NP-MRD: Showing NP-Card for 7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde (NP0146618)

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Record Information

Version

2.0

Created at

2022-09-02 02:03:09 UTC

Updated at

2022-09-02 02:03:10 UTC

NP-MRD ID

NP0146618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde

Description

5-[(5-{[3,4-Dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carbaldehyde 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. 7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde is found in Erysimum cheiranthoides, Erysimum leptophyllum and Erysimum marshallii. 5-[(5-{[3,4-Dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carbaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161507142D          

 60 67  0  0  0  0            999 V2000
   -3.0946   -4.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825   -4.0500    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  0  0  0  0  0  0  0  0  0  0
   -0.6582   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385   -4.5355    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
   -1.7507   -4.6807    0.0000 C   0  0  0  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
   -1.4991   -6.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -5.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1552   -6.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6569   -6.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887   -7.0583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4355   -7.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963   -7.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840   -8.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9961   -8.9006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2764   -9.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885   -9.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3688  -10.5977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446  -10.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0249  -11.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0675  -10.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5994  -10.7927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478   -9.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600   -9.2409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2476   -7.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5279   -8.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794   -6.8633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -7.0085    0.0000 O   0  0  0  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  0  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  0  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
    1.2751   -0.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  0  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  0  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  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -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  0  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  0  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  0  0  0  0  0  0  0  0  0  0
    0.9660   -3.4691    0.0000 O   0  0  0  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
    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  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  1  0  0  0  0
 13 14  1  0  0  0  0
 12 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
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 36 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 42 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 39 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 36 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 33 54  1  0  0  0  0
 44 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
 55 60  1  0  0  0  0
M  END

     RDKit          3D

122129  0  0  0  0  0  0  0  0999 V2000
    0.9038   -0.6972   -1.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6504   -1.9662   -0.8359 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8002   -3.0480   -0.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030   -2.8503    0.5291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7708   -1.7559    0.2981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -1.9272    0.3934 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8661   -1.7972   -0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3593   -1.7496   -0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6120   -0.3587   -0.0941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4930    0.5611   -1.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7914    1.5299   -1.3324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0426   -0.2517    0.3853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0272   -0.7354   -0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3562   -0.7795    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7943    0.5899    0.5576 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.5766    0.4384    1.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5798    1.1536   -0.5681 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.9226    0.6210   -0.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6363   -0.2989   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9101   -0.3908   -0.9500 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8572   -1.1925   -0.6607 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9179    0.5356   -1.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7172    1.2068   -1.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5591    2.6491   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0322    2.7993   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7168    1.6033    0.7589 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8307    2.1644    2.0464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3116    1.2119    0.6032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4217    1.6385    1.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4562    0.5437    2.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6585    0.0053    0.9855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8551    1.0950    0.5672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7632   -1.0923    1.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668   -2.5876    1.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144   -2.8650    1.3251 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1743   -2.8380    2.3918 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078   -1.7482    0.3108 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9292   -1.6878   -0.0471 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668   -0.5156    0.3716 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9959    0.3074   -0.6091 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2586    0.2604   -1.0794 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4482    1.5602   -1.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2192    2.5855   -0.9573 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3674    0.1578   -0.0540 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3413    1.0924   -0.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6241    0.5483   -0.5075 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0013    0.8091   -1.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2917    0.5902   -2.1531 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5333   -0.8253   -2.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7384   -1.0979   -3.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3384    1.0068   -1.1573 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0862   -0.1143   -0.7883 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7674    1.7158    0.0485 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.7666    1.7188    1.0269 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5771    0.9612    0.5722 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9007    1.8514    1.4395 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7185    0.3087    1.3113 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5643    0.0724    2.3650 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6318   -0.7748    1.3829 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2739   -1.9832    1.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7632   -0.1050   -0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5326   -0.0552   -1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0195   -0.9238   -1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2468   -2.2412   -1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396   -3.7765    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855   -2.9906    0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5819   -0.9354   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7351   -2.7063   -1.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8863   -2.0027   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5865   -2.5290    0.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1259    0.2846   -2.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2228   -0.8260    1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8457   -1.7281   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1720    0.0380   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0663   -1.2736   -0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1662   -1.3978    1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5515    0.9441    1.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.1536    0.9888   -2.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004161507142D          

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M  END
> <DATABASE_ID>
NP0146618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CC(O)C1OC1OC(CO)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O)OC1CCC2(C=O)C3CCC4(C)C(CCC4(O)C3CCC2(O)C1)C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C41H62O19/c1-18-34(59-37-33(51)31(49)35(26(15-43)58-37)60-36-32(50)30(48)29(47)25(14-42)57-36)24(45)12-28(55-18)56-20-3-8-39(17-44)22-4-7-38(2)21(19-11-27(46)54-16-19)6-10-41(38,53)23(22)5-9-40(39,52)13-20/h11,17-18,20-26,28-37,42-43,45,47-53H,3-10,12-16H2,1-2H3

> <INCHI_KEY>
ZGRREZOFNHXSDO-UHFFFAOYSA-N

> <FORMULA>
C41H62O19

> <MOLECULAR_WEIGHT>
858.928

> <EXACT_MASS>
858.388529776

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
122

> <JCHEM_AVERAGE_POLARIZABILITY>
89.32691734502251

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carbaldehyde

> <ALOGPS_LOGP>
-1.80

> <JCHEM_LOGP>
-2.4966217446666645

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.934356686813977

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182628432383881

> <JCHEM_PKA_STRONGEST_BASIC>
-3.192409706977294

> <JCHEM_POLAR_SURFACE_AREA>
301.04999999999995

> <JCHEM_REFRACTIVITY>
200.10240000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-7,11-dihydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -5.777  -7.831   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.261  -7.560   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.737  -6.112   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.221  -5.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.229  -7.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.752  -8.466   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.759  -9.644   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.268  -8.737   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.791 -10.186   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.798 -11.363   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.282 -11.092   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.290 -12.269   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.226 -11.998   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.219 -13.176   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.813 -13.718   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.180 -14.895   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.343 -16.343   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.859 -16.614   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.383 -18.063   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.899 -18.334   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.422 -19.782   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.390 -19.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.913 -20.689   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.126 -18.969   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.119 -20.146   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.649 -17.521   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.165 -17.250   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.329 -13.989   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.852 -15.437   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.322 -12.811   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.838 -13.082   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.380  -0.953   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       6.505  -5.709   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       1.803  -6.476   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      10.728   0.744   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      10.779   2.283   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      11.944  -0.202   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
CONECT   28   15   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   10   31                                                  
CONECT   31   30                                                            
CONECT   32    4   33                                                       
CONECT   33   32   34   54                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   39   52                                             
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36   40   49                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44   47                                             
CONECT   43   42                                                            
CONECT   44   42   45   55                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   42   48   49                                             
CONECT   48   47                                                            
CONECT   49   47   39   50                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   36   53   54                                             
CONECT   53   52                                                            
CONECT   54   52   33                                                       
CONECT   55   44   56   60                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60                                                       
CONECT   60   59   55                                                       
MASTER        0    0    0    0    0    0    0    0   60    0  134    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₁H₆₂O₁₉

Average Mass

858.9280 Da

Monoisotopic Mass

858.38853 Da

IUPAC Name

5-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carbaldehyde

Traditional Name

5-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-7,11-dihydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC1OC(CC(O)C1OC1OC(CO)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O)OC1CCC2(C=O)C3CCC4(C)C(CCC4(O)C3CCC2(O)C1)C1=CC(=O)OC1

InChI Identifier

InChI=1S/C41H62O19/c1-18-34(59-37-33(51)31(49)35(26(15-43)58-37)60-36-32(50)30(48)29(47)25(14-42)57-36)24(45)12-28(55-18)56-20-3-8-39(17-44)22-4-7-38(2)21(19-11-27(46)54-16-19)6-10-41(38,53)23(22)5-9-40(39,52)13-20/h11,17-18,20-26,28-37,42-43,45,47-53H,3-10,12-16H2,1-2H3

InChI Key

ZGRREZOFNHXSDO-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
Erysimum cheiranthoides	LOTUS Database	35616633
Erysimum leptophyllum	LOTUS Database	35616633
Erysimum marshallii	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
Oligosaccharide
19-oxosteroid
Hydroxysteroid
5-hydroxysteroid
Oxosteroid
14-hydroxysteroid
O-glycosyl compound
Glycosyl compound
2-furanone
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Acetal
Polyol
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Organic oxide
Aldehyde
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-2.5	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	301.05 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	200.1 m³·mol⁻¹	ChemAxon
Polarizability	89.33 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	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

73257211

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde (NP0146618)

MOL for NP0146618 (7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D MOL for NP0146618 (7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D SDF for NP0146618 (7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D-SDF for NP0146618 (7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

PDB for NP0146618 (7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D PDB for NP0146618 (7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

SMILES for NP0146618 (7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

INCHI for NP0146618 (7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

Structure for NP0146618 (7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D Structure for NP0146618 (7-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)