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Showing NP-Card for 2-methylindole (NP0272305)

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Record Information
Version2.0
Created at2022-09-08 18:53:07 UTC
Updated at2022-09-08 18:53:07 UTC
NP-MRD IDNP0272305
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-methylindole
Description2-Methyl-1H-indole belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. A methylindole that is 1H-indole substituted by a methyl group at position 2. 2-methylindole was first documented in 2014 (PMID: 24555774). 2-Methyl-1H-indole is an extremely weak acidic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0272305 (2-methylindole)


  Mrv1652304272019022D          

 10 11  0  0  0  0            999 V2000
   -2.4327    1.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9645    1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6320    0.1715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  2  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for NP0272305 (2-methylindole)

     RDKit          3D

 19 20  0  0  0  0  0  0  0  0999 V2000
   -3.2372   -0.2025    0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7381   -0.1086    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490    0.9170    0.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3861    0.6451    0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663    1.3119    0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819    0.7830    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7448   -0.4396   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5920   -1.1253   -0.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.5730   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9003   -1.0014   -0.4612 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4809   -0.4112    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508   -1.0459   -0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6969    0.7543   -0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2985    1.8059    1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5809    2.2664    1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7347    1.2969    0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746   -0.8915   -0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5937   -2.0915   -1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916   -1.8899   -0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  2  1  0
  9  4  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
M  END
Download

3D SDF for NP0272305 (2-methylindole)


  Mrv1652304272019022D          

 10 11  0  0  0  0            999 V2000
   -2.4327    1.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9645    1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6320    0.1715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  2  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272305

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2=CC=CC=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C9H9N/c1-7-6-8-4-2-3-5-9(8)10-7/h2-6,10H,1H3

> <INCHI_KEY>
BHNHHSOHWZKFOX-UHFFFAOYSA-N

> <FORMULA>
C9H9N

> <MOLECULAR_WEIGHT>
131.1745

> <EXACT_MASS>
131.073499293

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.154605135796249

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-1H-indole

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.2715691319999998

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.61609839096281

> <JCHEM_POLAR_SURFACE_AREA>
15.79

> <JCHEM_REFRACTIVITY>
42.2942

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methylindole

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0272305 (2-methylindole)

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PDB for NP0272305 (2-methylindole)
HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0      -4.541   2.622   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.800   2.478   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.207   1.852   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -3.046   0.320   0.000  0.00  0.00           N+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    9                                                       
CONECT    6    7    8                                                       
CONECT    7    1    6   10                                                  
CONECT    8    4    6    9                                                  
CONECT    9    5    8   10                                                  
CONECT   10    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0272305 (2-methylindole)
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SMILES for NP0272305 (2-methylindole)
CC1=CC2=CC=CC=C2N1
Download
INCHI for NP0272305 (2-methylindole)
InChI=1S/C9H9N/c1-7-6-8-4-2-3-5-9(8)10-7/h2-6,10H,1H3
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View in JSmol
Synonyms
ValueSource
2-MethylindoleChEBI
2-Methylindole sodium saltMeSH
Chemical FormulaC9H9N
Average Mass131.1745 Da
Monoisotopic Mass131.07350 Da
IUPAC Name2-methyl-1H-indole
Traditional Name2-methylindole
CAS Registry NumberNot Available
SMILES
CC1=CC2=CC=CC=C2N1
InChI Identifier
InChI=1S/C9H9N/c1-7-6-8-4-2-3-5-9(8)10-7/h2-6,10H,1H3
InChI KeyBHNHHSOHWZKFOX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene  to form 2,3-benzopyrrole.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndoles  
Direct ParentIndoles  
Alternative Parents
Substituents
  • Indole
    • 

  • Benzenoid
    • 

  • Substituted pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP2.57ALOGPS
logP2.27ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)16.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.29 m³·mol⁻¹ChemAxon
Polarizability15.15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7224  
PDB IDNot Available
ChEBI ID49402  
Good Scents IDNot Available
References
General References
  1. Jiang D, Pan X, Li M, Gu Y: 2-Methylindole as an indicative nucleophile for developing a three-component reaction of aldehyde with two different nucleophiles. ACS Comb Sci. 2014 Jun 9;16(6):287-92. doi: 10.1021/co500010x. Epub 2014 Mar 4. [PubMed:24555774  ] 
  2. LOTUS database [Link]