NP-MRD: Showing NP-Card for (2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene (NP0331068)

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Record Information

Version

1.0

Created at

2022-09-12 17:03:00 UTC

Updated at

2022-09-12 17:03:00 UTC

NP-MRD ID

NP0331068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene

Description

Hapalindole A 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. It was first documented in 2018 (PMID: 29178634). Based on a literature review very few articles have been published on Hapalindole A (PMID: 31777053).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122219032D          

 24 27  0  0  1  0            999 V2000
    4.3769   -1.3341    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    4.4208   -0.5102    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.4648    0.3136    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7732    0.7635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0378    0.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8236   -0.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9997   -0.4495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348    0.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8065    1.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481    1.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902    1.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1257    2.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    2.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6889    2.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172    1.5874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5526    1.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441    1.5113    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9795    1.8852    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2002    0.6875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0220    0.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5995   -0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4243   -0.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  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
 12 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  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  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

 47 50  0  0  0  0  0  0  0  0999 V2000
   -3.1148    1.1906   -2.4726 C   0  0  0  0  0  3  0  0  0  0  0  0
   -2.4986    0.9689   -1.5163 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.7355    0.6704   -0.3412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3919    0.2448   -0.7628 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5552    1.4031   -0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3672    2.7916   -0.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786    3.3659   -0.3477 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972    2.4187   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504    2.3409    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4614    1.1023    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7437   -0.0866    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4071   -0.0023   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8531    1.2207   -0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6071   -1.2123   -0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -2.2515    0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375   -1.7681   -1.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1307   -1.0004   -0.1355 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3383   -1.1263    1.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8347   -1.3394    1.1875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4713   -1.6192    2.8246 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421   -0.2367    0.4958 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2953    0.5386    1.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6501   -0.8684   -0.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7898   -0.2059   -0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7021    1.6723    0.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3435    0.0605   -1.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5652    3.2857   -0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    4.3851   -0.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3807    3.2717    0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5105    1.1050    0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823   -1.0069    0.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1051   -2.6645    0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2892   -1.8648    1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4429   -3.1435    0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308   -2.2326   -2.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7673   -2.4965   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2606   -0.9538   -2.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3653   -1.8601   -0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0942   -0.2378    1.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793   -2.0639    1.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9776   -2.2953    0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2609    0.0584    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4218    1.5957    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6420    0.5536    2.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4881   -1.8348   -0.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9393    0.7734   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5839   -0.6464   -1.0661 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  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
  4 17  1  0
 13  5  1  0
 13  8  2  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  6
 18 39  1  0
 18 40  1  0
 19 41  1  6
 22 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
  3 25  1  1
  4 26  1  6
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
M  CHG  2   1  -1   2   1
M  END


  Mrv1652309122219032D          

 24 27  0  0  1  0            999 V2000
    4.3769   -1.3341    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    4.4208   -0.5102    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.4648    0.3136    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7732    0.7635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0378    0.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8236   -0.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9997   -0.4495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348    0.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8065    1.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481    1.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902    1.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1257    2.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    2.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6889    2.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172    1.5874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5526    1.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441    1.5113    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9795    1.8852    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2002    0.6875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0220    0.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5995   -0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4243   -0.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  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
 12 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  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  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>
NP0331068

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2C[C@@H](Cl)[C@](C)(C=C)[C@H]([N+]#[C-])[C@H]2C2=CNC3=CC=CC1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C21H23ClN2/c1-6-21(4)16(22)10-14-18(19(21)23-5)12-11-24-15-9-7-8-13(17(12)15)20(14,2)3/h6-9,11,14,16,18-19,24H,1,10H2,2-4H3/t14-,16+,18-,19+,21-/m0/s1

> <INCHI_KEY>
UGBGKUYYYCTXAK-DJNKVENRSA-N

> <FORMULA>
C21H23ClN2

> <MOLECULAR_WEIGHT>
338.88

> <EXACT_MASS>
338.1549764

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.4389912003493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4R,5R,7S)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraene

> <JCHEM_LOGP>
2.9249475987907214

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.828886041042505

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.84082209829861

> <JCHEM_POLAR_SURFACE_AREA>
20.15

> <JCHEM_REFRACTIVITY>
108.4705

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R,5R,7S)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

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       8.170  -2.490   0.000  0.00  0.00           C-1
HETATM    2  N   UNK     0       8.252  -0.952   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       8.334   0.585   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.043   1.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.671   0.727   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.271  -0.760   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.733  -0.839   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.182   0.599   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.745   1.152   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.505   2.674   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.703   3.642   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.462   3.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.380   1.567   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.835   3.803   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.909   5.034   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.886   4.928   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.125   2.963   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.498   3.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.789   2.821   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0      11.162   3.519   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0       9.707   1.283   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.241   1.148   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.452  -0.064   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.992  -0.093   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                                                       
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   14                                                  
CONECT   13   12    5    8                                                  
CONECT   14   12   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

C₂₁H₂₃ClN₂

Average Mass

338.8800 Da

Monoisotopic Mass

338.15498 Da

IUPAC Name

(2R,3R,4R,5R,7S)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraene

Traditional Name

(2R,3R,4R,5R,7S)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraene

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2C[C@@H](Cl)[C@](C)(C=C)[C@H]([N+]#[C-])[C@H]2C2=CNC3=CC=CC1=C23

InChI Identifier

InChI=1S/C21H23ClN2/c1-6-21(4)16(22)10-14-18(19(21)23-5)12-11-24-15-9-7-8-13(17(12)15)20(14,2)3/h6-9,11,14,16,18-19,24H,1,10H2,2-4H3/t14-,16+,18-,19+,21-/m0/s1

InChI Key

UGBGKUYYYCTXAK-DJNKVENRSA-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

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Isoindole or derivatives
Benzenoid
Pyrrole
Heteroaromatic compound
Organic isocyanide
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Alkyl chloride
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Alkyl halide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.92	ChemAxon
pKa (Strongest Acidic)	15.84	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	108.47 m³·mol⁻¹	ChemAxon
Polarizability	37.44 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

160968

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

185159

PDB ID

8O0

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chilczuk T, Steinborn C, Breinlinger S, Zimmermann-Klemd AM, Huber R, Enke H, Enke D, Niedermeyer THJ, Grundemann C: Hapalindoles from the Cyanobacterium Hapalosiphon sp. Inhibit T Cell Proliferation. Planta Med. 2020 Jan;86(2):96-103. doi: 10.1055/a-1045-5178. Epub 2019 Nov 27. [PubMed:31777053 ]
Wong CP, Awakawa T, Nakashima Y, Mori T, Zhu Q, Liu X, Abe I: Two Distinct Substrate Binding Modes for the Normal and Reverse Prenylation of Hapalindoles by the Prenyltransferase AmbP3. Angew Chem Int Ed Engl. 2018 Jan 8;57(2):560-563. doi: 10.1002/anie.201710682. Epub 2017 Dec 15. [PubMed:29178634 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene (NP0331068)

MOL for NP0331068 ((2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

3D MOL for NP0331068 ((2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

3D SDF for NP0331068 ((2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

3D-SDF for NP0331068 ((2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

PDB for NP0331068 ((2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

3D PDB for NP0331068 ((2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

SMILES for NP0331068 ((2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

INCHI for NP0331068 ((2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

Structure for NP0331068 ((2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

3D Structure for NP0331068 ((2r,3r,4r,5r,7s)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)