NP-MRD: Showing NP-Card for Pseudoprotodioscin (NP0137320)

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Record Information

Version

2.0

Created at

2022-05-30 16:48:51 UTC

Updated at

2022-05-30 16:48:51 UTC

NP-MRD ID

NP0137320

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pseudoprotodioscin

Description

2-{[4-Hydroxy-2-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-6-{[7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosa-6,18-dien-16-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. Pseudoprotodioscin is found in Asparagus cochinchinensis, Aspergillus fumigatus, Borassus flabellifer, Dioscorea panthaica, Smilax china, Smilax excelsa, Smilax japonica, Smilax menispermoidea, Trachycarpus wagnerianus and Tribulus terrestris. 2-{[4-Hydroxy-2-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-6-{[7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosa-6,18-dien-16-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171501012D          

 72 80  0  0  0  0            999 V2000
    1.4327   -3.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6833   -2.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4893   -2.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0447   -2.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8507   -2.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4669   -3.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3853   -3.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791   -2.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030   -1.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7151   -1.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3313   -2.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1513   -1.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4826   -1.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3026   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7913   -1.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6112   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0999   -2.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7686   -3.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9486   -3.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4600   -2.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1286   -3.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6400   -2.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3087   -3.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4887   -3.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -2.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5915   -3.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9199   -2.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4086   -2.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2286   -2.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7172   -3.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5372   -3.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8685   -2.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3859   -4.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8746   -4.8744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6946   -4.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0259   -4.0279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8459   -3.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1772   -3.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3345   -4.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1545   -4.5109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0032   -5.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4919   -6.0220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1833   -5.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8520   -6.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5659   -4.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2346   -5.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0773   -3.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2573   -3.7267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9260   -4.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4147   -5.1469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0834   -5.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5720   -6.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2634   -5.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9321   -6.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7747   -5.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9547   -5.4195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1060   -4.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6173   -3.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1820   -1.7915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278   -1.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3218   -1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2337   -1.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0397   -1.4214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5952   -0.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4012   -0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566   -0.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9001    0.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5387    0.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2881    0.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0168   -0.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8228   -0.2833    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  2  0  0  0  0
  6  7  1  0  0  0  0
  6  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
  8 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  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
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 35 43  1  0  0  0  0
 43 44  1  0  0  0  0
 33 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 28 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  1  0  0  0  0
 49 57  1  0  0  0  0
 57 58  1  0  0  0  0
  9 59  1  0  0  0  0
  5 59  1  0  0  0  0
  2 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
 65 66  1  0  0  0  0
 64 67  1  0  0  0  0
 67 68  1  0  0  0  0
 67 69  1  0  0  0  0
 69 70  1  0  0  0  0
 69 71  1  0  0  0  0
 62 71  1  0  0  0  0
 71 72  1  0  0  0  0
M  END

     RDKit          3D

154162  0  0  0  0  0  0  0  0999 V2000
    5.8616    4.1685    1.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9339    3.4619    0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8312    2.5431    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9212    2.0781    0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9253    0.6158    1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0903   -0.2566   -0.0312 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0619   -1.6898    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3165    0.1771   -0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5175    0.1391   -0.2117 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1669   -0.9495    0.2275 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3307   -1.1994   -0.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5986   -2.5727   -0.4134 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5739   -3.0216   -1.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8499   -4.3783   -1.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1083   -2.8154    1.0089 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4284   -3.2266    1.0296 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0468   -1.4789    1.7602 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0188   -0.6059    1.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7061   -0.8182    1.6357 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8105   -1.2685    2.5934 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5524    2.1273   -1.2539 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4707    2.7951   -1.8120 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2925    1.9227   -2.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1385    2.7948   -1.7717 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8179    2.1509   -1.7053 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3738    1.5390   -3.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    1.3936   -2.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6601    1.1182   -1.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287    0.9798   -1.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5787   -0.2391   -0.9200 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8159    0.0956   -0.3685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8261   -0.6681   -0.9432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7397    0.1154   -1.6357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5240    0.9127   -0.8657 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8762    2.1589   -0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7690    2.9009    0.4138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2215    0.1375    0.2314 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0905    0.9067    0.9598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3840    0.4187    0.7946 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.1951    1.3682    0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4700    2.4597    0.9876 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.3523    3.3922    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1385    2.0971    2.2691 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.3898    2.7085    2.3230 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3633    0.6017    2.3141 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.8679    0.1811    3.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0049   -0.0416    2.1090 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1703    0.2155    3.1895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1475   -0.5181    1.0667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6151   -1.1962    2.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5151   -1.5410    0.0900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5935   -2.1601   -0.4832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6633   -3.5237   -0.3547 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7598   -3.8075    0.4451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6389   -4.7321   -0.0388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.1575   -6.1606    0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1022   -4.5165   -1.4505 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.2889   -3.7976   -1.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0591   -3.8680   -2.3182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.1566   -4.1989   -3.6471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7054   -4.1485   -1.7036 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7516   -3.5350   -2.5119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6616   -0.7034    0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997   -0.4957   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041    0.9338   -0.5279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4877    1.8657    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913    1.1248   -0.6517 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1506    1.5746    0.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5527    2.1741    0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833    3.3045   -0.4328 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7573    4.4886    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170    3.6991   -0.7023 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8723    4.6046    1.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5885    5.0170    1.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004171501012D          

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 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
  8 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  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
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 35 43  1  0  0  0  0
 43 44  1  0  0  0  0
 33 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 28 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  1  0  0  0  0
 49 57  1  0  0  0  0
 57 58  1  0  0  0  0
  9 59  1  0  0  0  0
  5 59  1  0  0  0  0
  2 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
 65 66  1  0  0  0  0
 64 67  1  0  0  0  0
 67 68  1  0  0  0  0
 67 69  1  0  0  0  0
 69 70  1  0  0  0  0
 69 71  1  0  0  0  0
 62 71  1  0  0  0  0
 71 72  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137320

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1=C(C)C2C(CC3C4CC=C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(C)C(O)C(O)C3O)C(O)C2OC2OC(C)C(O)C(O)C2O)O1)COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C51H82O21/c1-20(19-64-46-40(60)39(59)36(56)31(17-52)69-46)7-10-29-21(2)33-30(68-29)16-28-26-9-8-24-15-25(11-13-50(24,5)27(26)12-14-51(28,33)6)67-49-45(72-48-42(62)38(58)35(55)23(4)66-48)43(63)44(32(18-53)70-49)71-47-41(61)37(57)34(54)22(3)65-47/h8,20,22-23,25-28,30-49,52-63H,7,9-19H2,1-6H3

> <INCHI_KEY>
MDCUMTGKKLOMCW-UHFFFAOYSA-N

> <FORMULA>
C51H82O21

> <MOLECULAR_WEIGHT>
1031.196

> <EXACT_MASS>
1030.53485966

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
154

> <JCHEM_AVERAGE_POLARIZABILITY>
112.39711761326903

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[4-hydroxy-2-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-6-{[7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-6,18-dien-16-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
-1.1450526846666682

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.18725531988907

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.751489800569265

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648377298756638

> <JCHEM_POLAR_SURFACE_AREA>
325.83

> <JCHEM_REFRACTIVITY>
250.01270000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[4-hydroxy-2-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-6-{[7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-6,18-dien-16-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.674  -5.741   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.142  -4.273   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.647  -3.945   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.684  -5.083   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.188  -4.755   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.338  -5.779   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.186  -7.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.668  -5.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.339  -3.497   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.668  -2.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.818  -3.743   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.349  -3.573   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.968  -2.163   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.498  -1.993   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.410  -3.234   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.941  -3.065   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.853  -4.305   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.235  -5.716   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.704  -5.885   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.792  -4.645   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.173  -6.055   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.261  -4.814   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.643  -6.225   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.112  -6.394   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.200  -5.153   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.438  -6.491   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      20.384  -4.136   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      21.296  -5.377   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      22.827  -5.207   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      23.739  -6.448   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.269  -6.278   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      25.888  -4.868   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      23.120  -7.858   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      24.033  -9.099   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      25.563  -8.929   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      26.182  -7.519   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      27.712  -7.349   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      28.331  -5.939   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      28.624  -8.590   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      30.155  -8.420   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      28.006 -10.000   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      28.918 -11.241   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      26.475 -10.170   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      25.857 -11.580   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      21.590  -8.028   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      20.971  -9.438   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      20.678  -6.787   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      19.147  -6.956   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      18.529  -8.367   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      19.441  -9.608   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      18.822 -11.018   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      19.734 -12.259   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      17.292 -11.188   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      16.673 -12.598   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      16.379  -9.947   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      14.849 -10.116   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      16.998  -8.536   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      16.086  -7.296   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       7.806  -3.344   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       2.105  -3.135   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       0.601  -3.463   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      -0.436  -2.325   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -1.941  -2.653   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      -2.978  -1.515   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -4.482  -1.843   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      -5.519  -0.705   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      -2.510  -0.047   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      -3.547   1.091   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      -1.005   0.281   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      -0.538   1.748   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0       0.031  -0.857   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0       1.536  -0.529   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   60                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   59                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   25                                                  
CONECT    9    8   10   59                                                  
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   27                                                  
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    8   11   26                                             
CONECT   26   25                                                            
CONECT   27   17   28                                                       
CONECT   28   27   29   47                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   45                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   43                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   35   44                                                  
CONECT   44   43                                                            
CONECT   45   33   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   28   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   57                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   49   58                                                  
CONECT   58   57                                                            
CONECT   59    9    5                                                       
CONECT   60    2   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63   71                                                  
CONECT   63   62   64                                                       
CONECT   64   63   65   67                                                  
CONECT   65   64   66                                                       
CONECT   66   65                                                            
CONECT   67   64   68   69                                                  
CONECT   68   67                                                            
CONECT   69   67   70   71                                                  
CONECT   70   69                                                            
CONECT   71   69   62   72                                                  
CONECT   72   71                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  160    0
END

View in JSmol

Synonyms

Value	Source
Pseudo-protodioscin	MeSH

Chemical Formula

C₅₁H₈₂O₂₁

Average Mass

1031.1960 Da

Monoisotopic Mass

1030.53486 Da

IUPAC Name

2-{[4-hydroxy-2-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-6-{[7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-6,18-dien-16-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(CCC1=C(C)C2C(CC3C4CC=C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(C)C(O)C(O)C3O)C(O)C2OC2OC(C)C(O)C(O)C2O)O1)COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C51H82O21/c1-20(19-64-46-40(60)39(59)36(56)31(17-52)69-46)7-10-29-21(2)33-30(68-29)16-28-26-9-8-24-15-25(11-13-50(24,5)27(26)12-14-51(28,33)6)67-49-45(72-48-42(62)38(58)35(55)23(4)66-48)43(63)44(32(18-53)70-49)71-47-41(61)37(57)34(54)22(3)65-47/h8,20,22-23,25-28,30-49,52-63H,7,9-19H2,1-6H3

InChI Key

MDCUMTGKKLOMCW-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
Asparagus cochinchinensis	LOTUS Database	35616633
Aspergillus fumigatus	LOTUS Database	35616633
Borassus flabellifer	LOTUS Database	35616633
Dioscorea panthaica	LOTUS Database	35616633
Smilax china	LOTUS Database	35616633
Smilax excelsa	LOTUS Database	35616633
Smilax japonica	LOTUS Database	35616633
Smilax menispermoidea	LOTUS Database	35616633
Trachycarpus wagnerianus	LOTUS Database	35616633
Tribulus terrestris	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
Diterpene glycoside
Furostane-skeleton
Oligosaccharide
Diterpenoid
Terpene glycoside
Delta-5-steroid
Fatty acyl glycoside
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Fatty acyl
Oxane
Dihydrofuran
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Alcohol
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen 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	0.18	ALOGPS
logP	-1.1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	325.83 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	250.01 m³·mol⁻¹	ChemAxon
Polarizability	112.4 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

73817989

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pseudoprotodioscin (NP0137320)

MOL for NP0137320 (Pseudoprotodioscin)

3D MOL for NP0137320 (Pseudoprotodioscin)

3D SDF for NP0137320 (Pseudoprotodioscin)

3D-SDF for NP0137320 (Pseudoprotodioscin)

PDB for NP0137320 (Pseudoprotodioscin)

3D PDB for NP0137320 (Pseudoprotodioscin)

SMILES for NP0137320 (Pseudoprotodioscin)

INCHI for NP0137320 (Pseudoprotodioscin)

Structure for NP0137320 (Pseudoprotodioscin)

3D Structure for NP0137320 (Pseudoprotodioscin)