NP-MRD: Showing NP-Card for Polyphyllin B (NP0139059)

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Record Information

Version

1.0

Created at

2022-06-29 19:37:44 UTC

Updated at

2022-06-29 19:37:44 UTC

NP-MRD ID

NP0139059

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Polyphyllin B

Description

DIOSGENIN TETRAGLYCOSIDE, also known as formosanin C or paris saponin II, 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. Polyphyllin B is found in Allium senescens, Borassus flabellifer, Cestrum nocturnum, Chamaerops humilis, Dioscorea floribunda, Dioscorea pseudojaponica, Paris polyphylla, Smilax china, Trachycarpus fortunei, Trillium erectum and Ypsilandra thibetica. DIOSGENIN TETRAGLYCOSIDE is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151519212D          

 71 80  0  0  0  0            999 V2000
    4.3030   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -3.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4082   -2.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2223   -2.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7452   -2.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4540   -3.6564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6399   -3.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1155   -2.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9311   -2.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6640   -1.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2507   -2.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0743   -2.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4446   -1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2682   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7215   -2.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5451   -2.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9984   -2.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6282   -3.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8046   -3.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3512   -3.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9810   -3.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5276   -3.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1573   -3.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3337   -3.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8804   -3.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4351   -3.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0648   -3.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319   -3.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2076   -4.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8221   -2.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2754   -3.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0990   -3.5638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5523   -4.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3759   -4.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7462   -3.4679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1820   -4.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6353   -5.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4589   -5.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8292   -4.8944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6528   -4.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0231   -4.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1062   -5.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9298   -5.4878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3831   -6.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0128   -6.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4661   -7.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0958   -8.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2897   -7.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7431   -8.2450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6600   -6.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4836   -6.7705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2067   -6.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5770   -5.3919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7359   -6.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1892   -6.9623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9123   -6.3209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5420   -7.0582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3584   -5.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9881   -5.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9051   -4.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0815   -4.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7112   -5.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1645   -5.8234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7942   -6.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2476   -7.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9706   -6.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6003   -7.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5173   -5.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6937   -5.9672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8876   -5.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4343   -4.4928    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  5  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
 14 15  2  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
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 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
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 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
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 44 52  1  0  0  0  0
 52 53  1  0  0  0  0
 42 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 38 56  1  0  0  0  0
 56 57  1  0  0  0  0
 36 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 31 60  1  0  0  0  0
 60 61  1  0  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
 64 66  1  0  0  0  0
 66 67  1  0  0  0  0
 66 68  1  0  0  0  0
 68 69  1  0  0  0  0
 68 70  1  0  0  0  0
 62 70  1  0  0  0  0
 70 71  1  0  0  0  0
M  END

     RDKit          3D

153162  0  0  0  0  0  0  0  0999 V2000
   13.1641    2.8819   -1.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0609    2.5349   -0.8193 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6556    1.9996    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7233    2.1510    1.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3302    2.2331    1.0904 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1219    3.3123    0.2648 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2111    3.7417   -0.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0896    1.0088    0.4194 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7055    0.9132    0.3150 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1647   -0.4226    0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0043   -0.1845    1.6711 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8556   -0.9698    1.1957 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0706   -1.6584    2.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631   -2.1510    1.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2303   -1.8958    0.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672   -2.4508    0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790   -1.2980    0.0561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1492   -1.4917   -0.7502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255   -1.3089   -0.0485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7885   -0.0260   -0.4976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7979    0.2803    0.4339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1533    1.7276    0.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0469    2.5336    0.7220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0239   -0.5589    0.1882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1078    0.1623   -0.3178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2761   -0.0238    0.3938 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2853   -0.5829   -0.3863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6375    0.3799   -1.3600 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4360   -0.3923   -2.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4615    1.4838   -0.7480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.7463    1.5144   -1.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0741    2.6947   -1.8456 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.3495    2.4569   -3.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2626    3.6443   -3.9326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8327    4.1354   -4.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1488    4.7293   -3.4114 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.4391    4.6934   -3.9687 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2466    4.8112   -1.9219 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.4090    5.5039   -1.5865 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2716    3.4097   -1.2950 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.2961    3.4852    0.0734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3362    1.3411    0.7568 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7541    2.4306    1.4708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8014    1.2627    0.9758 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3142    2.3657    0.2596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318   -1.5818   -0.8642 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5639   -2.5763   -1.0243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3239   -2.2921   -0.4502 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6600   -3.2749    0.4294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052   -4.5802   -0.0040 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8196   -5.2353    0.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8007   -6.5861   -0.0399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1905   -7.1789    0.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7684   -7.3211    0.7903 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0548   -7.0711    2.1258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020   -6.7419    0.4806 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4827   -7.2754    1.4107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929   -5.2590    0.8006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7673   -5.1673    2.1758 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454   -0.0516   -0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9089   -0.2387   -1.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203   -1.0368   -0.3510 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6044   -1.9685   -1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9635   -0.2069    0.2540 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5137    1.0260    0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376    1.9105    1.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8759    1.2655    1.8904 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5940    1.6522    3.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1027    1.8638    1.3263 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2519    2.1791    2.1950 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7043    1.1996    3.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9336    2.0765   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8081    2.8576   -2.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6442    3.8450   -1.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3961    1.8141   -1.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8180    0.9158    0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6620    2.4182    0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8397    1.2277    2.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9856    3.0620    2.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8566    4.1698   -1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8079    4.5165    0.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004151519212D          

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 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 44 52  1  0  0  0  0
 52 53  1  0  0  0  0
 42 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 38 56  1  0  0  0  0
 56 57  1  0  0  0  0
 36 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 31 60  1  0  0  0  0
 60 61  1  0  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
 64 66  1  0  0  0  0
 66 67  1  0  0  0  0
 66 68  1  0  0  0  0
 68 69  1  0  0  0  0
 68 70  1  0  0  0  0
 62 70  1  0  0  0  0
 70 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C4CC=C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(C)C(OC4OC(C)C(O)C(O)C4O)C(O)C3O)C(O)C2OC2OC(C)C(O)C(O)C2O)OC11CCC(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C51H82O20/c1-20-10-15-51(62-19-20)21(2)32-30(71-51)17-29-27-9-8-25-16-26(11-13-49(25,6)28(27)12-14-50(29,32)7)66-48-44(70-46-39(59)36(56)34(54)23(4)64-46)41(61)43(31(18-52)67-48)69-47-40(60)37(57)42(24(5)65-47)68-45-38(58)35(55)33(53)22(3)63-45/h8,20-24,26-48,52-61H,9-19H2,1-7H3

> <INCHI_KEY>
OZIHYFWYFUSXIS-UHFFFAOYSA-N

> <FORMULA>
C51H82O20

> <MOLECULAR_WEIGHT>
1015.197

> <EXACT_MASS>
1014.53994504

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
153

> <JCHEM_AVERAGE_POLARIZABILITY>
111.02282533296196

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4,5-dihydroxy-6-{[4-hydroxy-2-(hydroxymethyl)-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-eneoxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-2-methyloxan-3-yl)oxy]-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
0.9846927713333311

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.19130319621308

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.7542746611023

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826294395625

> <JCHEM_POLAR_SURFACE_AREA>
294.59999999999997

> <JCHEM_REFRACTIVITY>
245.28800000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4,5-dihydroxy-6-{[4-hydroxy-2-(hydroxymethyl)-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-eneoxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-2-methyloxan-3-yl)oxy]-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       8.032  -6.134   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.552  -5.884   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.095  -4.443   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.615  -4.193   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.591  -5.384   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.048  -6.825   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.528  -7.075   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.282  -4.008   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      14.805  -4.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.173  -3.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.268  -4.616   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.805  -4.526   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.497  -3.150   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.034  -3.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.880  -4.347   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.418  -4.258   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.264  -5.545   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.573  -6.921   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.035  -7.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.189  -5.724   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.498  -7.100   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.652  -5.813   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.960  -7.189   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.423  -7.279   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.577  -5.992   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.746  -7.289   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.054  -5.760   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.686  -6.467   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.454  -7.989   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      25.801  -5.455   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      26.647  -6.742   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      28.185  -6.652   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      29.031  -7.939   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      30.568  -7.850   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      31.260  -6.473   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      28.340  -9.315   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      29.186 -10.602   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      30.723 -10.512   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      31.415  -9.136   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      32.952  -9.047   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      33.643  -7.671   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      33.798 -10.333   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      35.336 -10.244   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      36.182 -11.531   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      35.491 -12.907   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      36.337 -14.193   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      35.646 -15.570   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      37.874 -14.104   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      38.720 -15.391   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      38.565 -12.728   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      40.103 -12.638   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      37.719 -11.441   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      38.410 -10.065   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      33.107 -11.710   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      33.953 -12.996   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      31.570 -11.799   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      30.878 -13.175   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      26.802  -9.405   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      26.111 -10.781   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      25.956  -8.118   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      24.419  -8.208   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      23.728  -9.584   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      24.574 -10.870   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      23.883 -12.247   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      24.729 -13.533   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      22.345 -12.336   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      21.654 -13.712   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      21.499 -11.049   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      19.962 -11.139   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0      22.190  -9.673   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0      21.344  -8.386   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8   28                                             
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   25                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   12   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   11   26   27                                             
CONECT   26   25                                                            
CONECT   27   25    9   28                                                  
CONECT   28   27    5   29                                                  
CONECT   29   28                                                            
CONECT   30   17   31                                                       
CONECT   31   30   32   60                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   58                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   56                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   54                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   52                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   44   53                                                  
CONECT   53   52                                                            
CONECT   54   42   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   38   57                                                  
CONECT   57   56                                                            
CONECT   58   36   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   31   61                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63   70                                                  
CONECT   63   62   64                                                       
CONECT   64   63   65   66                                                  
CONECT   65   64                                                            
CONECT   66   64   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   69   70                                                  
CONECT   69   68                                                            
CONECT   70   68   62   71                                                  
CONECT   71   70                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  160    0
END

View in JSmol

Synonyms

Value	Source
Diosgenin 3-O-alpha-rhamnopyranosyl-(1-4)-alpha-rhamnopyranosyl-(1-4)-(alpha-rhamnopyranosyl-(1-2))-beta-glucopyranoside	MeSH
Formosanin C	MeSH
Paris saponin II	MeSH

Chemical Formula

C₅₁H₈₂O₂₀

Average Mass

1015.1970 Da

Monoisotopic Mass

1014.53995 Da

IUPAC Name

2-[(4,5-dihydroxy-6-{[4-hydroxy-2-(hydroxymethyl)-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-eneoxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-2-methyloxan-3-yl)oxy]-6-methyloxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3C4CC=C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(C)C(OC4OC(C)C(O)C(O)C4O)C(O)C3O)C(O)C2OC2OC(C)C(O)C(O)C2O)OC11CCC(C)CO1

InChI Identifier

InChI=1S/C51H82O20/c1-20-10-15-51(62-19-20)21(2)32-30(71-51)17-29-27-9-8-25-16-26(11-13-49(25,6)28(27)12-14-50(29,32)7)66-48-44(70-46-39(59)36(56)34(54)23(4)64-46)41(61)43(31(18-52)67-48)69-47-40(60)37(57)42(24(5)65-47)68-45-38(58)35(55)33(53)22(3)63-45/h8,20-24,26-48,52-61H,9-19H2,1-7H3

InChI Key

OZIHYFWYFUSXIS-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
Allium senescens	LOTUS Database	35616633
Borassus flabellifer	LOTUS Database	35616633
Cestrum nocturnum	LOTUS Database	35616633
Chamaerops humilis	LOTUS Database	35616633
Dioscorea floribunda	LOTUS Database	35616633
Dioscorea pseudojaponica	LOTUS Database	35616633
Paris polyphylla	LOTUS Database	35616633
Smilax china	LOTUS Database	35616633
Trachycarpus fortunei	LOTUS Database	35616633
Trillium erectum	LOTUS Database	35616633
Ypsilandra thibetica	LOTUS Database	35616633

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
Triterpenoid
Spirostane skeleton
Oligosaccharide
Delta-5-steroid
Glycosyl compound
O-glycosyl compound
Ketal
Oxane
Tetrahydrofuran
Secondary alcohol
Oxacycle
Polyol
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Organic oxygen compound
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	1.02	ALOGPS
logP	0.98	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	294.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	245.29 m³·mol⁻¹	ChemAxon
Polarizability	111.02 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

328441

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Polyphyllin B (NP0139059)

MOL for NP0139059 (Polyphyllin B)

3D MOL for NP0139059 (Polyphyllin B)

3D SDF for NP0139059 (Polyphyllin B)

3D-SDF for NP0139059 (Polyphyllin B)

PDB for NP0139059 (Polyphyllin B)

3D PDB for NP0139059 (Polyphyllin B)

SMILES for NP0139059 (Polyphyllin B)

INCHI for NP0139059 (Polyphyllin B)

Structure for NP0139059 (Polyphyllin B)

3D Structure for NP0139059 (Polyphyllin B)