NP-MRD: Showing NP-Card for Segoline A (NP0025424)

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Record Information

Version

1.0

Created at

2021-06-19 17:33:22 UTC

Updated at

2021-06-29 23:50:22 UTC

NP-MRD ID

NP0025424

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Segoline A

Provided By

JEOL Database JEOL Logo

Description

Segoline A belongs to the class of organic compounds known as pyrido[2,3,4-kl]acridines. These are organic heterocyclic compounds with a structure based on the pyrido[2,3,4-kl]acridine skeleton. Segoline A is found in Eudistoma bituminis and Eudistoma sp.. It was first documented in 2001 (Viracaoundin, I., et al.). Based on a literature review very few articles have been published on Segoline A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119333D          

 48 53  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192119333D          

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 20 22  1  0  0  0  0
  3  4  2  0  0  0  0
 25 24  1  0  0  0  0
 24 22  1  0  0  0  0
  3 12  1  0  0  0  0
 22 23  2  0  0  0  0
  4  5  1  0  0  0  0
 25 26  2  0  0  0  0
 12 11  1  0  0  0  0
 27 44  1  1  0  0  0
  7  8  1  0  0  0  0
 28 29  1  0  0  0  0
  4 33  1  0  0  0  0
 17 39  1  0  0  0  0
 16 38  1  0  0  0  0
 15 37  1  0  0  0  0
 14 36  1  0  0  0  0
  9 34  1  0  0  0  0
 10 35  1  0  0  0  0
 28 45  1  1  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 21 40  1  0  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
 24 43  1  0  0  0  0
 29 46  1  0  0  0  0
 29 47  1  0  0  0  0
 29 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025424

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C(=O)[C@]2([H])C3=C4N(C5=C([H])C([H])=C([H])C([H])=C5C5=C([H])C([H])=NC(C(OC([H])([H])[H])=C3[H])=C45)[C@@](C1=O)(C([H])([H])[H])[C@]2([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H19N3O3/c1-11-17-14-10-16(29-3)19-18-13(8-9-24-19)12-6-4-5-7-15(12)26(20(14)18)23(11,2)22(28)25-21(17)27/h4-11,17H,1-3H3,(H,25,27,28)/t11-,17+,23+/m1/s1

> <INCHI_KEY>
ZOOFKNHZEAAAAK-AQFVUADLSA-N

> <FORMULA>
C23H19N3O3

> <MOLECULAR_WEIGHT>
385.423

> <EXACT_MASS>
385.142641484

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
40.643843903720175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(16S,20S,23R)-13-methoxy-20,23-dimethyl-1,11,18-triazahexacyclo[10.8.2.1^{16,20}.0^{2,7}.0^{8,22}.0^{15,21}]tricosa-2,4,6,8,10,12(22),13,15(21)-octaene-17,19-dione

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
2.910701992

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.493366838495891

> <JCHEM_PKA_STRONGEST_BASIC>
4.084281415628632

> <JCHEM_POLAR_SURFACE_AREA>
71.53

> <JCHEM_REFRACTIVITY>
106.8133

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(16S,20S,23R)-13-methoxy-20,23-dimethyl-1,11,18-triazahexacyclo[10.8.2.1^{16,20}.0^{2,7}.0^{8,22}.0^{15,21}]tricosa-2,4,6,8,10,12(22),13,15(21)-octaene-17,19-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 48 53  0  0  0  0  0  0  0  0999 V2000
   -1.8043   -4.6550    1.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0070   -3.5487    2.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2434   -2.3313    1.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825   -1.4467    1.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341   -0.1428    1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3409    0.2942    0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3955   -0.6193    0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4919   -0.2250   -0.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5749   -1.1038   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5066   -2.3338   -0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4410   -2.7549    0.6361 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821   -1.9306    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259    1.0675   -1.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658    1.4018   -2.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2561    2.5681   -3.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1868    3.4144   -2.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454    3.1056   -1.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3498    1.9629   -1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135    1.6323   -0.0051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4870    2.6791    0.6140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2724    3.9385    1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510    2.9915   -0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    4.0549   -0.9927 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966    2.0015   -0.5368 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214    0.9492    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7456    0.1652    0.1081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8867    0.8136    1.5118 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2175    2.1304    1.8962 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2237    3.0786    2.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3281   -5.5596    2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -4.6002    2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8424   -4.7584    0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841   -1.7883    2.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4710   -0.8627   -1.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3271   -3.0421   -0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1950    0.7447   -2.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9887    2.7960   -3.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0681    4.3139   -3.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4189    3.7997   -1.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0034    3.6918    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6059    4.7147    1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239    4.4266    0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755    2.1295   -1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4833    0.4507    2.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5521    1.9272    2.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169    2.5738    3.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245    3.9588    2.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0060    3.4229    1.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 19  6  1  0
  7  6  1  0
 19 18  1  0
 13 14  2  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 19 20  1  0
  6  5  2  0
  5 27  1  0
 27 28  1  0
 28 20  1  0
 15 14  1  0
  3  2  1  0
 12  7  2  0
  2  1  1  0
 13  8  1  0
 27 25  1  0
 13 18  1  0
 20 21  1  1
 20 22  1  0
  3  4  2  0
 25 24  1  0
 24 22  1  0
  3 12  1  0
 22 23  2  0
  4  5  1  0
 25 26  2  0
 12 11  1  0
 27 44  1  1
  7  8  1  0
 28 29  1  0
  4 33  1  0
 17 39  1  0
 16 38  1  0
 15 37  1  0
 14 36  1  0
  9 34  1  0
 10 35  1  0
 28 45  1  1
  1 30  1  0
  1 31  1  0
  1 32  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
 24 43  1  0
 29 46  1  0
 29 47  1  0
 29 48  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.804  -4.655   1.706  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.007  -3.549   2.107  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.243  -2.331   1.508  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.183  -1.447   1.713  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.234  -0.143   1.225  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.341   0.294   0.488  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.396  -0.619   0.238  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.492  -0.225  -0.560  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.575  -1.104  -0.674  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.507  -2.334  -0.062  0.00  0.00           C+0
HETATM   11  N   UNK     0      -3.441  -2.755   0.636  0.00  0.00           N+0
HETATM   12  C   UNK     0      -2.382  -1.931   0.792  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.426   1.067  -1.291  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.366   1.402  -2.295  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.256   2.568  -3.046  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.187   3.414  -2.828  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.245   3.106  -1.843  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.350   1.963  -1.027  0.00  0.00           C+0
HETATM   19  N   UNK     0      -1.414   1.632  -0.005  0.00  0.00           N+0
HETATM   20  C   UNK     0      -0.487   2.679   0.614  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.272   3.938   1.043  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.651   2.991  -0.387  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.772   4.055  -0.993  0.00  0.00           O+0
HETATM   24  N   UNK     0       1.597   2.002  -0.537  0.00  0.00           N+0
HETATM   25  C   UNK     0       1.821   0.949   0.315  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.746   0.165   0.108  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.887   0.814   1.512  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.218   2.130   1.896  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.224   3.079   2.572  0.00  0.00           C+0
HETATM   30  H   UNK     0      -1.328  -5.560   2.098  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.802  -4.600   2.152  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.842  -4.758   0.617  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.684  -1.788   2.277  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.471  -0.863  -1.231  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.327  -3.042  -0.131  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.195   0.745  -2.537  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.989   2.796  -3.816  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.068   4.314  -3.427  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.419   3.800  -1.761  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.003   3.692   1.822  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.606   4.715   1.433  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.824   4.427   0.240  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.276   2.130  -1.274  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.483   0.451   2.359  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.552   1.927   2.658  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.717   2.574   3.410  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.725   3.959   2.987  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.006   3.423   1.889  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5   33                                                  
CONECT    5    6   27    4                                                  
CONECT    6   19    7    5                                                  
CONECT    7    6   12    8                                                  
CONECT    8    9   13    7                                                  
CONECT    9    8   10   34                                                  
CONECT   10    9   11   35                                                  
CONECT   11   10   12                                                       
CONECT   12    7    3   11                                                  
CONECT   13   14    8   18                                                  
CONECT   14   13   15   36                                                  
CONECT   15   16   14   37                                                  
CONECT   16   17   15   38                                                  
CONECT   17   18   16   39                                                  
CONECT   18   19   17   13                                                  
CONECT   19    6   18   20                                                  
CONECT   20   19   28   21   22                                             
CONECT   21   20   40   41   42                                             
CONECT   22   20   24   23                                                  
CONECT   23   22                                                            
CONECT   24   25   22   43                                                  
CONECT   25   27   24   26                                                  
CONECT   26   25                                                            
CONECT   27    5   28   25   44                                             
CONECT   28   27   20   29   45                                             
CONECT   29   28   46   47   48                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    4                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   21                                                            
CONECT   41   21                                                            
CONECT   42   21                                                            
CONECT   43   24                                                            
CONECT   44   27                                                            
CONECT   45   28                                                            
CONECT   46   29                                                            
CONECT   47   29                                                            
CONECT   48   29                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  106    0
END

RDKit          3D

48 53  0  0  0  0  0  0  0  0999 V2000
   -1.8043   -4.6550    1.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0070   -3.5487    2.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2434   -2.3313    1.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825   -1.4467    1.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341   -0.1428    1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3409    0.2942    0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3955   -0.6193    0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4919   -0.2250   -0.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5749   -1.1038   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5066   -2.3338   -0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4410   -2.7549    0.6361 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821   -1.9306    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259    1.0675   -1.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658    1.4018   -2.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2561    2.5681   -3.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1868    3.4144   -2.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454    3.1056   -1.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3498    1.9629   -1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135    1.6323   -0.0051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4870    2.6791    0.6140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2724    3.9385    1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510    2.9915   -0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    4.0549   -0.9927 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966    2.0015   -0.5368 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214    0.9492    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7456    0.1652    0.1081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8867    0.8136    1.5118 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2175    2.1304    1.8962 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2237    3.0786    2.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3281   -5.5596    2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -4.6002    2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8424   -4.7584    0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841   -1.7883    2.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4710   -0.8627   -1.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3271   -3.0421   -0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1950    0.7447   -2.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9887    2.7960   -3.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0681    4.3139   -3.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4189    3.7997   -1.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0034    3.6918    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6059    4.7147    1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239    4.4266    0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755    2.1295   -1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4833    0.4507    2.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5521    1.9272    2.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169    2.5738    3.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245    3.9588    2.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0060    3.4229    1.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 19  6  1  0
  7  6  1  0
 19 18  1  0
 13 14  2  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 19 20  1  0
  6  5  2  0
  5 27  1  0
 27 28  1  0
 28 20  1  0
 15 14  1  0
  3  2  1  0
 12  7  2  0
  2  1  1  0
 13  8  1  0
 27 25  1  0
 13 18  1  0
 20 21  1  1
 20 22  1  0
  3  4  2  0
 25 24  1  0
 24 22  1  0
  3 12  1  0
 22 23  2  0
  4  5  1  0
 25 26  2  0
 12 11  1  0
 27 44  1  1
  7  8  1  0
 28 29  1  0
  4 33  1  0
 17 39  1  0
 16 38  1  0
 15 37  1  0
 14 36  1  0
  9 34  1  0
 10 35  1  0
 28 45  1  1
  1 30  1  0
  1 31  1  0
  1 32  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
 24 43  1  0
 29 46  1  0
 29 47  1  0
 29 48  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₃H₁₉N₃O₃

Average Mass

385.4230 Da

Monoisotopic Mass

385.14264 Da

IUPAC Name

(16S,20S,23R)-13-methoxy-20,23-dimethyl-1,11,18-triazahexacyclo[10.8.2.1^{16,20}.0^{2,7}.0^{8,22}.0^{15,21}]tricosa-2,4,6,8,10,12(22),13,15(21)-octaene-17,19-dione

Traditional Name

(16S,20S,23R)-13-methoxy-20,23-dimethyl-1,11,18-triazahexacyclo[10.8.2.1^{16,20}.0^{2,7}.0^{8,22}.0^{15,21}]tricosa-2,4,6,8,10,12(22),13,15(21)-octaene-17,19-dione

CAS Registry Number

Not Available

SMILES

[H]N1C(=O)[C@]2([H])C3=C4N(C5=C([H])C([H])=C([H])C([H])=C5C5=C([H])C([H])=NC(C(OC([H])([H])[H])=C3[H])=C45)[C@@](C1=O)(C([H])([H])[H])[C@]2([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H19N3O3/c1-11-17-14-10-16(29-3)19-18-13(8-9-24-19)12-6-4-5-7-15(12)26(20(14)18)23(11,2)22(28)25-21(17)27/h4-11,17H,1-3H3,(H,25,27,28)/t11-,17+,23+/m1/s1

InChI Key

ZOOFKNHZEAAAAK-AQFVUADLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Eudistoma bituminis	JEOL database	Viracaoundin, I., et al, Tetrahedron Letts. 42, 2669 (2001)
Eudistoma sp.	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrido[2,3,4-kl]acridines. These are organic heterocyclic compounds with a structure based on the pyrido[2,3,4-kl]acridine skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Pyrido[2,3,4-kl]acridines

Alternative Parents

Substituents

Pyrido[2,3,4-kl]acridine
1,7-phenanthroline
Naphthyridine
Anisole
Phenol ether
Piperidinedione
Alkyl aryl ether
Delta-lactam
Piperidinone
Benzenoid
Piperidine
Pyridine
Heteroaromatic compound
Carboxylic acid imide, n-unsubstituted
Dicarboximide
Carboxylic acid imide
Lactam
Azacycle
Ether
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
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	3.17	ALOGPS
logP	2.91	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	11.49	ChemAxon
pKa (Strongest Basic)	4.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	106.81 m³·mol⁻¹	ChemAxon
Polarizability	40.64 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

C00000520

Chemspider ID

10275443

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14447872

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Viracaoundin, I., et al. (2001). Viracaoundin, I., et al, Tetrahedron Letts. 42, 2669 (2001). Tetrahedron Lett.

Showing NP-Card for Segoline A (NP0025424)

MOL for NP0025424 (Segoline A)

3D MOL for NP0025424 (Segoline A)

3D SDF for NP0025424 (Segoline A)

3D-SDF for NP0025424 (Segoline A)

PDB for NP0025424 (Segoline A)

3D PDB for NP0025424 (Segoline A)

SMILES for NP0025424 (Segoline A)

INCHI for NP0025424 (Segoline A)

Structure for NP0025424 (Segoline A)

3D Structure for NP0025424 (Segoline A)