NP-MRD: Showing NP-Card for Caucasicoside D (NP0073406)

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Record Information

Version

2.0

Created at

2022-04-28 18:40:06 UTC

Updated at

2022-04-28 18:40:06 UTC

NP-MRD ID

NP0073406

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Caucasicoside D

Description

[(3S,4R,5R,6S)-5-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-{[(1S,2S,4S,8S,9S,12S,13R,14R,16R)-16-hydroxy-7,9,13-trimethyl-6-[3-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)but-3-en-1-yl]-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosa-6,18-dien-14-yl]oxy}oxan-3-yl]oxidanesulfonic acid belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Caucasicoside D is found in Helleborus caucasicus. Based on a literature review very few articles have been published on [(3S,4R,5R,6S)-5-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-{[(1S,2S,4S,8S,9S,12S,13R,14R,16R)-16-hydroxy-7,9,13-trimethyl-6-[3-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)but-3-en-1-yl]-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosa-6,18-dien-14-yl]oxy}oxan-3-yl]oxidanesulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220402D          

 74 82  0  0  1  0            999 V2000
    8.1476    0.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4789    1.1708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9902    1.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1703    1.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6816    2.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8616    2.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5303    1.5629    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0190    0.8982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8390    0.9891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3276    0.3244    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9963   -0.4312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4850   -1.0959    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3050   -1.0050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7937   -1.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4624   -2.4253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6424   -2.5161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1537   -1.8514    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3337   -1.9423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5910   -2.9082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5077    0.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6877    0.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8677    0.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3790    0.7165    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7103    1.4721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0941    2.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3820    1.6041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5581    0.7981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8459    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2297    0.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8683    1.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0623    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882    0.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4932    1.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6042    3.0179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1596    3.6279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.2162    2.6658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6607    2.0558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9112    1.2697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0221    2.4897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5211    4.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091    4.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4646    5.0239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643   -0.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9706   -0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2989    1.2617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  6  0  0  0
 12 13  1  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
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  1  0  0  0
 22 26  1  6  0  0  0
 21 27  1  1  0  0  0
 28 27  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 31 34  1  1  0  0  0
 30 35  1  6  0  0  0
 29 36  1  1  0  0  0
 20 37  1  1  0  0  0
 16 38  1  6  0  0  0
 15 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  2  0  0  0  0
 40 43  1  0  0  0  0
  9 44  1  1  0  0  0
  8 45  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
  7 48  1  0  0  0  0
 48 49  1  1  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 47 51  1  0  0  0  0
 51 52  1  1  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 50 54  1  1  0  0  0
 53 55  1  0  0  0  0
 55 56  1  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
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 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
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 65 66  1  0  0  0  0
 61 66  1  0  0  0  0
 66 67  1  6  0  0  0
 65 68  1  1  0  0  0
 64 69  1  1  0  0  0
 63 70  1  1  0  0  0
 70 71  1  0  0  0  0
 52 72  1  0  0  0  0
 47 73  1  1  0  0  0
  2 74  1  1  0  0  0
M  END

     RDKit          3D

150158  0  0  0  0  0  0  0  0999 V2000
    9.0011   -2.7255   -2.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1929   -2.5388   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1245   -1.9680   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8799   -1.7198   -0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8330   -1.1512    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6801   -1.7179    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2804   -3.0471   -0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189   -0.8364    1.3360 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7921    0.4003    1.3368 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9767    1.4311    0.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5915    1.0520    1.0141 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4896    1.6902    0.2674 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3943    3.1400    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625    3.7376    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7620    3.0482   -0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341    3.7502   -1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1661    3.3826   -0.5735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9612    2.6300   -1.4236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9266    2.6189    0.7212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151    1.3167    0.4879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0576    0.4744   -0.2331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4125   -0.6199    0.5071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7100   -1.7258   -0.0274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1919   -1.9657   -1.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5266   -2.6259   -1.1425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4167   -2.4212   -2.1496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7654   -3.7233   -3.1029 S   0  0  1  0  0  6  0  0  0  0  0  0
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   -7.4079   -3.9971   -3.3185 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9444    2.3479    2.3016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0198    2.7258    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3200    1.9968    2.7866 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.4184    2.2045    4.1758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7576    0.5991    2.4855 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.1373    0.5001    1.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4627    0.1015    1.0069 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.5216   -1.0993    0.2684 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4547   -0.8327   -1.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8519   -0.4562   -1.5776 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.6688   -1.5759   -1.6730 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3899    0.5083   -0.5397 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.0815    1.5128   -1.1742 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2285    1.1411    0.2233 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.8313    2.0686    1.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5706   -0.3250    2.8036 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9083   -1.6468    2.7236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170    1.5647   -0.2126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8673    0.9624   -1.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1927    1.0495    0.6552 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1764   -0.4248    0.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4124   -1.0038    1.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5963   -0.4236    0.7499 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5566   -0.7741   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9967    0.0655    0.7161 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4532   -2.9352   -0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1570   -1.9232    0.3690 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6164   -0.9400   -0.5302 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0074   -1.1481   -0.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6870   -0.2185   -1.3130 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1038   -0.7251   -1.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8483    0.1679   -2.2625 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6661    1.0687   -0.4829 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282220402D          

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 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  1  0  0  0
 22 26  1  6  0  0  0
 21 27  1  1  0  0  0
 28 27  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 31 34  1  1  0  0  0
 30 35  1  6  0  0  0
 29 36  1  1  0  0  0
 20 37  1  1  0  0  0
 16 38  1  6  0  0  0
 15 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  2  0  0  0  0
 40 43  1  0  0  0  0
  9 44  1  1  0  0  0
  8 45  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
  7 48  1  0  0  0  0
 48 49  1  1  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 47 51  1  0  0  0  0
 51 52  1  1  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 50 54  1  1  0  0  0
 53 55  1  0  0  0  0
 55 56  1  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
 61 60  1  1  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 61 66  1  0  0  0  0
 66 67  1  6  0  0  0
 65 68  1  1  0  0  0
 64 69  1  1  0  0  0
 63 70  1  1  0  0  0
 70 71  1  0  0  0  0
 52 72  1  0  0  0  0
 47 73  1  1  0  0  0
  2 74  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0073406

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](CO[C@H]2O[C@@H]2C[C@H](O)CC3=CC[C@H]4[C@@H]5C[C@@H]6OC(CCC(=C)CO[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)=C(C)[C@@H]6[C@@]5(C)CC[C@@H]4[C@@]23C)OS(O)(=O)=O)[C@H](O)[C@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C49H76O24S/c1-19(16-64-44-40(59)38(57)36(55)30(15-50)69-44)6-9-28-20(2)33-29(68-28)14-26-24-8-7-22-12-23(51)13-32(49(22,5)25(24)10-11-48(26,33)4)70-47-43(37(56)31(18-66-47)73-74(61,62)63)72-46-41(60)42(34(53)21(3)67-46)71-45-39(58)35(54)27(52)17-65-45/h7,21,23-27,29-47,50-60H,1,6,8-18H2,2-5H3,(H,61,62,63)/t21-,23+,24+,25-,26-,27+,29-,30+,31-,32+,33-,34-,35-,36-,37-,38-,39+,40+,41+,42+,43+,44+,45-,46-,47-,48-,49-/m0/s1

> <INCHI_KEY>
JRCHRRYFOVYVSX-VWPVEVEJSA-N

> <FORMULA>
C49H76O24S

> <MOLECULAR_WEIGHT>
1081.18

> <EXACT_MASS>
1080.444724501

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_ATOM_COUNT>
150

> <JCHEM_AVERAGE_POLARIZABILITY>
109.45506930662904

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3S,4R,5R,6S)-5-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-{[(1S,2S,4S,8S,9S,12S,13R,14R,16R)-16-hydroxy-7,9,13-trimethyl-6-[3-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)but-3-en-1-yl]-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-6,18-dien-14-yl]oxy}oxan-3-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.05

> <JCHEM_LOGP>
-4.266313045042347

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.772747077428596

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.9500678612733493

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483775517229935

> <JCHEM_POLAR_SURFACE_AREA>
369.20000000000005

> <JCHEM_REFRACTIVITY>
250.79560000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,4R,5R,6S)-5-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-{[(1S,2S,4S,8S,9S,12S,13R,14R,16R)-16-hydroxy-7,9,13-trimethyl-6-[3-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)but-3-en-1-yl]-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-6,18-dien-14-yl]oxy}oxan-3-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      15.209   0.775   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.827   2.185   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.915   3.426   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.384   3.257   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.472   4.497   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.942   4.328   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.323   2.917   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.235   1.677   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.766   1.846   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.678   0.606   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.060  -0.805   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      13.972  -2.046   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      15.503  -1.876   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      16.415  -3.117   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.796  -4.527   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.266  -4.697   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.354  -3.456   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.823  -3.626   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.205  -5.036   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.674  -5.206   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.055  -6.616   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.968  -7.857   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.498  -7.687   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.117  -6.277   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.410  -8.928   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.349  -9.267   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       7.525  -6.786   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.906  -8.196   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.376  -8.365   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.757  -9.776   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.670 -11.017   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.200 -10.847   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.819  -9.437   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.051 -12.427   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.227  -9.945   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       4.464  -7.125   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       8.762  -3.965   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      13.647  -6.107   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      16.709  -5.768   0.000  0.00  0.00           O+0
HETATM   40  S   UNK     0      18.239  -5.598   0.000  0.00  0.00           S+0
HETATM   41  O   UNK     0      18.409  -7.129   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      18.070  -4.068   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      19.770  -5.429   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      12.148   0.436   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      10.617   0.266   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.086   0.097   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       8.174   1.337   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       8.793   2.748   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.642   3.772   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.313   2.994   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.642   1.490   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       5.312   0.712   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       4.162   1.736   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       4.781   3.147   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       2.658   1.408   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       1.621   2.546   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       0.116   2.218   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -0.351   0.750   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -0.921   3.356   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -2.425   3.028   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -3.462   4.166   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      -2.994   5.633   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      -4.031   6.772   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -5.536   6.443   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -6.003   4.976   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      -4.967   3.837   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      -5.434   2.370   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      -7.508   4.647   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0      -6.573   7.582   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0      -3.564   8.239   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0      -4.601   9.378   0.000  0.00  0.00           O+0
HETATM   72  C   UNK     0       5.160  -0.820   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0       7.412  -0.001   0.000  0.00  0.00           C+0
HETATM   74  O   UNK     0      17.358   2.355   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   74                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   48                                                  
CONECT    8    7    9   45                                                  
CONECT    9    8    4   10   44                                             
CONECT   10    9    1   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   39                                                  
CONECT   16   15   17   38                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   37                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23                                                            
CONECT   26   22                                                            
CONECT   27   21   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   36                                                  
CONECT   30   29   31   35                                                  
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   31                                                            
CONECT   35   30                                                            
CONECT   36   29                                                            
CONECT   37   20                                                            
CONECT   38   16                                                            
CONECT   39   15   40                                                       
CONECT   40   39   41   42   43                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   40                                                            
CONECT   44    9                                                            
CONECT   45    8   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48   51   73                                             
CONECT   48   47    7   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   54                                                  
CONECT   51   50   47   52                                                  
CONECT   52   51   53   72                                                  
CONECT   53   52   54   55                                                  
CONECT   54   53   50                                                       
CONECT   55   53   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62   66                                                  
CONECT   62   61   63                                                       
CONECT   63   62   64   70                                                  
CONECT   64   63   65   69                                                  
CONECT   65   64   66   68                                                  
CONECT   66   65   61   67                                                  
CONECT   67   66                                                            
CONECT   68   65                                                            
CONECT   69   64                                                            
CONECT   70   63   71                                                       
CONECT   71   70                                                            
CONECT   72   52                                                            
CONECT   73   47                                                            
CONECT   74    2                                                            
MASTER        0    0    0    0    0    0    0    0   74    0  164    0
END

View in JSmol

Synonyms

Value	Source
[(3S,4R,5R,6S)-5-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-{[(1S,2S,4S,8S,9S,12S,13R,14R,16R)-16-hydroxy-7,9,13-trimethyl-6-[3-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)but-3-en-1-yl]-5-oxapentacyclo[10.8.0.0,.0,.0,]icosa-6,18-dien-14-yl]oxy}oxan-3-yl]oxidanesulfonate	Generator
[(3S,4R,5R,6S)-5-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-{[(1S,2S,4S,8S,9S,12S,13R,14R,16R)-16-hydroxy-7,9,13-trimethyl-6-[3-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)but-3-en-1-yl]-5-oxapentacyclo[10.8.0.0,.0,.0,]icosa-6,18-dien-14-yl]oxy}oxan-3-yl]oxidanesulphonate	Generator
[(3S,4R,5R,6S)-5-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-{[(1S,2S,4S,8S,9S,12S,13R,14R,16R)-16-hydroxy-7,9,13-trimethyl-6-[3-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)but-3-en-1-yl]-5-oxapentacyclo[10.8.0.0,.0,.0,]icosa-6,18-dien-14-yl]oxy}oxan-3-yl]oxidanesulphonic acid	Generator

Chemical Formula

C₄₉H₇₆O₂₄S

Average Mass

1081.1800 Da

Monoisotopic Mass

1080.44472 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](CO[C@H]2O[C@@H]2C[C@H](O)CC3=CC[C@H]4[C@@H]5C[C@@H]6OC(CCC(=C)CO[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)=C(C)[C@@H]6[C@@]5(C)CC[C@@H]4[C@@]23C)OS(O)(=O)=O)[C@H](O)[C@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O

InChI Identifier

InChI=1S/C49H76O24S/c1-19(16-64-44-40(59)38(57)36(55)30(15-50)69-44)6-9-28-20(2)33-29(68-28)14-26-24-8-7-22-12-23(51)13-32(49(22,5)25(24)10-11-48(26,33)4)70-47-43(37(56)31(18-66-47)73-74(61,62)63)72-46-41(60)42(34(53)21(3)67-46)71-45-39(58)35(54)27(52)17-65-45/h7,21,23-27,29-47,50-60H,1,6,8-18H2,2-5H3,(H,61,62,63)/t21-,23+,24+,25-,26-,27+,29-,30+,31-,32+,33-,34-,35-,36-,37-,38-,39+,40+,41+,42+,43+,44+,45-,46-,47-,48-,49-/m0/s1

InChI Key

JRCHRRYFOVYVSX-VWPVEVEJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Helleborus caucasicus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal saponins

Alternative Parents

Substituents

Steroidal saponin
Furostane-skeleton
Oligosaccharide
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Delta-5-steroid
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Fatty acyl
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Oxane
Organic sulfuric acid or derivatives
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.05	ALOGPS
logP	-4.3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	369.2 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	250.8 m³·mol⁻¹	ChemAxon
Polarizability	109.46 Å³	ChemAxon
Number of Rings	9	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

162906328

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Caucasicoside D (NP0073406)

MOL for NP0073406 (Caucasicoside D)

3D MOL for NP0073406 (Caucasicoside D)

3D SDF for NP0073406 (Caucasicoside D)

3D-SDF for NP0073406 (Caucasicoside D)

PDB for NP0073406 (Caucasicoside D)

3D PDB for NP0073406 (Caucasicoside D)

SMILES for NP0073406 (Caucasicoside D)

INCHI for NP0073406 (Caucasicoside D)

Structure for NP0073406 (Caucasicoside D)

3D Structure for NP0073406 (Caucasicoside D)