NP-MRD: Showing NP-Card for {2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid (NP0260403)

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Record Information

Version

1.0

Created at

2022-09-08 02:33:47 UTC

Updated at

2022-09-08 02:33:47 UTC

NP-MRD ID

NP0260403

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid

Description

{2,12-Dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl}oxidanesulfonic acid belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. {2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid is found in Melissa officinalis. {2,12-Dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl}oxidanesulfonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231519352D          

 55 60  0  0  0  0            999 V2000
   -0.1105   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -3.8230    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -3.4105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4414   -4.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337   -6.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955   -6.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7707   -6.6288    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0529   -5.8535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5460   -6.9109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4886   -7.4040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882   -6.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8266   -3.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558   -2.9985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -6.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605   -7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605   -8.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -8.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.3954    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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  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  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  2  0  0  0  0
 21 24  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  2  0  0  0  0
 29 32  1  0  0  0  0
 25 33  1  0  0  0  0
 14 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
  8 36  1  0  0  0  0
 13 36  1  0  0  0  0
 36 37  1  0  0  0  0
 10 38  1  0  0  0  0
  5 38  1  0  0  0  0
 38 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
  5 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 47 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 45 54  1  0  0  0  0
 54 55  1  0  0  0  0
M  END

     RDKit          3D

113118  0  0  0  0  0  0  0  0999 V2000
    2.9999    0.5479    3.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787    0.6244    2.3989 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9447    1.7951    1.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3166    1.8824    0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3151    0.6220   -0.5174 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5790    0.4614   -1.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    0.3378   -2.5641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8556    0.4301   -0.8202 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399    0.2792   -1.7068 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8322    1.3549   -1.5868 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3627    1.3589   -0.3179 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0587    2.7123   -0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0472    2.7699   -1.1284 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4238    0.3053   -0.2280 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5413   -0.1352    1.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1389   -0.7987   -1.1880 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8164   -0.6283   -2.3988 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6647   -1.0300   -1.4510 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0745   -1.7841   -0.4481 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2139    0.9123   -1.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6675   -0.3643   -2.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0894   -1.1630   -1.0609 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1828   -2.6369   -1.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5921   -1.0453    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812   -1.3752    1.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089   -1.8681    1.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1506   -0.9574    0.2398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6432   -0.8932    0.3754 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1034   -2.2917    0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0404   -0.0455    1.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5066   -0.0639    1.8520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8975   -1.1868    2.5948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3729    0.0286    0.6485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3600   -0.9555    0.5868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8941   -0.5575    0.7739 S   0  0  0  0  0  6  0  0  0  0  0  0
   -9.0716    0.9468    0.5964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8868   -1.2016   -0.1351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4049   -0.8618    2.3682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6704    0.2667   -0.6511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6300   -0.3643   -1.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7859    1.7373   -1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2402    2.5937   -0.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3624    4.1930   -0.5150 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.0143    4.7023   -0.9460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3840    4.3463   -1.6013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8291    5.0478    0.8756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195   -0.3194   -0.8331 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4742    0.5537   -1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833    0.4629   -1.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5536   -0.9393   -1.0992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0874   -1.8344   -2.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9894   -0.6259    0.2405 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6575   -0.5848    1.5863 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6602   -1.8852    2.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3972    0.0960    4.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2617    1.5983    4.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2249    0.8471    2.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0329    1.5607    1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104    2.7340    2.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2506    2.1878    0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7907    2.6725   -0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5336    0.2135   -2.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6066    1.1884    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3203    3.5067   -0.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5628    2.6663    0.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7069    3.4535   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4147    0.7411   -0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0560   -0.9877    1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5310   -1.7443   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8599   -1.4516   -2.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6447   -1.6968   -2.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5188   -2.5195   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5205    1.6742   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647    1.3882   -2.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687   -0.9618   -2.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240   -0.1877   -3.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6787   -3.2810   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5777   -2.7272   -2.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9812   -3.0891   -0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388   -1.3020    2.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0369   -1.7146    2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5631   -2.9331    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8437    0.0554    0.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574   -3.0883    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0920   -2.4395    1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0996   -2.4573    0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5454   -0.4061    2.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6821    1.0031    1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6515    0.7892    2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004231519352D          

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  8 36  1  0  0  0  0
 13 36  1  0  0  0  0
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 10 38  1  0  0  0  0
  5 38  1  0  0  0  0
 38 39  1  0  0  0  0
  2 39  1  0  0  0  0
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 39 41  1  0  0  0  0
  5 42  1  0  0  0  0
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 45 54  1  0  0  0  0
 54 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(OS(O)(=O)=O)C(C)(COS(O)(=O)=O)C5CCC34C)C2C1(C)O)C(=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C36H58O17S2/c1-18-9-12-36(30(42)52-29-26(41)25(40)24(39)21(16-37)51-29)14-13-33(4)19(27(36)35(18,6)43)7-8-23-31(2)15-20(38)28(53-55(47,48)49)32(3,17-50-54(44,45)46)22(31)10-11-34(23,33)5/h7,18,20-29,37-41,43H,8-17H2,1-6H3,(H,44,45,46)(H,47,48,49)

> <INCHI_KEY>
DFXHRBSEENKJFW-UHFFFAOYSA-N

> <FORMULA>
C36H58O17S2

> <MOLECULAR_WEIGHT>
826.96

> <EXACT_MASS>
826.311542756

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
83.32201645965257

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl}oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
-2.345808794744015

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
-1.3360699237629978

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.97783733959489

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810936801758814

> <JCHEM_POLAR_SURFACE_AREA>
284.10999999999996

> <JCHEM_REFRACTIVITY>
190.85410000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -0.206  -5.803   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.114  -5.803   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   21  S   UNK     0      14.424  -7.136   0.000  0.00  0.00           S+0
HETATM   22  O   UNK     0      15.194  -5.803   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.090  -6.366   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      15.757  -7.906   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.058 -11.847   0.000  0.00  0.00           O+0
HETATM   29  S   UNK     0      14.505 -12.374   0.000  0.00  0.00           S+0
HETATM   30  O   UNK     0      15.032 -10.927   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      15.952 -12.900   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      13.979 -13.821   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.885 -11.335   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.410  -6.320   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.157  -5.597   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -0.976 -12.471   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -2.516 -12.471   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -3.286 -13.805   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -4.826 -13.805   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -5.596 -12.471   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -2.516 -15.138   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -3.286 -16.472   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -0.976 -15.138   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -0.206 -16.472   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -0.206 -13.805   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       1.334 -13.805   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   38   42                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   36                                             
CONECT    9    8                                                            
CONECT   10    8   11   38                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   36                                                  
CONECT   14   13   15   16   33                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25   19   26   27   33                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33   25   14   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    8   13   37                                             
CONECT   37   36                                                            
CONECT   38   10    5   39                                                  
CONECT   39   38    2   40   41                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42    5   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46   54                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   50                                                  
CONECT   48   47   49                                                       
CONECT   49   48                                                            
CONECT   50   47   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   45   55                                                  
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  120    0
END

View in JSmol

Synonyms

Value	Source
{2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl}oxidanesulfonate	Generator
{2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulphooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl}oxidanesulphonate	Generator
{2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulphooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl}oxidanesulphonic acid	Generator

Chemical Formula

C₃₆H₅₈O₁₇S₂

Average Mass

826.9600 Da

Monoisotopic Mass

826.31154 Da

IUPAC Name

{2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl}oxidanesulfonic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(OS(O)(=O)=O)C(C)(COS(O)(=O)=O)C5CCC34C)C2C1(C)O)C(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C36H58O17S2/c1-18-9-12-36(30(42)52-29-26(41)25(40)24(39)21(16-37)51-29)14-13-33(4)19(27(36)35(18,6)43)7-8-23-31(2)15-20(38)28(53-55(47,48)49)32(3,17-50-54(44,45)46)22(31)10-11-34(23,33)5/h7,18,20-29,37-41,43H,8-17H2,1-6H3,(H,44,45,46)(H,47,48,49)

InChI Key

DFXHRBSEENKJFW-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
Melissa officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Sulfated steroid skeleton
12-hydroxysteroid
Hydroxysteroid
Steroid
Hexose monosaccharide
Sulfuric acid ester
Alkyl sulfate
Monosaccharide
Oxane
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organooxygen compound
Primary alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
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	-0.03	ALOGPS
logP	-2.3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	284.11 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	190.85 m³·mol⁻¹	ChemAxon
Polarizability	83.32 Å³	ChemAxon
Number of Rings	6	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid (NP0260403)

MOL for NP0260403 ({2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid)

3D MOL for NP0260403 ({2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid)

3D SDF for NP0260403 ({2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid)

3D-SDF for NP0260403 ({2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid)

PDB for NP0260403 ({2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid)

3D PDB for NP0260403 ({2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid)

SMILES for NP0260403 ({2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid)

INCHI for NP0260403 ({2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid)

Structure for NP0260403 ({2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid)

3D Structure for NP0260403 ({2,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-4-[(sulfooxy)methyl]-8a-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl}oxidanesulfonic acid)