NP-MRD: Showing NP-Card for periglaucine B (NP0033722)

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Record Information

Version

2.0

Created at

2021-06-20 17:39:37 UTC

Updated at

2021-06-30 00:03:41 UTC

NP-MRD ID

NP0033722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

periglaucine B

Provided By

JEOL Database JEOL Logo

Description

Periglaucine B belongs to the class of organic compounds known as hasubanan alkaloids. These are alkaloids with a structure based on the hasubanan skeleton, a tetracyclic propellane. periglaucine B is found in Pericampylus glaucus. periglaucine B was first documented in 2011 (PMID: 21638524). Based on a literature review a small amount of articles have been published on periglaucine B (PMID: 33523640) (PMID: 26521650).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119393D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202119393D          

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    3.4074   -2.7648   -1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2013   -0.2480   -4.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511   -1.8032   -5.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  2  0  0  0  0
 22 21  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  1  1  0  0  0
  4  3  1  0  0  0  0
  7 24  1  0  0  0  0
 12 13  1  0  0  0  0
 21 27  1  0  0  0  0
 27 26  1  0  0  0  0
 26 25  1  0  0  0  0
 25 22  1  0  0  0  0
 13 14  1  0  0  0  0
  4  5  2  0  0  0  0
 14 19  1  0  0  0  0
  3  2  1  0  0  0  0
 24 19  2  0  0  0  0
  7  8  1  0  0  0  0
  3 16  1  0  0  0  0
 12 10  1  1  0  0  0
 16 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 12  1  0  0  0  0
 10 11  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 24 23  1  0  0  0  0
 16 17  1  1  0  0  0
 19 20  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  2  0  0  0  0
  2  1  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
  3 31  1  1  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
 14 43  1  6  0  0  0
 20 47  1  0  0  0  0
 23 48  1  0  0  0  0
 26 49  1  0  0  0  0
 26 50  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 11 38  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 18 44  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C2OC([H])([H])OC2=C([H])C2=C1[C@@]1([H])O[C@@]3(OC([H])([H])[H])[C@@]([H])(OC([H])([H])[H])C(=O)C([H])([H])[C@@]22C([H])([H])C([H])([H])N(C([H])([H])[H])[C@]32C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO6/c1-21-5-4-18-8-13(22)17(23-2)20(24-3)19(18,21)9-16(27-20)11-6-14-15(7-12(11)18)26-10-25-14/h6-7,16-17H,4-5,8-10H2,1-3H3/t16-,17-,18-,19-,20-/m0/s1

> <INCHI_KEY>
QJDYNQYLCIPODD-HVTWWXFQSA-N

> <FORMULA>
C20H23NO6

> <MOLECULAR_WEIGHT>
373.405

> <EXACT_MASS>
373.152537465

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.41018805037368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,11S,13S,14R,15S)-14,15-dimethoxy-20-methyl-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2(10),3,8-trien-16-one

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
1.5654392480000001

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.037670103632433

> <JCHEM_PKA_STRONGEST_BASIC>
7.207944626448076

> <JCHEM_POLAR_SURFACE_AREA>
66.46000000000001

> <JCHEM_REFRACTIVITY>
93.92110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,11S,13S,14R,15S)-14,15-dimethoxy-20-methyl-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2(10),3,8-trien-16-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 55  0  0  0  0  0  0  0  0999 V2000
   -2.2321   -6.8053   -2.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0695   -5.4125   -2.3156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3948   -4.7310   -1.2461 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1199   -4.9422   -1.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6694   -5.7398   -2.0689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9337   -4.2133   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7046   -2.6941   -0.3822 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2883   -2.0107    0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.8640    1.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0097   -2.5446    1.2066 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -2.1147    1.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -2.3712   -0.2537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1061   -0.9742   -0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9065   -1.2912   -2.3058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4660   -2.5938   -2.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172   -3.2117   -1.2587 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1026   -2.9515   -0.9151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0692   -3.4792   -1.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695   -1.4306   -2.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320   -0.9123   -3.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -1.0757   -3.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729   -1.7253   -3.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7519   -2.2573   -1.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719   -2.1242   -1.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799   -1.7699   -3.4035 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5179   -1.1045   -4.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1975   -0.6323   -5.0206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721   -7.3097   -1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7330   -7.2400   -2.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8637   -6.9698   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7491   -5.1471   -0.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -4.6099    0.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9888   -4.4794   -0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -2.5962    1.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930   -1.0149    0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0829   -0.7986    2.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517   -2.3214    2.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5095   -1.0658    1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545   -2.2347    2.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063   -2.7399    1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1393   -0.6548   -0.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446   -0.1830   -0.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3812   -0.5527   -2.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2483   -4.5356   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0104   -2.9508   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7939   -3.3311   -2.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299   -0.4025   -4.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4074   -2.7648   -1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2013   -0.2480   -4.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511   -1.8032   -5.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  2  0
 22 21  1  0
  6  4  1  0
  7  6  1  1
  4  3  1  0
  7 24  1  0
 12 13  1  0
 21 27  1  0
 27 26  1  0
 26 25  1  0
 25 22  1  0
 13 14  1  0
  4  5  2  0
 14 19  1  0
  3  2  1  0
 24 19  2  0
  7  8  1  0
  3 16  1  0
 12 10  1  1
 16 12  1  0
  8  9  1  0
  9 10  1  0
  7 12  1  0
 10 11  1  0
 14 15  1  0
 16 15  1  0
 24 23  1  0
 16 17  1  1
 19 20  1  0
 17 18  1  0
 20 21  2  0
  2  1  1  0
  6 32  1  0
  6 33  1  0
  3 31  1  1
 13 41  1  0
 13 42  1  0
 14 43  1  6
 20 47  1  0
 23 48  1  0
 26 49  1  0
 26 50  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.232  -6.805  -2.082  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.070  -5.412  -2.316  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.395  -4.731  -1.246  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.120  -4.942  -1.306  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.669  -5.740  -2.069  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.934  -4.213  -0.272  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.705  -2.694  -0.382  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.288  -2.011   0.879  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.120  -1.864   1.848  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.010  -2.545   1.207  0.00  0.00           N+0
HETATM   11  C   UNK     0      -2.278  -2.115   1.780  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.834  -2.371  -0.254  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.106  -0.974  -0.828  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.907  -1.291  -2.306  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.466  -2.594  -2.542  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.717  -3.212  -1.259  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.103  -2.951  -0.915  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.069  -3.479  -1.810  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.570  -1.431  -2.586  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.132  -0.912  -3.761  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.486  -1.076  -3.950  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.273  -1.725  -3.030  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.752  -2.257  -1.869  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.372  -2.124  -1.638  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.580  -1.770  -3.404  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.518  -1.105  -4.682  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.197  -0.632  -5.021  0.00  0.00           O+0
HETATM   28  H   UNK     0      -1.272  -7.310  -1.949  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.733  -7.240  -2.951  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.864  -6.970  -1.203  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.749  -5.147  -0.294  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.640  -4.610   0.707  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.989  -4.479  -0.404  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.103  -2.596   1.322  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.693  -1.015   0.656  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.083  -0.799   2.016  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.352  -2.321   2.816  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.510  -1.066   1.571  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.255  -2.235   2.870  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.106  -2.740   1.439  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.139  -0.655  -0.650  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.445  -0.183  -0.459  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.381  -0.553  -2.959  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.248  -4.536  -1.597  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.010  -2.951  -1.631  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.794  -3.331  -2.858  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.530  -0.403  -4.505  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.407  -2.765  -1.169  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.201  -0.248  -4.664  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.851  -1.803  -5.458  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   16   31                                             
CONECT    4    6    3    5                                                  
CONECT    5    4                                                            
CONECT    6    4    7   32   33                                             
CONECT    7    6   24    8   12                                             
CONECT    8    7    9   34   35                                             
CONECT    9    8   10   36   37                                             
CONECT   10   12    9   11                                                  
CONECT   11   10   38   39   40                                             
CONECT   12   13   10   16    7                                             
CONECT   13   12   14   41   42                                             
CONECT   14   13   19   15   43                                             
CONECT   15   14   16                                                       
CONECT   16    3   12   15   17                                             
CONECT   17   16   18                                                       
CONECT   18   17   44   45   46                                             
CONECT   19   14   24   20                                                  
CONECT   20   19   21   47                                                  
CONECT   21   22   27   20                                                  
CONECT   22   23   21   25                                                  
CONECT   23   22   24   48                                                  
CONECT   24    7   19   23                                                  
CONECT   25   26   22                                                       
CONECT   26   27   25   49   50                                             
CONECT   27   21   26                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   11                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   13                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   20                                                            
CONECT   48   23                                                            
CONECT   49   26                                                            
CONECT   50   26                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  110    0
END

RDKit          3D

50 55  0  0  0  0  0  0  0  0999 V2000
   -2.2321   -6.8053   -2.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0695   -5.4125   -2.3156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3948   -4.7310   -1.2461 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1199   -4.9422   -1.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6694   -5.7398   -2.0689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9337   -4.2133   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7046   -2.6941   -0.3822 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2883   -2.0107    0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.8640    1.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0097   -2.5446    1.2066 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -2.1147    1.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -2.3712   -0.2537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1061   -0.9742   -0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9065   -1.2912   -2.3058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4660   -2.5938   -2.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172   -3.2117   -1.2587 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1026   -2.9515   -0.9151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0692   -3.4792   -1.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695   -1.4306   -2.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320   -0.9123   -3.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -1.0757   -3.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729   -1.7253   -3.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7519   -2.2573   -1.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719   -2.1242   -1.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799   -1.7699   -3.4035 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5179   -1.1045   -4.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1975   -0.6323   -5.0206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721   -7.3097   -1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7330   -7.2400   -2.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8637   -6.9698   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7491   -5.1471   -0.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -4.6099    0.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9888   -4.4794   -0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -2.5962    1.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930   -1.0149    0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0829   -0.7986    2.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517   -2.3214    2.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5095   -1.0658    1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545   -2.2347    2.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063   -2.7399    1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1393   -0.6548   -0.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446   -0.1830   -0.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3812   -0.5527   -2.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2483   -4.5356   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0104   -2.9508   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7939   -3.3311   -2.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299   -0.4025   -4.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4074   -2.7648   -1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2013   -0.2480   -4.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511   -1.8032   -5.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  2  0
 22 21  1  0
  6  4  1  0
  7  6  1  1
  4  3  1  0
  7 24  1  0
 12 13  1  0
 21 27  1  0
 27 26  1  0
 26 25  1  0
 25 22  1  0
 13 14  1  0
  4  5  2  0
 14 19  1  0
  3  2  1  0
 24 19  2  0
  7  8  1  0
  3 16  1  0
 12 10  1  1
 16 12  1  0
  8  9  1  0
  9 10  1  0
  7 12  1  0
 10 11  1  0
 14 15  1  0
 16 15  1  0
 24 23  1  0
 16 17  1  1
 19 20  1  0
 17 18  1  0
 20 21  2  0
  2  1  1  0
  6 32  1  0
  6 33  1  0
  3 31  1  1
 13 41  1  0
 13 42  1  0
 14 43  1  6
 20 47  1  0
 23 48  1  0
 26 49  1  0
 26 50  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃NO₆

Average Mass

373.4050 Da

Monoisotopic Mass

373.15254 Da

IUPAC Name

(1S,11S,13S,14R,15S)-14,15-dimethoxy-20-methyl-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2(10),3,8-trien-16-one

Traditional Name

(1S,11S,13S,14R,15S)-14,15-dimethoxy-20-methyl-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2(10),3,8-trien-16-one

CAS Registry Number

Not Available

SMILES

[H]C1=C2OC([H])([H])OC2=C([H])C2=C1[C@@]1([H])O[C@@]3(OC([H])([H])[H])[C@@]([H])(OC([H])([H])[H])C(=O)C([H])([H])[C@@]22C([H])([H])C([H])([H])N(C([H])([H])[H])[C@]32C1([H])[H]

InChI Identifier

InChI=1S/C20H23NO6/c1-21-5-4-18-8-13(22)17(23-2)20(24-3)19(18,21)9-16(27-20)11-6-14-15(7-12(11)18)26-10-25-14/h6-7,16-17H,4-5,8-10H2,1-3H3/t16-,17-,18-,19-,20-/m0/s1

InChI Key

QJDYNQYLCIPODD-HVTWWXFQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pericampylus glaucus	JEOL database	Yan, M. -H., et al, J. Nat. Prod. 71, 760 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hasubanan alkaloids. These are alkaloids with a structure based on the hasubanan skeleton, a tetracyclic propellane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Hasubanan alkaloids

Sub Class

Not Available

Direct Parent

Hasubanan alkaloids

Alternative Parents

Substituents

Hasubanan skeleton
Phenanthrene
Tetralin
Benzodioxole
Indole or derivatives
Ketal
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tetrahydrofuran
Ketone
Tertiary amine
Cyclic ketone
Tertiary aliphatic amine
Oxacycle
Dialkyl ether
Ether
Azacycle
Acetal
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Amine
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenanthrenes (CHEBI:66732 )

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	1.1	ALOGPS
logP	1.57	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	16.04	ChemAxon
pKa (Strongest Basic)	7.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.92 m³·mol⁻¹	ChemAxon
Polarizability	38.41 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

Not Available

Chemspider ID

34966925

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24879470

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hsu IT, Tomanik M, Herzon SB: Metric-Based Analysis of Convergence in Complex Molecule Synthesis. Acc Chem Res. 2021 Feb 16;54(4):903-916. doi: 10.1021/acs.accounts.0c00817. Epub 2021 Feb 1. [PubMed:33523640 ]
King SM, Herzon SB: The Hasubanan and Acutumine Alkaloids. Alkaloids Chem Biol. 2014;73:161-222. doi: 10.1016/B978-0-12-411565-1.00003-2. Epub 2013 Dec 25. [PubMed:26521650 ]
Herzon SB, Calandra NA, King SM: Efficient entry to the hasubanan alkaloids: first enantioselective total syntheses of (-)-hasubanonine, (-)-runanine, (-)-delavayine, and (+)-periglaucine B. Angew Chem Int Ed Engl. 2011 Sep 12;50(38):8863-6. doi: 10.1002/anie.201102226. Epub 2011 Jun 3. [PubMed:21638524 ]
Yan, M. -H., et al. (2008). Yan, M. -H., et al, J. Nat. Prod. 71, 760 (2008) . J. Nat. Prod..

Showing NP-Card for periglaucine B (NP0033722)

MOL for NP0033722 (periglaucine B)

3D MOL for NP0033722 (periglaucine B)

3D SDF for NP0033722 (periglaucine B)

3D-SDF for NP0033722 (periglaucine B)

PDB for NP0033722 (periglaucine B)

3D PDB for NP0033722 (periglaucine B)

SMILES for NP0033722 (periglaucine B)

INCHI for NP0033722 (periglaucine B)

Structure for NP0033722 (periglaucine B)

3D Structure for NP0033722 (periglaucine B)