NP-MRD: Showing NP-Card for Spirohexenolide B (NP0008840)

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Record Information

Version

2.0

Created at

2020-12-09 06:20:06 UTC

Updated at

2021-07-15 17:01:34 UTC

NP-MRD ID

NP0008840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spirohexenolide B

Provided By

NPAtlas

Description

Spirohexenolide B is found in Streptomyces platensis. Spirohexenolide B was first documented in 2009 (PMID: 19883063).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106303D          

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M  END


  Mrv1652306242106303D          

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    0.0974   -0.7681    2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208    1.9694    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645    3.8558   -0.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5278    4.3257   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2422    4.0062    0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6356    0.2940   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1309    2.5702    0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5280    1.2714    1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0530    1.8381   -0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9722    1.1808    1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8219   -0.1225   -1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5076   -3.6551   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204   -3.6934   -1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913   -1.0619   -2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095    0.6566   -1.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060   -1.6691   -0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5374    0.2356   -2.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7160   -0.3320   -1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8804   -1.4908   -2.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038   -0.3353    1.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0379   -2.0709    1.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  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
 13 14  2  0  0  0  0
 14 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
 19 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24  2  1  0  0  0  0
 22  4  1  0  0  0  0
 29 14  1  0  0  0  0
 26 18  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 33  1  0  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
  6 37  1  0  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
  9 41  1  0  0  0  0
 10 42  1  0  0  0  0
 11 43  1  0  0  0  0
 11 44  1  0  0  0  0
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 15 48  1  0  0  0  0
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 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 24 52  1  1  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 29 56  1  0  0  0  0
 29 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])/C2=C([H])/C([H])([H])C([H])([H])\C([H])=C(\[H])/C(=C([H])\[C@]3(C([H])=C(C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@]33OC(=O)\C(C3=O)=C\1/OC\2([H])[H])C([H])([H])[H])/C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O4/c1-16-8-6-5-7-9-19-10-11-20(28-15-19)21-22(26)25(29-23(21)27)14-18(3)17(2)13-24(25,4)12-16/h6,8-13,18H,5,7,14-15H2,1-4H3/b8-6-,16-12-,19-9-,21-20?/t18-,24-,25+/m0/s1

> <INCHI_KEY>
HFHJEHWFJWGNEW-KZNHLIAISA-N

> <FORMULA>
C25H28O4

> <MOLECULAR_WEIGHT>
392.495

> <EXACT_MASS>
392.198759382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.15148012569356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,7S,10R,11Z,13Z,17Z)-7,8,10,12-tetramethyl-4,20-dioxatetracyclo[16.2.2.1^{2,5}.0^{5,10}]tricosa-1,8,11,13,17,21-hexaene-3,23-dione

> <ALOGPS_LOGP>
5.20

> <JCHEM_LOGP>
4.667503114999999

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.892385602877096

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
118.86429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,7S,10R,11Z,13Z,17Z)-7,8,10,12-tetramethyl-4,20-dioxatetracyclo[16.2.2.1^{2,5}.0^{5,10}]tricosa-1,8,11,13,17,21-hexaene-3,23-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
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   -2.0913   -1.0619   -2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  2  0
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 17 18  2  0
 18 19  1  0
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 22 21  1  1
 22 23  1  0
 23 24  1  0
 24 25  1  0
 22 26  1  0
 26 27  2  0
 17 28  1  0
 28 29  1  0
 24  2  1  0
 22  4  1  0
 29 14  1  0
 26 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  5 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
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 23 50  1  0
 23 51  1  0
 24 52  1  1
 25 53  1  0
 25 54  1  0
 25 55  1  0
 29 56  1  0
 29 57  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.030   0.901   0.641  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.681   0.339   0.293  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.587   0.690   0.884  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.157   0.222   0.654  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.902  -0.341   2.097  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.441   1.484   0.685  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.178   2.196  -0.229  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.196   3.687  -0.210  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.063   1.631  -1.146  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.248   1.050  -1.022  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.118   1.405   0.088  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.508   1.010   0.035  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.940  -0.326  -0.480  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.351  -1.406  -0.132  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.020  -2.727  -0.606  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.636  -2.940  -0.775  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.746  -2.235   0.058  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.423  -2.208   0.089  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.787  -2.620   0.870  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.862  -3.353   1.880  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.851  -1.989   0.194  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.246  -0.741  -0.350  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.288  -0.414  -1.398  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.661  -0.673  -0.804  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.754  -0.509  -1.787  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.045  -1.378  -1.023  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.086  -0.990  -2.198  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.377  -1.405   0.985  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.689  -1.242   1.278  0.00  0.00           C+0
HETATM   30  H   UNK     0      -5.741   0.082   0.734  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.936   1.537   1.547  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.334   1.532  -0.221  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.743   1.448   1.683  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.742  -0.912   2.430  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.837   0.539   2.816  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.097  -0.768   2.138  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.421   1.969   1.699  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.165   3.856  -0.712  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.528   4.326  -0.691  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.242   4.006   0.852  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.771   1.651  -2.245  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.636   0.294  -1.717  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.131   2.570   0.053  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.528   1.271   1.018  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.053   1.838  -0.550  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.972   1.181   1.064  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.822  -0.123  -1.157  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.508  -3.655  -0.903  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.520  -3.693  -1.616  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.091  -1.062  -2.284  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.309   0.657  -1.667  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.706  -1.669  -0.311  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.537   0.236  -2.571  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.716  -0.332  -1.265  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.880  -1.491  -2.328  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.904  -0.335   1.769  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.038  -2.071   1.908  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3   24                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3    5    6   22                                             
CONECT    5    4   34   35   36                                             
CONECT    6    4    7   37                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   38   39   40                                             
CONECT    9    7   10   41                                                  
CONECT   10    9   11   42                                                  
CONECT   11   10   12   43   44                                             
CONECT   12   11   13   45   46                                             
CONECT   13   12   14   47                                                  
CONECT   14   13   15   29                                                  
CONECT   15   14   16   48                                                  
CONECT   16   15   17   49                                                  
CONECT   17   16   18   28                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   26    4                                             
CONECT   23   22   24   50   51                                             
CONECT   24   23   25    2   52                                             
CONECT   25   24   53   54   55                                             
CONECT   26   22   27   18                                                  
CONECT   27   26                                                            
CONECT   28   17   29                                                       
CONECT   29   28   14   56   57                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   29                                                            
CONECT   57   29                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

RDKit          3D

57 60  0  0  0  0  0  0  0  0999 V2000
   -5.0299    0.9014    0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6812    0.3393    0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871    0.6902    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    0.2224    0.6543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9020   -0.3411    2.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408    1.4844    0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1780    2.1960   -0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1962    3.6865   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628    1.6309   -1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2481    1.0503   -1.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179    1.4049    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.0101    0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9397   -0.3264   -0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3505   -1.4062   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -2.7270   -0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6365   -2.9396   -0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7461   -2.2349    0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4229   -2.2085    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7866   -2.6200    0.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8623   -3.3528    1.8796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8510   -1.9890    0.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460   -0.7412   -0.3496 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2876   -0.4138   -1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607   -0.6726   -0.8040 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7537   -0.5089   -1.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451   -1.3782   -1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0860   -0.9903   -2.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768   -1.4047    0.9852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6891   -1.2423    1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7414    0.0821    0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9365    1.5368    1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3342    1.5316   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7428    1.4476    1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421   -0.9115    2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369    0.5388    2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0974   -0.7681    2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208    1.9694    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645    3.8558   -0.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5278    4.3257   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2422    4.0062    0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7705    1.6509   -2.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6356    0.2940   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1309    2.5702    0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5280    1.2714    1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0530    1.8381   -0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9722    1.1808    1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8219   -0.1225   -1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5076   -3.6551   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204   -3.6934   -1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913   -1.0619   -2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095    0.6566   -1.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060   -1.6691   -0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5374    0.2356   -2.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7160   -0.3320   -1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8804   -1.4908   -2.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038   -0.3353    1.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0379   -2.0709    1.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  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
 19 21  1  0
 22 21  1  1
 22 23  1  0
 23 24  1  0
 24 25  1  0
 22 26  1  0
 26 27  2  0
 17 28  1  0
 28 29  1  0
 24  2  1  0
 22  4  1  0
 29 14  1  0
 26 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  5 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 15 48  1  0
 16 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  1
 25 53  1  0
 25 54  1  0
 25 55  1  0
 29 56  1  0
 29 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₄

Average Mass

392.4950 Da

Monoisotopic Mass

392.19876 Da

IUPAC Name

(5S,7S,10R,11Z,13Z,17Z)-7,8,10,12-tetramethyl-4,20-dioxatetracyclo[16.2.2.1^{2,5}.0^{5,10}]tricosa-1,8,11,13,17,21-hexaene-3,23-dione

Traditional Name

(5S,7S,10R,11Z,13Z,17Z)-7,8,10,12-tetramethyl-4,20-dioxatetracyclo[16.2.2.1^{2,5}.0^{5,10}]tricosa-1,8,11,13,17,21-hexaene-3,23-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@]23OC(=O)\C(C2=O)=C2/OC\C(\C=C2)=C\CC\C=C/C(/C)=C\[C@@]3(C)C=C1C

InChI Identifier

InChI=1S/C25H28O4/c1-16-8-6-5-7-9-19-10-11-20(28-15-19)21-22(26)25(29-23(21)27)14-18(3)17(2)13-24(25,4)12-16/h6,8-13,18H,5,7,14-15H2,1-4H3/b8-6-,16-12-,19-9+,21-20-/t18-,24-,25+/m0/s1

InChI Key

HFHJEHWFJWGNEW-KZNHLIAISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Streptomyces platensis	NPAtlas	19883063

Chemical Taxonomy

Classification

Not classified

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	5.2	ALOGPS
logP	4.67	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	118.86 m³·mol⁻¹	ChemAxon
Polarizability	43.15 Å³	ChemAxon
Number of Rings	4	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

Not Available

References

General References

Kang M, Jones BD, Mandel AL, Hammons JC, DiPasquale AG, Rheingold AL, La Clair JJ, Burkart MD: Isolation, structure elucidation, and antitumor activity of spirohexenolides A and B. J Org Chem. 2009 Dec 4;74(23):9054-61. doi: 10.1021/jo901826d. [PubMed:19883063 ]

Showing NP-Card for Spirohexenolide B (NP0008840)

MOL for NP0008840 (Spirohexenolide B)

3D MOL for NP0008840 (Spirohexenolide B)

3D SDF for NP0008840 (Spirohexenolide B)

3D-SDF for NP0008840 (Spirohexenolide B)

PDB for NP0008840 (Spirohexenolide B)

3D PDB for NP0008840 (Spirohexenolide B)

SMILES for NP0008840 (Spirohexenolide B)

INCHI for NP0008840 (Spirohexenolide B)

Structure for NP0008840 (Spirohexenolide B)

3D Structure for NP0008840 (Spirohexenolide B)