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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-23 14:24:16 UTC
Update Date2021-10-13 04:49:12 UTC
HMDB IDHMDB0006524
Secondary Accession Numbers
  • HMDB06524
Metabolite Identification
Common Name3-Indoleacetonitrile
Description3-Indoleacetonitrile is a phytoalexin. Phytoalexins are antibiotics produced by plants that are under attack. Phytoalexins tend to fall into several classes including terpenoids, glycosteroids, and alkaloids; however, researchers often find it convenient to extend the definition to include all phytochemicals that are part of the plant's defensive arsenal. Phytoalexins produced in plants act as toxins to the attacking organism. They may puncture the cell wall, delay maturation, disrupt metabolism, or prevent the reproduction of the pathogen in question. However, phytoalexins are often targeted to specific predators; a plant that has anti-insect phytoalexins may not have the ability to repel a fungal attack. 3-Indoleacetonitrile is common in cruciferous vegetables such as cabbage, cauliflower, broccoli, and Brussels sprouts. Dietary indoles in cruciferous vegetables induce cytochrome P450 enzymes and have prevented tumours in various animal models. Consumption of Brassica vegetables is associated with a reduced risk of cancer of the alimentary tract in animal models and human populations (PMID:15612779 , 15884814 , 2342128 , 3014947 , 3880668 , 6334634 , 6419397 , 6426808 , 6584878 , 6725517 , 6838646 , 7123561 ).
Structure
Data?1586452417
Synonyms
ValueSource
(indol-3-yl)AcetonitrileChEBI
(Indole-3-yl)acetonitrileChEBI
3-(Cyanomethyl)indoleChEBI
3-IndolylacetonitrileChEBI
indol-3-YlacetonitrileChEBI
Indole-3-acetonitrileKegg
(3-Indolyl)acetonitrileHMDB
1H-indol-3-YlacetonitrileHMDB
1H-Indole-3-acetonitrileHMDB
3-Cyanomethyl-1H-indoleHMDB
3-IndolacetonitrileHMDB
3-Indolyl-acetonitrileHMDB
b-IndoleacetonitrileHMDB
beta-IndoleacetonitrileHMDB
IANHMDB
IndoleacetonitrileHMDB
Indolyl-3-acetonitrileHMDB
IndolylacetonitrilHMDB
IndolylacetonitrileHMDB
Usaf CB-29HMDB
3-IndoleacetonitrileChEBI
(1H-Indol-3-yl)acetonitrileHMDB
Chemical FormulaC10H8N2
Average Molecular Weight156.1839
Monoisotopic Molecular Weight156.068748266
IUPAC Name2-(1H-indol-3-yl)acetonitrile
Traditional Nameindole-3-acetonitrile
CAS Registry Number771-51-7
SMILES
N#CCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
InChI KeyDMCPFOBLJMLSNX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point35 - 37 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1587 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
logP10(2.73) g/LALOGPS
logP10(1.77) g/LChemAxon
logS10(-2.5) g/LALOGPS
pKa (Strongest Acidic)14.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area39.58 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.43 m³·mol⁻¹ChemAxon
Polarizability16.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.17531661259
DarkChem[M-H]-131.93231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-IndoleacetonitrileN#CCC1=CNC2=C1C=CC=C22836.9Standard polar33892256
3-IndoleacetonitrileN#CCC1=CNC2=C1C=CC=C21747.1Standard non polar33892256
3-IndoleacetonitrileN#CCC1=CNC2=C1C=CC=C21834.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Indoleacetonitrile,1TMS,isomer #1C[Si](C)(C)N1C=C(CC#N)C2=CC=CC=C211851.3Semi standard non polar33892256
3-Indoleacetonitrile,1TMS,isomer #1C[Si](C)(C)N1C=C(CC#N)C2=CC=CC=C211910.3Standard non polar33892256
3-Indoleacetonitrile,1TMS,isomer #1C[Si](C)(C)N1C=C(CC#N)C2=CC=CC=C212231.4Standard polar33892256
3-Indoleacetonitrile,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(CC#N)C2=CC=CC=C212048.7Semi standard non polar33892256
3-Indoleacetonitrile,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(CC#N)C2=CC=CC=C212115.1Standard non polar33892256
3-Indoleacetonitrile,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(CC#N)C2=CC=CC=C212333.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Indoleacetonitrile GC-MS (1 TMS)splash10-004i-2950000000-640d53401ab5b06bad682014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Indoleacetonitrile GC-EI-TOF (Non-derivatized)splash10-004i-1930000000-26ddd3b2caf5e0b3a5b62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Indoleacetonitrile GC-EI-TOF (Non-derivatized)splash10-00fr-9740000000-96b8f06c6fb07ce93a3c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Indoleacetonitrile GC-MS (Non-derivatized)splash10-004i-2950000000-640d53401ab5b06bad682017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Indoleacetonitrile GC-EI-TOF (Non-derivatized)splash10-004i-0930000000-32debced08db3d4bf8cb2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Indoleacetonitrile GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-0900000000-8282b286970c64cd17382017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Indoleacetonitrile GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-2900000000-be863c7acf7363ffeedc2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QQ , negative-QTOFsplash10-0a4i-0900000000-458b38914f7ddf5b481a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QQ , negative-QTOFsplash10-0a4i-4900000000-69f7e3dfc4f01efba4642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QQ , negative-QTOFsplash10-056r-9300000000-7e44794a04e8de3d1daf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-d454501befd7405d3a7c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-e95beea8400e01e0632a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-42b4258b99c8588269de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-dba18a56ff6cbe01fe5c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QTOF , positive-QTOFsplash10-00lr-0900000000-cc0c89a2abe2633a90032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QQ , positive-QTOFsplash10-0a4i-0900000000-1d1a4eca72f57a9b927c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QQ , positive-QTOFsplash10-02ai-5900000000-bac26e180028ec3a808f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QQ , positive-QTOFsplash10-016r-7900000000-8ee8a1b5f235ed461d7a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QQ , positive-QTOFsplash10-014i-4900000000-3e3f0478af07473aa1422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indoleacetonitrile LC-ESI-QQ , positive-QTOFsplash10-000i-9000000000-1af02646eabe1e90e4822017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 10V, Positive-QTOFsplash10-0a4i-0900000000-686ec8d86a82008f6a872015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 20V, Positive-QTOFsplash10-0006-0900000000-0f41c00c3703e04901e82015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 40V, Positive-QTOFsplash10-000x-1900000000-144022b6dfec80ddd4a32015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 10V, Positive-QTOFsplash10-0a4i-0900000000-686ec8d86a82008f6a872015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 20V, Positive-QTOFsplash10-0006-0900000000-0f41c00c3703e04901e82015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 40V, Positive-QTOFsplash10-000x-1900000000-144022b6dfec80ddd4a32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 10V, Negative-QTOFsplash10-0a4i-0900000000-9b52919ba61c73ce0ade2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 20V, Negative-QTOFsplash10-0a4i-0900000000-f8b24a877c386d550c922015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 40V, Negative-QTOFsplash10-004i-1900000000-fc82dffe3b09577e06ee2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 10V, Negative-QTOFsplash10-0a4i-0900000000-9b52919ba61c73ce0ade2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 20V, Negative-QTOFsplash10-0a4i-0900000000-f8b24a877c386d550c922015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indoleacetonitrile 40V, Negative-QTOFsplash10-004i-1900000000-fc82dffe3b09577e06ee2015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001365
KNApSAcK IDC00000107
Chemspider ID312357
KEGG Compound IDC02938
BioCyc IDINDOLEYL-CPD
BiGG ID1724337
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound351795
PDB IDNot Available
ChEBI ID17566
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1190891
References
Synthesis ReferenceAhmad, A.; Spenser, Ian D. 3-Indolepyruvic acid oxime as the precursor of 3-indoleacetonitrile. Canadian Journal of Chemistry (1960), 38 1625-34.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Michnovicz JJ, Bradlow HL: Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst. 1990 Jun 6;82(11):947-9. [PubMed:2342128 ]
  2. Ciska E, Pathak DR: Glucosinolate derivatives in stored fermented cabbage. J Agric Food Chem. 2004 Dec 29;52(26):7938-43. [PubMed:15612779 ]
  3. Smith TK, Lund EK, Clarke RG, Bennett RN, Johnson IT: Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro. J Agric Food Chem. 2005 May 18;53(10):3895-901. [PubMed:15884814 ]
  4. Bradlow HL, Hershcopf R, Martucci C, Fishman J: 16 alpha-hydroxylation of estradiol: a possible risk marker for breast cancer. Ann N Y Acad Sci. 1986;464:138-51. [PubMed:3014947 ]
  5. Degawa M, Kojima M, Hishinuma T, Hashimoto Y: Sex-dependent induction of hepatic enzymes for mutagenic activation of a tryptophan pyrolysate component, 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]-indole, by feeding in mice. Cancer Res. 1985 Jan;45(1):96-102. [PubMed:3880668 ]
  6. Bradfield CA, Bjeldanes LF: Effect of dietary indole-3-carbinol on intestinal and hepatic monooxygenase, glutathione S-transferase and epoxide hydrolase activities in the rat. Food Chem Toxicol. 1984 Dec;22(12):977-82. [PubMed:6334634 ]
  7. Eisele TA, Bailey GS, Nixon JE: The effect of indole-3-carbinol, an aflatoxin B1 hepatocarcinoma inhibitor, and other indole analogs on the rainbow trout hepatic mixed function oxidase system. Toxicol Lett. 1983 Oct-Nov;19(1-2):133-8. [PubMed:6419397 ]
  8. Nixon JE, Hendricks JD, Pawlowski NE, Pereira CB, Sinnhuber RO, Bailey GS: Inhibition of aflatoxin B1 carcinogenesis in rainbow trout by flavone and indole compounds. Carcinogenesis. 1984 May;5(5):615-9. [PubMed:6426808 ]
  9. Kappas A, Anderson KE, Conney AH, Pantuck EJ, Fishman J, Bradlow HL: Nutrition-endocrine interactions: induction of reciprocal changes in the delta 4-5 alpha-reduction of testosterone and the cytochrome P-450-dependent oxidation of estradiol by dietary macronutrients in man. Proc Natl Acad Sci U S A. 1983 Dec;80(24):7646-9. [PubMed:6584878 ]
  10. Anderson KE, Kappas A, Conney AH, Bradlow HL, Fishman J: The influence of dietary protein and carbohydrate on the principal oxidative biotransformations of estradiol in normal subjects. J Clin Endocrinol Metab. 1984 Jul;59(1):103-7. [PubMed:6725517 ]
  11. Bulger WH, Kupfer D: Effect of xenobiotic estrogens and structurally related compounds on 2-hydroxylation of estradiol and on other monooxygenase activities in rat liver. Biochem Pharmacol. 1983 Mar 15;32(6):1005-10. [PubMed:6838646 ]
  12. Shertzer HG: Indole-3-carbinol and indole-3-acetonitrile influence on hepatic microsomal metabolism. Toxicol Appl Pharmacol. 1982 Jun 30;64(2):353-61. [PubMed:7123561 ]
  13. Barngrover DA, Stevens HC, Dills WL Jr: D-Xylulose-1-phosphate: enzymatic assay and production in isolated rat hepatocytes. Biochem Biophys Res Commun. 1981 Sep 16;102(1):75-80. [PubMed:6458298 ]
  14. GHALAMBOR MA, HEATH EC: The metabolism of L-fucose. II. The enzymatic cleavage of L-fuculose 1-phosphate. J Biol Chem. 1962 Aug;237:2427-33. [PubMed:13898172 ]
  15. James HM, Bais R, Edwards JB, Rofe AM, Conyers AJ: Models for the metabolic production of oxalate from xylitol in humans: a role for fructokinase and aldolase. Aust J Exp Biol Med Sci. 1982 Feb;60(Pt 1):117-22. [PubMed:6284103 ]
  16. Bais R, James HM, Rofe AM, Conyers RA: The purification and properties of human liver ketohexokinase. A role for ketohexokinase and fructose-bisphosphate aldolase in the metabolic production of oxalate from xylitol. Biochem J. 1985 Aug 15;230(1):53-60. [PubMed:2996495 ]