NP-MRD: Showing NP-Card for (1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde (NP0153081)

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Record Information

Version

2.0

Created at

2022-09-02 09:40:59 UTC

Updated at

2022-09-02 09:41:00 UTC

NP-MRD ID

NP0153081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde

Description

(1S,2S,5S,7S,10R,11S,13S,14S,15R)-7,11,13-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carbaldehyde 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. Thus, (1S,2S,5S,7S,10R,11S,13S,14S,15R)-7,11,13-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carbaldehyde is considered to be a sterol. (1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde is found in Drimia elata. Based on a literature review very few articles have been published on (1S,2S,5S,7S,10R,11S,13S,14S,15R)-7,11,13-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carbaldehyde.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309022211412D          

 42 47  0  0  1  0            999 V2000
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    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
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
    6.8898   -0.5288    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2974   -2.2757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1095   -2.1305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6413   -2.7612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4534   -2.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9852   -3.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  1  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
    9.5489   -3.6824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2686   -4.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    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  2  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
    6.5807   -3.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  2  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
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  2  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
    3.0683   -2.4895    0.0000 C   0  0  2  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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  2  0  0  0  0
  6 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 36 42  2  0  0  0  0
M  END

     RDKit          3D

 84 89  0  0  0  0  0  0  0  0999 V2000
    4.5993   -1.3560    1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2311   -0.0839    0.2832 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6180    0.8522    1.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2267    0.5250    1.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3457    0.6183    0.4436 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8611   -0.3994   -0.5107 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0352   -0.2769   -1.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320   -0.8027   -1.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9613   -0.1087   -0.2646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9311   -0.9874    0.2756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    1.0632   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8553    1.3473    0.2005 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6992    0.2669    0.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0112    0.5582   -0.1367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8075    0.2237    0.9577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1528    0.3439    0.7250 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8762    0.0825    2.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2566    0.1868    1.8721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5583   -0.7635   -0.2302 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.9205   -0.6934   -0.4680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8139   -0.5152   -1.5236 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0408   -1.5958   -2.3566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3472   -0.3223   -1.3220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8502    0.3477   -2.4639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1498    1.5732    1.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6461    1.6767    1.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0733    0.3511    0.8194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0554   -0.5710    2.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5110   -0.2810    3.0894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2850   -0.2961   -0.8652 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6194   -1.4129   -1.6462 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5969    0.9187   -1.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1207    0.8157   -1.7911 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5221   -0.2148   -2.6034 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4396    0.6100   -0.3282 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7123   -0.0541   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9854   -1.3157   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2048   -1.9422   -0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1672   -1.2692    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2701   -1.8187    0.6465 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8889   -0.0694    0.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7499    0.5367    0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4659   -2.2669    0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8992   -1.5005    1.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6023   -1.2752    1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3106    0.9564    2.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6019    1.8689    0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9145    1.2577    2.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1358   -0.5054    2.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4384    1.6505    0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503   -1.4009   -0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9664    0.8155   -2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -0.8762   -2.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0041   -0.7374   -2.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1681   -1.8799   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5187   -1.8182    0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1476    1.9323   -1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2079    0.7016   -1.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4381    2.2348   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1559    1.6270   -0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3970    1.3227    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5541    0.7550    2.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6714   -0.9606    2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7266   -0.6727    2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2494   -1.7258    0.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2452   -1.6244   -0.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2236    0.4289   -1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9338   -1.5050   -2.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8073   -1.2957   -1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4865    1.0967   -2.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002    0.8262    2.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4817    2.5579    1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2355    1.8624    2.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522    2.5262    0.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4381   -1.2921   -2.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3451    1.8657   -1.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1472    0.8041   -2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5716    1.7612   -2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4137   -0.0938   -3.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5350    1.6553    0.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2725   -1.8568   -1.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3955   -2.9333   -0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6239    1.5247    1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  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  1
  9 11  1  0
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 12 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 28 29  2  0
 12 13  1  0
 13 14  1  0
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 15 16  1  0
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  6 30  1  0
 30 31  1  6
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 30  2  1  0
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 35  2  1  0
 27  5  1  0
 23 14  1  0
 27  9  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  3 46  1  0
  3 47  1  0
  4 48  1  0
  4 49  1  0
  5 50  1  6
  6 51  1  1
  7 52  1  0
  7 53  1  0
  8 54  1  0
  8 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 12 59  1  6
 25 71  1  0
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 14 60  1  6
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 18 64  1  0
 19 65  1  1
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 22 68  1  0
 23 69  1  1
 24 70  1  0
 31 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  6
 34 80  1  0
 35 81  1  1
 42 84  1  0
 38 83  1  0
 37 82  1  0
M  END

  Mrv1652309022211412D          

 42 47  0  0  1  0            999 V2000
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    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
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
    6.8898   -0.5288    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2974   -2.2757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1095   -2.1305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6413   -2.7612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4534   -2.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9852   -3.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  1  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
    9.5489   -3.6824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2686   -4.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    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  2  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
    6.5807   -3.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  2  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
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  2  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
    3.0683   -2.4895    0.0000 C   0  0  2  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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  2  0  0  0  0
  6 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 36 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0153081

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@H]3[C@@H](CC[C@]4(O)C[C@H](CC[C@]34C=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@]1(O)C[C@H](O)[C@@H]2C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O12/c1-27-7-5-17-18(30(27,39)11-19(33)22(27)15-2-3-21(34)40-13-15)6-9-29(38)10-16(4-8-28(17,29)14-32)41-26-25(37)24(36)23(35)20(12-31)42-26/h2-3,13-14,16-20,22-26,31,33,35-39H,4-12H2,1H3/t16-,17-,18+,19-,20+,22-,23+,24-,25+,26+,27+,28-,29-,30-/m0/s1

> <INCHI_KEY>
LJMMDGJVOPWTGH-KYHHGZFYSA-N

> <FORMULA>
C30H42O12

> <MOLECULAR_WEIGHT>
594.654

> <EXACT_MASS>
594.267626792

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
60.92169030518983

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,7S,10R,11S,13S,14S,15R)-7,11,13-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

> <ALOGPS_LOGP>
-0.68

> <JCHEM_LOGP>
-2.074650369333334

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.102176887325168

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.197971680154131

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9057798718150805

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
144.72720000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7S,10R,11S,13S,14S,15R)-7,11,13-trihydroxy-15-methyl-14-(6-oxopyran-3-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

> <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       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.861  -0.987   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      18.871  -3.977   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.380  -4.883   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      22.372  -6.061   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      20.333  -7.780   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      17.825  -6.874   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      17.301  -8.322   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      16.832  -5.696   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.284  -6.510   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.892  -8.295   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.947  -9.510   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       2.312  -6.868   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30   35                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   27                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    5    9   28                                             
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30    6    2   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    2   36                                                  
CONECT   36   35   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   36                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₁₂

Average Mass

594.6540 Da

Monoisotopic Mass

594.26763 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@]4(O)C[C@H](CC[C@]34C=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@]1(O)C[C@H](O)[C@@H]2C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C30H42O12/c1-27-7-5-17-18(30(27,39)11-19(33)22(27)15-2-3-21(34)40-13-15)6-9-29(38)10-16(4-8-28(17,29)14-32)41-26-25(37)24(36)23(35)20(12-31)42-26/h2-3,13-14,16-20,22-26,31,33,35-39H,4-12H2,1H3/t16-,17-,18+,19-,20+,22-,23+,24-,25+,26+,27+,28-,29-,30-/m0/s1

InChI Key

LJMMDGJVOPWTGH-KYHHGZFYSA-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 elata	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
19-oxosteroid
14-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Oxosteroid
16-beta-hydroxysteroid
16-hydroxysteroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Pyranone
Pyran
Monosaccharide
Oxane
Tertiary alcohol
Heteroaromatic compound
Cyclic alcohol
Secondary alcohol
Lactone
Oxacycle
Acetal
Polyol
Organoheterocyclic compound
Aldehyde
Alcohol
Primary alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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

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

113385394

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14888414

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde (NP0153081)

MOL for NP0153081 ((1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D MOL for NP0153081 ((1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D SDF for NP0153081 ((1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D-SDF for NP0153081 ((1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

PDB for NP0153081 ((1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D PDB for NP0153081 ((1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

SMILES for NP0153081 ((1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

INCHI for NP0153081 ((1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

Structure for NP0153081 ((1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D Structure for NP0153081 ((1r,2s,3as,3br,5as,7s,9as,9bs,11ar)-2,3a,5a-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)