NP-MRD: Showing NP-Card for (1s,2s,3ar,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate (NP0325427)

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Record Information

Version

2.0

Created at

2022-09-12 06:10:52 UTC

Updated at

2022-09-12 06:10:52 UTC

NP-MRD ID

NP0325427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(1S,2S,3aR,5R,10R,11S,13R,13aR)-1,11,13-tris(acetyloxy)-10-[(2S)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-3a-yl acetate 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,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate is found in Euphorbia paralias. Based on a literature review very few articles have been published on (1S,2S,3aR,5R,10R,11S,13R,13aR)-1,11,13-tris(acetyloxy)-10-[(2S)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-3a-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122208102D          

 43 44  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  1  0  0  0  0  0  0  0  0  0
    6.4310    0.2517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2253    0.0285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4292   -0.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8157    0.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6099    0.3816    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
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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
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  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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 18 64  1  0
 18 65  1  0
M  END


  Mrv1652309122208102D          

 43 44  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  1  0  0  0  0  0  0  0  0  0
    6.4310    0.2517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2253    0.0285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4292   -0.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8157    0.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6099    0.3816    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  0  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
    3.1558   -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
    2.0345   -2.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296   -3.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5231   -2.0701    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886    1.0142    0.0000 O   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  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 38 33  1  6  0  0  0
 25 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>
NP0325427

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O11/c1-12-18(4)39-28-27(42-22(8)35)19(5)26(41-21(7)34)24-25(40-20(6)33)17(3)15-32(24,43-23(9)36)29(37)16(2)13-14-31(10,11)30(28)38/h13-14,16-18,24-28H,5,12,15H2,1-4,6-11H3/b14-13+/t16-,17+,18+,24-,25+,26+,27+,28-,32-/m1/s1

> <INCHI_KEY>
BVIVCJVEOCNDHW-YQLCRDMKSA-N

> <FORMULA>
C32H46O11

> <MOLECULAR_WEIGHT>
606.709

> <EXACT_MASS>
606.304012301

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
63.622379858245765

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
4.144846862666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.368600568119607

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.100409293174678

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2349883569545375

> <JCHEM_POLAR_SURFACE_AREA>
148.57

> <JCHEM_REFRACTIVITY>
153.9317

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-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  O   UNK     0      12.005   0.470   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      13.487   0.053   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.868  -1.439   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.589   1.129   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.072   0.712   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.656  -1.949   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.149  -1.568   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.638  -3.489   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.147  -4.942   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.158  -3.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.295  -4.243   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.509  -5.567   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.969  -5.548   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.552  -7.031   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.645  -4.762   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.543  -5.838   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.891  -3.419   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.322  -4.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.798  -5.073   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.229  -6.504   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.843  -3.864   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.421  -3.877   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.531  -2.621   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.991  -2.602   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.451  -1.386   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.993   0.084   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.490   0.423   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.446  -0.709   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.032   1.893   0.000  0.00  0.00           O+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   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    8   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30   38                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   33   25   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   88    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₃₂H₄₆O₁₁

Average Mass

606.7090 Da

Monoisotopic Mass

606.30401 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C32H46O11/c1-12-18(4)39-28-27(42-22(8)35)19(5)26(41-21(7)34)24-25(40-20(6)33)17(3)15-32(24,43-23(9)36)29(37)16(2)13-14-31(10,11)30(28)38/h13-14,16-18,24-28H,5,12,15H2,1-4,6-11H3/b14-13+/t16-,17+,18+,24-,25+,26+,27+,28-,32-/m1/s1

InChI Key

BVIVCJVEOCNDHW-YQLCRDMKSA-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 paralias	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
Alpha-acyloxy ketone
Cyclic ketone
Ketone
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.14	ChemAxon
pKa (Strongest Acidic)	15.1	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	148.57 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	153.93 m³·mol⁻¹	ChemAxon
Polarizability	63.62 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163045062

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,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate (NP0325427)

MOL for NP0325427 ((1s,2s,3ar,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

3D MOL for NP0325427 ((1s,2s,3ar,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

3D SDF for NP0325427 ((1s,2s,3ar,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

3D-SDF for NP0325427 ((1s,2s,3ar,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

PDB for NP0325427 ((1s,2s,3ar,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

3D PDB for NP0325427 ((1s,2s,3ar,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

SMILES for NP0325427 ((1s,2s,3ar,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

INCHI for NP0325427 ((1s,2s,3ar,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

Structure for NP0325427 ((1s,2s,3ar,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)

3D Structure for NP0325427 ((1s,2s,3ar,5r,10r,11s,13r,13ar)-3a,11,13-tris(acetyloxy)-10-[(2s)-butan-2-yloxy]-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1h,2h,3h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl acetate)