NP-MRD: Showing NP-Card for (-)-Abutiloside M (NP0074658)

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Record Information

Version

2.0

Created at

2022-04-28 19:56:58 UTC

Updated at

2022-04-28 19:56:58 UTC

NP-MRD ID

NP0074658

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Abutiloside M

Description

(2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1'S,2S,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'R,16'S,20'S)-20'-methoxy-5,7',9',13'-tetramethyl-5-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5'-oxaspiro[oxolane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosan]-18'-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol 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. (-)-Abutiloside M is found in Solanum abutiloides. Based on a literature review very few articles have been published on (2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1'S,2S,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'R,16'S,20'S)-20'-methoxy-5,7',9',13'-tetramethyl-5-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5'-oxaspiro[oxolane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosan]-18'-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221562D          

 75 84  0  0  1  0            999 V2000
    5.7766    1.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1445    0.5286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5559   -0.0495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8242    0.3317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9607    1.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2290    1.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6404    0.9484    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0083    0.2100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5527   -0.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -0.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3614    0.3112    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8169    0.9991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4491    1.7375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6256    1.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1700    1.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379    0.3619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0823   -0.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3466    1.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3003    1.2522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4039    3.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3151    2.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7547   -2.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3868   -2.9759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8424   -3.6637    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4745   -4.4022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6511   -4.4528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1955   -3.7650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5634   -3.0265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720   -3.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832   -5.1912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9301   -5.0900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6658   -3.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1078   -2.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2844   -2.3894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058   -0.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9046    2.4253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    3.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4513   -0.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6776   -0.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7331    1.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4648    0.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3284   -0.0882    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5124   -0.2099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1209   -0.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7156    0.2546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5081    0.0256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7061   -0.7753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4986   -1.0044    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0933   -0.4325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8953    0.3684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1028    0.5974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4900    0.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2826    0.7112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8858   -0.6615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6966   -1.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1114   -1.3472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5430   -0.8848    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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  1  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12  7  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 11 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
 15 20  1  0  0  0  0
 19 21  1  6  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  1  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
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 33 35  1  6  0  0  0
 32 36  1  1  0  0  0
 31 37  1  6  0  0  0
 30 38  1  6  0  0  0
 26 39  1  6  0  0  0
 25 40  1  6  0  0  0
 41 40  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 41 46  1  0  0  0  0
 45 47  1  1  0  0  0
 44 48  1  6  0  0  0
 43 49  1  1  0  0  0
 42 50  1  1  0  0  0
 24 51  1  6  0  0  0
 51 52  1  0  0  0  0
 16 53  1  6  0  0  0
 13 54  1  1  0  0  0
 54 55  1  0  0  0  0
  8 56  1  6  0  0  0
  3 57  1  1  0  0  0
  2 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
  2 61  1  0  0  0  0
 60 62  1  1  0  0  0
 62 63  1  0  0  0  0
 64 63  1  6  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
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 64 69  1  0  0  0  0
 68 70  1  6  0  0  0
 70 71  1  0  0  0  0
 67 72  1  6  0  0  0
 66 73  1  6  0  0  0
 65 74  1  1  0  0  0
 60 75  1  6  0  0  0
M  END

     RDKit          3D

159168  0  0  0  0  0  0  0  0999 V2000
    1.2638    2.6983    2.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6363    1.5469    2.5188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5609    1.5159    1.1328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8608    1.4503    0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4798    0.3209    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961    0.4522   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066   -0.6818    0.4069 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9112   -0.8655   -0.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9468   -0.8402    0.6536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4210   -2.1760    0.7946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3423   -2.1455    1.8378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6678   -3.4923    2.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1973   -4.3874    1.5139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5597   -1.4389    1.2546 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6545   -1.7817   -0.0718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8958   -2.2412   -0.4837 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.7369   -3.5354   -0.9680 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9422   -4.0907   -1.3897 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.8726   -4.3957   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5833   -3.2208   -2.4744 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.8010   -3.9488   -3.6439 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6376   -2.0812   -2.8408 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.1828   -1.2361   -3.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3974   -1.3012   -1.5620 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.5255   -0.5969   -1.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1461    0.0600    1.2295 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.2861    0.7166    0.7883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0022    0.1131    0.2173 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.0093    5.7043   -0.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0055    4.4476   -0.7497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8090    5.4496   -1.3437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5665    3.1285   -1.1638 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9975    3.3031   -2.5062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9989   -2.0306    0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7311   -1.9382    1.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070   -1.0013    0.3719 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6995   -1.4821   -1.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5122   -0.8984    1.0529 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2497   -2.1927    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6259   -2.1416    1.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3818   -1.0634    0.8374 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4558   -1.3873   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6536    0.2709    1.0785 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6386    1.1814    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9547    0.6730    0.9387 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9183    0.4869   -0.0511 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8023   -0.4700    0.5002 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7124   -1.0598   -0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8983   -0.0647   -0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9082    0.1104    1.0951 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5955   -1.0597    1.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5602    1.3774    1.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8507    1.5970    1.3013 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3266    1.7097    0.0605 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2582    0.6752   -0.2640 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6270    0.9152   -1.5862 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9531   -0.3670   -2.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3132   -0.0740   -3.6309 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8282    1.8360   -1.5235 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.9395    1.0729   -1.1710 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282221562D          

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   10.4986   -1.0044    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0933   -0.4325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8953    0.3684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1028    0.5974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4900    0.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2826    0.7112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8858   -0.6615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6966   -1.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1114   -1.3472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5430   -0.8848    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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  1  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12  7  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 11 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
 15 20  1  0  0  0  0
 19 21  1  6  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  1  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
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 33 35  1  6  0  0  0
 32 36  1  1  0  0  0
 31 37  1  6  0  0  0
 30 38  1  6  0  0  0
 26 39  1  6  0  0  0
 25 40  1  6  0  0  0
 41 40  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 41 46  1  0  0  0  0
 45 47  1  1  0  0  0
 44 48  1  6  0  0  0
 43 49  1  1  0  0  0
 42 50  1  1  0  0  0
 24 51  1  6  0  0  0
 51 52  1  0  0  0  0
 16 53  1  6  0  0  0
 13 54  1  1  0  0  0
 54 55  1  0  0  0  0
  8 56  1  6  0  0  0
  3 57  1  1  0  0  0
  2 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
  2 61  1  0  0  0  0
 60 62  1  1  0  0  0
 62 63  1  0  0  0  0
 64 63  1  6  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 64 69  1  0  0  0  0
 68 70  1  6  0  0  0
 70 71  1  0  0  0  0
 67 72  1  6  0  0  0
 66 73  1  6  0  0  0
 65 74  1  1  0  0  0
 60 75  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0074658

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C=C2C[C@H](CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](C[C@@H]4O[C@]5(CC[C@@](C)(CO[C@@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)O5)[C@@H](C)[C@H]34)[C@H]12)O[C@@H]1O[C@H](CO)[C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C52H84O23/c1-20-32-28(74-52(20)13-12-49(4,75-52)19-66-45-39(61)38(60)35(57)29(17-53)70-45)16-26-31-25(9-11-51(26,32)6)50(5)10-8-24(14-23(50)15-27(31)65-7)69-48-44(73-47-41(63)37(59)34(56)22(3)68-47)42(64)43(30(18-54)71-48)72-46-40(62)36(58)33(55)21(2)67-46/h15,20-22,24-48,53-64H,8-14,16-19H2,1-7H3/t20-,21-,22-,24-,25-,26-,27+,28-,29+,30+,31+,32-,33-,34-,35-,36+,37+,38-,39+,40+,41+,42-,43-,44+,45+,46-,47-,48+,49-,50-,51-,52-/m0/s1

> <INCHI_KEY>
DYVAXAUOLHCWSG-XHCXKHOPSA-N

> <FORMULA>
C52H84O23

> <MOLECULAR_WEIGHT>
1077.221

> <EXACT_MASS>
1076.540338965

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_ATOM_COUNT>
159

> <JCHEM_AVERAGE_POLARIZABILITY>
114.96375820622262

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5R,6R)-4-hydroxy-6-(hydroxymethyl)-2-[(1'S,2S,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'R,16'S,20'S)-20'-methoxy-5,7',9',13'-tetramethyl-5-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5'-oxaspiro[oxolane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.43

> <JCHEM_LOGP>
-1.731247793666666

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.187214216125957

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.751444895638507

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483773201108614

> <JCHEM_POLAR_SURFACE_AREA>
344.29

> <JCHEM_REFRACTIVITY>
254.5495000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5R,6R)-4-hydroxy-6-(hydroxymethyl)-2-[(1'S,2S,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'R,16'S,20'S)-20'-methoxy-5,7',9',13'-tetramethyl-5-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5'-oxaspiro[oxolane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <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  O   UNK     0      10.783   2.365   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.470   0.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.371  -0.092   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.005   0.619   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.260   2.138   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.894   2.849   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.795   1.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.482   0.392   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.632  -0.892   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.095  -0.797   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.408   0.581   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.258   1.865   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.572   3.243   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.034   3.338   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.184   2.054   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.871   0.675   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.020  -0.608   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.483  -0.514   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.203   0.865   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.647   2.148   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.741   0.959   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.591  -0.325   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.904  -1.703   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.755  -2.987   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.292  -2.893   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.978  -1.514   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.128  -0.230   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.815   1.148   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.964   2.432   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.651   3.810   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.801   5.094   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.264   5.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.577   3.621   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.427   2.337   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.040   3.527   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.413   6.284   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -4.487   6.473   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -6.188   3.905   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -6.515  -1.420   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -5.142  -4.177   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.455  -5.555   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -5.306  -6.839   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -4.619  -8.217   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -3.082  -8.312   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -2.232  -7.028   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -2.918  -5.650   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -0.694  -7.122   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -2.395  -9.690   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -5.469  -9.501   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -6.843  -6.744   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -2.068  -4.366   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -0.531  -4.460   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       3.557  -0.703   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       5.422   4.527   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       4.735   5.906   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       8.309  -0.907   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      10.598  -1.616   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      12.568   2.066   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      13.934   1.354   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      13.680  -0.165   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      12.156  -0.392   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      15.159  -0.592   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      16.269   0.475   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      17.749   0.048   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      18.118  -1.447   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      19.597  -1.875   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      20.707  -0.807   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      20.338   0.688   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      18.859   1.115   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0      21.448   1.755   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0      22.927   1.328   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0      22.187  -1.235   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      19.967  -3.370   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      17.008  -2.515   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0      14.080  -1.652   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   58   61                                             
CONECT    3    2    4   57                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    4    9   56                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14   54                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   11   17   53                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   51                                                  
CONECT   25   24   26   40                                                  
CONECT   26   25   27   39                                                  
CONECT   27   26   22   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31   38                                                  
CONECT   31   30   32   37                                                  
CONECT   32   31   33   36                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33   29                                                       
CONECT   35   33                                                            
CONECT   36   32                                                            
CONECT   37   31                                                            
CONECT   38   30                                                            
CONECT   39   26                                                            
CONECT   40   25   41                                                       
CONECT   41   40   42   46                                                  
CONECT   42   41   43   50                                                  
CONECT   43   42   44   49                                                  
CONECT   44   43   45   48                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45   41                                                       
CONECT   47   45                                                            
CONECT   48   44                                                            
CONECT   49   43                                                            
CONECT   50   42                                                            
CONECT   51   24   52                                                       
CONECT   52   51                                                            
CONECT   53   16                                                            
CONECT   54   13   55                                                       
CONECT   55   54                                                            
CONECT   56    8                                                            
CONECT   57    3                                                            
CONECT   58    2   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61   62   75                                             
CONECT   61   60    2                                                       
CONECT   62   60   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65   69                                                  
CONECT   65   64   66   74                                                  
CONECT   66   65   67   73                                                  
CONECT   67   66   68   72                                                  
CONECT   68   67   69   70                                                  
CONECT   69   68   64                                                       
CONECT   70   68   71                                                       
CONECT   71   70                                                            
CONECT   72   67                                                            
CONECT   73   66                                                            
CONECT   74   65                                                            
CONECT   75   60                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  168    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₂H₈₄O₂₃

Average Mass

1077.2210 Da

Monoisotopic Mass

1076.54034 Da

IUPAC Name

(2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5R,6R)-4-hydroxy-6-(hydroxymethyl)-2-[(1'S,2S,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'R,16'S,20'S)-20'-methoxy-5,7',9',13'-tetramethyl-5-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5'-oxaspiro[oxolane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C=C2C[C@H](CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](C[C@@H]4O[C@]5(CC[C@@](C)(CO[C@@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)O5)[C@@H](C)[C@H]34)[C@H]12)O[C@@H]1O[C@H](CO)[C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C52H84O23/c1-20-32-28(74-52(20)13-12-49(4,75-52)19-66-45-39(61)38(60)35(57)29(17-53)70-45)16-26-31-25(9-11-51(26,32)6)50(5)10-8-24(14-23(50)15-27(31)65-7)69-48-44(73-47-41(63)37(59)34(56)22(3)68-47)42(64)43(30(18-54)71-48)72-46-40(62)36(58)33(55)21(2)67-46/h15,20-22,24-48,53-64H,8-14,16-19H2,1-7H3/t20-,21-,22-,24-,25-,26-,27+,28-,29+,30+,31+,32-,33-,34-,35-,36+,37+,38-,39+,40+,41+,42-,43-,44+,45+,46-,47-,48+,49-,50-,51-,52-/m0/s1

InChI Key

DYVAXAUOLHCWSG-XHCXKHOPSA-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
Solanum abutiloides	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
Furospirostane-skeleton
Triterpenoid
Spirostane skeleton
Oligosaccharide
Delta-5-steroid
O-glycosyl compound
Glycosyl compound
Ketal
Oxane
Tetrahydrofuran
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
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	-0.43	ALOGPS
logP	-1.7	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	344.29 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	254.55 m³·mol⁻¹	ChemAxon
Polarizability	114.96 Å³	ChemAxon
Number of Rings	10	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

162859167

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Abutiloside M (NP0074658)

MOL for NP0074658 ((-)-Abutiloside M)

3D MOL for NP0074658 ((-)-Abutiloside M)

3D SDF for NP0074658 ((-)-Abutiloside M)

3D-SDF for NP0074658 ((-)-Abutiloside M)

PDB for NP0074658 ((-)-Abutiloside M)

3D PDB for NP0074658 ((-)-Abutiloside M)

SMILES for NP0074658 ((-)-Abutiloside M)

INCHI for NP0074658 ((-)-Abutiloside M)

Structure for NP0074658 ((-)-Abutiloside M)

3D Structure for NP0074658 ((-)-Abutiloside M)