NP-MRD: Showing NP-Card for (3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+ (NP0042098)

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Record Information

Version

2.0

Created at

2021-06-20 23:50:36 UTC

Updated at

2021-06-30 00:16:59 UTC

NP-MRD ID

NP0042098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+

Provided By

JEOL Database JEOL Logo

Description

CHEMBL4165646 belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. (3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+ is found in Clerodendrum trichotomum. (3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+ was first documented in 2013 (Wang, W.-X., et al.). Based on a literature review very few articles have been published on CHEMBL4165646.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101503D          

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     RDKit          3D

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  Mrv1652306212101503D          

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 16 17  1  0  0  0  0
  2  1  1  0  0  0  0
 13  8  1  0  0  0  0
 17 18  1  6  0  0  0
 22 23  2  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  0  0  0  0
 23 47  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
 21 44  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 10 33  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  2 29  1  1  0  0  0
  6 32  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 18 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2O[C@@]([H])(C([H])([H])[H])C([H])([H])C2=C(O[H])C2=C1[C@@]1(C(=C([H])C2=O)[C@]2(O[C@@]2(C([H])([H])[H])C([H])([H])C1([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O5/c1-9-7-10-15(22)13-11(21)8-12-18(2,14(13)16(23)17(10)24-9)5-6-19(3)20(12,4)25-19/h8-9,22-23H,5-7H2,1-4H3/t9-,18-,19-,20+/m0/s1

> <INCHI_KEY>
PKEXFWWHNQGVIY-QKMKBPDTSA-N

> <FORMULA>
C20H22O5

> <MOLECULAR_WEIGHT>
342.391

> <EXACT_MASS>
342.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.06006711427816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5S,7R,15S)-12,18-dihydroxy-2,5,7,15-tetramethyl-6,16-dioxapentacyclo[9.7.0.0^{2,8}.0^{5,7}.0^{13,17}]octadeca-1(11),8,12,17-tetraen-10-one

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
3.293590930333333

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.060243546129813

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.200805293465244

> <JCHEM_PKA_STRONGEST_BASIC>
-4.194332171953724

> <JCHEM_POLAR_SURFACE_AREA>
79.28999999999999

> <JCHEM_REFRACTIVITY>
92.9222

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7R,15S)-12,18-dihydroxy-2,5,7,15-tetramethyl-6,16-dioxapentacyclo[9.7.0.0^{2,8}.0^{5,7}.0^{13,17}]octadeca-1(11),8,12,17-tetraen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 47 51  0  0  0  0  0  0  0  0999 V2000
   -3.8828   -2.4856    4.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -1.4170    3.7287 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4506   -1.7539    4.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761   -1.2524    3.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788   -1.0723    2.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678   -1.3435    3.9899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -0.6334    1.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3218   -0.3806    0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549   -0.6136    0.7652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746   -0.4669   -0.2339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207   -1.0253    2.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8427   -1.2736    2.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8847    0.0649   -0.8201 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6225   -1.1080   -1.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1887    1.3872   -1.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5591    1.8714   -2.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0445    1.9531   -2.8485 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5336    3.1765   -3.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5766    0.7300   -3.3766 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987    1.0455   -2.0418 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4822    1.3614   -2.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092    0.3750   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1596    0.1068    0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6315   -0.4531    1.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3973   -0.7334    2.4356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9388   -2.6207    5.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8759   -2.2116    3.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290   -3.4453    3.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -0.4512    4.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968   -2.8316    4.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2191   -1.2394    5.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -1.2076    3.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386   -0.7127    0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0483   -0.9566   -2.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0515   -2.0418   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4456   -1.2849   -1.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404    2.1747   -0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014    1.3122   -1.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1053    2.8599   -2.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1099    1.2209   -3.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8336    3.4646   -4.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5060    3.0330   -4.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6158    4.0122   -2.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680    0.4660   -1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    1.7100   -2.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7028    2.1388   -1.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2234    0.3093    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  7  5  1  0
  4  5  2  0
 11  9  2  0
 23 24  1  0
 20 21  1  6
 13 15  1  0
 24 25  2  0
 24  7  1  0
  9 10  1  0
 11  4  1  0
 15 16  1  0
  8  7  2  0
 22 20  1  0
 20 17  1  0
 13 22  1  0
  4  3  1  0
  3  2  1  0
  2 12  1  0
 12 11  1  0
 13 14  1  6
  5  6  1  0
 16 17  1  0
  2  1  1  0
 13  8  1  0
 17 18  1  6
 22 23  2  0
 17 19  1  0
 20 19  1  0
 23 47  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 10 33  1  0
  3 30  1  0
  3 31  1  0
  2 29  1  1
  6 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 18 41  1  0
 18 42  1  0
 18 43  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      -3.883  -2.486   4.099  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.867  -1.417   3.729  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.451  -1.754   4.220  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.676  -1.252   3.065  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.679  -1.072   2.906  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.468  -1.343   3.990  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.179  -0.633   1.656  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.322  -0.381   0.556  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.055  -0.614   0.765  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.975  -0.467  -0.234  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.521  -1.025   2.005  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.843  -1.274   2.281  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.885   0.065  -0.820  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.623  -1.108  -1.799  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.189   1.387  -1.246  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.559   1.871  -2.642  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.045   1.953  -2.849  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.534   3.176  -3.567  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.577   0.730  -3.377  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.999   1.046  -2.042  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.482   1.361  -2.027  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.409   0.375  -0.813  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.160   0.107   0.271  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.632  -0.453   1.517  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.397  -0.733   2.436  0.00  0.00           O+0
HETATM   26  H   UNK     0      -3.939  -2.621   5.183  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.876  -2.212   3.727  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.629  -3.445   3.635  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.190  -0.451   4.141  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.297  -2.832   4.340  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.219  -1.239   5.157  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.407  -1.208   3.726  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.839  -0.713   0.153  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.048  -0.957  -2.792  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.052  -2.042  -1.413  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.446  -1.285  -1.958  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.440   2.175  -0.520  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.901   1.312  -1.225  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.105   2.860  -2.787  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.110   1.221  -3.402  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.834   3.465  -4.359  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.506   3.033  -4.045  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.616   4.012  -2.865  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.068   0.466  -1.792  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.848   1.710  -2.998  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.703   2.139  -1.288  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.223   0.309   0.315  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3   12    1   29                                             
CONECT    3    4    2   30   31                                             
CONECT    4    5   11    3                                                  
CONECT    5    7    4    6                                                  
CONECT    6    5   32                                                       
CONECT    7    5   24    8                                                  
CONECT    8    9    7   13                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9   33                                                       
CONECT   11    9    4   12                                                  
CONECT   12    2   11                                                       
CONECT   13   15   22   14    8                                             
CONECT   14   13   34   35   36                                             
CONECT   15   13   16   37   38                                             
CONECT   16   15   17   39   40                                             
CONECT   17   20   16   18   19                                             
CONECT   18   17   41   42   43                                             
CONECT   19   17   20                                                       
CONECT   20   21   22   17   19                                             
CONECT   21   20   44   45   46                                             
CONECT   22   20   13   23                                                  
CONECT   23   24   22   47                                                  
CONECT   24   23   25    7                                                  
CONECT   25   24                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    6                                                            
CONECT   33   10                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   16                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   18                                                            
CONECT   44   21                                                            
CONECT   45   21                                                            
CONECT   46   21                                                            
CONECT   47   23                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  102    0
END

RDKit          3D

47 51  0  0  0  0  0  0  0  0999 V2000
   -3.8828   -2.4856    4.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -1.4170    3.7287 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4506   -1.7539    4.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761   -1.2524    3.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788   -1.0723    2.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678   -1.3435    3.9899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -0.6334    1.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3218   -0.3806    0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549   -0.6136    0.7652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746   -0.4669   -0.2339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207   -1.0253    2.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8427   -1.2736    2.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8847    0.0649   -0.8201 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6225   -1.1080   -1.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1887    1.3872   -1.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5591    1.8714   -2.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0445    1.9531   -2.8485 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5336    3.1765   -3.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5766    0.7300   -3.3766 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987    1.0455   -2.0418 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4822    1.3614   -2.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092    0.3750   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1596    0.1068    0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6315   -0.4531    1.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3973   -0.7334    2.4356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9388   -2.6207    5.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8759   -2.2116    3.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290   -3.4453    3.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -0.4512    4.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968   -2.8316    4.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2191   -1.2394    5.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -1.2076    3.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386   -0.7127    0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0483   -0.9566   -2.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0515   -2.0418   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4456   -1.2849   -1.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404    2.1747   -0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014    1.3122   -1.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1053    2.8599   -2.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1099    1.2209   -3.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8336    3.4646   -4.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5060    3.0330   -4.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6158    4.0122   -2.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680    0.4660   -1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    1.7100   -2.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7028    2.1388   -1.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2234    0.3093    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  7  5  1  0
  4  5  2  0
 11  9  2  0
 23 24  1  0
 20 21  1  6
 13 15  1  0
 24 25  2  0
 24  7  1  0
  9 10  1  0
 11  4  1  0
 15 16  1  0
  8  7  2  0
 22 20  1  0
 20 17  1  0
 13 22  1  0
  4  3  1  0
  3  2  1  0
  2 12  1  0
 12 11  1  0
 13 14  1  6
  5  6  1  0
 16 17  1  0
  2  1  1  0
 13  8  1  0
 17 18  1  6
 22 23  2  0
 17 19  1  0
 20 19  1  0
 23 47  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 10 33  1  0
  3 30  1  0
  3 31  1  0
  2 29  1  1
  6 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₅

Average Mass

342.3910 Da

Monoisotopic Mass

342.14672 Da

IUPAC Name

(2S,5S,7R,15S)-12,18-dihydroxy-2,5,7,15-tetramethyl-6,16-dioxapentacyclo[9.7.0.0^{2,8}.0^{5,7}.0^{13,17}]octadeca-1(11),8,12,17-tetraen-10-one

Traditional Name

(2S,5S,7R,15S)-12,18-dihydroxy-2,5,7,15-tetramethyl-6,16-dioxapentacyclo[9.7.0.0^{2,8}.0^{5,7}.0^{13,17}]octadeca-1(11),8,12,17-tetraen-10-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C2O[C@@]([H])(C([H])([H])[H])C([H])([H])C2=C(O[H])C2=C1[C@@]1(C(=C([H])C2=O)[C@]2(O[C@@]2(C([H])([H])[H])C([H])([H])C1([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H22O5/c1-9-7-10-15(22)13-11(21)8-12-18(2,14(13)16(23)17(10)24-9)5-6-19(3)20(12,4)25-19/h8-9,22-23H,5-7H2,1-4H3/t9-,18-,19-,20+/m0/s1

InChI Key

PKEXFWWHNQGVIY-QKMKBPDTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Clerodendrum trichotomum	JEOL database	Wang, W.-X., et al, Phytochemistry 89, 89 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Naphthofuran
Naphthalene
Coumaran
Aryl ketone
Alkyl aryl ether
Oxepane
Phenol
Vinylogous acid
Ketone
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	3.25	ALOGPS
logP	3.29	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.2	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	92.92 m³·mol⁻¹	ChemAxon
Polarizability	37.06 Å³	ChemAxon
Number of Rings	5	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

90633679

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71682092

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang, W.-X., et al. (2013). Wang, W.-X., et al, Phytochemistry 89, 89 (2013) . Phytochem..

Showing NP-Card for (3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+ (NP0042098)

MOL for NP0042098 ((3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+)

3D MOL for NP0042098 ((3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+)

3D SDF for NP0042098 ((3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+)

3D-SDF for NP0042098 ((3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+)

PDB for NP0042098 ((3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+)

3D PDB for NP0042098 ((3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+)

SMILES for NP0042098 ((3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+)

INCHI for NP0042098 ((3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+)

Structure for NP0042098 ((3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+)

3D Structure for NP0042098 ((3S,4R,10R,16S)-3,4:12,16-diepoxy-11,14-dihydroxy-17(15-16),18(4-3)-diabe+)