NP-MRD: Showing NP-Card for 3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate (NP0289893)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 20:17:50 UTC

Updated at

2022-09-09 20:17:50 UTC

NP-MRD ID

NP0289893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate

Description

3A,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H-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. 3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate is found in Euphorbia platyphyllos and Euphorbia serrulata. 3A,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H-cyclopenta[12]annulen-1-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201505162D          

 47 49  0  0  0  0            999 V2000
   -0.7074   -1.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7105   -1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4273   -1.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088   -0.8254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386   -0.3443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869   -0.6841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202    0.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2105   -1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3774   -0.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1605   -0.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7768   -0.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098   -1.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570   -1.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4345   -1.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261   -2.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -1.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1761   -1.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9593   -0.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599   -0.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592   -3.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6754   -3.5810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4586   -3.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6255   -2.5136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748   -3.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2760   -3.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091   -4.0998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253   -4.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085   -4.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5584   -5.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598   -2.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7793   -3.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2266   -3.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8766   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2604   -2.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404   -2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0320   -3.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486   -3.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2736   -3.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0402   -4.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -5.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483   -6.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -6.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848   -4.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  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
 13 11  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 36 33  1  4  0  0  0
 36 37  2  0  0  0  0
  4 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 42 47  1  0  0  0  0
M  END

     RDKit          3D

 91 93  0  0  0  0  0  0  0  0999 V2000
   -4.6844    1.3253    3.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8707    1.7264    2.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9704    2.9054    2.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0308    0.8790    2.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2037    1.1725    0.9230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7694    0.6925   -0.3759 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9888    0.0251   -0.1197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1594    0.3066   -0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4022   -0.4493   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1480    1.1950   -1.7195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151   -0.3736   -0.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9470   -1.3326    0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656    0.4390   -1.6335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648   -1.1589   -2.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367   -2.3122   -2.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466   -3.0221   -1.7134 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2269   -4.1565   -2.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -2.3926   -1.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1182   -1.9053   -2.5607 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4808   -2.2804   -0.2531 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9777   -3.0059    0.8137 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707   -4.3356    0.9660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1811   -4.9396    2.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0663   -5.1213    0.0616 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8495   -2.8859   -0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4941   -1.7434   -1.2873 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0204   -2.0411   -1.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1528   -0.6204   -0.4611 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0948    0.5476   -1.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291    1.6106   -0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7324    1.4685   -0.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9305    2.8510   -1.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0948    3.0754   -2.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1153    4.2665   -3.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9966    5.2687   -3.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8441    5.0510   -2.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8052    3.8607   -1.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135   -0.9084    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2793   -0.0269    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1461    0.3029    1.8592 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2506   -0.6378    2.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9287    1.1801    2.7995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.2833    1.3345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9733    2.2566    2.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485    3.5161    2.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    4.4829    3.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1909    3.8696    1.3572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2626    0.3903    4.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5731    2.0992    4.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7619    1.2393    3.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008    2.2920    0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9489    1.4019   -1.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5068   -0.5764    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3102   -1.4684   -0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2946    0.0383   -0.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583   -1.8756    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6929   -2.1781   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5229   -1.0398    1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601    1.5764   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9137    0.4106   -2.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2119    0.4282   -1.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1772   -0.7769   -2.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2111   -2.8196   -3.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9223   -3.6338   -0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717   -3.7306   -3.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681   -4.5151   -2.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9896   -4.9318   -2.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8036   -5.4070    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529   -4.1473    3.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8815   -5.6976    2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4307   -3.0593    0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7412   -3.8060   -1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2926   -1.6508   -2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020   -1.3006   -1.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3977   -2.0148   -0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1288   -3.0585   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9390   -0.5194    0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4081    2.3090   -3.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4564    4.4456   -4.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197    6.2026   -3.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5276    5.8418   -1.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.6775   -0.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9412    0.9328    0.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786   -1.0398    3.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7453   -0.0484    3.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071   -1.4607    2.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3312    1.4289    3.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262    1.9228    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021    5.3405    3.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3476    4.8802    3.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2193    3.9897    4.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 25  1  0
 25 20  1  0
 20 21  1  1
 21 22  1  0
 22 23  1  0
 22 24  2  0
 20 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  1  0
 40 42  1  1
 40 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 45 47  2  0
 43  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  6 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 38 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 28 26  1  0
 37 32  1  0
 18 20  1  0
 27 74  1  0
 27 75  1  0
 27 76  1  0
 26 73  1  6
 25 71  1  0
 25 72  1  0
 23 68  1  0
 23 69  1  0
 23 70  1  0
 39 83  1  0
 41 84  1  0
 41 85  1  0
 41 86  1  0
 42 87  1  0
 43 88  1  6
 46 89  1  0
 46 90  1  0
 46 91  1  0
  5 51  1  6
  1 48  1  0
  1 49  1  0
  1 50  1  0
  6 52  1  6
  9 53  1  0
  9 54  1  0
  9 55  1  0
 12 56  1  0
 12 57  1  0
 12 58  1  0
 13 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 15 63  1  0
 16 64  1  1
 17 65  1  0
 17 66  1  0
 17 67  1  0
 28 77  1  1
 33 78  1  0
 34 79  1  0
 35 80  1  0
 36 81  1  0
 37 82  1  0
M  END


  Mrv1533004201505162D          

 47 49  0  0  0  0            999 V2000
   -0.7074   -1.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7105   -1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4273   -1.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088   -0.8254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386   -0.3443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869   -0.6841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202    0.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2105   -1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3774   -0.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1605   -0.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7768   -0.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098   -1.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570   -1.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4345   -1.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261   -2.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -1.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1761   -1.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9593   -0.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599   -0.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592   -3.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6754   -3.5810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4586   -3.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6255   -2.5136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748   -3.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2760   -3.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091   -4.0998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253   -4.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085   -4.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5584   -5.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598   -2.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7793   -3.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2266   -3.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8766   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2604   -2.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404   -2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0320   -3.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486   -3.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2736   -3.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0402   -4.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -5.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483   -6.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -6.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848   -4.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  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
 13 11  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 36 33  1  4  0  0  0
 36 37  2  0  0  0  0
  4 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 42 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289893

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2(OC(C)=O)C(=CC(C)(O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(C)(C)C=CC(C)C2=O)C1OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C35H44O12/c1-19-15-16-33(7,8)30(44-22(4)37)28(43-21(3)36)31(45-23(5)38)34(9,42)18-26-27(46-32(41)25-13-11-10-12-14-25)20(2)17-35(26,29(19)40)47-24(6)39/h10-16,18-20,27-28,30-31,42H,17H2,1-9H3

> <INCHI_KEY>
MGQBTBLHNLYVIS-UHFFFAOYSA-N

> <FORMULA>
C35H44O12

> <MOLECULAR_WEIGHT>
656.725

> <EXACT_MASS>
656.283276857

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
67.75978462427375

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H-cyclopenta[12]annulen-1-yl benzoate

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
3.956506114999998

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.799515771286956

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.502116742937435

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4435362081355327

> <JCHEM_POLAR_SURFACE_AREA>
168.8

> <JCHEM_REFRACTIVITY>
167.23939999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1H,2H,3H,5H,9H,10H,11H-cyclopenta[12]annulen-1-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -1.320  -3.036   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.188  -3.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.326  -2.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.664  -3.073   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.817  -1.541   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.565  -0.643   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.162  -1.277   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.718   0.890   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.126  -2.589   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.276  -3.613   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.438  -1.081   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.287  -0.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.900  -0.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.050  -1.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.738  -3.129   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.946  -2.174   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.278  -3.174   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.889  -4.152   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.351  -3.668   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.662  -2.160   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.124  -1.676   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.512  -1.136   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.577  -5.661   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.727  -6.685   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.189  -6.200   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.501  -4.692   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.340  -7.224   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.115  -6.145   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.804  -7.653   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.954  -8.677   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.416  -8.193   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.642 -10.185   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.965  -5.121   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.188  -6.645   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.156  -6.432   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.503  -5.605   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.353  -4.581   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.822  -4.751   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.060  -6.089   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.837  -7.418   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.377  -7.410   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       0.075  -8.756   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.853 -10.086   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.090 -11.424   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.450 -11.433   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -2.227 -10.103   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -1.465  -8.765   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9   37                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   37                                                       
CONECT   37   36    4   38                                                  
CONECT   38   37    2   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   47                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   42                                                       
MASTER        0    0    0    0    0    0    0    0   47    0   98    0
END

View in JSmol

Synonyms

Value	Source
3a,9,10,11-Tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1H,2H,3H,3ah,4H,5H,8H,9H,10H,11H,12H-cyclopenta[12]annulen-1-yl benzoic acid	Generator

Chemical Formula

C₃₅H₄₄O₁₂

Average Mass

656.7250 Da

Monoisotopic Mass

656.28328 Da

IUPAC Name

3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H-cyclopenta[12]annulen-1-yl benzoate

Traditional Name

3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1H,2H,3H,5H,9H,10H,11H-cyclopenta[12]annulen-1-yl benzoate

CAS Registry Number

Not Available

SMILES

CC1CC2(OC(C)=O)C(=CC(C)(O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(C)(C)C=CC(C)C2=O)C1OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C35H44O12/c1-19-15-16-33(7,8)30(44-22(4)37)28(43-21(3)36)31(45-23(5)38)34(9,42)18-26-27(46-32(41)25-13-11-10-12-14-25)20(2)17-35(26,29(19)40)47-24(6)39/h10-16,18-20,27-28,30-31,42H,17H2,1-9H3

InChI Key

MGQBTBLHNLYVIS-UHFFFAOYSA-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 platyphyllos	LOTUS Database	35616633
Euphorbia serrulata	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
Pentacarboxylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Alpha-acyloxy ketone
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
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	2.81	ALOGPS
logP	3.96	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.5	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	168.8 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	167.24 m³·mol⁻¹	ChemAxon
Polarizability	67.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

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

73079455

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate (NP0289893)

MOL for NP0289893 (3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate)

3D MOL for NP0289893 (3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate)

3D SDF for NP0289893 (3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate)

3D-SDF for NP0289893 (3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate)

PDB for NP0289893 (3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate)

3D PDB for NP0289893 (3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate)

SMILES for NP0289893 (3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate)

INCHI for NP0289893 (3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate)

Structure for NP0289893 (3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate)

3D Structure for NP0289893 (3a,9,10,11-tetrakis(acetyloxy)-12-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1h,2h,3h,5h,9h,10h,11h-cyclopenta[12]annulen-1-yl benzoate)