Record Information
Version1.0
Creation date2010-04-08 22:13:27 UTC
Update date2019-11-26 03:15:35 UTC
Primary IDFDB018028
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-3-Cyanomethyl-3-hydroxy-1H-indol-2(3H)-one
Description2-(2,3-Dihydroxy-3H-indol-3-yl)acetonitrile belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. 2-(2,3-Dihydroxy-3H-indol-3-yl)acetonitrile is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2-(2,3-Dihydroxy-3H-indol-3-yl)acetonitrile has been detected, but not quantified in, brassicas. This could make 2-(2,3-dihydroxy-3H-indol-3-yl)acetonitrile a potential biomarker for the consumption of these foods.
CAS Number137761-24-1
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility5.93 g/LALOGPS
logP0.54ALOGPS
logP0.21ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)11.24ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area73.12 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity50.65 m³·mol⁻¹ChemAxon
Polarizability18.23 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H8N2O2
IUPAC name2-(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetonitrile
InChI IdentifierInChI=1S/C10H8N2O2/c11-6-5-10(14)7-3-1-2-4-8(7)12-9(10)13/h1-4,14H,5H2,(H,12,13)
InChI KeyIXOBWMNTICTXOJ-UHFFFAOYSA-N
Isomeric SMILESOC1(CC#N)C(=O)NC2=C1C=CC=C2
Average Molecular Weight188.1827
Monoisotopic Molecular Weight188.05857751
Classification
Description belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolines
Direct ParentIndolines
Alternative Parents
Substituents
  • Dihydroindole
  • Benzenoid
  • Tertiary alcohol
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carbonitrile
  • Azacycle
  • Nitrile
  • 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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 63.83%; H 4.28%; N 14.89%; O 17.00%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -37.1 (c, 0.21 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-1900000000-1cd756668eff04515e9eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7790000000-f15719a571f7959d62ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-e4f9845c617470b83113JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-8456e8f24b07732ac450JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-7900000000-02ca0348c558c5216dbeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-57e8015cd86712eede83JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-6855cc5f39e233597266JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-7900000000-dc8876fbba413ffba18cJSpectraViewer
ChemSpider ID9833148
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID11658413
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38633
CRC / DFC (Dictionary of Food Compounds) IDLDQ29-A:LDQ30-U
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference