Showing metabocard for 3-Indoleacetonitrile (MMDBc0047993)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-12-11 00:19:26 UTC
Update Date2024-10-17 03:42:31 UTC
Metabolite IDMMDBc0047993
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fab51755090>


  Mrv1652309042000322D          

 12 13  0  0  0  0            999 V2000
   -1.6433    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982   -0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392   -0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239    1.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.9748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fab51755090>

HMDB0006524
     RDKit          3D
3-Indoleacetonitrile
 20 21  0  0  0  0  0  0  0  0999 V2000
    2.7048   -2.6089    1.2056 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5567   -1.7595    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3578   -0.7155   -0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2972    0.2264   -0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    1.4921    0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081    1.9718    0.6669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537    1.0587    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307    1.0757    0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8502   -0.0230    0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1598   -1.1068   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7875   -1.1270   -0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0549   -0.0262   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810   -1.2155   -1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2935   -0.1632   -0.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3728    2.0268    0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462    2.9138    1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092    1.9692    0.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9527   -0.0251    0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7197   -1.9723   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2402   -1.9915   -0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
 12  7  1  0
  3 13  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fab51755090>


  Mrv1652309042000322D          

 12 13  0  0  0  0            999 V2000
   -1.6433    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982   -0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392   -0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239    1.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.9748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047993

> <DATABASE_NAME>
MIME

> <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_KEY>
DMCPFOBLJMLSNX-UHFFFAOYSA-N

> <FORMULA>
C10H8N2

> <MOLECULAR_WEIGHT>
156.1839

> <EXACT_MASS>
156.068748266

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.737495134746684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(1H-indol-3-yl)acetonitrile

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
1.7677049649999999

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.20338292150119

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.252795576930861

> <JCHEM_POLAR_SURFACE_AREA>
39.58

> <JCHEM_REFRACTIVITY>
47.431400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole-3-acetonitrile

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007fab51755090>

HMDB0006524
     RDKit          3D
3-Indoleacetonitrile
 20 21  0  0  0  0  0  0  0  0999 V2000
    2.7048   -2.6089    1.2056 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5567   -1.7595    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3578   -0.7155   -0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2972    0.2264   -0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    1.4921    0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081    1.9718    0.6669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537    1.0587    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307    1.0757    0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8502   -0.0230    0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1598   -1.1068   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7875   -1.1270   -0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0549   -0.0262   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810   -1.2155   -1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2935   -0.1632   -0.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3728    2.0268    0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462    2.9138    1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092    1.9692    0.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9527   -0.0251    0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7197   -1.9723   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2402   -1.9915   -0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
 12  7  1  0
  3 13  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
M  END
Download

PDB for #<Metabolite:0x00007fab51755090>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -3.067   0.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.543  -0.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.513  -2.131   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.007  -1.811   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.791   2.131   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.561   0.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.531  -0.347   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.876   0.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.715   1.811   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.210  -0.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.543   0.280   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.543   1.820   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for #<Metabolite:0x00007fab51755090>

COMPND    HMDB0006524
HETATM    1  N1  UNL     1       2.705  -2.609   1.206  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.557  -1.759   0.424  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.358  -0.716  -0.572  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.297   0.226  -0.123  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.433   1.492   0.397  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.208   1.972   0.667  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.754   1.059   0.341  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.131   1.076   0.428  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.850  -0.023   0.010  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.160  -1.107  -0.481  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.787  -1.127  -0.568  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.055  -0.026  -0.151  1.00  0.00           C  
HETATM   13  H1  UNL     1       2.081  -1.215  -1.543  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.294  -0.163  -0.802  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.373   2.027   0.568  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.046   2.914   1.073  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.609   1.969   0.825  1.00  0.00           H  
HETATM   18  H6  UNL     1      -3.953  -0.025   0.070  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.720  -1.972  -0.812  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.240  -1.992  -0.957  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4   13   14
CONECT    4    5    5   12
CONECT    5    6   15
CONECT    6    7   16
CONECT    7    8    8   12
CONECT    8    9   17
CONECT    9   10   10   18
CONECT   10   11   19
CONECT   11   12   12   20
END
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SMILES for #<Metabolite:0x00007fab51755090>

N#CCC1=CNC2=C1C=CC=C2
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INCHI for #<Metabolite:0x00007fab51755090>

InChI=1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
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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
Molecular FormulaC10H8N2
Average Mass156.1839
Monoisotopic Mass156.068748266
IUPAC Name2-(1H-indol-3-yl)acetonitrile
Traditional Nameindole-3-acetonitrile
CAS Registry NumberNot Available
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