NP-MRD: Showing NP-Card for (1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate (NP0146377)

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Record Information

Version

2.0

Created at

2022-09-02 01:46:00 UTC

Updated at

2022-09-02 01:46:00 UTC

NP-MRD ID

NP0146377

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate

Description

Sapinsignoid D belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. Based on a literature review very few articles have been published on Sapinsignoid D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203462D          

 44 47  0  0  1  0            999 V2000
   -3.0962  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3817  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6673  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2383  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4761  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7630  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4774  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1919  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1919  -11.8331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9064  -10.5956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6209  -11.0081    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2084  -11.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6209  -12.4370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2084  -13.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4459  -12.4370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9811  -13.1187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8584  -11.7225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6741  -11.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2789  -12.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0469  -11.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6919  -12.3737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2173  -12.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5356  -13.4482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2679  -13.8282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5479  -14.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2226  -14.7479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7672  -14.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5241  -15.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2724  -13.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7473  -13.2050    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4459  -11.0081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0334  -10.2936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5066   -9.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5602   -9.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9088   -8.8701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4356   -8.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6138   -8.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7843   -7.4466    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  6  0  0  0
 21 19  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 29 28  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 36 35  1  1  0  0  0
 36 29  1  0  0  0  0
 21 36  1  0  0  0  0
 23 37  1  0  0  0  0
 37 17  1  0  0  0  0
 37 38  1  1  0  0  0
 17 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
M  END

     RDKit          3D

 96 99  0  0  0  0  0  0  0  0999 V2000
   12.1130   -0.8428   -1.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9385   -1.0547    0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8832   -2.0711    0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5034   -1.6818    0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0698   -0.3819    0.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7889    0.2065    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4918   -0.4201    0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1687   -1.7665   -0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7290   -2.0416    0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7942   -2.2552   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4232   -2.5154   -0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4086   -2.7428   -0.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0283   -3.0000   -0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759   -1.9499   -0.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9288   -1.8651   -2.1871 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8675   -0.8720   -0.8849 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7398   -2.2284   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0481    0.2182    0.1107 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4549   -0.2171    1.3188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2810    1.4422   -0.3113 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6669    2.6636    0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8351    3.2593    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9555    4.4616    1.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2867    5.5972    0.5943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0539    2.8973   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1339    1.4256   -0.5885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7282    1.2144   -1.8804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5707    1.0215   -0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5620    1.7198   -0.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5506   -0.3211    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7403   -1.2666    0.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3453   -0.5613    0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4667    0.5643    0.4221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8211    1.1328   -0.0486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8186    1.1906   -1.1283 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0803    1.8854   -2.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3797    1.3484   -0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114    1.2400    0.7357 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8641    1.3424    1.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8802    1.2200    2.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9241    1.5433    0.7921 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2418   -0.2973   -1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1453   -3.0310    0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8256   -2.1930    1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8876   -2.5522    0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9074    0.3707    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7890    1.2722    0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8148    0.4497   -0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3984   -0.5214    1.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6766    0.3252    0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2428   -1.7759   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7819   -2.5544    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0039   -2.2468   -1.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2179   -2.5223    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6624   -0.9854   -1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6838   -2.0921    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0618    3.4496   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.2138   -1.2971   -0.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4060   -2.2296    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0706   -1.5180    1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4435    1.1567    1.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5242    1.2746    1.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909    1.5804   -3.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9409    2.9897   -2.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9259    1.1459    3.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3431    0.3278    3.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3563    2.0982    3.4068 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 17 16  1  1
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  1
 21 36  1  0
 36 35  1  0
 35 33  2  0
 33 34  1  0
 33 31  1  0
 31 32  2  0
 31 29  1  0
 29 30  1  6
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 28 25  1  0
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 37 38  1  0
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 37 17  1  0
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 23 21  1  0
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  1 45  1  0
  1 46  1  0
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 22 74  1  0
 36 87  1  1
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 34 84  1  0
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 28 80  1  0
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 26 77  1  0
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 27 79  1  0
 24 76  1  0
 23 75  1  6
 37 88  1  1
 39 89  1  0
 39 90  1  0
 39 91  1  0
 40 92  1  0
 40 93  1  0
 43 94  1  0
 43 95  1  0
 43 96  1  0
M  END


  Mrv1652309022203462D          

 44 47  0  0  1  0            999 V2000
   -3.0962  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3817  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6673  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2383  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4761  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7630  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4774  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1919  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1919  -11.8331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9064  -10.5956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6209  -11.0081    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2084  -11.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6209  -12.4370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2084  -13.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4459  -12.4370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9811  -13.1187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8584  -11.7225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6741  -11.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2789  -12.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0469  -11.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6919  -12.3737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2173  -12.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5356  -13.4482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2679  -13.8282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5479  -14.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2226  -14.7479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7672  -14.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5241  -15.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2724  -13.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7473  -13.2050    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4459  -11.0081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0334  -10.2936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5066   -9.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5602   -9.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9088   -8.8701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4356   -8.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6138   -8.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7843   -7.4466    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  6  0  0  0
 21 19  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 29 28  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 36 35  1  1  0  0  0
 36 29  1  0  0  0  0
 21 36  1  0  0  0  0
 23 37  1  0  0  0  0
 37 17  1  0  0  0  0
 37 38  1  1  0  0  0
 17 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0146377

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC\C=C\C=C\CC(=O)O[C@@]12C[C@@H](C)[C@]3(O)[C@@H]4C=C(C)C(=O)[C@@]4(O)CC(CO)=C[C@H]3[C@@H]1[C@@]2(C)COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C36H52O8/c1-6-7-8-9-10-11-12-13-14-15-16-17-30(39)44-35-20-25(3)36(42)28(31(35)33(35,5)23-43-26(4)38)19-27(22-37)21-34(41)29(36)18-24(2)32(34)40/h13-16,18-19,25,28-29,31,37,41-42H,6-12,17,20-23H2,1-5H3/b14-13+,16-15+/t25-,28+,29-,31-,33-,34-,35+,36-/m1/s1

> <INCHI_KEY>
UYPOIYOXALXFNN-UFANGNBOSA-N

> <FORMULA>
C36H52O8

> <MOLECULAR_WEIGHT>
612.804

> <EXACT_MASS>
612.366218634

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
70.93232753589922

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
4.720891648333331

> <ALOGPS_LOGS>
-5.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.007016548252988

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.574627074720077

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7316132676212703

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
172.0635

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.13e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.780 -19.778   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.446 -20.548   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.112 -19.778   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.779 -20.548   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.445 -19.778   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.889 -20.548   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.222 -19.778   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.556 -20.548   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.890 -19.778   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.224 -20.548   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.557 -19.778   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.891 -20.548   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.225 -19.778   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.558 -20.548   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.558 -22.088   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.892 -19.778   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      14.226 -20.548   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.456 -21.882   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.226 -23.216   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.456 -24.549   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.766 -23.216   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.898 -24.488   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      16.536 -21.882   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.058 -21.653   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.187 -22.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.621 -22.137   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      21.825 -23.098   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      19.072 -24.236   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.800 -25.103   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      19.167 -25.813   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      17.823 -26.643   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      19.082 -27.529   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      16.365 -27.141   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.912 -28.612   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.442 -25.909   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.328 -24.649   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.766 -20.548   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.996 -19.215   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      15.879 -17.953   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.112 -17.953   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      14.763 -16.557   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      13.880 -15.296   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.346 -15.430   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      14.531 -13.900   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   37   38                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   36                                             
CONECT   22   21                                                            
CONECT   23   21   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30   31   36                                             
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   29   21                                                  
CONECT   37   23   17   38                                                  
CONECT   38   37   17   39   40                                             
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₅₂O₈

Average Mass

612.8040 Da

Monoisotopic Mass

612.36622 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C\C=C\CC(=O)O[C@@]12C[C@@H](C)[C@]3(O)[C@@H]4C=C(C)C(=O)[C@@]4(O)CC(CO)=C[C@H]3[C@@H]1[C@@]2(C)COC(C)=O

InChI Identifier

InChI=1S/C36H52O8/c1-6-7-8-9-10-11-12-13-14-15-16-17-30(39)44-35-20-25(3)36(42)28(31(35)33(35,5)23-43-26(4)38)19-27(22-37)21-34(41)29(36)18-24(2)32(34)40/h13-16,18-19,25,28-29,31,37,41-42H,6-12,17,20-23H2,1-5H3/b14-13+,16-15+/t25-,28+,29-,31-,33-,34-,35+,36-/m1/s1

InChI Key

UYPOIYOXALXFNN-UFANGNBOSA-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

Not Available

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
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary 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	5.11	ALOGPS
logP	4.72	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	172.06 m³·mol⁻¹	ChemAxon
Polarizability	70.93 Å³	ChemAxon
Number of Rings	4	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

28521280

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57408646

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate (NP0146377)

MOL for NP0146377 ((1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate)

3D MOL for NP0146377 ((1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate)

3D SDF for NP0146377 ((1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate)

3D-SDF for NP0146377 ((1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate)

PDB for NP0146377 ((1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate)

3D PDB for NP0146377 ((1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate)

SMILES for NP0146377 ((1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate)

INCHI for NP0146377 ((1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate)

Structure for NP0146377 ((1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate)

3D Structure for NP0146377 ((1r,2s,6r,10s,11r,12s,13s,15r)-12-[(acetyloxy)methyl]-1,6-dihydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (3e,5e)-tetradeca-3,5-dienoate)