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Indole-3-acetonitrile

PubChem CID: 351795

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Compound Synonyms 3-Indoleacetonitrile, 771-51-7, Indole-3-acetonitrile, 2-(1H-indol-3-yl)acetonitrile, 3-Indolylacetonitrile, 1H-Indole-3-acetonitrile, 3-(Cyanomethyl)indole, Indolylacetonitrile, Indoleacetonitrile, Indolylacetonitril, 3-Indolacetonitrile, Acetonitrile, 3-indolyl-, Indol-3-ylacetonitrile, 1H-Indol-3-ylacetonitrile, USAF CB-29, (3-Indolyl)acetonitrile, (indol-3-yl)acetonitrile, 3-Cyanomethyl-1H-indole, CCRIS 5807, (1H-indol-3-yl)-acetonitrile, NSC 523272, AG97OFW8JW, (Indole-3-yl)acetonitrile, EINECS 212-232-1, (1H-Indol-3-yl)acetonitrile, BRN 0125488, CHEBI:17566, AI3-50105, Indolyl-3-acetonitrile, indole-3-ylacetonitrile, MFCD00005628, NSC-523272, CHEMBL1812654, DTXSID5061118, 5-22-03-00074 (Beilstein Handbook Reference), IAN, 3-cyanomethylindole, b-Indoleacetonitrile, beta-Indoleacetonitrile, 3-indolyl-Acetonitrile, .beta.-Indoleacetonitrile, UNII-AG97OFW8JW, beta-indole-3-acetonitrile, bmse000488, 1H-indole-3-ylacetonitrile, 3-Indoleacetonitrile, 98%, 1H-Indol-3-ylacetonitrile #, BIDD:GT0196, SCHEMBL149254, Indole-3-acetonitrile (8CI), WLN: T56 BMJ D1CN, 2(1H-indol-3-yl)acetonitrile, DTXCID1047944, DMCPFOBLJMLSNX-UHFFFAOYSA-, MSK1974, 2-(1H-indol-3-yl)-acetonitrile, GLXC-26570, HY-Y0136, BDBM50350241, NSC523272, s6043, STK802120, AKOS000120379, 1ST1974, CS-W008768, FI16427, MB00159, PS-3276, AC-10572, PD124092, Indolyl-3-acetonitrile, 3-Indoleacetonitrile, I0024, NS00014724, EN300-20368, 3-Indoleacetonitrile, purum, >=96.0% (GC), C02938, BRD-K65452854-001-01-5, Q27102461, Z104477894, 71C17B3A-CA19-4822-A4E7-D424F7074B4C, InChI=1/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2, 3BO
Ghose Rule False
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 39.6
Hydrogen Bond Donor Count 1.0
Pfizer 3 75 Rule False
Scaffold Graph Level C1CCC2CCCC2C1
Np Classifier Class Aminoacids
Deep Smiles N#CCcc[nH]cc5cccc6
Heavy Atom Count 12.0
Classyfire Class Indoles and derivatives
Description Myrosinase-induced hydrolysis product of indole glucosinolates, found in cabbage and other crucifers 3-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, 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 tumors 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), 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 reproduction of the pathogen in question. However, phytoalexins are often targeted to specific predators
Scaffold Graph Node Level C1CCC2NCCC2C1
Classyfire Subclass Indoles
Isotope Atom Count 0.0
Molecular Complexity 203.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Uniprot Id P48776, n.a.
Iupac Name 2-(1H-indol-3-yl)acetonitrile
Prediction Hob 1.0
Class Indoles and derivatives
Veber Rule True
Classyfire Superclass Organoheterocyclic compounds
Xlogp 1.6
Superclass Organoheterocyclic compounds
Subclass Indoles
Gsk 4 400 Rule True
Molecular Formula C10H8N2
Scaffold Graph Node Bond Level c1ccc2[nH]ccc2c1
Prediction Swissadme 0.0
Inchi Key DMCPFOBLJMLSNX-UHFFFAOYSA-N
Silicos It Class Soluble
Fcsp3 0.1
Logs -2.435
Rotatable Bond Count 1.0
State Solid
Logd 1.64
Synonyms (3-Indolyl)acetonitrile, (indol-3-yl)acetonitrile, (Indole-3-yl)acetonitrile, &beta, -indoleacetonitrile, 1H-indol-3-ylacetonitrile, 1H-Indole-3-acetonitrile, 3-(Cyanomethyl)indole, 3-Cyanomethyl-1H-indole, 3-Indolacetonitrile, 3-Indoleacetonitrile, 3-indolyl-Acetonitrile, 3-Indolylacetonitrile, Acetonitrile, 3-indolyl-, B-indoleacetonitrile, Benzene, pentafluoromethyl-, Beta-indoleacetonitrile, Beta-indolylacetonitrile, IAN, Indol-3-ylacetonitrile, Indole-3-acetonitrile, Indole-3-acetonitrile (8CI), indole-3-ylacetonitrile, Indoleacetonitrile, Indoleacetonitrile (van), Indoleyl-CPD, Indolyl-3-acetonitrile, Indolylacetonitril, Indolylacetonitrile, Usaf cb-29, (indol-3-yl)Acetonitrile, indol-3-Ylacetonitrile, 1H-indol-3-Ylacetonitrile, 3-Indolyl-acetonitrile, b-Indoleacetonitrile, beta-Indoleacetonitrile, Usaf CB-29, (1H-Indol-3-yl)acetonitrile, 3-indoleacetonitrile, 3-indolylacetonitrile, indolacetonitrite, indole acetonitrile, indole-3-acetonitrile
Substituent Name Indole, Benzenoid, Substituted pyrrole, Heteroaromatic compound, Pyrrole, Azacycle, Nitrile, Carbonitrile, Hydrocarbon derivative, Organonitrogen compound, Aromatic heteropolycyclic compound
Esol Class Soluble
Functional Groups CC#N, c[nH]c
Compound Name Indole-3-acetonitrile
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 156.069
Formal Charge 0.0
Monoisotopic Mass 156.069
Hydrogen Bond Acceptor Count 1.0
Molecular Weight 156.18
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 0.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteropolycyclic compounds
Lipinski Rule Of 5 True
Esol -2.3053656
Inchi InChI=1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
Smiles C1=CC=C2C(=C1)C(=CN2)CC#N
Nring 2.0
Np Classifier Biosynthetic Pathway Amino acids and Peptides, Shikimates and Phenylpropanoids
Defined Bond Stereocenter Count 0.0
Egan Rule True
Taxonomy Direct Parent 3-alkylindoles
Np Classifier Superclass Small peptides

  • 1. Outgoing r'ship FOUND_IN to/from Acmella Oleracea (Plant) Rel Props:Reference:
  • 2. Outgoing r'ship FOUND_IN to/from Brassica Alba (Plant) Rel Props:Reference:
  • 3. Outgoing r'ship FOUND_IN to/from Brassica Campestris (Plant) Rel Props:Reference:
  • 4. Outgoing r'ship FOUND_IN to/from Brassica Carinata (Plant) Rel Props:Reference:
  • 5. Outgoing r'ship FOUND_IN to/from Brassica Integrifolia (Plant) Rel Props:Reference:
  • 6. Outgoing r'ship FOUND_IN to/from Brassica Juncea (Plant) Rel Props:Reference:
  • 7. Outgoing r'ship FOUND_IN to/from Brassica Napus (Plant) Rel Props:Reference:
  • 8. Outgoing r'ship FOUND_IN to/from Brassica Nigra (Plant) Rel Props:Reference:
  • 9. Outgoing r'ship FOUND_IN to/from Brassica Oleracea (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 10. Outgoing r'ship FOUND_IN to/from Brassica Rapa (Plant) Rel Props:Source_db:fooddb_chem_all
  • 11. Outgoing r'ship FOUND_IN to/from Brassica Rutabaga (Plant) Rel Props:Reference:
  • 12. Outgoing r'ship FOUND_IN to/from Brassica Varigiata (Plant) Rel Props:Reference:
  • 13. Outgoing r'ship FOUND_IN to/from Cardamine Impatiens (Plant) Rel Props:Reference:
  • 14. Outgoing r'ship FOUND_IN to/from Carthamus Lanatus (Plant) Rel Props:Reference:
  • 15. Outgoing r'ship FOUND_IN to/from Citrullus Aromatica (Plant) Rel Props:Reference:
  • 16. Outgoing r'ship FOUND_IN to/from Citrullus Colocynthis (Plant) Rel Props:Reference:
  • 17. Outgoing r'ship FOUND_IN to/from Citrullus Lanatus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 18. Outgoing r'ship FOUND_IN to/from Citrullus Vulgaris (Plant) Rel Props:Reference:
  • 19. Outgoing r'ship FOUND_IN to/from Cucurbita Citrullus (Plant) Rel Props:Reference:
  • 20. Outgoing r'ship FOUND_IN to/from Diospyros Kaki (Plant) Rel Props:Source_db:fooddb_chem_all
  • 21. Outgoing r'ship FOUND_IN to/from Impatiens Angustifolia (Plant) Rel Props:Reference:
  • 22. Outgoing r'ship FOUND_IN to/from Impatiens Balsamina (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 23. Outgoing r'ship FOUND_IN to/from Impatiens Bicolor (Plant) Rel Props:Reference:
  • 24. Outgoing r'ship FOUND_IN to/from Impatiens Chinensis (Plant) Rel Props:Reference:
  • 25. Outgoing r'ship FOUND_IN to/from Impatiens Edgeworthii (Plant) Rel Props:Reference:
  • 26. Outgoing r'ship FOUND_IN to/from Impatiens Gigantea (Plant) Rel Props:Reference:
  • 27. Outgoing r'ship FOUND_IN to/from Impatiens Glandulifera (Plant) Rel Props:Reference:
  • 28. Outgoing r'ship FOUND_IN to/from Impatiens Latifolia (Plant) Rel Props:Reference:
  • 29. Outgoing r'ship FOUND_IN to/from Impatiens Minor (Plant) Rel Props:Reference:
  • 30. Outgoing r'ship FOUND_IN to/from Impatiens Pulcherrima (Plant) Rel Props:Reference:
  • 31. Outgoing r'ship FOUND_IN to/from Impatiens Scabrida (Plant) Rel Props:Reference:
  • 32. Outgoing r'ship FOUND_IN to/from Impatiens Siculifer (Plant) Rel Props:Reference:
  • 33. Outgoing r'ship FOUND_IN to/from Impatiens Trilobata (Plant) Rel Props:Reference:
  • 34. Outgoing r'ship FOUND_IN to/from Impatiens Tripetala (Plant) Rel Props:Reference:
  • 35. Outgoing r'ship FOUND_IN to/from Isatis Costata (Plant) Rel Props:Reference:
  • 36. Outgoing r'ship FOUND_IN to/from Isatis Tinctoria (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/8148009
  • 37. Outgoing r'ship FOUND_IN to/from Lycopersicon Esculentum (Plant) Rel Props:Source_db:fooddb_chem_all
  • 38. Outgoing r'ship FOUND_IN to/from Momordica Balsamina (Plant) Rel Props:Reference:
  • 39. Outgoing r'ship FOUND_IN to/from Moringa Oleifera (Plant) Rel Props:Source_db:fooddb_chem_all
  • 40. Outgoing r'ship FOUND_IN to/from Neptunia Oleracea (Plant) Rel Props:Reference:
  • 41. Outgoing r'ship FOUND_IN to/from Portulaca Oleracea (Plant) Rel Props:Reference:
  • 42. Outgoing r'ship FOUND_IN to/from Raphanus Sativus (Plant) Rel Props:Source_db:fooddb_chem_all
  • 43. Outgoing r'ship FOUND_IN to/from Spilanthes Oleracea (Plant) Rel Props:Reference:
  • 44. Outgoing r'ship FOUND_IN to/from Spinacia Oleracea (Plant) Rel Props:Reference:
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