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Showing NP-Card for 2-[6-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]acetonitrile (NP0331019)

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Record Information
Version2.0
Created at2022-09-12 16:56:48 UTC
Updated at2022-09-12 16:56:48 UTC
NP-MRD IDNP0331019
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-[6-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]acetonitrile
Description3-Cyanomethyl-6-prenylindole 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. 2-[6-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]acetonitrile was first documented in 2014 (PMID: 24443904). Based on a literature review very few articles have been published on 3-cyanomethyl-6-prenylindole.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0331019 (2-[6-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]acetonitrile)


  Mrv1652309122218562D          

 17 18  0  0  0  0            999 V2000
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9878   -1.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 10 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
  6 17  1  0  0  0  0
M  END
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3D MOL for NP0331019 (2-[6-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]acetonitrile)

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3D SDF for NP0331019 (2-[6-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]acetonitrile)

  Mrv1652309122218562D          

 17 18  0  0  0  0            999 V2000
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9878   -1.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 10 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
  6 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331019

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC=C2C(CC#N)=CNC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16N2/c1-11(2)3-4-12-5-6-14-13(7-8-16)10-17-15(14)9-12/h3,5-6,9-10,17H,4,7H2,1-2H3

> <INCHI_KEY>
WXAZQTKZTNNGIV-UHFFFAOYSA-N

> <FORMULA>
C15H16N2

> <MOLECULAR_WEIGHT>
224.307

> <EXACT_MASS>
224.131348523

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.619599449531222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]acetonitrile

> <JCHEM_LOGP>
3.496271964333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.21207728007808

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.23347855235669

> <JCHEM_POLAR_SURFACE_AREA>
39.58

> <JCHEM_REFRACTIVITY>
71.67420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]acetonitrile

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0331019 (2-[6-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]acetonitrile)
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PDB for NP0331019 (2-[6-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]acetonitrile)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.680  -1.012   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.711  -2.157   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   10   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16    6                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

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3D PDB for NP0331019 (2-[6-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]acetonitrile)
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SMILES for NP0331019 (2-[6-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]acetonitrile)
CC(C)=CCC1=CC=C2C(CC#N)=CNC2=C1
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INCHI for NP0331019 (2-[6-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]acetonitrile)
InChI=1S/C15H16N2/c1-11(2)3-4-12-5-6-14-13(7-8-16)10-17-15(14)9-12/h3,5-6,9-10,17H,4,7H2,1-2H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H16N2
Average Mass224.3070 Da
Monoisotopic Mass224.13135 Da
IUPAC Name2-[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]acetonitrile
Traditional Name2-[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]acetonitrile
CAS Registry NumberNot Available
SMILES
CC(C)=CCC1=CC=C2C(CC#N)=CNC2=C1
InChI Identifier
InChI=1S/C15H16N2/c1-11(2)3-4-12-5-6-14-13(7-8-16)10-17-15(14)9-12/h3,5-6,9-10,17H,4,7H2,1-2H3
InChI KeyWXAZQTKZTNNGIV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
    • 

  • Cyanide
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • 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
logP3.5ChemAxon
pKa (Strongest Acidic)14.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area39.58 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.67 m³·mol⁻¹ChemAxon
Polarizability26.62 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9184802  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11009616  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Zhang J, Wang JD, Liu CX, Yuan JH, Wang XJ, Xiang WS: A new prenylated indole derivative from endophytic actinobacteria Streptomyces sp. neau-D50. Nat Prod Res. 2014;28(7):431-7. doi: 10.1080/14786419.2013.871546. Epub 2014 Jan  21. [PubMed:24443904  ] 
  2. LOTUS database [Link]