NP-MRD: Showing NP-Card for (6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole (NP0254046)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-07 18:05:44 UTC

Updated at

2022-09-07 18:05:45 UTC

NP-MRD ID

NP0254046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole

Description

It was first documented in 2012 (PMID: 22470225). Based on a literature review a significant number of articles have been published on 12-epi-Fischerindole I isonitrile (PMID: 32302487) (PMID: 30155122) (PMID: 25303730) (PMID: 36099392).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072220052D          

 24 27  0  0  1  0            999 V2000
    5.1019   -2.8955    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    4.6170   -2.2281    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.1321   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522    0.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369    0.5279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5218   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6778   -0.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1929   -1.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676    0.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8032    1.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7531    0.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.1395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1622   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -0.9794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0062   -1.0657    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -1.6469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6615   -2.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -2.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1106   -2.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
  8 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17  4  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  2  0  0  0  0
M  CHG  2   1  -1   2   1
M  END

     RDKit          3D

 45 48  0  0  0  0  0  0  0  0999 V2000
   -1.0755   -3.0181   -1.4921 C   0  0  0  0  0  3  0  0  0  0  0  0
   -1.1442   -1.9946   -0.9137 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.2650   -0.7878   -0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2328   -0.0937    0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064   -0.3121   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090    0.9361    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1257    0.7359   -0.0944 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4124   -0.5912   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668   -1.3157   -0.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5450   -2.6930   -0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3548   -3.3835   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1843   -2.6482   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082   -1.2706   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719    1.9928    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5553    2.6354   -1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2812    2.9490    1.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    1.2250    0.7302 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6771    1.8820    0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6969    1.1969   -0.1997 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5142    1.5298   -1.9176 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6678   -0.2905   -0.0011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1246   -0.6551    1.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6133   -0.9309   -0.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0791   -2.1585   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940    1.4705   -0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020   -0.7538   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881   -3.2464   -0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3953   -4.4586   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2725   -3.2050   -0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2605    3.3539   -1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4435    1.9113   -2.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5150    3.1818   -1.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6521    2.2959    2.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183    3.5294    1.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0779    3.5975    0.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757    1.0419    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650    2.9611    0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1506    1.8834    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7349    1.5415    0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4049   -1.3342    1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3312    0.2498    2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1095   -1.2074    1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9225   -0.3879   -1.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977   -2.7615    0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7621   -2.6022   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  6
 23 24  2  3
 21  3  1  0
  3  2  1  0
  2  1  3  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 13  8  1  0
  4 17  1  0
 13  5  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  1
 18 37  1  0
 18 38  1  0
 19 39  1  1
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 24 45  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
M  CHG  2   1  -1   2   1
M  END


  Mrv1652309072220052D          

 24 27  0  0  1  0            999 V2000
    5.1019   -2.8955    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    4.6170   -2.2281    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.1321   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522    0.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369    0.5279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5218   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6778   -0.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1929   -1.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676    0.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8032    1.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7531    0.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.1395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1622   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -0.9794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0062   -1.0657    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -1.6469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6615   -2.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -2.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1106   -2.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
  8 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17  4  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  2  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
NP0254046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2C[C@@H](Cl)[C@@](C)(C=C)C([N+]#[C-])=C2C2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C21H21ClN2/c1-6-21(4)15(22)11-13-17(19(21)23-5)16-12-9-7-8-10-14(12)24-18(16)20(13,2)3/h6-10,13,15,24H,1,11H2,2-4H3/t13-,15+,21+/m0/s1

> <INCHI_KEY>
ZVBCZYGMKQOJFW-QDUSTFBWSA-N

> <FORMULA>
C21H21ClN2

> <MOLECULAR_WEIGHT>
336.86

> <EXACT_MASS>
336.1393264

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
37.421425819193445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6aS,8R,9S)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5H,6H,6aH,7H,8H,9H-indeno[2,1-b]indole

> <JCHEM_LOGP>
2.5298138981240537

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.596292628838892

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.765552414116925

> <JCHEM_POLAR_SURFACE_AREA>
20.15

> <JCHEM_REFRACTIVITY>
109.65180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6aS,8R,9S)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5H,6aH,7H,8H-indeno[2,1-b]indole

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       9.524  -5.405   0.000  0.00  0.00           C-1
HETATM    2  N   UNK     0       8.618  -4.159   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       7.713  -2.913   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.340  -1.506   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.804  -1.030   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804   0.510   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      11.269   0.985   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      12.174  -0.260   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.706  -0.421   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.332  -1.828   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.427  -3.074   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.895  -2.913   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.269  -1.506   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.340   0.985   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.966   2.392   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.006   1.755   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.434  -0.260   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.903  -0.421   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.276  -1.828   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       3.745  -1.989   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0       6.182  -3.074   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.968  -4.022   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.289  -4.610   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.673  -5.286   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5    8                                                  
CONECT   14    6   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14    4   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₁ClN₂

Average Mass

336.8600 Da

Monoisotopic Mass

336.13933 Da

IUPAC Name

(6aS,8R,9S)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5H,6H,6aH,7H,8H,9H-indeno[2,1-b]indole

Traditional Name

(6aS,8R,9S)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5H,6aH,7H,8H-indeno[2,1-b]indole

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2C[C@@H](Cl)[C@@](C)(C=C)C([N+]#[C-])=C2C2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C21H21ClN2/c1-6-21(4)15(22)11-13-17(19(21)23-5)16-12-9-7-8-10-14(12)24-18(16)20(13,2)3/h6-10,13,15,24H,1,11H2,2-4H3/t13-,15+,21+/m0/s1

InChI Key

ZVBCZYGMKQOJFW-QDUSTFBWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.53	ChemAxon
pKa (Strongest Acidic)	14.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	109.65 m³·mol⁻¹	ChemAxon
Polarizability	37.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9798948

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11624200

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim H, Krunic A, Lantvit D, Shen Q, Kroll DJ, Swanson SM, Orjala J: Nitrile-Containing Fischerindoles from the Cultured Cyanobacterium Fischerella sp. Tetrahedron. 2012 Apr 15;68(15):3205-3209. doi: 10.1016/j.tet.2012.02.048. [PubMed:22470225 ]
Khatri Y, Hohlman RM, Mendoza J, Li S, Lowell AN, Asahara H, Sherman DH: Multicomponent Microscale Biosynthesis of Unnatural Cyanobacterial Indole Alkaloids. ACS Synth Biol. 2020 Jun 19;9(6):1349-1360. doi: 10.1021/acssynbio.0c00038. Epub 2020 May 7. [PubMed:32302487 ]
Liu Y, Cheng LJ, Yue HT, Che W, Xie JH, Zhou QL: Divergent enantioselective synthesis of hapalindole-type alkaloids using catalytic asymmetric hydrogenation of a ketone to construct the chiral core structure. Chem Sci. 2016 Jul 1;7(7):4725-4729. doi: 10.1039/c6sc00686h. Epub 2016 Apr 12. [PubMed:30155122 ]
Lu Z, Yang M, Chen P, Xiong X, Li A: Total synthesis of hapalindole-type natural products. Angew Chem Int Ed Engl. 2014 Dec 8;53(50):13840-4. doi: 10.1002/anie.201406626. Epub 2014 Oct 10. [PubMed:25303730 ]
Freebody J: "The Root of All Evil is Inactivity": The Response of French Psychiatrists to New Approaches to Patient Work and Occupation, 1918-1939. 2021. [PubMed:36099392 ]
LOTUS database [Link]

Showing NP-Card for (6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole (NP0254046)

MOL for NP0254046 ((6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole)

3D MOL for NP0254046 ((6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole)

3D SDF for NP0254046 ((6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole)

3D-SDF for NP0254046 ((6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole)

PDB for NP0254046 ((6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole)

3D PDB for NP0254046 ((6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole)

SMILES for NP0254046 ((6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole)

INCHI for NP0254046 ((6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole)

Structure for NP0254046 ((6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole)

3D Structure for NP0254046 ((6ar,8r,9s)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h-indeno[2,1-b]indole)