NP-MRD: Showing NP-Card for 3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate (NP0156112)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 13:16:52 UTC

Updated at

2022-09-02 13:16:53 UTC

NP-MRD ID

NP0156112

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate

Description

11-Hydroxy-2,15-dimethyl-14-(2-oxo-2H-pyran-5-yl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-6-en-13-yl acetate belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. 3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate is found in Drimia maritima. Based on a literature review very few articles have been published on 11-hydroxy-2,15-dimethyl-14-(2-oxo-2H-pyran-5-yl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-6-en-13-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215162D          

 43 48  0  0  0  0            999 V2000
    2.5485   -0.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -0.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1419   -0.3243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630   -1.4167    0.0000 O   0  0  0  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  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  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
    6.6095   -1.3047    0.0000 C   0  0  0  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  0  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
    9.2974   -2.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5489   -3.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2686   -4.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8004   -5.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8928   -4.1678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6413   -2.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4534   -2.6160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1095   -2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3898   -1.3546    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  0  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  0  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  0  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
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492   -4.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0429   -5.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  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
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  9 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 37 43  2  0  0  0  0
M  END

     RDKit          3D

 87 92  0  0  0  0  0  0  0  0999 V2000
   -7.4697   -0.4073   -3.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7822   -1.1099   -2.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1797   -2.2419   -2.0706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7053   -0.5484   -1.8443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0117   -1.1858   -0.7577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5908   -1.3741   -1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930   -0.1418   -0.7287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8470    0.6983   -1.8819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755   -0.2742   -0.3368 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1186   -1.4308    0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954   -1.4153    1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -0.1654    0.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490   -0.2544    0.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    0.9113    0.2334 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2879    0.3419   -0.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5139    0.3641    0.1184 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9831   -0.8910    0.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -1.4746   -0.4444 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1784   -1.6893    0.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7112   -0.4865    0.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9949   -0.8425   -1.7777 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9266   -1.1543   -2.6138 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2589    0.6197   -1.6916 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6217    0.8819   -1.5423 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5072    1.2476   -0.5732 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7725    2.3303   -1.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401    1.9871   -0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0968    1.7381   -0.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    1.1496    0.4465 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6752    2.1239    1.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0679    1.0539    0.2844 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7263    1.0998    1.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1990    0.7995    1.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806    0.5404    0.2723 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2314    1.9108   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0524   -0.2704    0.4021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2582   -0.8953    1.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0830   -0.3235    2.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2364   -0.9368    3.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5678   -2.1286    4.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7196   -2.6844    5.2862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7988   -2.6147    3.2213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6161   -2.0688    2.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7483   -1.1576   -4.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3054    0.1905   -3.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7136    0.2565   -4.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5458   -2.1471   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245   -2.3226   -0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6094   -1.4738   -2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7063    0.1420   -2.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8382   -0.3633   -1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -1.5073    1.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -2.3615   -0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557   -2.3226    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -1.4904    2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8179   -1.2447    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076    1.2260    1.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232    0.8535    1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4689   -2.5277   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0595   -2.3463    1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8892   -2.2399   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6928   -0.4534    0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8998   -1.3127   -2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8713   -2.1618   -2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9896    1.0694   -2.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7603    1.7189   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1781    1.7363    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3797    2.8126   -1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    2.0728   -1.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513    2.9980   -0.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131    2.7415   -0.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9612    1.0538   -1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277    2.4792    1.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3661    1.6938    2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0730    3.0480    1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254    1.8694   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696    0.3854    2.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5794    2.0948    2.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839   -0.0027    2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7641    1.6722    2.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6118    2.7288    0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3252    1.8106   -1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2795    2.1153    0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9572    0.4104    0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5885    0.5908    2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8672   -0.5527    4.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9417   -2.5708    1.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  6
 34 36  1  0
 36 37  1  0
 37 43  2  0
 43 42  1  0
 42 40  1  0
 40 41  2  0
 40 39  1  0
 39 38  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 36  5  1  0
 38 37  1  0
 25 16  1  0
 34  7  1  0
 31  9  1  0
 29 12  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  5 47  1  1
  6 48  1  0
  6 49  1  0
  8 50  1  0
  9 51  1  6
 10 52  1  0
 10 53  1  0
 11 54  1  0
 11 55  1  0
 13 56  1  0
 14 57  1  1
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 30 73  1  0
 30 74  1  0
 30 75  1  0
 31 76  1  6
 32 77  1  0
 32 78  1  0
 33 79  1  0
 33 80  1  0
 35 81  1  0
 35 82  1  0
 35 83  1  0
 36 84  1  6
 43 87  1  0
 39 86  1  0
 38 85  1  0
 16 58  1  1
 18 59  1  6
 19 60  1  0
 19 61  1  0
 20 62  1  0
 21 63  1  6
 22 64  1  0
 23 65  1  6
 24 66  1  0
 25 67  1  1
 26 68  1  0
M  END


  Mrv1652309022215162D          

 43 48  0  0  0  0            999 V2000
    2.5485   -0.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -0.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1419   -0.3243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630   -1.4167    0.0000 O   0  0  0  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  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  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
    6.6095   -1.3047    0.0000 C   0  0  0  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  0  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
    9.2974   -2.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5489   -3.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2686   -4.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8004   -5.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8928   -4.1678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6413   -2.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4534   -2.6160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1095   -2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3898   -1.3546    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  0  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  0  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  0  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
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492   -4.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0429   -5.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  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
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  9 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 37 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0156112

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2(O)C3CCC4=CC(CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C32H44O11/c1-16(34)41-22-13-32(39)21-6-5-18-12-19(42-29-28(38)27(37)26(36)23(14-33)43-29)8-10-30(18,2)20(21)9-11-31(32,3)25(22)17-4-7-24(35)40-15-17/h4,7,12,15,19-23,25-29,33,36-39H,5-6,8-11,13-14H2,1-3H3

> <INCHI_KEY>
YNJFTCNGKDLURQ-UHFFFAOYSA-N

> <FORMULA>
C32H44O11

> <MOLECULAR_WEIGHT>
604.693

> <EXACT_MASS>
604.288362237

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
63.823276401217015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-hydroxy-2,15-dimethyl-14-(2-oxo-2H-pyran-5-yl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-13-yl acetate

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
0.31582044399999865

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.151158570648686

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.204184470856973

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810836832070953

> <JCHEM_POLAR_SURFACE_AREA>
172.21

> <JCHEM_REFRACTIVITY>
152.29840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-2,15-dimethyl-14-(6-oxopyran-3-yl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.757  -0.136   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.580  -1.129   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.132  -0.605   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.832  -5.696   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      17.825  -6.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.301  -8.322   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.294  -9.499   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      20.333  -7.780   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      21.380  -4.883   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      18.871  -3.977   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      19.394  -2.529   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.892  -8.295   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.947  -9.510   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       2.312  -6.868   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   34                                             
CONECT    8    7                                                            
CONECT    9    7   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   14   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   12   30   31                                             
CONECT   30   29                                                            
CONECT   31   29    9   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    7   35   36                                             
CONECT   35   34                                                            
CONECT   36   34    5   37                                                  
CONECT   37   36   38   43                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   37                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
11-Hydroxy-2,15-dimethyl-14-(2-oxo-2H-pyran-5-yl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0,.0,]heptadec-6-en-13-yl acetic acid	Generator

Chemical Formula

C₃₂H₄₄O₁₁

Average Mass

604.6930 Da

Monoisotopic Mass

604.28836 Da

IUPAC Name

11-hydroxy-2,15-dimethyl-14-(2-oxo-2H-pyran-5-yl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-13-yl acetate

Traditional Name

11-hydroxy-2,15-dimethyl-14-(6-oxopyran-3-yl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-13-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2(O)C3CCC4=CC(CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C32H44O11/c1-16(34)41-22-13-32(39)21-6-5-18-12-19(42-29-28(38)27(37)26(36)23(14-33)43-29)8-10-30(18,2)20(21)9-11-31(32,3)25(22)17-4-7-24(35)40-15-17/h4,7,12,15,19-23,25-29,33,36-39H,5-6,8-11,13-14H2,1-3H3

InChI Key

YNJFTCNGKDLURQ-UHFFFAOYSA-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
Drimia maritima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
Steroidal glycoside
Steroid ester
14-hydroxysteroid
Hydroxysteroid
Delta-4-steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Pyranone
Pyran
Monosaccharide
Oxane
Tertiary alcohol
Cyclic alcohol
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.08	ALOGPS
logP	0.32	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	152.3 m³·mol⁻¹	ChemAxon
Polarizability	63.82 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

162846049

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate (NP0156112)

MOL for NP0156112 (3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate)

3D MOL for NP0156112 (3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate)

3D SDF for NP0156112 (3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate)

3D-SDF for NP0156112 (3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate)

PDB for NP0156112 (3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate)

3D PDB for NP0156112 (3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate)

SMILES for NP0156112 (3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate)

INCHI for NP0156112 (3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate)

Structure for NP0156112 (3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate)

3D Structure for NP0156112 (3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate)