NP-MRD: Showing NP-Card for jatrophalone (NP0041070)

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Record Information

Version

2.0

Created at

2021-06-20 23:04:41 UTC

Updated at

2021-06-30 00:15:22 UTC

NP-MRD ID

NP0041070

Secondary Accession Numbers

None

Natural Product Identification

Common Name

jatrophalone

Provided By

JEOL Database JEOL Logo

Description

Jatrophaketone belongs to the class of organic compounds known as jatropholane and crotopholane diterpenoids. These are diterpenoids with a structure based either on the jatropholane or the crotopholane skeleton. Jatropholanes arise by 5,13- and 6,10-cyclisation of a casbane precursor. Subsequent cleavage of the 2,15-cyclopropane bond affords crotofolane. jatrophalone is found in Jatropha curcas. jatrophalone was first documented in 2012 (Liu, J.-Q., et al.). Based on a literature review very few articles have been published on Jatrophaketone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101043D          

 50 53  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212101043D          

 50 53  0  0  0  0            999 V2000
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    0.9664    1.0156    5.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5729   -0.5472    5.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 22  1  0  0  0  0
 17 19  1  0  0  0  0
  8  2  1  0  0  0  0
  7  6  1  0  0  0  0
 19  7  1  0  0  0  0
 19 21  1  1  0  0  0
  2  3  1  0  0  0  0
  7 33  1  6  0  0  0
  8  9  1  0  0  0  0
  2  1  2  3  0  0  0
  3  4  1  0  0  0  0
 22 23  1  6  0  0  0
  5  4  1  0  0  0  0
 22 24  1  0  0  0  0
  9 10  2  0  0  0  0
 10 17  1  0  0  0  0
  8 34  1  1  0  0  0
 19 20  1  0  0  0  0
  7  8  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 15  1  0  0  0  0
 15  9  1  0  0  0  0
 17 18  2  0  0  0  0
 15 16  2  0  0  0  0
  6  5  1  0  0  0  0
 12 14  1  6  0  0  0
 12 13  1  0  0  0  0
  6 22  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
 20 41  1  0  0  0  0
 20 42  1  0  0  0  0
 20 43  1  0  0  0  0
  5 31  1  1  0  0  0
  6 32  1  1  0  0  0
 21 44  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 23 45  1  0  0  0  0
 23 46  1  0  0  0  0
 23 47  1  0  0  0  0
 24 48  1  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 14 40  1  0  0  0  0
 13 37  1  0  0  0  0
 13 38  1  0  0  0  0
 13 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041070

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1(C(=O)C2=C(C(=O)[C@](O[H])(C([H])([H])[H])[C@]3([H])[C@]4([H])[C@]([H])(C([H])([H])C([H])([H])C(=C([H])[H])[C@@]23[H])C4(C([H])([H])[H])C([H])([H])[H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-9-6-7-11-14(18(11,2)3)15-12(9)13-10(16(21)20(15,5)24)8-19(4,23)17(13)22/h11-12,14-15,23-24H,1,6-8H2,2-5H3/t11-,12-,14-,15-,19+,20-/m0/s1

> <INCHI_KEY>
DGXURLBVVBVHIO-KOWFQURMSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.21209656048957

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,8S,9R,10S,12S)-4,8-dihydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadec-2(6)-ene-3,7-dione

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
2.2760439886666672

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.383013861971417

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.76384655118365

> <JCHEM_PKA_STRONGEST_BASIC>
-3.604540231174231

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
90.9476

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,8S,9R,10S,12S)-4,8-dihydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadec-2(6)-ene-3,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -0.5343    2.0732   -1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968    1.4450   -0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5358    2.2523    1.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5633    2.5023    2.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4664    1.3132    3.0688 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0567   -0.0205    2.5782 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5249   -0.2264    1.1388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6989   -0.0564    0.1685 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5452   -0.8647   -1.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4646   -1.6488   -1.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691   -2.3054   -2.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0155   -1.8798   -3.2916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9560   -1.0857   -4.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -3.0176   -3.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -1.0186   -2.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6776   -0.5637   -2.0892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710   -1.8587   -0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437   -2.3150   -0.9006 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -1.5793    0.9781 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5629   -2.8055    1.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5490   -1.4813    1.6525 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373    0.7595    3.6341 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1576    1.4141    3.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962    0.2127    5.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0522    1.5702   -2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7016    3.1394   -1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8608    3.2268    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455    1.7475    1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4089    2.8201    1.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9394    3.3422    2.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424    1.2733    3.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5361   -0.8666    2.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541    0.5539    0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6068   -0.4290    0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1752   -1.9504   -3.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4516   -3.3936   -2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9602   -0.7828   -4.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3504   -0.1793   -4.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391   -1.6950   -5.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7614   -2.6796   -3.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0766   -3.7287    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4715   -2.8778    1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5679   -2.8009    2.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1592   -2.0925    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345    1.7849    2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774    0.7039    3.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    2.2666    3.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1688   -0.2501    5.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9664    1.0156    5.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5729   -0.5472    5.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 22  1  0
 17 19  1  0
  8  2  1  0
  7  6  1  0
 19  7  1  0
 19 21  1  1
  2  3  1  0
  7 33  1  6
  8  9  1  0
  2  1  2  3
  3  4  1  0
 22 23  1  6
  5  4  1  0
 22 24  1  0
  9 10  2  0
 10 17  1  0
  8 34  1  1
 19 20  1  0
  7  8  1  0
 10 11  1  0
 11 12  1  0
 12 15  1  0
 15  9  1  0
 17 18  2  0
 15 16  2  0
  6  5  1  0
 12 14  1  6
 12 13  1  0
  6 22  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
  5 31  1  1
  6 32  1  1
 21 44  1  0
  1 25  1  0
  1 26  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 11 35  1  0
 11 36  1  0
 14 40  1  0
 13 37  1  0
 13 38  1  0
 13 39  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      -0.534   2.073  -1.249  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.897   1.445  -0.113  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.536   2.252   1.005  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.563   2.502   2.163  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.466   1.313   3.069  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.057  -0.021   2.578  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.525  -0.226   1.139  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.699  -0.056   0.169  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.545  -0.865  -1.077  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.465  -1.649  -1.450  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.369  -2.305  -2.783  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.016  -1.880  -3.292  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.956  -1.086  -4.588  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.852  -3.018  -3.465  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.544  -1.019  -2.146  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.678  -0.564  -2.089  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.571  -1.859  -0.510  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.644  -2.315  -0.901  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.285  -1.579   0.978  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.563  -2.805   1.549  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.549  -1.481   1.653  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.837   0.760   3.634  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.158   1.414   3.311  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.796   0.213   5.044  0.00  0.00           C+0
HETATM   25  H   UNK     0      -0.052   1.570  -2.079  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.702   3.139  -1.380  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.861   3.227   0.618  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.446   1.748   1.353  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.409   2.820   1.775  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.939   3.342   2.761  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.342   1.273   3.714  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.536  -0.867   2.918  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.254   0.554   0.886  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.607  -0.429   0.664  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.175  -1.950  -3.434  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.452  -3.394  -2.688  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.960  -0.783  -4.906  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.350  -0.179  -4.482  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.539  -1.695  -5.397  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.761  -2.680  -3.581  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.077  -3.729   1.253  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.472  -2.878   1.198  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.568  -2.801   2.644  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.159  -2.092   1.192  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.235   1.785   2.287  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.977   0.704   3.462  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.323   2.267   3.978  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.169  -0.250   5.277  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.966   1.016   5.768  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.573  -0.547   5.179  0.00  0.00           H+0
CONECT    1    2   25   26                                                  
CONECT    2    8    3    1                                                  
CONECT    3    2    4   27   28                                             
CONECT    4    3    5   29   30                                             
CONECT    5   22    4    6   31                                             
CONECT    6    7    5   22   32                                             
CONECT    7    6   19   33    8                                             
CONECT    8    2    9   34    7                                             
CONECT    9    8   10   15                                                  
CONECT   10    9   17   11                                                  
CONECT   11   10   12   35   36                                             
CONECT   12   11   15   14   13                                             
CONECT   13   12   37   38   39                                             
CONECT   14   12   40                                                       
CONECT   15   12    9   16                                                  
CONECT   16   15                                                            
CONECT   17   19   10   18                                                  
CONECT   18   17                                                            
CONECT   19   17    7   21   20                                             
CONECT   20   19   41   42   43                                             
CONECT   21   19   44                                                       
CONECT   22    5   23   24    6                                             
CONECT   23   22   45   46   47                                             
CONECT   24   22   48   49   50                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   13                                                            
CONECT   38   13                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   20                                                            
CONECT   42   20                                                            
CONECT   43   20                                                            
CONECT   44   21                                                            
CONECT   45   23                                                            
CONECT   46   23                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  106    0
END

RDKit          3D

50 53  0  0  0  0  0  0  0  0999 V2000
   -0.5343    2.0732   -1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968    1.4450   -0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5358    2.2523    1.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5633    2.5023    2.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4664    1.3132    3.0688 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0567   -0.0205    2.5782 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5249   -0.2264    1.1388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6989   -0.0564    0.1685 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5452   -0.8647   -1.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4646   -1.6488   -1.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691   -2.3054   -2.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0155   -1.8798   -3.2916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9560   -1.0857   -4.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -3.0176   -3.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -1.0186   -2.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6776   -0.5637   -2.0892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710   -1.8587   -0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437   -2.3150   -0.9006 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -1.5793    0.9781 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5629   -2.8055    1.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5490   -1.4813    1.6525 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373    0.7595    3.6341 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1576    1.4141    3.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962    0.2127    5.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0522    1.5702   -2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7016    3.1394   -1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8608    3.2268    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455    1.7475    1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4089    2.8201    1.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9394    3.3422    2.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424    1.2733    3.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5361   -0.8666    2.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541    0.5539    0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6068   -0.4290    0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1752   -1.9504   -3.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4516   -3.3936   -2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9602   -0.7828   -4.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3504   -0.1793   -4.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391   -1.6950   -5.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7614   -2.6796   -3.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0766   -3.7287    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4715   -2.8778    1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5679   -2.8009    2.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1592   -2.0925    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345    1.7849    2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774    0.7039    3.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    2.2666    3.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1688   -0.2501    5.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9664    1.0156    5.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5729   -0.5472    5.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 22  1  0
 17 19  1  0
  8  2  1  0
  7  6  1  0
 19  7  1  0
 19 21  1  1
  2  3  1  0
  7 33  1  6
  8  9  1  0
  2  1  2  3
  3  4  1  0
 22 23  1  6
  5  4  1  0
 22 24  1  0
  9 10  2  0
 10 17  1  0
  8 34  1  1
 19 20  1  0
  7  8  1  0
 10 11  1  0
 11 12  1  0
 12 15  1  0
 15  9  1  0
 17 18  2  0
 15 16  2  0
  6  5  1  0
 12 14  1  6
 12 13  1  0
  6 22  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
  5 31  1  1
  6 32  1  1
 21 44  1  0
  1 25  1  0
  1 26  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 11 35  1  0
 11 36  1  0
 14 40  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₄

Average Mass

330.4240 Da

Monoisotopic Mass

330.18311 Da

IUPAC Name

(1S,4R,8S,9R,10S,12S)-4,8-dihydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadec-2(6)-ene-3,7-dione

Traditional Name

(1S,4R,8S,9R,10S,12S)-4,8-dihydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadec-2(6)-ene-3,7-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@]1(C(=O)C2=C(C(=O)[C@](O[H])(C([H])([H])[H])[C@]3([H])[C@]4([H])[C@]([H])(C([H])([H])C([H])([H])C(=C([H])[H])[C@@]23[H])C4(C([H])([H])[H])C([H])([H])[H])C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H26O4/c1-9-6-7-11-14(18(11,2)3)15-12(9)13-10(16(21)20(15,5)24)8-19(4,23)17(13)22/h11-12,14-15,23-24H,1,6-8H2,2-5H3/t11-,12-,14-,15-,19+,20-/m0/s1

InChI Key

DGXURLBVVBVHIO-KOWFQURMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Jatropha curcas	JEOL database	Liu, J.-Q., et al, Tetrahedron 68, 972 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jatropholane and crotopholane diterpenoids. These are diterpenoids with a structure based either on the jatropholane or the crotopholane skeleton. Jatropholanes arise by 5,13- and 6,10-cyclisation of a casbane precursor. Subsequent cleavage of the 2,15-cyclopropane bond affords crotofolane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Jatropholane and crotopholane diterpenoids

Alternative Parents

Substituents

Jatropholane or crotopholane diterpenoid
Cyclohexenone
Acyloin
Tertiary alcohol
Cyclic alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.43	ALOGPS
logP	2.28	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	12.76	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.95 m³·mol⁻¹	ChemAxon
Polarizability	36.21 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

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

57328374

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu, J.-Q., et al. (2012). Liu, J.-Q., et al, Tetrahedron 68, 972 (2012). Tetrahedron.

Showing NP-Card for jatrophalone (NP0041070)

MOL for NP0041070 (jatrophalone)

3D MOL for NP0041070 (jatrophalone)

3D SDF for NP0041070 (jatrophalone)

3D-SDF for NP0041070 (jatrophalone)

PDB for NP0041070 (jatrophalone)

3D PDB for NP0041070 (jatrophalone)

SMILES for NP0041070 (jatrophalone)

INCHI for NP0041070 (jatrophalone)

Structure for NP0041070 (jatrophalone)

3D Structure for NP0041070 (jatrophalone)