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Showing NP-Card for 9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h,10h,10ah-indeno[2,1-b]indole (NP0219676)

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Record Information
Version2.0
Created at2022-09-05 20:45:03 UTC
Updated at2022-09-05 20:45:04 UTC
NP-MRD IDNP0219676
Secondary Accession NumbersNone
Natural Product Identification
Common Name9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h,10h,10ah-indeno[2,1-b]indole
DescriptionFischerindoles 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. 9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h,10h,10ah-indeno[2,1-b]indole was first documented in 2019 (PMID: 31284716). Based on a literature review a small amount of articles have been published on fischerindoles (PMID: 34354850) (PMID: 34032254) (PMID: 33289164) (PMID: 32052896).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0219676 (9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h,10h,10ah-indeno[2,1-b]indole)


  Mrv1652309052222452D          

 23 26  0  0  0  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  0  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  0  0  0  0  0  0  0  0  0  0
    3.3116   -1.6469    0.0000 C   0  0  0  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  1  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
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
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3D MOL for NP0219676 (9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h,10h,10ah-indeno[2,1-b]indole)

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3D SDF for NP0219676 (9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h,10h,10ah-indeno[2,1-b]indole)

  Mrv1652309052222452D          

 23 26  0  0  0  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  0  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  0  0  0  0  0  0  0  0  0  0
    3.3116   -1.6469    0.0000 C   0  0  0  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  1  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
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
NP0219676

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CCC(C)(C=C)C([N+]#[C-])C2C2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2/c1-6-21(4)12-11-14-17(19(21)22-5)16-13-9-7-8-10-15(13)23-18(16)20(14,2)3/h6-10,14,17,19,23H,1,11-12H2,2-4H3

> <INCHI_KEY>
NEYJIGPAQAKWSI-UHFFFAOYSA-N

> <FORMULA>
C21H24N2

> <MOLECULAR_WEIGHT>
304.437

> <EXACT_MASS>
304.193948781

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.15251542557309

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-ethenyl-10-isocyano-6,6,9-trimethyl-5H,6H,6aH,7H,8H,9H,10H,10aH-indeno[2,1-b]indole

> <JCHEM_LOGP>
2.721167933457389

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.4444023705965

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.792399872912913

> <JCHEM_POLAR_SURFACE_AREA>
20.15

> <JCHEM_REFRACTIVITY>
103.78150000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9-ethenyl-10-isocyano-6,6,9-trimethyl-5H,6aH,7H,8H,10H,10aH-indeno[2,1-b]indole

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0219676 (9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h,10h,10ah-indeno[2,1-b]indole)
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PDB for NP0219676 (9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h,10h,10ah-indeno[2,1-b]indole)
HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-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  C   UNK     0       6.182  -3.074   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.968  -4.022   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.289  -4.610   0.000  0.00  0.00           C+0
HETATM   23  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   20                                                  
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                                                       
CONECT   20   19    3   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

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3D PDB for NP0219676 (9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h,10h,10ah-indeno[2,1-b]indole)
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SMILES for NP0219676 (9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h,10h,10ah-indeno[2,1-b]indole)
CC1(C)C2CCC(C)(C=C)C([N+]#[C-])C2C2=C1NC1=CC=CC=C21
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INCHI for NP0219676 (9-ethenyl-10-isocyano-6,6,9-trimethyl-5h,6ah,7h,8h,10h,10ah-indeno[2,1-b]indole)
InChI=1S/C21H24N2/c1-6-21(4)12-11-14-17(19(21)22-5)16-13-9-7-8-10-15(13)23-18(16)20(14,2)3/h6-10,14,17,19,23H,1,11-12H2,2-4H3
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SynonymsNot Available
Chemical FormulaC21H24N2
Average Mass304.4370 Da
Monoisotopic Mass304.19395 Da
IUPAC Name9-ethenyl-10-isocyano-6,6,9-trimethyl-5H,6H,6aH,7H,8H,9H,10H,10aH-indeno[2,1-b]indole
Traditional Name9-ethenyl-10-isocyano-6,6,9-trimethyl-5H,6aH,7H,8H,10H,10aH-indeno[2,1-b]indole
CAS Registry NumberNot Available
SMILES
CC1(C)C2CCC(C)(C=C)C([N+]#[C-])C2C2=C1NC1=CC=CC=C21
InChI Identifier
InChI=1S/C21H24N2/c1-6-21(4)12-11-14-17(19(21)22-5)16-13-9-7-8-10-15(13)23-18(16)20(14,2)3/h6-10,14,17,19,23H,1,11-12H2,2-4H3
InChI KeyNEYJIGPAQAKWSI-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
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Azacycle
    • 

  • Organic isocyanide
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • 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
logP2.72ChemAxon
pKa (Strongest Acidic)15.79ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity103.78 m³·mol⁻¹ChemAxon
Polarizability36.15 ųChemAxon
Number of Rings4ChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound134716588  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Knoot CJ, Khatri Y, Hohlman RM, Sherman DH, Pakrasi HB: Engineered Production of Hapalindole Alkaloids in the Cyanobacterium Synechococcus sp. UTEX 2973. ACS Synth Biol. 2019 Aug 16;8(8):1941-1951. doi: 10.1021/acssynbio.9b00229. Epub  2019 Jul 19. [PubMed:31284716  ] 
  2. Hohlman RM, Newmister SA, Sanders JN, Khatri Y, Li S, Keramati NR, Lowell AN, Houk KN, Sherman DH: Structural diversification of hapalindole and fischerindole natural products via cascade biocatalysis. ACS Catal. 2021 Apr 16;11(8):4670-4681. doi: 10.1021/acscatal.0c05656. Epub 2021  Apr 5. [PubMed:34354850  ] 
  3. Hohlman RM, Sherman DH: Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity. Nat Prod Rep. 2021 Sep 23;38(9):1567-1588. doi: 10.1039/d1np00007a. [PubMed:34032254  ] 
  4. Nowruzi B, Porzani SJ: Toxic compounds produced by cyanobacteria belonging to several species of the order Nostocales: A review. J Appl Toxicol. 2020 Dec 2. doi: 10.1002/jat.4088. [PubMed:33289164  ] 
  5. Li S, Newmister SA, Lowell AN, Zi J, Chappell CR, Yu F, Hohlman RM, Orjala J, Williams RM, Sherman DH: Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor-Induced Combinatorial Pairing of Stig Cyclases. Angew Chem Int Ed Engl. 2020 May 18;59(21):8166-8172. doi:  10.1002/anie.201913686. Epub 2020 Mar 19. [PubMed:32052896  ] 
  6. LOTUS database [Link]