NP-MRD: Showing NP-Card for Diterpenoid EF-D (NP0052005)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 23:11:57 UTC

Updated at

2022-04-27 23:11:57 UTC

NP-MRD ID

NP0052005

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Diterpenoid EF-D

Description

(1R,2S,6R,10R,11R,13S,15R)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]Pentadeca-3,8-dien-13-yl (2R)-2-methylbutanoate belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. Diterpenoid EF-D is found in Euphorbia caerulescens and Euphorbia fortissima. Based on a literature review very few articles have been published on (1R,2S,6R,10R,11R,13S,15R)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]Pentadeca-3,8-dien-13-yl (2R)-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201112D          

 34 37  0  0  1  0            999 V2000
    5.5966    0.2916    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0582   -0.3921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8115   -1.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0422   -1.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3296   -1.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2103   -0.2453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7742    0.3570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5345    1.1464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7311    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1672    0.7314    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4068   -0.0581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6033    0.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0941   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192    0.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5650    1.2952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7522    2.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1499    2.6626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5416    2.3383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1438    1.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7288    3.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5182    3.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0984    1.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2914    0.9997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9768   -2.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319   -2.6543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5524   -2.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.5411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6177   -1.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8512   -0.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5015   -0.6719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8796    0.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042    0.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5633    1.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6346   -0.9824    0.0000 O   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  2  0  0  0  0
  6  5  1  6  0  0  0
  7  6  1  0  0  0  0
  7  1  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 16  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 22  1  1  0  0  0
  7 23  1  1  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
  1 32  1  6  0  0  0
 31 33  1  0  0  0  0
  2 34  1  6  0  0  0
M  END

     RDKit          3D

 72 75  0  0  0  0  0  0  0  0999 V2000
    6.3254    0.7926    2.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5395    0.7197    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5498   -0.1439   -0.1139 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6154   -1.5656    0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1575    0.3943    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867    1.4263    0.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1669   -0.2957   -0.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068   -0.0730   -0.7255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0866   -1.2608   -1.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2129   -1.6229   -0.7320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2440   -3.1425   -0.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215   -0.9186    0.5097 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4696   -1.3189    1.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8177   -1.1690    1.1749 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8465   -2.3600    2.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1061   -2.7341    2.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6348   -3.8977    2.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9923   -1.8676    1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2106   -1.6633    1.4187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0552   -1.1862    0.3888 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1169   -1.9677   -0.7337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5859    0.1938    0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865    1.1435   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4212    2.0600   -1.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3397    2.7620   -0.5310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2086    3.7095   -0.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1508    4.4204   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2136    3.9871   -2.2053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3898    1.2675   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342    0.5693    0.3864 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0265    0.9613   -0.0951 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4366    1.2697   -1.4450 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4981    2.2969   -1.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143    1.0585   -2.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6648    1.6887    2.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3163    1.0177    2.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8571   -0.0946    2.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5453    1.7312    0.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5476    0.2978    0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.1729   -1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0483   -2.2664   -0.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036   -1.8891    0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2990   -1.6608    1.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7778   -2.1250   -1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9762   -1.0874   -2.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187   -1.4288   -1.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394   -3.5328   -0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046   -3.5283    0.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075   -3.6257   -1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5398   -2.2906    1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9486   -0.3183    1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0255   -2.8714    2.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6246   -4.7941    2.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6555   -3.7004    3.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0169   -4.1021    3.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4534   -1.4764   -1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8655    0.5589    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5786    0.0947   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510    1.5195   -2.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886    2.8048   -1.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9091    4.1878    0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0840    5.5195   -0.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2044    4.1152   -0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9978    2.0681   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5211    0.9265    1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855    1.5539    0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918    1.8850   -1.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1492    2.9113   -2.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5649    3.0491   -0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    2.0668   -3.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2858    0.4910   -2.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2759    0.6326   -3.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 23 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  1
 32 34  1  0
 31  8  1  0
 32  8  1  0
 30 12  1  0
 20 14  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  6
  4 41  1  0
  4 42  1  0
  4 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  6
 11 47  1  0
 11 48  1  0
 11 49  1  0
 13 50  1  0
 14 51  1  1
 15 52  1  0
 17 53  1  0
 17 54  1  0
 17 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 24 59  1  0
 24 60  1  0
 27 61  1  0
 27 62  1  0
 27 63  1  0
 29 64  1  0
 30 65  1  1
 31 66  1  1
 33 67  1  0
 33 68  1  0
 33 69  1  0
 34 70  1  0
 34 71  1  0
 34 72  1  0
M  END


  Mrv1652304282201112D          

 34 37  0  0  1  0            999 V2000
    5.5966    0.2916    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0582   -0.3921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8115   -1.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0422   -1.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3296   -1.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2103   -0.2453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7742    0.3570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5345    1.1464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7311    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1672    0.7314    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4068   -0.0581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6033    0.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0941   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192    0.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5650    1.2952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7522    2.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1499    2.6626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5416    2.3383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1438    1.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7288    3.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5182    3.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0984    1.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2914    0.9997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9768   -2.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319   -2.6543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5524   -2.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.5411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6177   -1.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8512   -0.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5015   -0.6719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8796    0.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042    0.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5633    1.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6346   -0.9824    0.0000 O   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  2  0  0  0  0
  6  5  1  6  0  0  0
  7  6  1  0  0  0  0
  7  1  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 16  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 22  1  1  0  0  0
  7 23  1  1  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
  1 32  1  6  0  0  0
 31 33  1  0  0  0  0
  2 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052005

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)O[C@@]12C[C@@H](C)[C@]3(O)[C@@H]4C=C(C)C(=O)[C@@]4(O)CC(COC(C)=O)=C[C@@H]3[C@@H]1C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O7/c1-8-14(2)23(30)34-26-11-16(4)27(32)19(21(26)24(26,6)7)10-18(13-33-17(5)28)12-25(31)20(27)9-15(3)22(25)29/h9-10,14,16,19-21,31-32H,8,11-13H2,1-7H3/t14-,16-,19-,20-,21-,25-,26+,27-/m1/s1

> <INCHI_KEY>
QOSLYAARSBMQOF-CZQUJOTESA-N

> <FORMULA>
C27H38O7

> <MOLECULAR_WEIGHT>
474.594

> <EXACT_MASS>
474.261753564

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.61189650325832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,6R,10R,11R,13S,15R)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl (2R)-2-methylbutanoate

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.822805746666666

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.037693842512272

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.575740432151242

> <JCHEM_PKA_STRONGEST_BASIC>
-3.271835702664961

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
126.62009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6R,10R,11R,13S,15R)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl (2R)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      10.447   0.544   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.309  -0.732   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.848  -2.201   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.412  -2.758   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.082  -1.982   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.859  -0.458   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.912   0.666   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.464   2.140   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.965   2.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.912   1.365   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.359  -0.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.860   0.241   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.909  -0.971   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.396   0.720   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.788   2.418   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.137   3.918   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.013   4.970   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.611   4.365   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.735   3.312   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.960   5.865   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.434   6.312   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.517   3.264   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.877   1.866   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.290  -4.293   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.900  -4.955   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.631  -4.081   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.241  -4.743   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.753  -2.546   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.789  -0.307   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.003  -1.254   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.842   1.232   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.394   1.758   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.118   2.094   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.385  -1.834   0.000  0.00  0.00           O+0
CONECT    1    2    7   32                                                  
CONECT    2    1    3   29   34                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    1    8   23                                             
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   15                                             
CONECT   11   10    6   12                                                  
CONECT   12   11   10   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22    8                                                            
CONECT   23    7                                                            
CONECT   24    4   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    2   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31    1                                                       
CONECT   33   31                                                            
CONECT   34    2                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,6R,10R,11R,13S,15R)-8-[(Acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0,.0,]pentadeca-3,8-dien-13-yl (2R)-2-methylbutanoic acid	Generator

Chemical Formula

C₂₇H₃₈O₇

Average Mass

474.5940 Da

Monoisotopic Mass

474.26175 Da

IUPAC Name

(1R,2S,6R,10R,11R,13S,15R)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl (2R)-2-methylbutanoate

Traditional Name

(1R,2S,6R,10R,11R,13S,15R)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl (2R)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@@]12C[C@@H](C)[C@]3(O)[C@@H]4C=C(C)C(=O)[C@@]4(O)CC(COC(C)=O)=C[C@@H]3[C@@H]1C2(C)C

InChI Identifier

InChI=1S/C27H38O7/c1-8-14(2)23(30)34-26-11-16(4)27(32)19(21(26)24(26,6)7)10-18(13-33-17(5)28)12-25(31)20(27)9-15(3)22(25)29/h9-10,14,16,19-21,31-32H,8,11-13H2,1-7H3/t14-,16-,19-,20-,21-,25-,26+,27-/m1/s1

InChI Key

QOSLYAARSBMQOF-CZQUJOTESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 caerulescens	LOTUS Database	35616633
Euphorbia fortissima	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Phorbol esters

Alternative Parents

Substituents

Phorbol ester
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
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	3.01	ALOGPS
logP	2.82	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.62 m³·mol⁻¹	ChemAxon
Polarizability	51.61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

163031749

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Diterpenoid EF-D (NP0052005)

MOL for NP0052005 (Diterpenoid EF-D)

3D MOL for NP0052005 (Diterpenoid EF-D)

3D SDF for NP0052005 (Diterpenoid EF-D)

3D-SDF for NP0052005 (Diterpenoid EF-D)

PDB for NP0052005 (Diterpenoid EF-D)

3D PDB for NP0052005 (Diterpenoid EF-D)

SMILES for NP0052005 (Diterpenoid EF-D)

INCHI for NP0052005 (Diterpenoid EF-D)

Structure for NP0052005 (Diterpenoid EF-D)

3D Structure for NP0052005 (Diterpenoid EF-D)