NP-MRD: Showing NP-Card for cladieunicellin E (NP0040134)

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Record Information

Version

2.0

Created at

2021-06-20 22:22:59 UTC

Updated at

2021-06-30 00:13:52 UTC

NP-MRD ID

NP0040134

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cladieunicellin E

Provided By

JEOL Database JEOL Logo

Description

(1S,2R,9R,10R)-4alpha,8beta-Dihydroxy-4,8,14-trimethyl-11beta-isopropyl-14beta-acetoxy-2,9-epoxybicyclo[8.4.0]Tetradecane-5-one belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton. cladieunicellin E is found in Cladiella sp. cladieunicellin E was first documented in 2011 (Chen, Y.-H., et al.). Based on a literature review very few articles have been published on (1S,2R,9R,10R)-4alpha,8beta-Dihydroxy-4,8,14-trimethyl-11beta-isopropyl-14beta-acetoxy-2,9-epoxybicyclo[8.4.0]Tetradecane-5-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100233D          

 64 66  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212100233D          

 64 66  0  0  0  0            999 V2000
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    2.8090   -1.9139   -1.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -3.3202   -2.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4949   -3.6292    0.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0259   -4.4997    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0325   -4.3148   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3361   -1.6149    0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817    0.2237   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6381    5.9020    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8631    4.7111    1.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4616    4.4560   -0.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076    3.5599    3.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9445    1.6429    2.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2952    1.3932    4.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270   -1.0740    3.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -1.8859    2.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792   -0.9397    4.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4041    0.2803    3.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9786   -0.1712    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 13  1  0  0  0  0
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 28 15  1  0  0  0  0
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 15 14  1  0  0  0  0
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 14  5  1  0  0  0  0
 24 26  1  6  0  0  0
 15 16  1  0  0  0  0
 27 64  1  1  0  0  0
 14 13  1  0  0  0  0
 15 49  1  6  0  0  0
 16 17  1  0  0  0  0
 24 25  1  0  0  0  0
  5  6  1  0  0  0  0
 17 20  1  0  0  0  0
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  7  8  1  0  0  0  0
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 27 24  1  0  0  0  0
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  7  5  1  0  0  0  0
  5  4  1  1  0  0  0
 24 23  1  0  0  0  0
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  8  9  1  0  0  0  0
  2  1  1  0  0  0  0
 23 22  1  0  0  0  0
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  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040134

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1(C(=O)C([H])([H])C([H])([H])[C@](O[H])(C([H])([H])[H])[C@]2([H])O[C@]([H])(C1([H])[H])[C@]1([H])[C@@]2([H])[C@]([H])(C([H])([H])C([H])([H])[C@]1(OC(=O)C([H])([H])[H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O6/c1-12(2)14-7-10-22(6,28-13(3)23)18-15-11-21(5,26)16(24)8-9-20(4,25)19(27-15)17(14)18/h12,14-15,17-19,25-26H,7-11H2,1-6H3/t14-,15-,17-,18-,19-,20-,21+,22-/m1/s1

> <INCHI_KEY>
XTZRJSQVKAGUBF-BIQOJAMWSA-N

> <FORMULA>
C22H36O6

> <MOLECULAR_WEIGHT>
396.524

> <EXACT_MASS>
396.251188879

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
43.05407392563116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3R,6R,7R,8R,9R,13S)-9,13-dihydroxy-3,9,13-trimethyl-12-oxo-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-3-yl acetate

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.8998186800000008

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.0833286004655

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.127231298749354

> <JCHEM_PKA_STRONGEST_BASIC>
-3.223158002421844

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
104.04349999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,6R,7R,8R,9R,13S)-9,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-12-oxo-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
   -5.0929   -2.7694   -1.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820   -1.4031   -1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0783   -2.5063   -0.6686 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2647   -2.8256   -1.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3449   -3.8054   -0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263   -0.7975   -0.2240 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8666    0.1696   -0.8233 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.8716    4.0070    1.3807 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1393    1.5475    2.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9786   -0.1712    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 22  1  0
  9 13  1  0
 17 18  1  0
 13 27  1  0
 20 21  2  0
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  9 10  1  0
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 23 22  1  0
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 19 55  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.093  -2.769  -1.145  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.482  -1.403  -1.220  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.966  -0.409  -0.701  0.00  0.00           O+0
HETATM    4  O   UNK     0      -3.333  -1.460  -1.942  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.503  -0.274  -2.159  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.327   0.818  -2.859  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.417  -0.747  -3.143  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.559  -1.859  -2.546  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.164  -1.391  -1.276  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.078  -2.506  -0.669  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.265  -2.826  -1.587  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.345  -3.805  -0.319  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.826  -0.798  -0.224  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.867   0.170  -0.823  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.139   1.522  -0.810  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.021   2.680  -0.310  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.234   3.901   0.191  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.194   5.021   0.602  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.462   4.414  -0.904  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.299   3.603   1.393  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.872   4.007   1.381  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.852   2.870   2.603  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.139   1.548   2.929  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.656   0.275   2.197  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.260  -0.975   3.005  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.085   0.317   2.183  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.069   0.124   0.754  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.025   1.385   0.080  0.00  0.00           O+0
HETATM   29  H   UNK     0      -4.400  -3.458  -0.654  0.00  0.00           H+0
HETATM   30  H   UNK     0      -6.014  -2.723  -0.556  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.339  -3.121  -2.150  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.053   1.280  -2.184  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.691   1.618  -3.253  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.899   0.397  -3.693  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.775   0.087  -3.449  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.888  -1.140  -4.053  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.168  -2.170  -3.304  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.187  -2.732  -2.337  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.833  -0.575  -1.588  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.511  -2.128   0.265  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.809  -1.914  -1.854  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.947  -3.320  -2.510  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.970  -3.495  -1.082  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.495  -3.629   0.359  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.026  -4.500   0.187  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.033  -4.315  -1.210  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.336  -1.615   0.294  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.682   0.224  -0.096  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.722   1.773  -1.790  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.679   2.983  -1.133  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.680   2.329   0.491  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.803   5.347  -0.248  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.638   5.902   0.945  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.863   4.711   1.411  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.462   4.456  -0.577  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.708   3.560   3.445  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.934   2.744   2.523  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.945   1.643   2.790  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.295   1.393   4.006  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.827  -1.074   3.087  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.659  -1.886   2.544  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.679  -0.940   4.017  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.404   0.280   3.101  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.979  -0.171   0.867  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5   14    6    7    4                                             
CONECT    6    5   32   33   34                                             
CONECT    7    8    5   35   36                                             
CONECT    8    7    9   37   38                                             
CONECT    9   13   10    8   39                                             
CONECT   10    9   11   12   40                                             
CONECT   11   10   41   42   43                                             
CONECT   12   10   44   45   46                                             
CONECT   13    9   27   47   14                                             
CONECT   14   15   48    5   13                                             
CONECT   15   28   14   16   49                                             
CONECT   16   15   17   50   51                                             
CONECT   17   18   16   20   19                                             
CONECT   18   17   52   53   54                                             
CONECT   19   17   55                                                       
CONECT   20   22   21   17                                                  
CONECT   21   20                                                            
CONECT   22   20   23   56   57                                             
CONECT   23   24   22   58   59                                             
CONECT   24   26   25   27   23                                             
CONECT   25   24   60   61   62                                             
CONECT   26   24   63                                                       
CONECT   27   13   28   64   24                                             
CONECT   28   27   15                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   18                                                            
CONECT   53   18                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   23                                                            
CONECT   59   23                                                            
CONECT   60   25                                                            
CONECT   61   25                                                            
CONECT   62   25                                                            
CONECT   63   26                                                            
CONECT   64   27                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  132    0
END

RDKit          3D

64 66  0  0  0  0  0  0  0  0999 V2000
   -5.0929   -2.7694   -1.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820   -1.4031   -1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9659   -0.4089   -0.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3327   -1.4597   -1.9425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026   -0.2737   -2.1593 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3267    0.8183   -2.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4170   -0.7474   -3.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5594   -1.8590   -2.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1644   -1.3910   -1.2764 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0783   -2.5063   -0.6686 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2647   -2.8256   -1.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3449   -3.8054   -0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263   -0.7975   -0.2240 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8666    0.1696   -0.8233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1395    1.5221   -0.8097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0208    2.6797   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2342    3.9014    0.1912 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1936    5.0206    0.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622    4.4135   -0.9044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2985    3.6026    1.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8716    4.0070    1.3807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8523    2.8701    2.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1393    1.5475    2.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6560    0.2754    2.1974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2603   -0.9753    3.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847    0.3166    2.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0691    0.1243    0.7543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0254    1.3851    0.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4004   -3.4580   -0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0136   -2.7233   -0.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3389   -3.1212   -2.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0532    1.2796   -2.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    1.6179   -3.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8987    0.3970   -3.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7749    0.0871   -3.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8877   -1.1404   -4.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1676   -2.1698   -3.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865   -2.7323   -2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8334   -0.5748   -1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111   -2.1284    0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090   -1.9139   -1.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -3.3202   -2.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -3.4950   -1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4949   -3.6292    0.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0259   -4.4997    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0325   -4.3148   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3361   -1.6149    0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817    0.2237   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7219    1.7730   -1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6793    2.9832   -1.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6798    2.3291    0.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8034    5.3468   -0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381    5.9020    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8631    4.7111    1.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4616    4.4560   -0.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076    3.5599    3.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9339    2.7437    2.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445    1.6429    2.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2952    1.3932    4.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270   -1.0740    3.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -1.8859    2.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792   -0.9397    4.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4041    0.2803    3.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9786   -0.1712    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 22  1  0
  9 13  1  0
 17 18  1  0
 13 27  1  0
 20 21  2  0
 27 28  1  0
  9 10  1  0
 28 15  1  0
 13 47  1  1
 15 14  1  0
 14 48  1  1
 14  5  1  0
 24 26  1  6
 15 16  1  0
 27 64  1  1
 14 13  1  0
 15 49  1  6
 16 17  1  0
 24 25  1  0
  5  6  1  0
 17 20  1  0
 10 11  1  0
  7  8  1  0
 10 12  1  0
 27 24  1  0
 17 19  1  6
  7  5  1  0
  5  4  1  1
 24 23  1  0
  4  2  1  0
  8  9  1  0
  2  1  1  0
 23 22  1  0
  2  3  2  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  6
 16 50  1  0
 16 51  1  0
 23 58  1  0
 23 59  1  0
 22 56  1  0
 22 57  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 10 40  1  1
 26 63  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 12 46  1  0
 19 55  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(1S,2R,9R,10R)-4a,8b-Dihydroxy-4,8,14-trimethyl-11b-isopropyl-14b-acetoxy-2,9-epoxybicyclo[8.4.0]tetradecane-5-one	Generator
(1S,2R,9R,10R)-4Α,8β-dihydroxy-4,8,14-trimethyl-11β-isopropyl-14β-acetoxy-2,9-epoxybicyclo[8.4.0]tetradecane-5-one	Generator

Chemical Formula

C₂₂H₃₆O₆

Average Mass

396.5240 Da

Monoisotopic Mass

396.25119 Da

IUPAC Name

(1R,2S,3R,6R,7R,8R,9R,13S)-9,13-dihydroxy-3,9,13-trimethyl-12-oxo-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-3-yl acetate

Traditional Name

(1R,2S,3R,6R,7R,8R,9R,13S)-9,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-12-oxo-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-3-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1(C(=O)C([H])([H])C([H])([H])[C@](O[H])(C([H])([H])[H])[C@]2([H])O[C@]([H])(C1([H])[H])[C@]1([H])[C@@]2([H])[C@]([H])(C([H])([H])C([H])([H])[C@]1(OC(=O)C([H])([H])[H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H36O6/c1-12(2)14-7-10-22(6,28-13(3)23)18-15-11-21(5,26)16(24)8-9-20(4,25)19(27-15)17(14)18/h12,14-15,17-19,25-26H,7-11H2,1-6H3/t14-,15-,17-,18-,19-,20-,21+,22-/m1/s1

InChI Key

XTZRJSQVKAGUBF-BIQOJAMWSA-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
Cladiella sp.	JEOL database	Chen, Y.-H., et al, Chem. Pharm. Bull. 59, 353 (2011).

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Eunicellane and asbestinane diterpenoids

Alternative Parents

Substituents

Cladiellane diterpenoid
Eunicellane-type diterpenoid
Acyloin
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.01	ALOGPS
logP	1.9	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.13	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	104.04 m³·mol⁻¹	ChemAxon
Polarizability	43.05 Å³	ChemAxon
Number of Rings	3	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

27025447

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51039971

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen, Y.-H., et al. (2011). Chen, Y.-H., et al, Chem. Pharm. Bull. 59, 353 (2011).. Chem. Pharm. Bull..

Showing NP-Card for cladieunicellin E (NP0040134)

MOL for NP0040134 (cladieunicellin E)

3D MOL for NP0040134 (cladieunicellin E)

3D SDF for NP0040134 (cladieunicellin E)

3D-SDF for NP0040134 (cladieunicellin E)

PDB for NP0040134 (cladieunicellin E)

3D PDB for NP0040134 (cladieunicellin E)

SMILES for NP0040134 (cladieunicellin E)

INCHI for NP0040134 (cladieunicellin E)

Structure for NP0040134 (cladieunicellin E)

3D Structure for NP0040134 (cladieunicellin E)