Show more...
Record Information
Version2.0
Created at2022-09-06 19:23:35 UTC
Updated at2022-09-06 19:23:36 UTC
NP-MRD IDNP0236483
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-(2,3-dihydroxyindol-3-yl)acetonitrile
Description(-)-3-Cyanomethyl-3-hydroxy-1H-indol-2(3H)-one 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 (-)-3-Cyanomethyl-3-hydroxy-1H-indol-2(3H)-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (-)-3-Cyanomethyl-3-hydroxy-1H-indol-2(3H)-one has been detected, but not quantified in, brassicas. 2-(2,3-dihydroxyindol-3-yl)acetonitrile is found in Brassica oleracea and Pseudomonas cichorii. This could make (-)-3-cyanomethyl-3-hydroxy-1H-indol-2(3H)-one a potential biomarker for the consumption of these foods.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC10H8N2O2
Average Mass188.1827 Da
Monoisotopic Mass188.05858 Da
IUPAC Name2-(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetonitrile
Traditional Name2-(3-hydroxy-2-oxo-1H-indol-3-yl)acetonitrile
CAS Registry NumberNot Available
SMILES
OC1(CC#N)C(=O)NC2=C1C=CC=C2
InChI Identifier
InChI=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
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Brassica oleraceaLOTUS Database
Pseudomonas cichoriiLOTUS Database
Chemical Taxonomy
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038633
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018028
KNApSAcK IDNot Available
Chemspider ID9833148
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11658413
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]