NP-MRD: Showing NP-Card for (1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one (NP0219487)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 20:29:33 UTC

Updated at

2022-09-05 20:29:34 UTC

NP-MRD ID

NP0219487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one

Description

Puqietinone belongs to the class of organic compounds known as 22,26-epiminocholestanes. These are steroid alkaloids obtained by reduction of spirosolane through opening of the E-ring. (1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one is found in Fritillaria monantha and Fritillaria puqiensis. (1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one was first documented in 2005 (PMID: 15730259). Based on a literature review a small amount of articles have been published on Puqietinone (PMID: 22658466) (PMID: 19686814) (PMID: 17080553).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052222292D          

 31 35  0  0  1  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7071   -2.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9401   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  3  2  1  6  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  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  2  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 17  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 11 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END

     RDKit          3D

 78 82  0  0  0  0  0  0  0  0999 V2000
    2.1601   -0.6652    1.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -0.7145    0.1839 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7522   -0.6272   -0.3054 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5818   -1.7883    0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9913   -1.5720   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5371   -0.4050    0.5842 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8126    0.1231   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4954    0.6408    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4120    0.6112   -0.1473 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8837    1.1597   -1.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.1750   -0.6342 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5741    1.6459   -0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1350    2.1427   -0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6361    1.0061   -0.0706 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0804    0.9352   -0.4663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7418    2.2484   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2091    2.0396   -0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9217    2.7010   -1.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7921    0.9546    0.4390 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2861    0.8947    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7463    0.0119    1.5416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7243   -0.8793    1.0884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6131   -0.7857    2.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7404   -1.3973    0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1361   -0.3750    0.0925 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4262   -0.7564   -1.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552   -0.2197    0.2928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9585   -1.4857   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4491   -1.3804   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375   -0.1877   -0.7674 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3932   -0.2706   -2.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1419   -0.4934    2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4960    0.1203    2.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285   -1.6474    2.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9879   -1.7706   -0.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7823   -0.8490   -1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1422   -2.7426   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5939   -1.7443    1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9298   -1.2447   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6246   -2.4667   -0.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8098   -0.8470    1.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7212   -0.2878    0.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9152    1.2117    0.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9550   -0.1892   -1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1694    0.6564    1.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0076    1.6345    0.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5963    2.2154   -1.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9894    1.1468   -1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    0.5876   -2.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9068    0.0901   -1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8058    1.8736    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2770    2.1967   -0.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0348    2.3945   -1.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080    3.0935   -0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5043    0.9072    1.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1101    0.7776   -1.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4793    2.7004    0.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367    2.9447   -1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5101    1.1579    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6587    1.9171    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7206    0.5797   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1753    0.6071    2.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5392   -0.8238    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0147   -0.2859    2.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0687   -1.6839    2.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4564   -2.0581    0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0577   -2.0717    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6134   -0.5158   -2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401   -1.8711   -1.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3496   -0.3384   -1.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921   -0.0197    1.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2075   -2.2573    0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3504   -1.9076   -1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517   -1.1985    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321   -2.3281   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241    0.7285   -2.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4613   -0.7999   -2.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2711   -0.8788   -2.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 30 11  1  0
  9  3  1  0
 30 14  1  0
 27 15  1  0
 25 19  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  6
 11 50  1  6
 12 51  1  0
 12 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  1
 15 56  1  6
 16 57  1  0
 16 58  1  0
 19 59  1  1
 20 60  1  0
 20 61  1  0
 21 62  1  1
 22 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 24 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  1
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
  3 36  1  6
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  1
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
 10 47  1  0
 10 48  1  0
 10 49  1  0
M  END


  Mrv1652309052222292D          

 31 35  0  0  1  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7071   -2.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9401   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  3  2  1  6  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  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  2  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 17  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 11 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0219487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@@H]1CC[C@H]2[C@@H]3CC(=O)[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@@H]1CC[C@@H](C)CN1C

> <INCHI_IDENTIFIER>
InChI=1S/C28H47NO2/c1-17-6-9-25(29(5)16-17)18(2)21-7-8-22-20-15-26(31)24-14-19(30)10-12-28(24,4)23(20)11-13-27(21,22)3/h17-25,30H,6-16H2,1-5H3/t17-,18+,19+,20+,21+,22+,23+,24-,25+,27-,28-/m1/s1

> <INCHI_KEY>
HEOBUSMYCWXIQQ-OXZWOSNHSA-N

> <FORMULA>
C28H47NO2

> <MOLECULAR_WEIGHT>
429.689

> <EXACT_MASS>
429.360679757

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.42055446093691

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,7S,10S,11S,14S,15S)-14-[(1S)-1-[(2S,5R)-1,5-dimethylpiperidin-2-yl]ethyl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-8-one

> <JCHEM_LOGP>
5.155051888000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.709549437410562

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.234294654958099

> <JCHEM_PKA_STRONGEST_BASIC>
9.914053888660016

> <JCHEM_POLAR_SURFACE_AREA>
40.540000000000006

> <JCHEM_REFRACTIVITY>
127.34349999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7S,10S,11S,14S,15S)-14-[(1S)-1-[(2S,5R)-1,5-dimethylpiperidin-2-yl]ethyl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.320  -5.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.676  -4.226   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.622  -3.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    2   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   30                                                  
CONECT   15   14   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   15   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   11   14   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₇NO₂

Average Mass

429.6890 Da

Monoisotopic Mass

429.36068 Da

IUPAC Name

(1S,2R,5S,7S,10S,11S,14S,15S)-14-[(1S)-1-[(2S,5R)-1,5-dimethylpiperidin-2-yl]ethyl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-8-one

Traditional Name

(1S,2R,5S,7S,10S,11S,14S,15S)-14-[(1S)-1-[(2S,5R)-1,5-dimethylpiperidin-2-yl]ethyl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-8-one

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@@H]1CC[C@H]2[C@@H]3CC(=O)[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@@H]1CC[C@@H](C)CN1C

InChI Identifier

InChI=1S/C28H47NO2/c1-17-6-9-25(29(5)16-17)18(2)21-7-8-22-20-15-26(31)24-14-19(30)10-12-28(24,4)23(20)11-13-27(21,22)3/h17-25,30H,6-16H2,1-5H3/t17-,18+,19+,20+,21+,22+,23+,24-,25+,27-,28-/m1/s1

InChI Key

HEOBUSMYCWXIQQ-OXZWOSNHSA-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
Fritillaria monantha	LOTUS Database	35616633
Fritillaria puqiensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 22,26-epiminocholestanes. These are steroid alkaloids obtained by reduction of spirosolane through opening of the E-ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

22,26-epiminocholestanes

Alternative Parents

Substituents

22,26-epiminocholestane skeleton
Progestogin-skeleton
Pregnane-skeleton
3-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-beta-hydroxysteroid
6-oxosteroid
Piperidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.16	ChemAxon
pKa (Strongest Acidic)	15.23	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	127.34 m³·mol⁻¹	ChemAxon
Polarizability	53.42 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00028660

Chemspider ID

24709227

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44583920

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jiang Y, Li H, Li P, Cai Z, Ye W: Steroidal alkaloids from the bulbs of Fritillaria puqiensis. J Nat Prod. 2005 Feb;68(2):264-7. doi: 10.1021/np0497649. [PubMed:15730259 ]
Xin GZ, Cao L, Shi ZQ, Li HJ, Wen XD, Chen J, Qi LW, Li P: Direct pharmacokinetic analysis of puqietinone by in vivo microdialysis sampling and turbulent-flow chromatography coupled with liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jun 15;899:127-34. doi: 10.1016/j.jchromb.2012.05.012. Epub 2012 May 17. [PubMed:22658466 ]
An JJ, Zhou JL, Li HJ, Jiang Y, Li P: Puqienine E: an angiotensin converting enzyme inhibitory steroidal alkaloid from Fritillaria puqiensis. Fitoterapia. 2010 Apr;81(3):149-52. doi: 10.1016/j.fitote.2009.08.012. Epub 2009 Aug 15. [PubMed:19686814 ]
Zhou Y, Ji H, Lin BQ, Jiang Y, Li P: The effects of five alkaloids from Bulbus Fritillariae on the concentration of cAMP in HEK cells transfected with muscarinic M(2) receptor plasmid. Am J Chin Med. 2006;34(5):901-10. doi: 10.1142/S0192415X06004375. [PubMed:17080553 ]
LOTUS database [Link]

Showing NP-Card for (1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one (NP0219487)

MOL for NP0219487 ((1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D MOL for NP0219487 ((1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D SDF for NP0219487 ((1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D-SDF for NP0219487 ((1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

PDB for NP0219487 ((1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D PDB for NP0219487 ((1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

SMILES for NP0219487 ((1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

INCHI for NP0219487 ((1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

Structure for NP0219487 ((1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D Structure for NP0219487 ((1s,3as,3bs,5as,7s,9ar,9bs,11as)-1-[(1s)-1-[(2s,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)