NP-MRD: Showing NP-Card for 4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one (NP0242032)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 02:14:44 UTC

Updated at

2022-09-07 02:14:44 UTC

NP-MRD ID

NP0242032

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one

Description

4-[(1S,2S,5S,7R,10R,11S,13R,14R,15R)-5-{[(2R,3R,4S,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-11,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. 4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one is found in Adenium obesum. Based on a literature review very few articles have been published on 4-[(1S,2S,5S,7R,10R,11S,13R,14R,15R)-5-{[(2R,3R,4S,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-11,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204142D          

 39 44  0  0  1  0            999 V2000
   -0.6870   -5.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067   -5.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385   -4.5355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7507   -4.6807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0310   -5.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825   -4.0500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0946   -4.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0022   -3.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -3.1289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   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  2  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
    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
    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7742    1.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7927   -2.5812    0.0000 O   0  0  0  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
    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850   -3.0585    0.0000 O   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  2  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
   -0.6582   -3.7596    0.0000 C   0  0  2  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  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  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
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 19 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 36 35  1  6  0  0  0
 14 36  1  0  0  0  0
 36 37  1  0  0  0  0
 11 37  1  0  0  0  0
  9 38  1  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END

     RDKit          3D

 85 90  0  0  0  0  0  0  0  0999 V2000
   -7.2948    0.2815   -2.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2041   -0.4721   -2.4906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2292   -0.6871   -1.1134 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2834   -2.1578   -0.8785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6114   -2.4890   -0.5269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3392   -2.5713    0.2149 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0159   -3.0243   -0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2277   -1.6539    1.2154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6947   -0.4405    0.8665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3176   -0.3858    0.9781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101    0.5196    1.8298 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8948    0.0051    2.8991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4407    0.0494    2.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -0.1072    1.0666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4656   -1.4688    0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3132    0.1465    0.8791 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2281   -0.8973    1.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -0.2409    1.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0329   -0.1509   -0.0907 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8991   -1.3564   -0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8504    1.0893   -0.3313 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1620    1.1473    0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4791    2.1491    1.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8305    1.9895    1.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4564    2.7268    2.4582 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3525    0.8622    1.0847 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3574    0.3066    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8861    1.1191   -1.8454 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2344    2.4163   -2.2256 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    0.8063   -2.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8971   -0.0688   -1.0711 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7565   -1.3353   -1.6497 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840    0.3656   -0.5760 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2052    1.8073   -0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    2.1635    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8750    0.9887    0.2878 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0496    1.5646    1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0303    0.0080   -0.5327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2831    1.3772   -0.5894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2625   -0.2063   -2.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2874    1.2244   -2.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1819    0.5761   -3.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1537   -0.1692   -0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0360   -2.7605   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5917   -3.2072    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7926   -3.4967    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8685   -4.1222   -0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218   -2.7931   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1638   -2.5572    0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0919    0.3535    1.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725    1.0774    2.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233    0.6871    3.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -0.9994    3.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0044    1.0408    2.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1108   -0.7069    3.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4141   -2.0845    0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1013   -1.4498   -0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9781   -2.0367    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    1.0897    1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3275   -1.8157    0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -1.1580    2.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2998   -0.8808    1.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    0.7393    1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6916   -1.1990   -1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1994   -1.8664    0.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2180   -2.1265   -0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2006    1.9483   -0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8450    2.9682    1.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2214   -0.7346    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.2261   -0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5899    0.4303   -2.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0574    2.4256   -2.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218    0.3242   -3.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9240    1.7662   -2.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2001   -1.2021   -2.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877   -0.2109   -1.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9983    2.5300   -0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8239    1.9059   -1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3520    2.6710    0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028    2.9231   -0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2150    0.6109   -0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7485    2.4244    1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457    1.9672    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1644   -0.1803   -1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0804    1.6721   -1.5114 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  6
 14 36  1  0
 36 35  1  0
 35 34  1  0
 34 33  1  0
 33 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  6
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 36 37  1  0
  9 38  1  0
 38 39  1  0
 38  3  1  0
 37 11  1  0
 16 14  1  0
 31 19  1  0
 27 22  1  0
 31 33  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  1
  4 44  1  6
  5 45  1  0
  6 46  1  1
  7 47  1  0
  7 48  1  0
  7 49  1  0
  9 50  1  1
 11 51  1  1
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 15 56  1  0
 15 57  1  0
 15 58  1  0
 36 81  1  6
 35 79  1  0
 35 80  1  0
 34 77  1  0
 34 78  1  0
 33 76  1  6
 16 59  1  1
 17 60  1  0
 17 61  1  0
 18 62  1  0
 18 63  1  0
 20 64  1  0
 20 65  1  0
 20 66  1  0
 21 67  1  1
 28 71  1  6
 29 72  1  0
 30 73  1  0
 30 74  1  0
 32 75  1  0
 23 68  1  0
 27 69  1  0
 27 70  1  0
 37 82  1  0
 37 83  1  0
 38 84  1  6
 39 85  1  0
M  END


  Mrv1652309072204142D          

 39 44  0  0  1  0            999 V2000
   -0.6870   -5.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067   -5.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385   -4.5355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7507   -4.6807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0310   -5.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825   -4.0500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0946   -4.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0022   -3.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -3.1289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   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  2  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
    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
    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7742    1.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7927   -2.5812    0.0000 O   0  0  0  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
    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850   -3.0585    0.0000 O   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  2  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
   -0.6582   -3.7596    0.0000 C   0  0  2  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  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  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
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 19 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 36 35  1  6  0  0  0
 14 36  1  0  0  0  0
 36 37  1  0  0  0  0
 11 37  1  0  0  0  0
  9 38  1  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0242032

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@H](O)[C@@H](C)O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H]([C@H](O)C[C@]43O)C3=CC(=O)OC3)C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O9/c1-15-24(33)26(36-4)25(34)27(38-15)39-18-7-9-28(2)17(12-18)5-6-20-19(28)8-10-29(3)23(16-11-22(32)37-14-16)21(31)13-30(20,29)35/h11,15,17-21,23-27,31,33-35H,5-10,12-14H2,1-4H3/t15-,17-,18+,19+,20-,21-,23+,24-,25-,26+,27+,28+,29-,30+/m1/s1

> <INCHI_KEY>
CPFNIKYEDJFRAT-JALCIOOHSA-N

> <FORMULA>
C30H46O9

> <MOLECULAR_WEIGHT>
550.689

> <EXACT_MASS>
550.314183061

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
60.08932501795546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1S,2S,5S,7R,10R,11S,13R,14R,15R)-5-{[(2R,3R,4S,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-11,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
1.6049966086666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.288114273639913

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.831024134054796

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9014290478101277

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
140.81029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,2S,5S,7R,10R,11S,13R,14R,15R)-5-{[(2R,3R,4S,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-11,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.282 -11.092   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.759  -9.644   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.752  -8.466   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.268  -8.737   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.791 -10.186   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.261  -7.560   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.777  -7.831   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.737  -6.112   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.221  -5.841   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.728   0.744   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.779   2.283   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      11.944  -0.202   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.813  -4.818   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.505  -5.709   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.229  -7.018   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.287  -6.747   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   38                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   37                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   36                                             
CONECT   15   14                                                            
CONECT   16   14   17   33                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   31                                             
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   22                                                       
CONECT   28   21   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   19   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   16   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   14   37                                                  
CONECT   37   36   11                                                       
CONECT   38    9    3   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₉

Average Mass

550.6890 Da

Monoisotopic Mass

550.31418 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](O)[C@@H](C)O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H]([C@H](O)C[C@]43O)C3=CC(=O)OC3)C2)[C@@H]1O

InChI Identifier

InChI=1S/C30H46O9/c1-15-24(33)26(36-4)25(34)27(38-15)39-18-7-9-28(2)17(12-18)5-6-20-19(28)8-10-29(3)23(16-11-22(32)37-14-16)21(31)13-30(20,29)35/h11,15,17-21,23-27,31,33-35H,5-10,12-14H2,1-4H3/t15-,17-,18+,19+,20-,21-,23+,24-,25-,26+,27+,28+,29-,30+/m1/s1

InChI Key

CPFNIKYEDJFRAT-JALCIOOHSA-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
Adenium obesum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
Steroidal glycoside
16-hydroxysteroid
16-alpha-hydroxysteroid
Hydroxysteroid
14-hydroxysteroid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163187600

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one (NP0242032)

MOL for NP0242032 (4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D MOL for NP0242032 (4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D SDF for NP0242032 (4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D-SDF for NP0242032 (4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

PDB for NP0242032 (4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D PDB for NP0242032 (4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

SMILES for NP0242032 (4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

INCHI for NP0242032 (4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

Structure for NP0242032 (4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D Structure for NP0242032 (4-[(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,3a-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)