NP-MRD: Showing NP-Card for [(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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 (NP0302051)

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Record Information

Version

2.0

Created at

2022-09-10 15:22:19 UTC

Updated at

2022-09-10 15:22:19 UTC

NP-MRD ID

NP0302051

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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

[(2R,3R,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1R,4S,5S,8R,9R,12S,13S,16S)-8-[(2R,4E)-6-methoxy-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. [(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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. Based on a literature review very few articles have been published on [(2R,3R,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1R,4S,5S,8R,9R,12S,13S,16S)-8-[(2R,4E)-6-methoxy-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

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102217222D          

 57 62  0  0  1  0            999 V2000
    9.9286    4.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1092    4.2461    0.0000 O   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
    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 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
    7.3051    3.0174    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
    5.9934    2.4506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6662    3.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5011    1.7886    0.0000 C   0  0  1  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  1  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  2  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  1  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  1  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  2  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  2  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  2  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  2  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  2  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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3503    4.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788    4.1013    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5545    5.9403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122    3.8667    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170    5.8045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6046    3.0645    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    3.1632    0.0000 O   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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11  9  1  1  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  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  1  0  0  0
 22 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 34 40  1  0  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
 40 45  1  0  0  0  0
 45 46  1  1  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  2  0  0  0  0
 45 50  1  0  0  0  0
 32 50  1  0  0  0  0
 50 51  1  1  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  2  0  0  0  0
 30 55  1  0  0  0  0
 19 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  1  0  0  0  0
M  END

     RDKit          3D

125130  0  0  0  0  0  0  0  0999 V2000
   10.3609   -1.0540   -3.6948 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6190   -2.1539   -2.9298 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3274   -2.0611   -1.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0753   -0.9631   -0.8824 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7980   -3.3750   -0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8810   -1.9297   -1.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2089   -0.7865   -1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7368   -0.7320   -0.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6234    0.1986    0.2042 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1446    1.5510   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    0.1716    0.9616 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4977    1.1911    2.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423    1.8895    2.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510    0.8763    1.5388 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1068   -0.2477    2.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9651    1.3925    1.0334 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1853    1.9809    2.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1378    2.0119    2.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332    1.0075    1.3236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9085    1.3973    0.0199 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2489    1.1252   -0.6471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1564    0.3437    0.3206 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9198   -0.6722   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3800   -0.7877   -0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0764    0.4275    0.3224 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0319    1.4966   -0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0525   -0.2327    1.2168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6069   -1.3944    0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3311   -1.2994   -1.0996 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5353   -2.5448   -1.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8825   -2.9572   -1.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6003   -3.2926   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0267   -3.7206   -0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0756   -3.2478    0.3190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0883   -0.1199   -1.6351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4672   -0.3854   -1.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0094   -0.3145   -3.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4510   -0.5834   -3.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3075   -0.0249   -4.0570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8332    1.0548   -0.7174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2612    0.6838    0.5766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2321    1.3654    1.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6036    0.8911    2.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7549    2.3662    0.7288 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3924    3.4928   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9655    4.8037   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1155    0.6104    1.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570   -0.0880    3.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0145    1.7484    2.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9004   -0.1351   -3.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7214   -1.2694   -4.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2869   -0.8117   -3.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1629   -1.1295   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7807   -1.0448    0.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7665    0.0519   -1.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8861   -4.1740   -1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1548   -3.6337   -0.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8319   -3.2338   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2850   -2.8130   -0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7557    0.1060   -1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -0.4167   -1.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4483   -1.7444   -0.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4110   -0.2030    0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4664    2.3905   -0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3556    1.5833   -1.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1171    1.8222    0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3123   -0.8363    1.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7340    0.6798    3.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3243    1.8997    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    1.9953    3.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434    2.8778    1.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0600   -0.4706    3.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4578    0.1753    3.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974   -1.1635    2.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571    2.2323    0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
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 57125  1  0
M  END


  Mrv1652309102217222D          

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  6  7  2  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11  9  1  1  0  0  0
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 55 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302051

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C)(C)\C=C\C[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3C=C[C@@]45OC[C@]3(CC[C@]12C)[C@@H]4CC[C@H](O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O)C5(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C45H68O12/c1-26(14-13-19-40(6,7)50-12)31-17-20-43(11)33-18-21-45-34(44(33,25-52-45)23-22-42(31,43)10)15-16-35(41(45,8)9)57-39-38(55-30(5)49)37(54-29(4)48)36(53-28(3)47)32(56-39)24-51-27(2)46/h13,18-19,21,26,31-39H,14-17,20,22-25H2,1-12H3/b19-13+/t26-,31-,32-,33+,34+,35+,36-,37-,38-,39+,42-,43+,44+,45-/m1/s1

> <INCHI_KEY>
OMGGPLTZARDXEH-SFFZUTDPSA-N

> <FORMULA>
C45H68O12

> <MOLECULAR_WEIGHT>
801.027

> <EXACT_MASS>
800.47107763

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
125

> <JCHEM_AVERAGE_POLARIZABILITY>
88.6788936750529

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1R,4S,5S,8R,9R,12S,13S,16S)-8-[(2R,4E)-6-methoxy-6-methylhept-4-en-2-yl]-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0^{1,13}.0^{4,12}.0^{5,9}]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_LOGP>
6.114725109999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.668464381393562

> <JCHEM_POLAR_SURFACE_AREA>
142.12000000000003

> <JCHEM_REFRACTIVITY>
210.35880000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1R,4S,5S,8R,9R,12S,13S,16S)-8-[(2R,4E)-6-methoxy-6-methylhept-4-en-2-yl]-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0^{1,13}.0^{4,12}.0^{5,9}]nonadec-2-en-16-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      18.533   7.748   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.004   7.926   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      16.085   6.690   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.849   7.609   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.321   5.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.166   5.454   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.636   5.632   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.717   4.397   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.188   4.575   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.577   5.988   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.269   3.339   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.728   1.869   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.473   0.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.237   1.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.899   0.394   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.710   1.592   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.364   0.007   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.812  -0.370   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.682   0.790   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.894   2.200   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.815   3.505   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.562   2.772   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.191   4.235   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.719   4.533   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.729   3.356   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.380   4.751   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.800   1.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.441   3.347   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.964   3.785   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.847   2.725   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.370   3.163   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.011   4.661   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.465   5.098   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.824   6.596   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.301   7.034   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.418   5.974   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -5.895   6.412   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.012   5.352   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.254   7.909   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.707   7.656   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.066   9.153   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -2.543   9.591   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -3.660   8.531   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.902  11.089   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       0.769   7.218   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       1.887   8.278   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       1.528   9.775   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.051  10.213   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       2.645  10.835   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       1.129   5.720   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       2.605   5.283   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       3.722   6.342   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       3.363   7.840   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       5.199   5.905   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       2.206   1.228   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.722   0.817   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       1.717  -0.233   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   25                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   25                                             
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   27   55                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16   23   27                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   11   14   26                                             
CONECT   26   25                                                            
CONECT   27   22   19   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   55                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   50                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   34   41   45                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   40   46   50                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   45   32   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   30   19   56   57                                             
CONECT   56   55                                                            
CONECT   57   55                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3R,4R,5R,6R)-3,4,5-Tris(acetyloxy)-6-{[(1R,4S,5S,8R,9R,12S,13S,16S)-8-[(2R,4E)-6-methoxy-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

Chemical Formula

C₄₅H₆₈O₁₂

Average Mass

801.0270 Da

Monoisotopic Mass

800.47108 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(C)(C)\C=C\C[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3C=C[C@@]45OC[C@]3(CC[C@]12C)[C@@H]4CC[C@H](O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O)C5(C)C

InChI Identifier

InChI=1S/C45H68O12/c1-26(14-13-19-40(6,7)50-12)31-17-20-43(11)33-18-21-45-34(44(33,25-52-45)23-22-42(31,43)10)15-16-35(41(45,8)9)57-39-38(55-30(5)49)37(54-29(4)48)36(53-28(3)47)32(56-39)24-51-27(2)46/h13,18-19,21,26,31-39H,14-17,20,22-25H2,1-12H3/b19-13+/t26-,31-,32-,33+,34+,35+,36-,37-,38-,39+,42-,43+,44+,45-/m1/s1

InChI Key

OMGGPLTZARDXEH-SFFZUTDPSA-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
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	6.11	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	142.12 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	210.36 m³·mol⁻¹	ChemAxon
Polarizability	88.68 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

162915460

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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 (NP0302051)

MOL for NP0302051 ([(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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 NP0302051 ([(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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 NP0302051 ([(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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 NP0302051 ([(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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 NP0302051 ([(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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 NP0302051 ([(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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 NP0302051 ([(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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 NP0302051 ([(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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 NP0302051 ([(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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 NP0302051 ([(2r,3r,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(1r,4s,5s,8r,9r,12s,13s,16s)-8-[(2r,4e)-6-methoxy-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)