NP-MRD: Showing NP-Card for 2-deoxyecdysone (NP0302120)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 15:28:39 UTC

Updated at

2022-09-10 15:28:39 UTC

NP-MRD ID

NP0302120

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-deoxyecdysone

Description

2-Deoxyecdysone belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. Thus, 2-deoxyecdysone is considered to be a sterol lipid molecule. 2-deoxyecdysone is found in Locusta migratoria, Poranopsis discifera, Schistocerca gregaria, Silene brahuica, Silene latifolia, Silene nutans, Silene otites, Silene viridiflora, Silene vulgaris and Tyrophagus putrescentiae. 2-Deoxyecdysone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1652301251918552D          

 34 37  0  0  1  0            999 V2000
   26.2994  -21.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0190  -20.7150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.5798  -20.7643    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.3275  -22.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0224  -19.9224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.4686  -20.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0578  -21.5886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8672  -21.1799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.6153  -19.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5869  -22.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7455  -19.5033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.2959  -19.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0154  -19.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4650  -19.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8672  -22.0042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.1547  -20.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8599  -20.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6149  -23.1779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7490  -18.6928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.1547  -22.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4526  -21.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4546  -18.2876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.0224  -18.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4526  -22.0042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   29.1602  -18.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4475  -17.4493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7261  -22.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8588  -18.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5643  -18.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2698  -18.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5608  -19.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2595  -19.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5725  -21.5571    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.8599  -22.8355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  6  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  1  0  0  0
  6 14  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  1  0  0  0
 10 18  2  0  0  0  0
 11 19  1  1  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 19 23  1  6  0  0  0
 20 24  1  0  0  0  0
 22 25  1  0  0  0  0
 22 26  1  6  0  0  0
 24 27  1  1  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
  9 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 14  1  0  0  0  0
 21 24  1  0  0  0  0
  3 33  1  6  0  0  0
 15 34  1  1  0  0  0
M  END

     RDKit          3D

 76 79  0  0  0  0  0  0  0  0999 V2000
   -2.8268    0.7788   -1.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5499   -0.3826   -1.0627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1371   -0.1668    0.3121 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2065   -1.4552    0.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5773    0.2975    0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1083    0.4724    1.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5446    0.9355    1.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2989   -0.1284    0.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5601    2.2131    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0625    1.1439    2.7249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2363   -0.9970   -1.0157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8819   -1.5318   -2.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -1.5410   -2.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -1.4452   -1.0397 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4432   -2.6038   -0.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3426   -1.2071   -0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948   -1.9523   -1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6605   -1.7837   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5166   -2.6889   -1.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1603   -0.6314    0.0299 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6625   -1.0125    1.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9798    0.1810    2.2433 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2577    0.1668    2.7472 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    1.4425    1.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3760    1.5346    1.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0571    0.4021    0.0542 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0937    1.0300   -1.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7755   -0.2609    0.4169 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6694    0.6910    0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351   -0.0889    0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008   -0.3231   -0.6286 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3256    0.8511   -1.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9560    0.8131   -2.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4790    0.6751   -2.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5762    1.7617   -1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2510   -1.2081   -1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5508    0.5452    0.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5020   -2.0836    0.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507    1.3009   -0.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2217   -0.4354   -0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0685   -0.5455    2.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4804    1.2096    2.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3574   -0.0922    1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2875    0.0668   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9142   -1.1528    0.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6868    2.8305    0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5005    2.7734    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5054    1.9854   -0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9907    0.8130    2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091   -1.9471   -0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2996   -0.9097   -3.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069   -2.5651   -2.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0738   -0.7514   -3.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208   -2.5089   -2.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1076   -3.0415    0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0195   -2.6638   -1.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0371   -0.2437   -0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6142   -1.5703    1.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793   -1.7266    1.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1849    0.2419    3.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5028    1.1237    2.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4337    1.3987    0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1193    2.3440    2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1005    2.4962    0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7459    1.3756    1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1473    1.2213   -1.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7121    0.2978   -2.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716    1.9250   -1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9998   -0.8759    1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922    0.9937    1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6648    1.5714    0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3838    0.3609    1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6226   -1.0642    1.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2144    0.6905   -2.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1253    1.8267   -1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3905    0.8037   -1.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  6
 31 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
 11  2  1  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 16 28  1  0
 26 20  1  0
 26 28  1  0
 14 31  1  0
 28 69  1  1
 29 70  1  0
 29 71  1  0
 30 72  1  0
 30 73  1  0
 32 74  1  0
 32 75  1  0
 32 76  1  0
 11 50  1  1
 12 51  1  0
 12 52  1  0
 13 53  1  0
 13 54  1  0
 15 55  1  0
 17 56  1  0
 20 57  1  6
 21 58  1  0
 21 59  1  0
 22 60  1  1
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 27 66  1  0
 27 67  1  0
 27 68  1  0
  2 36  1  6
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 37  1  1
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
M  END

 
  Mrv1652301251918552D          

 34 37  0  0  1  0            999 V2000
   26.2994  -21.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0190  -20.7150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.5798  -20.7643    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.3275  -22.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0224  -19.9224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.4686  -20.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0578  -21.5886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8672  -21.1799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.6153  -19.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5869  -22.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7455  -19.5033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.2959  -19.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0154  -19.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4650  -19.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8672  -22.0042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.1547  -20.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8599  -20.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6149  -23.1779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7490  -18.6928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.1547  -22.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4526  -21.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4546  -18.2876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.0224  -18.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4526  -22.0042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   29.1602  -18.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4475  -17.4493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7261  -22.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8588  -18.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5643  -18.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2698  -18.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5608  -19.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2595  -19.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5725  -21.5571    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.8599  -22.8355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  6  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  1  0  0  0
  6 14  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  1  0  0  0
 10 18  2  0  0  0  0
 11 19  1  1  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 19 23  1  6  0  0  0
 20 24  1  0  0  0  0
 22 25  1  0  0  0  0
 22 26  1  6  0  0  0
 24 27  1  1  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
  9 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 14  1  0  0  0  0
 21 24  1  0  0  0  0
  3 33  1  6  0  0  0
 15 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0302120

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@]3(C)[C@H](CC[C@@]3(O)C1=CC(=O)[C@]1([H])C[C@@H](O)CC[C@]21C)[C@H](C)[C@H](O)CCC(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O5/c1-16(22(29)9-10-24(2,3)31)18-8-13-27(32)20-15-23(30)21-14-17(28)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-19,21-22,28-29,31-32H,6-14H2,1-5H3/t16-,17-,18+,19-,21-,22+,25+,26+,27+/m0/s1

> <INCHI_KEY>
CRAPXAGGASWTPU-VQOIUDCISA-N

> <FORMULA>
C27H44O5

> <MOLECULAR_WEIGHT>
448.644

> <EXACT_MASS>
448.318874517

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.040020451091245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
2.766111846666667

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.708903937871465

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.729161021298179

> <JCHEM_PKA_STRONGEST_BASIC>
-2.627362688414686

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
126.06320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-JAN-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JAN-19         0                                  
HETATM    1  C   UNK     0      49.092 -39.523   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      50.435 -38.668   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      47.749 -38.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      49.145 -41.145   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      50.442 -37.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      53.141 -38.635   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      50.508 -40.299   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      46.419 -39.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      47.815 -37.201   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      47.762 -41.837   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      51.792 -36.406   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.086 -36.419   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      50.429 -35.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.135 -37.201   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      46.419 -41.075   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.089 -38.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      46.405 -37.977   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      47.814 -43.265   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      51.798 -34.893   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      45.089 -41.844   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      43.778 -39.536   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      53.115 -34.137   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      50.442 -33.803   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      43.778 -41.075   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      54.432 -34.906   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      53.102 -32.572   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      42.422 -41.844   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      55.736 -34.143   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      57.053 -34.913   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      58.370 -34.150   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      57.047 -36.819   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      58.351 -35.669   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0      47.735 -40.240   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      46.405 -42.626   0.000  0.00  0.00           H+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6    7                                             
CONECT    3    1    8    9   33                                             
CONECT    4    1   10                                                       
CONECT    5    2   11   12   13                                             
CONECT    6    2   14                                                       
CONECT    7    2                                                            
CONECT    8    3   15   16   17                                             
CONECT    9    3   12                                                       
CONECT   10    4   18   15                                                  
CONECT   11    5   19   14                                                  
CONECT   12    5    9                                                       
CONECT   13    5                                                            
CONECT   14    6   11                                                       
CONECT   15    8   20   10   34                                             
CONECT   16    8   21                                                       
CONECT   17    8                                                            
CONECT   18   10                                                            
CONECT   19   11   22   23                                                  
CONECT   20   15   24                                                       
CONECT   21   16   24                                                       
CONECT   22   19   25   26                                                  
CONECT   23   19                                                            
CONECT   24   20   27   21                                                  
CONECT   25   22   28                                                       
CONECT   26   22                                                            
CONECT   27   24                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33    3                                                            
CONECT   34   15                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
2-Deoxy-alpha-ecdysone	ChEBI
2-Deoxy-a-ecdysone	Generator
2-Deoxy-α-ecdysone	Generator

Chemical Formula

C₂₇H₄₄O₅

Average Mass

448.6440 Da

Monoisotopic Mass

448.31887 Da

IUPAC Name

(1R,2R,5S,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

(1R,2R,5S,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

Not Available

SMILES

[H][C@]12CC[C@]3(C)[C@H](CC[C@@]3(O)C1=CC(=O)[C@]1([H])C[C@@H](O)CC[C@]21C)[C@H](C)[C@H](O)CCC(C)(C)O

InChI Identifier

InChI=1S/C27H44O5/c1-16(22(29)9-10-24(2,3)31)18-8-13-27(32)20-15-23(30)21-14-17(28)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-19,21-22,28-29,31-32H,6-14H2,1-5H3/t16-,17-,18+,19-,21-,22+,25+,26+,27+/m0/s1

InChI Key

CRAPXAGGASWTPU-VQOIUDCISA-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
Locusta migratoria	LOTUS Database	35616633
Poranopsis discifera	LOTUS Database	35616633
Schistocerca gregaria	LOTUS Database	35616633
Silene brahuica	LOTUS Database	35616633
Silene latifolia	LOTUS Database	35616633
Silene nutans	LOTUS Database	35616633
Silene otites	LOTUS Database	35616633
Silene viridiflora	LOTUS Database	35616633
Silene vulgaris	LOTUS Database	35616633
Tyrophagus putrescentiae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Tetrahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
Cholestane-skeleton
Tetrahydroxy bile acid, alcohol, or derivatives
Ecdysteroid
25-hydroxysteroid
22-hydroxysteroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
6-oxosteroid
3-beta-hydroxysteroid
Delta-7-steroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Ketone
Secondary alcohol
Hydrocarbon derivative
Alcohol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:19566 )
enone (CHEBI:19566 )
6-oxo steroid (CHEBI:19566 )
22-hydroxy steroid (CHEBI:19566 )
25-hydroxy steroid (CHEBI:19566 )
14alpha-hydroxy steroid (CHEBI:19566 )
Cholesterol and derivatives (LMST01010182 )

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	2.91	ALOGPS
logP	2.77	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	13.73	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.06 m³·mol⁻¹	ChemAxon
Polarizability	52.04 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16495

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13939876

PDB ID

Not Available

ChEBI ID

19566

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-deoxyecdysone (NP0302120)

MOL for NP0302120 (2-deoxyecdysone)

3D MOL for NP0302120 (2-deoxyecdysone)

3D SDF for NP0302120 (2-deoxyecdysone)

3D-SDF for NP0302120 (2-deoxyecdysone)

PDB for NP0302120 (2-deoxyecdysone)

3D PDB for NP0302120 (2-deoxyecdysone)

SMILES for NP0302120 (2-deoxyecdysone)

INCHI for NP0302120 (2-deoxyecdysone)

Structure for NP0302120 (2-deoxyecdysone)

3D Structure for NP0302120 (2-deoxyecdysone)