NP-MRD: Showing NP-Card for 2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0226818)

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Record Information

Version

2.0

Created at

2022-09-06 05:58:38 UTC

Updated at

2022-09-06 05:58:38 UTC

NP-MRD ID

NP0226818

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-{[15-(5-Hydroxy-6-methyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}heptan-2-yl)-7,7,12,16-tetramethyl-14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 2-{[15-(5-Hydroxy-6-methyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}heptan-2-yl)-7,7,12,16-tetramethyl-14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171513572D          

 77 85  0  0  0  0            999 V2000
    6.8256    2.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6974    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802    3.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5693    4.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0757    5.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521    4.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6392    3.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649    5.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9348    4.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6239    5.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8067    5.5993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4958    6.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785    6.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3677    7.2405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0021    7.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    7.7790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8194    6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3257    7.5533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1303    6.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9475    6.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3971    1.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1995    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123   -0.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441   -1.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562   -0.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9002   -1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1805   -0.5824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0562   -0.0471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362   -0.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -1.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801   -0.4827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195    1.0691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5072    1.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6524    0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4284    0.0388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5736   -0.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3495   -1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4947   -1.8657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9429   -1.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0881   -2.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1669   -1.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5362   -1.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0217   -0.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458    0.0676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  7 10  1  0  0  0  0
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 11 12  1  0  0  0  0
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 20 21  1  0  0  0  0
  2 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
 25 26  1  0  0  0  0
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 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
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 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
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 34 35  1  0  0  0  0
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 36 37  1  0  0  0  0
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 38 39  1  0  0  0  0
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 40 41  1  0  0  0  0
 29 42  1  0  0  0  0
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 43 46  1  0  0  0  0
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 47 48  1  0  0  0  0
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 27 51  1  0  0  0  0
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 67 76  1  0  0  0  0
 76 77  1  0  0  0  0
M  END

     RDKit          3D

167175  0  0  0  0  0  0  0  0999 V2000
    3.9159    1.3568   -2.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9850    0.3700   -1.2719 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5802    0.2639    0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0047   -0.2605   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1039   -1.5997   -0.6633 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3946   -2.5538    0.0415 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5882   -2.0006   -0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3249   -1.0184   -1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7455   -3.3704   -1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0532   -2.0722    0.6611 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4030   -2.4268    0.6716 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6347   -3.5970    1.3451 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9005   -4.0805    1.2653 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0914   -5.0370    0.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8492   -4.4558   -1.1355 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0195   -3.1080    1.3748 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6804   -3.1829    2.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6857   -1.6927    1.0706 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4684   -0.8639    1.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2432   -1.3438    1.3298 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0685   -1.3896    2.7284 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6056    0.9250   -1.3790 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3885    2.2737   -0.7680 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2700    3.3200   -1.6126 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2420    2.1311    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6129    1.0380   -0.5003 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3094    1.7363   -1.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5072    0.4035    0.5428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6143    1.3020    0.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0195    0.7397    0.9453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3504    0.4180    2.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2969    1.1817    2.8605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6529    2.0953    3.7763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6107    3.0733    4.0264 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9815    4.2900    4.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0181    5.2105    4.8721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8071    2.5831    4.7720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7557    3.6102    4.7691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4300    1.4392    3.9711 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.3191    0.4239    3.6414 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8024   -0.0255    4.8705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1943   -0.3973    0.0289 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.9233   -2.0086    0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6349    0.1185   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6828   -1.6839   -1.4368 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5920   -2.7073   -1.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6463   -2.4607   -2.2372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8709   -2.4239   -1.5713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0464   -3.5423   -0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0690   -4.8044   -1.5942 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.1206   -4.7185   -2.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7458   -4.8936   -2.3270 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004171513572D          

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   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0562   -0.0471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362   -0.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -1.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801   -0.4827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195    1.0691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5072    1.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6524    0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4284    0.0388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5736   -0.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3495   -1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4947   -1.8657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9429   -1.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0881   -2.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1669   -1.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5362   -1.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0217   -0.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458    0.0676    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 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  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 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
 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  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
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  0  0  0  0
 29 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 43 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
 42 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 27 51  1  0  0  0  0
 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 22 54  1  0  0  0  0
 25 54  1  0  0  0  0
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 46 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
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 57 64  1  0  0  0  0
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 23 66  1  0  0  0  0
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 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 69 72  1  0  0  0  0
 72 73  1  0  0  0  0
 72 74  1  0  0  0  0
 74 75  1  0  0  0  0
 74 76  1  0  0  0  0
 67 76  1  0  0  0  0
 76 77  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226818

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(O)C(C)(C)OC1OC(CO)C(O)C(O)C1O)C1C(CC2(C)C3CC(OC4OC(CO)C(O)C(O)C4O)C4C5(CC35CCC12C)CCC(OC1OCC(O)C(O)C1O)C4(C)C)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C53H90O24/c1-21(8-9-29(58)49(4,5)77-47-42(69)38(65)35(62)27(18-56)75-47)31-24(72-46-41(68)37(64)34(61)26(17-55)74-46)15-51(7)28-14-23(71-45-40(67)36(63)33(60)25(16-54)73-45)43-48(2,3)30(76-44-39(66)32(59)22(57)19-70-44)10-11-53(43)20-52(28,53)13-12-50(31,51)6/h21-47,54-69H,8-20H2,1-7H3

> <INCHI_KEY>
AFYCRSVRZJCGCA-UHFFFAOYSA-N

> <FORMULA>
C53H90O24

> <MOLECULAR_WEIGHT>
1111.279

> <EXACT_MASS>
1110.582203778

> <JCHEM_ACCEPTOR_COUNT>
24

> <JCHEM_ATOM_COUNT>
167

> <JCHEM_AVERAGE_POLARIZABILITY>
117.21640666714055

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.14

> <JCHEM_LOGP>
-3.663313665999999

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.09728281490003

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.678059180062332

> <JCHEM_PKA_STRONGEST_BASIC>
-3.672684471052242

> <JCHEM_POLAR_SURFACE_AREA>
397.5200000000001

> <JCHEM_REFRACTIVITY>
261.2565000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-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      12.741   5.119   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.635   6.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.110   6.967   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.529   8.394   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.475   9.609   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.004   8.604   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.793   7.079   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.215  10.130   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.478   8.815   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.898  10.241   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.372  10.452   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.792  11.879   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.267  12.089   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.686  13.516   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.737  13.094   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.157  14.521   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.263  12.884   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.208  14.100   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.843  11.457   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.369  11.247   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.130  -0.723   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.122  -1.900   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.638  -1.629   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.631  -2.807   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.147  -2.536   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.670  -1.087   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.108  -4.255   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.101  -5.432   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.592  -4.526   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.069  -5.974   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.599  -3.349   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.083  -3.620   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.674   0.186   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.812   0.858   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -0.888   1.089   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       0.105  -0.088   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      -0.418  -1.536   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -1.934  -1.807   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      -2.457  -3.256   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      -2.927  -0.630   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -4.443  -0.901   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      -2.404   0.818   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      -3.396   1.996   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      12.147   2.112   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      12.418   0.596   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      13.866   0.073   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      14.137  -1.443   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      15.586  -1.967   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0      15.857  -3.483   0.000  0.00  0.00           O+0
HETATM   72  C   UNK     0      12.960  -2.436   0.000  0.00  0.00           C+0
HETATM   73  O   UNK     0      13.231  -3.952   0.000  0.00  0.00           O+0
HETATM   74  C   UNK     0      11.512  -1.913   0.000  0.00  0.00           C+0
HETATM   75  O   UNK     0      10.334  -2.906   0.000  0.00  0.00           O+0
HETATM   76  C   UNK     0      11.241  -0.397   0.000  0.00  0.00           C+0
HETATM   77  O   UNK     0       9.792   0.126   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20                                                            
CONECT   22    2   23   54                                                  
CONECT   23   22   24   66                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   54                                             
CONECT   26   25                                                            
CONECT   27   25   28   51                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   42                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   31   41                                                  
CONECT   41   40                                                            
CONECT   42   29   43   49                                                  
CONECT   43   42   44   45   46                                             
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   43   47   56                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   42   50   51                                             
CONECT   50   49   51                                                       
CONECT   51   50   27   49   52                                             
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   22   25   55                                             
CONECT   55   54                                                            
CONECT   56   46   57                                                       
CONECT   57   56   58   64                                                  
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   57   65                                                  
CONECT   65   64                                                            
CONECT   66   23   67                                                       
CONECT   67   66   68   76                                                  
CONECT   68   67   69                                                       
CONECT   69   68   70   72                                                  
CONECT   70   69   71                                                       
CONECT   71   70                                                            
CONECT   72   69   73   74                                                  
CONECT   73   72                                                            
CONECT   74   72   75   76                                                  
CONECT   75   74                                                            
CONECT   76   74   67   77                                                  
CONECT   77   76                                                            
MASTER        0    0    0    0    0    0    0    0   77    0  170    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₃H₉₀O₂₄

Average Mass

1111.2790 Da

Monoisotopic Mass

1110.58220 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(CCC(O)C(C)(C)OC1OC(CO)C(O)C(O)C1O)C1C(CC2(C)C3CC(OC4OC(CO)C(O)C(O)C4O)C4C5(CC35CCC12C)CCC(OC1OCC(O)C(O)C1O)C4(C)C)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C53H90O24/c1-21(8-9-29(58)49(4,5)77-47-42(69)38(65)35(62)27(18-56)75-47)31-24(72-46-41(68)37(64)34(61)26(17-55)74-46)15-51(7)28-14-23(71-45-40(67)36(63)33(60)25(16-54)73-45)43-48(2,3)30(76-44-39(66)32(59)22(57)19-70-44)10-11-53(43)20-52(28,53)13-12-50(31,51)6/h21-47,54-69H,8-20H2,1-7H3

InChI Key

AFYCRSVRZJCGCA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Triterpene saponin
Triterpene glycoside
Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
24-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Oxane
Fatty acyl
Monosaccharide
Secondary alcohol
Organoheterocyclic compound
Polyol
Acetal
Oxacycle
Organooxygen compound
Primary alcohol
Alcohol
Hydrocarbon derivative
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	-1.1	ALOGPS
logP	-3.7	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	11.68	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	397.52 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	261.26 m³·mol⁻¹	ChemAxon
Polarizability	117.22 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

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-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0226818)

MOL for NP0226818 (2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0226818 (2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0226818 (2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0226818 (2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0226818 (2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0226818 (2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0226818 (2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0226818 (2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0226818 (2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0226818 (2-({3-hydroxy-2-methyl-6-[7,7,12,16-tetramethyl-9,14-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]heptan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)