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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:17:26 UTC
Update Date2019-07-23 06:28:05 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 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid has been detected, but not quantified in, 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.
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 acidGenerator
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point78 - 80 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-1920000000-341a149da27672ffa231Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-3119000000-dc21343dcf4903151141Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0290000000-70f8a8822eee1d2eb1f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0920000000-5d5f8a1f1635a91fdbdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06to-5900000000-a72d8e05f5bbf07d8a89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1390000000-53331e4005631dc2f52fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3950000000-2c7f1ebda7a3d553c961Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-5900000000-295fa2abc6f3b1fe4e56Spectrum
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
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.. .