NP-MRD: Showing NP-Card for methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate (NP0151054)

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Record Information

Version

2.0

Created at

2022-09-02 07:18:38 UTC

Updated at

2022-09-02 07:18:38 UTC

NP-MRD ID

NP0151054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate

Description

Kopsifoline D 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. methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate is found in Kopsia fruticosa. methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate was first documented in 2014 (PMID: 24499015). Based on a literature review a small amount of articles have been published on Kopsifoline D (PMID: 26813287) (PMID: 35735178) (PMID: 34766779) (PMID: 31830791).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022209182D          

 24 29  0  0  1  0            999 V2000
    3.3054   -2.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062   -1.5880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224   -0.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3378   -1.0697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2231   -0.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3629   -0.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602    0.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3193    0.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1077    1.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6684    2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5161    2.3002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610    2.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299    2.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6561    1.3825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8012    0.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5744    0.1520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0706    0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8797    0.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1446    1.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6004    2.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7913    2.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5264    1.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536    1.4584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9225    0.5608    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  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  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 14 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 11  1  6  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  5 24  1  0  0  0  0
M  END

     RDKit          3D

 44 49  0  0  0  0  0  0  0  0999 V2000
    5.2873    1.0960   -1.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0851    0.3580   -0.9028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    0.9149   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9992    2.1252   -0.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6604    0.2179   -0.2401 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2884   -0.8147   -1.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6557   -1.5945   -0.0946 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6301   -3.0512   -0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5132   -3.6520   -0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155   -2.9538   -0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7646   -1.5644   -0.4191 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8535   -0.7559   -1.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2893    0.5815   -1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7965    0.4067    0.1416 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6685    1.2158    0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9983    1.1808    1.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6146    2.1687    2.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8275    3.2243    2.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896    3.2891    2.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9111    2.2934    1.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4481    2.0712    0.9964 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5638    0.9829    0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6723   -1.0531    0.3685 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8071   -1.0573    0.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2506    1.7838   -1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1494    0.4050   -1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4495    1.7658   -0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7503   -0.6301   -2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -1.4091   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5782   -3.5919   -0.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236   -4.7350   -0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5110   -3.4786    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2267   -3.1716   -1.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762   -0.7131   -1.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4560   -1.2581   -2.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6186    1.0645   -1.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2029    1.2841   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6349    0.3462    0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6743    2.1195    2.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3185    4.0042    3.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472    4.1576    2.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.2855    1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7596   -1.5186    0.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6048   -0.7687    1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  6
  5 24  1  0
 24  7  1  0
  7  6  1  0
  7  8  1  6
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 13  1  6
 14 23  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  6  5  1  0
 23 11  1  0
 20 15  1  0
 22  5  1  0
 23  7  1  0
 22 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 24 43  1  0
 24 44  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 23 42  1  1
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv1652309022209182D          

 24 29  0  0  1  0            999 V2000
    3.3054   -2.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062   -1.5880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224   -0.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3378   -1.0697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2231   -0.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3629   -0.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602    0.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3193    0.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1077    1.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6684    2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5161    2.3002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610    2.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299    2.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6561    1.3825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8012    0.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5744    0.1520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0706    0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8797    0.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1446    1.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6004    2.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7913    2.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5264    1.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536    1.4584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9225    0.5608    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  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  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 14 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 11  1  6  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  5 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0151054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12CC3(C1)C=CCN1CC[C@]4([C@H]31)C1=CC=CC=C1N=C24

> <INCHI_IDENTIFIER>
InChI=1S/C20H20N2O2/c1-24-17(23)19-11-18(12-19)7-4-9-22-10-8-20(16(18)22)13-5-2-3-6-14(13)21-15(19)20/h2-7,16H,8-12H2,1H3/t16-,18?,19?,20-/m0/s1

> <INCHI_KEY>
FHPMIUVZUHCUPX-ACAXCVFMSA-N

> <FORMULA>
C20H20N2O2

> <MOLECULAR_WEIGHT>
320.392

> <EXACT_MASS>
320.152477892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.13146537039543

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,19S)-8,16-diazahexacyclo[10.6.1.1^{10,12}.0^{1,9}.0^{2,7}.0^{16,19}]icosa-2,4,6,8,13-pentaene-10-carboxylate

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.9502020833333336

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.828123405513274

> <JCHEM_POLAR_SURFACE_AREA>
41.9

> <JCHEM_REFRACTIVITY>
93.47650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,19S)-8,16-diazahexacyclo[10.6.1.1^{10,12}.0^{1,9}.0^{2,7}.0^{16,19}]icosa-2,4,6,8,13-pentaene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.170  -4.399   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.612  -2.964   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.575  -1.763   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.097  -1.997   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.016  -0.328   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.411  -0.144   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.032   1.459   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.463   1.762   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.068   3.282   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.114   4.483   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.697   4.294   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.900   5.337   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.963   4.194   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.825   2.581   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.096   0.917   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       8.539   0.284   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       9.465   1.542   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.975   1.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.470   3.302   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.454   4.459   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.944   4.158   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.449   2.699   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.140   2.722   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.455   1.047   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15   24                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   23   24                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   22   23                                             
CONECT   15   14    5   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   14                                                  
CONECT   23   14   11    7                                                  
CONECT   24    7    5                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀N₂O₂

Average Mass

320.3920 Da

Monoisotopic Mass

320.15248 Da

IUPAC Name

methyl (1R,19S)-8,16-diazahexacyclo[10.6.1.1^{10,12}.0^{1,9}.0^{2,7}.0^{16,19}]icosa-2,4,6,8,13-pentaene-10-carboxylate

Traditional Name

methyl (1R,19S)-8,16-diazahexacyclo[10.6.1.1^{10,12}.0^{1,9}.0^{2,7}.0^{16,19}]icosa-2,4,6,8,13-pentaene-10-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C12CC3(C1)C=CCN1CC[C@]4([C@H]31)C1=CC=CC=C1N=C24

InChI Identifier

InChI=1S/C20H20N2O2/c1-24-17(23)19-11-18(12-19)7-4-9-22-10-8-20(16(18)22)13-5-2-3-6-14(13)21-15(19)20/h2-7,16H,8-12H2,1H3/t16-,18?,19?,20-/m0/s1

InChI Key

FHPMIUVZUHCUPX-ACAXCVFMSA-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

Species Name	Source	Reference
Kopsia fruticosa	LOTUS Database	35616633

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
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Ketimine
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Imine
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Amine
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	2.71	ALOGPS
logP	2.95	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	8.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	41.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.48 m³·mol⁻¹	ChemAxon
Polarizability	35.13 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

C00051154

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101733512

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sears JE, Boger DL: Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications. Acc Chem Res. 2016 Feb 16;49(2):241-51. doi: 10.1021/acs.accounts.5b00510. Epub 2016 Jan 27. [PubMed:26813287 ]
Lee K, Boger DL: Total syntheses of (-)-kopsifoline D and (-)-deoxoapodine: divergent total synthesis via late-stage key strategic bond formation. J Am Chem Soc. 2014 Feb 26;136(8):3312-7. doi: 10.1021/ja500548e. Epub 2014 Feb 17. [PubMed:24499015 ]
Zhao LP, Li PJ, Wang L, Tang Y: Allenamide-Initiated Cascade [2+2+2] Annulation Enabling the Divergent Total Synthesis of (-)-Deoxoapodine, (-)-Kopsifoline D and (+/-)-Melotenine A. Angew Chem Int Ed Engl. 2022 Aug 22;61(34):e202207360. doi: 10.1002/anie.202207360. Epub 2022 Jul 13. [PubMed:35735178 ]
Myeong IS, Avci NH, Movassaghi M: Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E. Org Lett. 2021 Dec 3;23(23):9118-9122. doi: 10.1021/acs.orglett.1c03448. Epub 2021 Nov 12. [PubMed:34766779 ]
Zhou YG, Wong HNC, Peng XS: Total Syntheses of (-)-Deoxoapodine, (-)-Kopsifoline D, and (-)-Beninine. J Org Chem. 2020 Jan 17;85(2):967-976. doi: 10.1021/acs.joc.9b02918. Epub 2019 Dec 26. [PubMed:31830791 ]
LOTUS database [Link]

Showing NP-Card for methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate (NP0151054)

MOL for NP0151054 (methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate)

3D MOL for NP0151054 (methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate)

3D SDF for NP0151054 (methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate)

3D-SDF for NP0151054 (methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate)

PDB for NP0151054 (methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate)

3D PDB for NP0151054 (methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate)

SMILES for NP0151054 (methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate)

INCHI for NP0151054 (methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate)

Structure for NP0151054 (methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate)

3D Structure for NP0151054 (methyl (1r,19s)-8,16-diazahexacyclo[10.6.1.1¹⁰,¹².0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6,8,13-pentaene-10-carboxylate)