NP-MRD: Showing NP-Card for (1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0151995)

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Record Information

Version

2.0

Created at

2022-09-02 08:23:46 UTC

Updated at

2022-09-02 08:23:46 UTC

NP-MRD ID

NP0151995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate

Description

(1S,2S,3aR,4R,5R,11R,13R,13aR)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate belongs to the class of organic compounds known as jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton. (1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate is found in Euphorbia guyoniana and Euphorbia hyberna. Based on a literature review very few articles have been published on (1S,2S,3aR,4R,5R,11R,13R,13aR)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210232D          

 43 45  0  0  1  0            999 V2000
    4.1024    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3063    0.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1312    0.0965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3544    0.8907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1538    1.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3769    1.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7301    0.5043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8407   -0.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2445   -1.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0439   -0.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2345   -1.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5073   -2.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0487   -1.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5151   -2.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0940   -2.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2691   -2.9723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0459   -3.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597   -2.5511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9693   -3.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732   -3.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2338    1.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575    1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0332    1.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
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  2 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  END

     RDKit          3D

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   -2.6929    2.2298   -2.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8332   -0.5466   -0.8717 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022210232D          

 43 45  0  0  1  0            999 V2000
    4.1024    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3063    0.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1312    0.0965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3544    0.8907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1538    1.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3769    1.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7301    0.5043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8407   -0.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2445   -1.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0439   -0.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2345   -1.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5073   -2.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0487   -1.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5151   -2.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0940   -2.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2691   -2.9723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0459   -3.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597   -2.5511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9693   -3.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732   -3.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9674   -4.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5828   -4.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558   -1.8317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8509   -2.5983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3682   -2.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913   -1.4039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0664   -1.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3843   -0.7424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1389    0.0452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340    0.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -0.3799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886    1.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2837    1.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383    1.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5977    2.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4026    2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6480    1.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658   -1.0068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5869   -0.2974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0106    0.2930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338    1.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575    1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0332    1.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 38 28  1  6  0  0  0
 23 38  1  0  0  0  0
 38 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0151995

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O10/c1-18-14-15-32(7,8)26(37)16-25(40-21(4)34)20(3)29(41-22(5)35)27-28(43-31(38)24-12-10-9-11-13-24)19(2)17-33(27,39)30(18)42-23(6)36/h9-15,18-19,25,27-30,39H,3,16-17H2,1-2,4-8H3/b15-14+/t18-,19+,25-,27-,28+,29+,30-,33-/m1/s1

> <INCHI_KEY>
QPKPYRGCZAZZJU-STMFRTFUSA-N

> <FORMULA>
C33H42O10

> <MOLECULAR_WEIGHT>
598.689

> <EXACT_MASS>
598.277797552

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
62.92773685948314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3aR,4R,5R,11R,13R,13aR)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
4.2336067260000005

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.086422267604593

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.40035474749294

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4984809093559956

> <JCHEM_POLAR_SURFACE_AREA>
142.50000000000003

> <JCHEM_REFRACTIVITY>
155.54079999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3aR,4R,5R,11R,13R,13aR)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,4H,5H,10H,11H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       7.658   1.691   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.038   0.199   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.578   0.180   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.995   1.663   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.487   2.043   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.904   3.526   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.563   0.941   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.903  -0.606   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.656  -1.949   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.149  -1.568   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.638  -3.489   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.147  -4.942   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.158  -3.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.295  -4.243   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.509  -5.567   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.969  -5.548   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.552  -7.031   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.645  -4.762   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.543  -5.838   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.923  -7.330   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.406  -7.747   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.821  -8.406   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.891  -3.419   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.322  -4.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.421  -3.877   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.531  -2.621   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.991  -2.602   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.451  -1.386   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.993   0.084   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.490   0.423   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.446  -0.709   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.032   1.893   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.530   2.231   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.072   3.702   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.116   4.834   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.618   4.495   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.076   3.025   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.909  -1.879   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.696  -0.555   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.620   0.547   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.036   2.030   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.961   3.132   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       7.529   2.410   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   25   38                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   38                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   28   23   39                                                  
CONECT   39   38    2   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,3AR,4R,5R,11R,13R,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3ah,4H,5H,8H,9H,10H,11H,12H,13H,13ah-cyclopenta[12]annulen-1-yl benzoic acid	Generator

Chemical Formula

C₃₃H₄₂O₁₀

Average Mass

598.6890 Da

Monoisotopic Mass

598.27780 Da

IUPAC Name

(1S,2S,3aR,4R,5R,11R,13R,13aR)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate

Traditional Name

(1S,2S,3aR,4R,5R,11R,13R,13aR)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,4H,5H,10H,11H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C33H42O10/c1-18-14-15-32(7,8)26(37)16-25(40-21(4)34)20(3)29(41-22(5)35)27-28(43-31(38)24-12-10-9-11-13-24)19(2)17-33(27,39)30(18)42-23(6)36/h9-15,18-19,25,27-30,39H,3,16-17H2,1-2,4-8H3/b15-14+/t18-,19+,25-,27-,28+,29+,30-,33-/m1/s1

InChI Key

QPKPYRGCZAZZJU-STMFRTFUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Euphorbia guyoniana	LOTUS Database	35616633
Euphorbia hyberna	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Jatrophane and cyclojatrophane diterpenoids

Alternative Parents

Substituents

Jatrophane diterpenoid
Tetracarboxylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Ketone
Carboxylic acid ester
Cyclic ketone
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	2.43	ALOGPS
logP	4.23	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	13.4	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	142.5 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	155.54 m³·mol⁻¹	ChemAxon
Polarizability	62.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

8754820

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10579438

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0151995)

MOL for NP0151995 ((1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D MOL for NP0151995 ((1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D SDF for NP0151995 ((1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D-SDF for NP0151995 ((1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

PDB for NP0151995 ((1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D PDB for NP0151995 ((1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

SMILES for NP0151995 ((1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

INCHI for NP0151995 ((1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

Structure for NP0151995 ((1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D Structure for NP0151995 ((1s,2s,3ar,4r,5r,11r,13r,13ar)-4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)