NP-MRD: Showing NP-Card for [3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate (NP0169350)

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Record Information

Version

2.0

Created at

2022-09-03 05:17:08 UTC

Updated at

2022-09-03 05:17:08 UTC

NP-MRD ID

NP0169350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate

Description

[3,4,5-Tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]Nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate 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. [3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate is found in Momordica charantia. [3,4,5-Tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]Nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161509302D          

 56 61  0  0  0  0            999 V2000
    5.6662    3.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9934    2.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8128    2.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3051    3.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1246    2.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6169    3.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1092    4.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9548    4.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2789    3.0918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5011    1.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7473    1.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0746    0.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125    1.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314    0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5945    0.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4090    0.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780   -0.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9727    0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5503    1.1787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0438    1.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796    1.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3166    2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1353    2.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761    1.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250    2.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5713    0.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789    1.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5879    2.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9893    1.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1984    1.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0060    2.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7850    2.7313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9774    3.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683    3.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3669    3.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1579    3.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565    2.8671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3503    4.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788    4.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5712    4.9035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621    5.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9607    4.5703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5545    5.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122    3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0108    4.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184    5.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274    5.4712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170    5.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6046    3.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3955    2.8300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9941    3.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017    4.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    3.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1817    0.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867    0.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197   -0.1246    0.0000 C   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
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  2 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
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 18 26  1  0  0  0  0
 26 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
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 33 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 39 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 44 49  1  0  0  0  0
 31 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
 29 54  1  0  0  0  0
 18 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
M  END

     RDKit          3D

122127  0  0  0  0  0  0  0  0999 V2000
   -7.8638    0.9621   -5.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1652    0.6168   -4.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3141    0.8907   -4.0917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2717    0.0259   -3.6613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5807   -0.3013   -2.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2966   -0.9308   -1.7450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2394   -0.0701   -1.8003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5775    0.0873   -0.6174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5369    0.9616   -0.6295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2989    0.4766   -0.3162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3273    0.4382   -1.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042   -0.4798   -1.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944   -0.0333    0.1449 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8410    0.6123   -0.1850 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6202   -0.1209   -1.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1033    0.1809   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5511   -0.5656    0.2593 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5543   -2.0576   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9182   -0.2855    0.7598 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5858    0.9681    0.3566 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8232    1.1645   -1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9767    1.0304    1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8885   -0.0077    0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0376    0.2558   -0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9323   -0.8121   -0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3896   -1.3113   -1.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3415   -0.2867   -0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9459   -1.8944    0.2918 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7551   -0.4044    2.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4517    0.2627    2.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887   -0.3039    1.4025 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9643   -1.5696    1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850    0.7815    1.0961 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6790    0.9126    2.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4638    1.3962    2.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945    1.1516    0.7507 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1543    2.2426   -0.0412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680    1.9817   -0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734    1.0476    0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2134    2.4274    1.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9764    0.1690    2.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5119    0.4312    0.4735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3884    1.4651    0.3485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5644    2.5431    1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5865    3.5534    0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8294    2.5783    2.1893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3116   -0.8436    0.7833 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5563   -0.4938    1.3471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9822   -0.8756    2.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3143   -0.4421    3.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2649   -1.5797    3.3064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5216   -1.6453   -0.4602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8864   -2.0889   -0.4614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2504   -3.4140   -0.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6944   -3.7492   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3315   -4.2750   -0.3982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6623    0.6454   -6.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8965    0.5228   -6.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7223    2.0742   -6.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3972   -1.0203   -2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8556    0.6294   -1.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0671   -1.7412   -2.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1401   -0.9213   -0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810   -0.6206   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8819   -0.0666   -2.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0076    1.3946   -1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480   -1.5278   -0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658   -0.5469   -1.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.8389    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4346    0.3768   -2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3970   -1.1638   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0939    1.2758   -0.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6199   -0.1349   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6560   -2.4272   -0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9016   -2.6640    0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3793   -2.1540   -0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6287   -1.1244    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0675    1.8858    0.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1492    1.8744   -1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8466    1.6384   -1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9364    0.1840   -1.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3931    2.0123    0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9552    1.1622    2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6398   -1.0550    0.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3189    1.2933   -0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2973   -1.1279   -1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6084   -2.3917   -2.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8717   -0.6952   -2.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4553    0.3876   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5769    0.2775    0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0188   -1.1538   -0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7992   -1.9365    0.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5644   -0.0125    2.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6573   -1.4867    2.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0473   -0.0124    3.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
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 40105  1  0
 40106  1  0
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 41108  1  0
 41109  1  0
 41110  1  0
M  END


  Mrv1533004161509302D          

 56 61  0  0  0  0            999 V2000
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 41 42  2  0  0  0  0
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 39 44  1  0  0  0  0
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 54 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC=CC(C)(C)O)C1CCC2(C)C3C=CC45OCC3(CCC12C)C4CCC(OC1OC(COC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O)C5(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C44H66O12/c1-25(13-12-18-39(6,7)49)30-16-19-42(11)32-17-20-44-33(43(32,24-51-44)22-21-41(30,42)10)14-15-34(40(44,8)9)56-38-37(54-29(5)48)36(53-28(4)47)35(52-27(3)46)31(55-38)23-50-26(2)45/h12,17-18,20,25,30-38,49H,13-16,19,21-24H2,1-11H3

> <INCHI_KEY>
AOOVSOSBQZZYPP-UHFFFAOYSA-N

> <FORMULA>
C44H66O12

> <MOLECULAR_WEIGHT>
787.0

> <EXACT_MASS>
786.455427565

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
122

> <JCHEM_AVERAGE_POLARIZABILITY>
87.71497324215865

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
6.09

> <JCHEM_LOGP>
5.47159860633333

> <ALOGPS_LOGS>
-6.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.781315978829436

> <JCHEM_PKA_STRONGEST_BASIC>
-1.579825593357731

> <JCHEM_POLAR_SURFACE_AREA>
153.12

> <JCHEM_REFRACTIVITY>
205.60760000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.01e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      10.577   5.988   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.188   4.575   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.717   4.397   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.636   5.632   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.166   5.454   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.085   6.690   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.004   7.926   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.849   7.609   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      17.321   5.771   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.269   3.339   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.728   1.869   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.473   0.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.237   1.897   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.899   0.394   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.710   1.592   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.364   0.007   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.812  -0.370   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.682   0.790   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.894   2.200   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.815   3.505   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.562   2.772   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.191   4.235   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.719   4.533   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.729   3.356   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.380   4.751   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.800   1.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.441   3.347   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.964   3.785   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.847   2.725   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.370   3.163   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.011   4.661   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.465   5.098   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.824   6.596   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.301   7.034   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -4.418   5.974   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -5.895   6.412   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -7.012   5.352   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -6.254   7.909   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.707   7.656   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.066   9.153   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -2.543   9.591   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -3.660   8.531   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.902  11.089   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.769   7.218   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       1.887   8.278   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       1.528   9.775   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       0.051  10.213   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       2.645  10.835   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       1.129   5.720   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       2.605   5.283   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       3.722   6.342   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       3.363   7.840   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       5.199   5.905   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       2.206   1.228   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       0.722   0.817   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       1.717  -0.233   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    2   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   24                                             
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   26   54                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22   26                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   10   13   25                                             
CONECT   25   24                                                            
CONECT   26   21   18   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   54                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   49                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   39                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   33   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   39   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   44   31   50                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54   29   18   55   56                                             
CONECT   55   54                                                            
CONECT   56   54                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  122    0
END

View in JSmol

Synonyms

Value	Source
[3,4,5-Tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0,.0,.0,]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetic acid	Generator
[3,4,5-Tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₄₄H₆₆O₁₂

Average Mass

787.0000 Da

Monoisotopic Mass

786.45543 Da

IUPAC Name

[3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate

Traditional Name

[3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(CC=CC(C)(C)O)C1CCC2(C)C3C=CC45OCC3(CCC12C)C4CCC(OC1OC(COC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O)C5(C)C

InChI Identifier

InChI=1S/C44H66O12/c1-25(13-12-18-39(6,7)49)30-16-19-42(11)32-17-20-44-33(43(32,24-51-44)22-21-41(30,42)10)14-15-34(40(44,8)9)56-38-37(54-29(5)48)36(53-28(4)47)35(52-27(3)46)31(55-38)23-50-26(2)45/h12,17-18,20,25,30-38,49H,13-16,19,21-24H2,1-11H3

InChI Key

AOOVSOSBQZZYPP-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
Momordica charantia	LOTUS Database	35616633

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
Cucurbitacin skeleton
Triterpenoid
Tetracarboxylic acid or derivatives
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Acetal
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	6.09	ALOGPS
logP	5.47	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	17.78	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	153.12 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	205.61 m³·mol⁻¹	ChemAxon
Polarizability	87.71 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 [3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate (NP0169350)

MOL for NP0169350 ([3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate)

3D MOL for NP0169350 ([3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate)

3D SDF for NP0169350 ([3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate)

3D-SDF for NP0169350 ([3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate)

PDB for NP0169350 ([3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate)

3D PDB for NP0169350 ([3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate)

SMILES for NP0169350 ([3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate)

INCHI for NP0169350 ([3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate)

Structure for NP0169350 ([3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate)

3D Structure for NP0169350 ([3,4,5-tris(acetyloxy)-6-{[8-(6-hydroxy-6-methylhept-4-en-2-yl)-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate)