NP-MRD: Showing NP-Card for 7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+ (NP0043023)

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Record Information

Version

1.0

Created at

2021-06-21 00:32:26 UTC

Updated at

2021-06-30 00:18:28 UTC

NP-MRD ID

NP0043023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+

Provided By

JEOL Database JEOL Logo

Description

CHEMBL3092692 belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. 7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+ is found in Salvia cavaleriei. It was first documented in 2013 (Zheng, H., et al.). Based on a literature review very few articles have been published on CHEMBL3092692.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102323D          

 67 70  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212102323D          

 67 70  0  0  0  0            999 V2000
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    1.4454    1.0938    3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    1.4019    0.5981 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2588    1.6151    0.1803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1671    3.0853    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    3.3854    0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8837    4.1763    0.2581 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2502    3.7339    0.7814 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6878    2.4825    0.0170 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0696    2.2751    0.2787 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7684   -0.6923   -0.8879 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.6065   -0.1975    0.5477 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2361   -1.8642   -3.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9986   -3.2506   -1.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7541   -0.6650    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7942   -1.1402    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
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 13  5  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0043023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]2([H])C([H])([H])C(=O)[C@]3([H])[C@@]1(C(=O)[C@]2([H])C([H])([H])OC([H])([H])C([H])([H])[H])[C@]([H])(O[H])C([H])([H])[C@]1([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])[C@@]31C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O7/c1-6-30-11-14-13-9-15(26)19-23(5)8-7-18(31-12(2)25)22(3,4)16(23)10-17(27)24(19,20(13)28)21(14)29/h13-14,16-20,27-28H,6-11H2,1-5H3/t13-,14+,16+,17+,18-,19-,20+,23+,24-/m0/s1

> <INCHI_KEY>
FGAPYAJNPFGUCX-KAMFQRNMSA-N

> <FORMULA>
C24H36O7

> <MOLECULAR_WEIGHT>
436.545

> <EXACT_MASS>
436.246103499

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.06428422553448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4S,6S,9R,10S,13S,14S,16R)-14-(ethoxymethyl)-2,16-dihydroxy-5,5,9-trimethyl-11,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-6-yl acetate

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.1750264946666664

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.709210347252103

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.795072412202899

> <JCHEM_PKA_STRONGEST_BASIC>
-3.053268890302621

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
112.15079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,6S,9R,10S,13S,14S,16R)-14-(ethoxymethyl)-2,16-dihydroxy-5,5,9-trimethyl-11,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 67 70  0  0  0  0  0  0  0  0999 V2000
    1.3622    7.6300    3.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746    6.1751    4.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7386    5.3949    3.1519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229    4.0075    3.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710    3.2406    2.2494 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8044    1.8103    2.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4454    1.0938    3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    1.4019    0.5981 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2588    1.6151    0.1803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1671    3.0853    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    3.3854    0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8837    4.1763    0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502    3.7339    0.7814 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6878    2.4825    0.0170 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0696    2.2751    0.2787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626    0.9640   -1.1981 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4725    1.7306   -2.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084    1.0404   -1.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2647    0.1731   -2.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8653   -1.2971   -2.3538 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4758   -1.8086   -1.1438 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2348   -2.7518    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4078   -2.3142   -2.2847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200   -1.4947   -2.2502 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3341   -1.2934   -3.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0555   -2.9796   -1.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2544   -0.5528   -1.1270 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7684   -0.6923   -0.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864   -0.0639    0.4437 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6065   -0.1975    0.5477 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3726    2.8122   -2.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2572   -3.1275   -0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0664   -0.3508   -4.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259   -1.3463   -3.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0127   -2.0795   -4.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6305   -3.6565   -2.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9986   -3.2506   -1.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3368   -3.1910   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2110   -0.9310   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0646   -1.7463   -0.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3561   -0.2655   -1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541   -0.6650    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7942   -1.1402    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
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 14 44  1  6
 12 41  1  0
 12 42  1  0
  5 39  1  1
 15 45  1  0
  4 37  1  0
  4 38  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 31 67  1  0
 26 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
  2 35  1  0
  2 36  1  0
  1 32  1  0
  1 33  1  0
  1 34  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       1.362   7.630   3.898  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.975   6.175   4.070  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.739   5.395   3.152  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.423   4.008   3.249  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.271   3.241   2.249  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.804   1.810   2.078  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.445   1.094   3.005  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.749   1.402   0.598  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.259   1.615   0.180  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.167   3.085   0.345  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.351   3.385   0.503  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.884   4.176   0.258  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.250   3.734   0.781  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.688   2.482   0.017  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.070   2.275   0.279  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.163   0.964  -1.198  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.473   1.731  -2.380  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.708   1.040  -1.363  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.265   0.173  -2.496  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.865  -1.297  -2.354  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.476  -1.809  -1.144  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.749  -2.278  -1.256  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.235  -2.752   0.079  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.408  -2.314  -2.285  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.320  -1.495  -2.250  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.334  -1.293  -3.632  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.056  -2.980  -1.868  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.254  -0.553  -1.127  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.768  -0.692  -0.888  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.186  -0.064   0.444  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.607  -0.198   0.548  0.00  0.00           O+0
HETATM   32  H   UNK     0       1.173   7.960   2.871  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.799   8.268   4.584  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.432   7.769   4.084  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.094   6.048   3.864  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.185   5.851   5.095  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.637   3.653   4.265  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.353   3.857   3.066  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.312   3.215   2.597  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.340   1.098   0.950  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.524   5.046   0.817  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.966   4.480  -0.791  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.971   4.551   0.662  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.592   2.611  -1.061  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.240   1.307   0.254  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.373   2.812  -2.253  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.531   1.508  -2.517  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.014   1.521  -3.333  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.020   2.075  -1.552  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.194   0.739  -0.425  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.950   0.560  -3.470  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.358   0.262  -2.476  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.236  -1.864  -3.218  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.257  -3.127  -0.020  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.598  -3.564   0.438  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.236  -1.921   0.789  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.066  -0.351  -4.106  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.426  -1.346  -3.575  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.013  -2.079  -4.326  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.631  -3.656  -2.511  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.999  -3.251  -1.988  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.337  -3.191  -0.831  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.211  -0.931  -0.201  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.065  -1.746  -0.855  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.356  -0.266  -1.707  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.754  -0.665   1.254  0.00  0.00           H+0
HETATM   67  H   UNK     0       3.794  -1.140   0.723  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    3    1   35   36                                             
CONECT    3    4    2                                                       
CONECT    4    5    3   37   38                                             
CONECT    5   13    6    4   39                                             
CONECT    6    8    5    7                                                  
CONECT    7    6                                                            
CONECT    8    6   30    9   14                                             
CONECT    9   40    8   10   16                                             
CONECT   10   11    9   12                                                  
CONECT   11   10                                                            
CONECT   12   13   10   41   42                                             
CONECT   13    5   43   14   12                                             
CONECT   14   15    8   13   44                                             
CONECT   15   14   45                                                       
CONECT   16   17   18   28    9                                             
CONECT   17   16   46   47   48                                             
CONECT   18   16   19   49   50                                             
CONECT   19   20   18   51   52                                             
CONECT   20   19   21   25   53                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   54   55   56                                             
CONECT   24   22                                                            
CONECT   25   28   26   27   20                                             
CONECT   26   25   57   58   59                                             
CONECT   27   25   60   61   62                                             
CONECT   28   29   25   16   63                                             
CONECT   29   28   30   64   65                                             
CONECT   30   29    8   31   66                                             
CONECT   31   30   67                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    2                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    9                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   27                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   29                                                            
CONECT   65   29                                                            
CONECT   66   30                                                            
CONECT   67   31                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  140    0
END

RDKit          3D

67 70  0  0  0  0  0  0  0  0999 V2000
    1.3622    7.6300    3.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746    6.1751    4.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7386    5.3949    3.1519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229    4.0075    3.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710    3.2406    2.2494 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8044    1.8103    2.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4454    1.0938    3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    1.4019    0.5981 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2588    1.6151    0.1803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1671    3.0853    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    3.3854    0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8837    4.1763    0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502    3.7339    0.7814 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6878    2.4825    0.0170 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0696    2.2751    0.2787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626    0.9640   -1.1981 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4725    1.7306   -2.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084    1.0404   -1.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2647    0.1731   -2.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8653   -1.2971   -2.3538 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4758   -1.8086   -1.1438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7486   -2.2782   -1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2348   -2.7518    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4078   -2.3142   -2.2847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200   -1.4947   -2.2502 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3341   -1.2934   -3.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0555   -2.9796   -1.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2544   -0.5528   -1.1270 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7684   -0.6923   -0.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864   -0.0639    0.4437 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6065   -0.1975    0.5477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726    7.9602    2.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7985    8.2682    4.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4323    7.7687    4.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    6.0477    3.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851    5.8513    5.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6371    3.6527    4.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3526    3.8567    3.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116    3.2153    2.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3398    1.0982    0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238    5.0465    0.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656    4.4802   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714    4.5512    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5916    2.6113   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2404    1.3070    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726    2.8122   -2.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5312    1.5082   -2.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0141    1.5214   -3.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0200    2.0748   -1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1938    0.7394   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9496    0.5598   -3.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3578    0.2623   -2.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361   -1.8642   -3.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2572   -3.1275   -0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5981   -3.5642    0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2360   -1.9206    0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0664   -0.3508   -4.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259   -1.3463   -3.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0127   -2.0795   -4.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6305   -3.6565   -2.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9986   -3.2506   -1.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3368   -3.1910   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2110   -0.9310   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0646   -1.7463   -0.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3561   -0.2655   -1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541   -0.6650    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7942   -1.1402    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 40  1  1
 28 29  1  0
 13  5  1  0
 29 30  1  0
  8  6  1  1
 30  8  1  0
 14 15  1  0
  5  6  1  0
  9  8  1  0
  5  4  1  0
 25 28  1  0
 16 17  1  6
 16 18  1  0
 30 31  1  0
 16 28  1  0
 25 26  1  6
 25 27  1  0
 19 20  1  0
  6  7  2  0
 19 18  1  0
 10 11  2  0
  9 10  1  0
 13 43  1  1
  8 14  1  0
 20 21  1  0
 14 13  1  0
 21 22  1  0
 13 12  1  0
 22 23  1  0
 12 10  1  0
 22 24  2  0
 20 25  1  0
  4  3  1  0
 28 63  1  1
  3  2  1  0
 16  9  1  0
  2  1  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  6
 18 49  1  0
 18 50  1  0
 29 64  1  0
 29 65  1  0
 30 66  1  1
 14 44  1  6
 12 41  1  0
 12 42  1  0
  5 39  1  1
 15 45  1  0
  4 37  1  0
  4 38  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 31 67  1  0
 26 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
  2 35  1  0
  2 36  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₆O₇

Average Mass

436.5450 Da

Monoisotopic Mass

436.24610 Da

IUPAC Name

(1R,2R,4S,6S,9R,10S,13S,14S,16R)-14-(ethoxymethyl)-2,16-dihydroxy-5,5,9-trimethyl-11,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-6-yl acetate

Traditional Name

(1R,2R,4S,6S,9R,10S,13S,14S,16R)-14-(ethoxymethyl)-2,16-dihydroxy-5,5,9-trimethyl-11,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-6-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@@]2([H])C([H])([H])C(=O)[C@]3([H])[C@@]1(C(=O)[C@]2([H])C([H])([H])OC([H])([H])C([H])([H])[H])[C@]([H])(O[H])C([H])([H])[C@]1([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])[C@@]31C([H])([H])[H]

InChI Identifier

InChI=1S/C24H36O7/c1-6-30-11-14-13-9-15(26)19-23(5)8-7-18(31-12(2)25)22(3,4)16(23)10-17(27)24(19,20(13)28)21(14)29/h13-14,16-20,27-28H,6-11H2,1-5H3/t13-,14+,16+,17+,18-,19-,20+,23+,24-/m0/s1

InChI Key

FGAPYAJNPFGUCX-KAMFQRNMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Salvia cavaleriei	JEOL database	Zheng, H., et al, J. Nat. Prod. 76, 2253 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Cyclic alcohol
Carboxylic acid ester
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.74	ALOGPS
logP	1.18	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.8	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	112.15 m³·mol⁻¹	ChemAxon
Polarizability	47.06 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31129902

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76324560

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zheng, H., et al. (2013). Zheng, H., et al, J. Nat. Prod. 76, 2253 (2013). J. Nat. Prod..

Showing NP-Card for 7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+ (NP0043023)

MOL for NP0043023 (7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+)

3D MOL for NP0043023 (7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+)

3D SDF for NP0043023 (7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+)

3D-SDF for NP0043023 (7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+)

PDB for NP0043023 (7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+)

3D PDB for NP0043023 (7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+)

SMILES for NP0043023 (7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+)

INCHI for NP0043023 (7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+)

Structure for NP0043023 (7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+)

3D Structure for NP0043023 (7alpha,14beta-dihydroxy-17beta-ethyoxymethyl-3beta-acetoxy-ent-kaur-11,15+)