NP-MRD: Showing NP-Card for (3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one (NP0278234)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 03:11:32 UTC

Updated at

2022-09-09 03:11:32 UTC

NP-MRD ID

NP0278234

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one

Description

Pachystermine A belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. (3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one is found in Pachysandra terminalis. (3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one was first documented in 2000 (PMID: 10706399). Based on a literature review very few articles have been published on Pachystermine A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092205112D          

 33 37  0  0  1  0            999 V2000
   -3.1507   -3.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8704   -2.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4022   -2.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -2.5583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5867   -1.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -0.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.9700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -0.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4220   -1.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   -3.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813   -3.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2361   -3.8420    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 17 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 29 28  1  1  0  0  0
 10 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  2  0  0  0  0
  6 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

 81 85  0  0  0  0  0  0  0  0999 V2000
    8.4633   -0.1785   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0664    0.2847    0.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4021    1.7520    0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6418    0.1029    0.7699 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1090   -1.3312    0.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8427   -0.6697    0.4427 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -0.9375    0.7871 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8491    0.1774    1.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667    0.1453    1.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7452   -0.1534    0.2455 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1948    0.9716   -0.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7320   -0.2795    0.3720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3459    0.7698    1.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8766    0.6410    1.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2325    0.8696   -0.2351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5782    2.1589   -0.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7984   -0.3258   -1.0399 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3533    0.0432   -2.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6107    0.8719   -2.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6791    0.9556   -0.5684 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5500   -0.1643   -0.1529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9660    0.1538   -0.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5448   -0.5155    1.2180 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9982    0.4741    2.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3676   -1.7118    1.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2983   -0.4107   -0.9885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8736   -1.7974   -1.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6048   -1.9495   -1.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729   -1.4822   -0.2609 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7412   -1.2651   -0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119   -1.3616   -1.5563 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6230    0.2625   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4043    0.8687   -1.3628 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5935   -0.1746   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1683   -1.2253   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1550    0.4956   -1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6943   -0.2652    1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2743    1.9982    1.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6900    2.3990    0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4534    1.8862    0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3676    0.6235    1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1567   -1.8137    1.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4695   -1.9232   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890   -1.8577    1.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2827    1.1723    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864    0.0241    2.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853   -0.5144    2.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0066    1.1804    1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7529    1.9390   -0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0807    0.7012   -1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3080    1.1327   -0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153   -1.2643    0.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0857    0.5543    2.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0217    1.7878    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0801   -0.3755    1.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2479    1.4391    1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1269    2.7027   -1.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5959    2.8399    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466    2.0646   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760   -1.2155   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6867   -0.8853   -2.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176    0.6135   -2.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5185    0.3582   -2.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5849    1.8505   -2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1461    1.9177   -0.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2843   -1.1089   -0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7162   -0.2368    0.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0715    1.2713   -0.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1871   -0.3101   -1.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0476    0.3492    2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7922    1.4764    1.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3147    0.4124    3.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2728   -1.4932    1.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7908   -2.5609    1.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7368   -2.0931    0.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071    0.2907   -1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2420   -1.8442   -2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4015   -2.5441   -0.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8126   -3.0559   -1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0265   -1.4899   -2.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1374   -2.1975    0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
  6 32  1  0
 32 33  2  0
 32  4  1  0
 30  7  1  0
 29 10  1  0
 26 12  1  0
 17 15  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  1
  5 42  1  0
  5 43  1  0
  7 44  1  1
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 11 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  1
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 16 57  1  0
 16 58  1  0
 16 59  1  0
 20 65  1  6
 19 63  1  0
 19 64  1  0
 18 61  1  0
 18 62  1  0
 17 60  1  1
 26 76  1  6
 27 77  1  0
 27 78  1  0
 28 79  1  0
 28 80  1  0
 29 81  1  1
 21 66  1  6
 22 67  1  0
 22 68  1  0
 22 69  1  0
 24 70  1  0
 24 71  1  0
 24 72  1  0
 25 73  1  0
 25 74  1  0
 25 75  1  0
M  END


  Mrv1652309092205112D          

 33 37  0  0  1  0            999 V2000
   -3.1507   -3.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8704   -2.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4022   -2.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -2.5583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5867   -1.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -0.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.9700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -0.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4220   -1.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   -3.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813   -3.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2361   -3.8420    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 17 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 29 28  1  1  0  0  0
 10 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  2  0  0  0  0
  6 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0278234

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1CN([C@H]2CC[C@]3(C)[C@H]4CC[C@]5(C)[C@@H](CC[C@H]5[C@@H]4CC[C@H]3C2=O)C(C)N(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H48N2O2/c1-17(2)20-16-31(27(20)33)25-13-15-29(5)23-12-14-28(4)21(18(3)30(6)7)10-11-22(28)19(23)8-9-24(29)26(25)32/h17-25H,8-16H2,1-7H3/t18?,19-,20-,21-,22-,23-,24-,25-,28+,29+/m0/s1

> <INCHI_KEY>
MHFGHEARXPBTQH-PTKYFECBSA-N

> <FORMULA>
C29H48N2O2

> <MOLECULAR_WEIGHT>
456.715

> <EXACT_MASS>
456.371578794

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.3356594462755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-1-[(1S,2R,5S,7R,10S,11S,14R,15S)-14-[1-(dimethylamino)ethyl]-2,15-dimethyl-6-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]-3-(propan-2-yl)azetidin-2-one

> <JCHEM_LOGP>
5.229142400333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.866008385342806

> <JCHEM_PKA_STRONGEST_BASIC>
9.600296987933813

> <JCHEM_POLAR_SURFACE_AREA>
40.620000000000005

> <JCHEM_REFRACTIVITY>
134.01399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-1-[(1S,2R,5S,7R,10S,11S,14R,15S)-14-[1-(dimethylamino)ethyl]-2,15-dimethyl-6-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]-3-isopropylazetidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.881  -6.495   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.358  -5.047   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.351  -3.869   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.842  -4.775   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.962  -3.512   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -1.698  -4.392   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.302  -0.173   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      11.407  -1.811   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      12.353  -0.595   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.988  -3.237   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.287  -6.747   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.579  -5.656   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.307  -7.172   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   29                                             
CONECT   11   10                                                            
CONECT   12   10   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   20                                             
CONECT   16   15                                                            
CONECT   17   15   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   17   12   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   10   30                                                  
CONECT   30   29    7   31                                                  
CONECT   31   30                                                            
CONECT   32    6    4   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₈N₂O₂

Average Mass

456.7150 Da

Monoisotopic Mass

456.37158 Da

IUPAC Name

(3R)-1-[(1S,2R,5S,7R,10S,11S,14R,15S)-14-[1-(dimethylamino)ethyl]-2,15-dimethyl-6-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]-3-(propan-2-yl)azetidin-2-one

Traditional Name

(3R)-1-[(1S,2R,5S,7R,10S,11S,14R,15S)-14-[1-(dimethylamino)ethyl]-2,15-dimethyl-6-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]-3-isopropylazetidin-2-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1CN([C@H]2CC[C@]3(C)[C@H]4CC[C@]5(C)[C@@H](CC[C@H]5[C@@H]4CC[C@H]3C2=O)C(C)N(C)C)C1=O

InChI Identifier

InChI=1S/C29H48N2O2/c1-17(2)20-16-31(27(20)33)25-13-15-29(5)23-12-14-28(4)21(18(3)30(6)7)10-11-22(28)19(23)8-9-24(29)26(25)32/h17-25H,8-16H2,1-7H3/t18?,19-,20-,21-,22-,23-,24-,25-,28+,29+/m0/s1

InChI Key

MHFGHEARXPBTQH-PTKYFECBSA-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
Pachysandra terminalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

22-azasteroid
Pregnane-skeleton
Pregnane-type alkaloid
Steroidal alkaloid
Oxosteroid
4-oxosteroid
Azasteroid
Monobactam
Alkaloid or derivatives
Beta-lactam
Tertiary carboxylic acid amide
Tertiary amine
Amino acid or derivatives
Azetidine
Carboxamide group
Tertiary aliphatic amine
Lactam
Ketone
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organic oxide
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
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	5.23	ChemAxon
pKa (Strongest Acidic)	19.87	ChemAxon
pKa (Strongest Basic)	9.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	134.01 m³·mol⁻¹	ChemAxon
Polarizability	56.34 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

C00053620

Chemspider ID

21131

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22532

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Funayama S, Noshita T, Shinoda K, Haga N, Nozoe S, Hayashi M, Komiyama K: Cytotoxic alkaloids of Pachysandra terminalis. Biol Pharm Bull. 2000 Feb;23(2):262-4. doi: 10.1248/bpb.23.262. [PubMed:10706399 ]
LOTUS database [Link]

Showing NP-Card for (3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one (NP0278234)

MOL for NP0278234 ((3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

3D MOL for NP0278234 ((3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

3D SDF for NP0278234 ((3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

3D-SDF for NP0278234 ((3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

PDB for NP0278234 ((3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

3D PDB for NP0278234 ((3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

SMILES for NP0278234 ((3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

INCHI for NP0278234 ((3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

Structure for NP0278234 ((3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

3D Structure for NP0278234 ((3r)-1-[(1r,3as,3bs,5ar,7s,9ar,9bs,11as)-1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)