2=CC=C(O)C=C212149.3Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TMS,isomer #2COC(=O)CC1(O)C(=O)NC2=CC=C(O[Si](C)(C)C)C=C212177.5Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TMS,isomer #3COC(=O)CC1(O)C(=O)N([Si](C)(C)C)C2=CC=C(O)C=C212085.3Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TMS,isomer #1COC(=O)CC1(O[Si](C)(C)C)C(=O)NC2=CC=C(O[Si](C)(C)C)C=C212245.7Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TMS,isomer #2COC(=O)CC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=C(O)C=C212070.7Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TMS,isomer #3COC(=O)CC1(O)C(=O)N([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C212152.1Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,3TMS,isomer #1COC(=O)CC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C212203.2Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,3TMS,isomer #1COC(=O)CC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C212184.6Standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TBDMS,isomer #1COC(=O)CC1(O[Si](C)(C)C(C)(C)C)C(=O)NC2=CC=C(O)C=C212381.1Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TBDMS,isomer #2COC(=O)CC1(O)C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C212425.7Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TBDMS,isomer #3COC(=O)CC1(O)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C212348.5Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TBDMS,isomer #1COC(=O)CC1(O[Si](C)(C)C(C)(C)C)C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C212670.5Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TBDMS,isomer #2COC(=O)CC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C212570.8Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TBDMS,isomer #3COC(=O)CC1(O)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C212640.2Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,3TBDMS,isomer #1COC(=O)CC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C212848.6Semi standard non polar33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,3TBDMS,isomer #1COC(=O)CC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C212816.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-1920000000-341a149da27672ffa2312017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-3119000000-dc21343dcf49031511412017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 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 - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 10V, Positive-QTOFsplash10-052r-0290000000-70f8a8822eee1d2eb1f72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 20V, Positive-QTOFsplash10-03di-0920000000-5d5f8a1f1635a91fdbdc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 40V, Positive-QTOFsplash10-06to-5900000000-a72d8e05f5bbf07d8a892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 10V, Negative-QTOFsplash10-000i-1390000000-53331e4005631dc2f52f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 20V, Negative-QTOFsplash10-03di-3950000000-2c7f1ebda7a3d553c9612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 40V, Negative-QTOFsplash10-001l-5900000000-295fa2abc6f3b1fe4e562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 10V, Positive-QTOFsplash10-000i-0190000000-dbb0178dbb630b1c4d642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 20V, Positive-QTOFsplash10-052r-0690000000-b9ec47421043a61378952021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 40V, Positive-QTOFsplash10-0a4i-7900000000-ac0322a62f5ca31abb072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 10V, Negative-QTOFsplash10-0udi-0190000000-9de2f90d912bddc140af2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 20V, Negative-QTOFsplash10-01t9-0910000000-d077b917e584095e909f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 40V, Negative-QTOFsplash10-0006-9400000000-d29b858e645a8ddbc7c62021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018418
KNApSAcK IDNot Available
Chemspider ID22943185
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound45782784
PDB IDNot Available
ChEBI IDNot Available
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .