NP-MRD: Showing NP-Card for rapulaside A (NP0028590)

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Record Information

Version

2.0

Created at

2021-06-19 20:26:16 UTC

Updated at

2021-06-29 23:55:28 UTC

NP-MRD ID

NP0028590

Secondary Accession Numbers

None

Natural Product Identification

Common Name

rapulaside A

Provided By

JEOL Database JEOL Logo

Description

rapulaside A is found in Heracleum rapula. rapulaside A was first documented in 2005 (Xiao, W., et al.). Based on a literature review very few articles have been published on methyl (4S,5S,6R,7S,8E,11R,12R,13S,16S)-6-ethenyl-5-methyl-2-oxo-16-(2-oxoethyl)-11,13-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-3,10,14-trioxatricyclo[10.3.1.1⁴,⁷]Heptadeca-1(15),8-diene-8-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122263D          

 98102  0  0  0  0            999 V2000
   -0.1172   -6.9016   -3.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0526   -5.6965   -4.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -4.3342   -3.4137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6824   -4.2387   -1.9321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9326   -3.3552   -2.0379 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6404   -2.4609   -3.2310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8021   -1.7384   -3.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -0.6376   -2.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4057   -0.2958   -2.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2216    0.1541   -2.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817    0.6409   -2.9363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    1.3776   -2.4240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013    1.8466   -1.0804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0156    3.0938   -1.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2362    4.1699   -1.5707 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7485    4.5818   -0.6147 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2359    5.1519    0.6051 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1971    4.0755    1.6998 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3945    3.2938    1.6929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1168    5.8653    0.4576 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2535    6.9330    1.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1975    6.4474   -0.9488 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4016    7.2134   -1.1052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752    5.3273   -1.9902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7617    5.9003   -3.2437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0305    0.8572   -0.1492 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4113    0.4936   -0.7836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2122   -0.5178    0.0545 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7989    0.1647    1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524    0.1645    2.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0878   -0.3254    0.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4273   -0.7502    1.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984   -0.2672    2.5186 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7107   -1.0074    2.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7083   -0.6474    3.3593 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9535   -1.4894    3.0487 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6189   -2.8774    2.9752 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1963   -0.8914    4.7842 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1487   -0.4350    5.7495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8896   -0.1273    4.9920 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3605   -0.4421    6.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -0.4637    3.9092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2620    0.4006    4.1148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311   -1.4110   -0.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662   -2.4968   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4058   -3.7304   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628   -4.7879   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0835   -5.9762   -0.4823 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -4.2511   -0.1891 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5249   -5.2077    0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1703   -3.4975   -4.2505 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5650   -2.8543   -5.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385   -7.0479   -2.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0872   -7.8034   -4.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4053   -5.6836   -5.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193   -3.8329   -3.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0351   -5.2020   -1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8152   -3.9750   -2.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795   -2.8188   -1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003   -1.7901   -3.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    0.4592   -3.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081    2.0210   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052    3.8287   -2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972    5.8809    0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849    4.5285    2.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386    3.3891    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8891    3.5531    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    5.1859    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673    6.5447    2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    7.1550   -1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4390    7.7892   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    4.9376   -2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3799    6.6388   -3.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2486    1.3951    0.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0078    1.4200   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6127   -1.3612    0.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0607   -0.9395   -0.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7310    0.7303    1.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580    0.0095    0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828    0.7994    2.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758    0.4095    3.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7398   -1.3546    3.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3576   -1.2111    2.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371   -2.9290    2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0276   -1.9600    4.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875   -0.5023    6.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0838    0.9530    5.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5446   -0.0681    6.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4922   -1.4925    4.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9431    0.1562    3.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703   -2.2655    0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1674   -5.7066    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479   -4.6728    0.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7411   -5.9373   -0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0213   -4.1147   -4.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256   -3.6143   -6.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925   -2.2220   -5.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3043   -2.2275   -6.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
 27 26  1  0  0  0  0
 17 16  1  0  0  0  0
 16 15  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 27 10  1  0  0  0  0
 26 13  1  0  0  0  0
 13 12  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  2  0  0  0  0
 10  8  1  0  0  0  0
 33 42  1  0  0  0  0
  8  9  2  0  0  0  0
 42 40  1  0  0  0  0
  8  7  1  0  0  0  0
 40 38  1  0  0  0  0
 27 28  1  0  0  0  0
 38 35  1  0  0  0  0
 28 29  1  0  0  0  0
 35 34  1  0  0  0  0
 29 30  2  0  0  0  0
 34 33  1  0  0  0  0
 29 78  1  0  0  0  0
 26 31  1  0  0  0  0
 38 39  1  0  0  0  0
 31 44  1  0  0  0  0
 40 41  1  0  0  0  0
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 36 37  1  0  0  0  0
 47 49  1  0  0  0  0
 31 32  1  0  0  0  0
  4  5  1  0  0  0  0
 26 74  1  1  0  0  0
 13 14  1  0  0  0  0
 18 19  1  0  0  0  0
 49 50  1  0  0  0  0
  7  6  1  0  0  0  0
 15 24  1  0  0  0  0
 51 52  1  0  0  0  0
 24 22  1  0  0  0  0
  3  2  1  0  0  0  0
 22 20  1  0  0  0  0
  2  1  2  3  0  0  0
 20 17  1  0  0  0  0
  4 57  1  1  0  0  0
  5  6  1  0  0  0  0
  6 60  1  1  0  0  0
  6 51  1  0  0  0  0
  3 56  1  1  0  0  0
 51  3  1  0  0  0  0
 27 75  1  6  0  0  0
 17 18  1  0  0  0  0
 15 14  1  0  0  0  0
 35 36  1  0  0  0  0
 33 32  1  0  0  0  0
 15 63  1  6  0  0  0
 20 68  1  1  0  0  0
 21 69  1  0  0  0  0
 22 70  1  6  0  0  0
 23 71  1  0  0  0  0
 24 72  1  6  0  0  0
 25 73  1  0  0  0  0
 18 65  1  0  0  0  0
 18 66  1  0  0  0  0
 17 64  1  1  0  0  0
 19 67  1  0  0  0  0
 33 80  1  6  0  0  0
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  1 53  1  0  0  0  0
  1 54  1  0  0  0  0
M  END

     RDKit          3D

 98102  0  0  0  0  0  0  0  0999 V2000
   -0.1172   -6.9016   -3.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0526   -5.6965   -4.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -4.3342   -3.4137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6824   -4.2387   -1.9321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9326   -3.3552   -2.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6404   -2.4609   -3.2310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8021   -1.7384   -3.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -0.6376   -2.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4057   -0.2958   -2.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2216    0.1541   -2.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817    0.6409   -2.9363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    1.3776   -2.4240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013    1.8466   -1.0804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0156    3.0938   -1.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2362    4.1699   -1.5707 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7485    4.5818   -0.6147 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2359    5.1519    0.6051 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1971    4.0755    1.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3945    3.2938    1.6929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1168    5.8653    0.4576 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2535    6.9330    1.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1975    6.4474   -0.9488 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4016    7.2134   -1.1052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752    5.3273   -1.9902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7617    5.9003   -3.2437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0305    0.8572   -0.1492 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4113    0.4936   -0.7836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2122   -0.5178    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7989    0.1647    1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524    0.1645    2.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0878   -0.3254    0.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4273   -0.7502    1.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984   -0.2672    2.5186 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7107   -1.0074    2.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7083   -0.6474    3.3593 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9535   -1.4894    3.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6189   -2.8774    2.9752 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1963   -0.8914    4.7842 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1487   -0.4350    5.7495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8896   -0.1273    4.9920 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3605   -0.4421    6.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -0.4637    3.9092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2620    0.4006    4.1148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311   -1.4110   -0.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192122263D          

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  3  2  1  0  0  0  0
 22 20  1  0  0  0  0
  2  1  2  3  0  0  0
 20 17  1  0  0  0  0
  4 57  1  1  0  0  0
  5  6  1  0  0  0  0
  6 60  1  1  0  0  0
  6 51  1  0  0  0  0
  3 56  1  1  0  0  0
 51  3  1  0  0  0  0
 27 75  1  6  0  0  0
 17 18  1  0  0  0  0
 15 14  1  0  0  0  0
 35 36  1  0  0  0  0
 33 32  1  0  0  0  0
 15 63  1  6  0  0  0
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  2 55  1  0  0  0  0
  1 53  1  0  0  0  0
  1 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028590

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C3C(=O)O[C@@]4([H])C([H])([H])[C@]([H])(\C(=C([H])/O[C@]([H])(O[C@]5([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]5([H])O[H])[C@]2([H])[C@]3([H])C([H])([H])C([H])=O)C(=O)OC([H])([H])[H])[C@@]([H])(C([H])=C([H])[H])[C@]4([H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C33H46O19/c1-4-13-12(2)18-7-15(13)17(28(43)45-3)11-47-31(52-33-27(42)25(40)23(38)20(9-36)50-33)21-14(5-6-34)16(29(44)48-18)10-46-30(21)51-32-26(41)24(39)22(37)19(8-35)49-32/h4,6,10-15,18-27,30-33,35-42H,1,5,7-9H2,2-3H3/b17-11+/t12-,13-,14+,15-,18-,19+,20+,21+,22+,23+,24-,25-,26+,27+,30-,31+,32-,33-/m0/s1

> <INCHI_KEY>
QMDDOXYGVQQWAK-HQBCCELPSA-N

> <FORMULA>
C33H46O19

> <MOLECULAR_WEIGHT>
746.712

> <EXACT_MASS>
746.263329261

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
72.62985010054183

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (4S,5S,6R,7S,8E,11R,12R,13S,16S)-6-ethenyl-5-methyl-2-oxo-16-(2-oxoethyl)-11,13-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-3,10,14-trioxatricyclo[10.3.1.1^{4,7}]heptadeca-1(15),8-diene-8-carboxylate

> <ALOGPS_LOGP>
-0.88

> <JCHEM_LOGP>
-3.0762881706666643

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.425438306414282

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.905133553935965

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760227608

> <JCHEM_POLAR_SURFACE_AREA>
286.89

> <JCHEM_REFRACTIVITY>
167.39470000000009

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.22e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4S,5S,6R,7S,8E,11R,12R,13S,16S)-6-ethenyl-5-methyl-2-oxo-16-(2-oxoethyl)-11,13-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-3,10,14-trioxatricyclo[10.3.1.1^{4,7}]heptadeca-1(15),8-diene-8-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 98102  0  0  0  0  0  0  0  0999 V2000
   -0.1172   -6.9016   -3.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0526   -5.6965   -4.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -4.3342   -3.4137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6824   -4.2387   -1.9321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9326   -3.3552   -2.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6404   -2.4609   -3.2310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8021   -1.7384   -3.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -0.6376   -2.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4057   -0.2958   -2.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2216    0.1541   -2.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817    0.6409   -2.9363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    1.3776   -2.4240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013    1.8466   -1.0804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0156    3.0938   -1.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2362    4.1699   -1.5707 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7485    4.5818   -0.6147 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2359    5.1519    0.6051 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1971    4.0755    1.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3945    3.2938    1.6929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1168    5.8653    0.4576 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2535    6.9330    1.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1975    6.4474   -0.9488 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4016    7.2134   -1.1052 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4113    0.4936   -0.7836 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.7989    0.1647    1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6189   -2.8774    2.9752 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1963   -0.8914    4.7842 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.3605   -0.4421    6.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4058   -3.7304   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1703   -3.4975   -4.2505 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5650   -2.8543   -5.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 53  1  0
  1 54  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.117  -6.902  -3.475  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.053  -5.697  -4.033  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.159  -4.334  -3.414  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.682  -4.239  -1.932  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.933  -3.355  -2.038  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.640  -2.461  -3.231  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.802  -1.738  -3.656  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.229  -0.638  -2.978  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.406  -0.296  -2.963  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.222   0.154  -2.242  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.182   0.641  -2.936  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.152   1.378  -2.424  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.301   1.847  -1.080  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.016   3.094  -1.041  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.236   4.170  -1.571  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.749   4.582  -0.615  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.236   5.152   0.605  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.197   4.075   1.700  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.395   3.294   1.693  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.117   5.865   0.458  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.254   6.933   1.403  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.198   6.447  -0.949  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.402   7.213  -1.105  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.175   5.327  -1.990  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.762   5.900  -3.244  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.030   0.857  -0.149  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.411   0.494  -0.784  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.212  -0.518   0.055  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.799   0.165   1.262  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.252   0.165   2.362  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.088  -0.325   0.210  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.427  -0.750   1.537  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.498  -0.267   2.519  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.711  -1.007   2.388  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.708  -0.647   3.359  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.954  -1.489   3.049  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.619  -2.877   2.975  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.196  -0.891   4.784  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.149  -0.435   5.750  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.890  -0.127   4.992  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.361  -0.442   6.291  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.133  -0.464   3.909  0.00  0.00           C+0
HETATM   43  O   UNK     0      -1.262   0.401   4.115  0.00  0.00           O+0
HETATM   44  O   UNK     0      -0.231  -1.411  -0.725  0.00  0.00           O+0
HETATM   45  C   UNK     0       0.566  -2.497  -0.463  0.00  0.00           C+0
HETATM   46  C   UNK     0       0.406  -3.730  -0.985  0.00  0.00           C+0
HETATM   47  C   UNK     0       1.363  -4.788  -0.525  0.00  0.00           C+0
HETATM   48  O   UNK     0       1.083  -5.976  -0.482  0.00  0.00           O+0
HETATM   49  O   UNK     0       2.565  -4.251  -0.189  0.00  0.00           O+0
HETATM   50  C   UNK     0       3.525  -5.208   0.266  0.00  0.00           C+0
HETATM   51  C   UNK     0      -1.170  -3.498  -4.250  0.00  0.00           C+0
HETATM   52  C   UNK     0      -0.565  -2.854  -5.494  0.00  0.00           C+0
HETATM   53  H   UNK     0      -0.439  -7.048  -2.450  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.087  -7.803  -4.046  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.405  -5.684  -5.065  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.819  -3.833  -3.465  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.035  -5.202  -1.550  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.815  -3.975  -2.251  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.180  -2.819  -1.125  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.800  -1.790  -3.050  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.018   0.459  -3.994  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.708   2.021  -0.691  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.305   3.829  -2.461  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.997   5.881   0.911  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.085   4.529   2.690  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.639   3.389   1.554  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.889   3.553   0.889  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.963   5.186   0.619  0.00  0.00           H+0
HETATM   69  H   UNK     0      -1.367   6.545   2.289  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.376   7.155  -1.117  0.00  0.00           H+0
HETATM   71  H   UNK     0      -2.439   7.789  -0.314  0.00  0.00           H+0
HETATM   72  H   UNK     0      -2.186   4.938  -2.163  0.00  0.00           H+0
HETATM   73  H   UNK     0      -1.380   6.639  -3.410  0.00  0.00           H+0
HETATM   74  H   UNK     0      -1.249   1.395   0.782  0.00  0.00           H+0
HETATM   75  H   UNK     0      -3.008   1.420  -0.791  0.00  0.00           H+0
HETATM   76  H   UNK     0      -2.613  -1.361   0.401  0.00  0.00           H+0
HETATM   77  H   UNK     0      -4.061  -0.940  -0.493  0.00  0.00           H+0
HETATM   78  H   UNK     0      -4.731   0.730   1.089  0.00  0.00           H+0
HETATM   79  H   UNK     0       0.958   0.010   0.171  0.00  0.00           H+0
HETATM   80  H   UNK     0       0.683   0.799   2.343  0.00  0.00           H+0
HETATM   81  H   UNK     0       2.976   0.410   3.229  0.00  0.00           H+0
HETATM   82  H   UNK     0       4.740  -1.355   3.797  0.00  0.00           H+0
HETATM   83  H   UNK     0       4.358  -1.211   2.070  0.00  0.00           H+0
HETATM   84  H   UNK     0       2.837  -2.929   2.393  0.00  0.00           H+0
HETATM   85  H   UNK     0       2.028  -1.960   4.965  0.00  0.00           H+0
HETATM   86  H   UNK     0       2.688  -0.502   6.611  0.00  0.00           H+0
HETATM   87  H   UNK     0       1.084   0.953   5.011  0.00  0.00           H+0
HETATM   88  H   UNK     0      -0.545  -0.068   6.291  0.00  0.00           H+0
HETATM   89  H   UNK     0      -0.492  -1.492   4.035  0.00  0.00           H+0
HETATM   90  H   UNK     0      -1.943   0.156   3.443  0.00  0.00           H+0
HETATM   91  H   UNK     0       1.370  -2.265   0.226  0.00  0.00           H+0
HETATM   92  H   UNK     0       3.167  -5.707   1.172  0.00  0.00           H+0
HETATM   93  H   UNK     0       4.448  -4.673   0.505  0.00  0.00           H+0
HETATM   94  H   UNK     0       3.741  -5.937  -0.521  0.00  0.00           H+0
HETATM   95  H   UNK     0      -2.021  -4.115  -4.572  0.00  0.00           H+0
HETATM   96  H   UNK     0      -0.226  -3.614  -6.204  0.00  0.00           H+0
HETATM   97  H   UNK     0       0.293  -2.222  -5.240  0.00  0.00           H+0
HETATM   98  H   UNK     0      -1.304  -2.228  -6.003  0.00  0.00           H+0
CONECT    1    2   53   54                                                  
CONECT    2    3    1   55                                                  
CONECT    3    4    2   56   51                                             
CONECT    4    3   46    5   57                                             
CONECT    5    4    6   58   59                                             
CONECT    6    7    5   60   51                                             
CONECT    7    8    6                                                       
CONECT    8   10    9    7                                                  
CONECT    9    8                                                            
CONECT   10   27   11    8                                                  
CONECT   11   12   10   61                                                  
CONECT   12   13   11                                                       
CONECT   13   26   12   14   62                                             
CONECT   14   13   15                                                       
CONECT   15   16   24   14   63                                             
CONECT   16   17   15                                                       
CONECT   17   16   20   18   64                                             
CONECT   18   19   17   65   66                                             
CONECT   19   18   67                                                       
CONECT   20   21   22   17   68                                             
CONECT   21   20   69                                                       
CONECT   22   23   24   20   70                                             
CONECT   23   22   71                                                       
CONECT   24   25   15   22   72                                             
CONECT   25   24   73                                                       
CONECT   26   27   13   31   74                                             
CONECT   27   26   10   28   75                                             
CONECT   28   27   29   76   77                                             
CONECT   29   28   30   78                                                  
CONECT   30   29                                                            
CONECT   31   26   44   32   79                                             
CONECT   32   31   33                                                       
CONECT   33   42   34   32   80                                             
CONECT   34   35   33                                                       
CONECT   35   38   34   36   81                                             
CONECT   36   37   35   82   83                                             
CONECT   37   36   84                                                       
CONECT   38   40   35   39   85                                             
CONECT   39   38   86                                                       
CONECT   40   42   38   41   87                                             
CONECT   41   40   88                                                       
CONECT   42   33   40   43   89                                             
CONECT   43   42   90                                                       
CONECT   44   31   45                                                       
CONECT   45   44   46   91                                                  
CONECT   46   45    4   47                                                  
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50                                                       
CONECT   50   49   92   93   94                                             
CONECT   51   52    6    3   95                                             
CONECT   52   51   96   97   98                                             
CONECT   53    1                                                            
CONECT   54    1                                                            
CONECT   55    2                                                            
CONECT   56    3                                                            
CONECT   57    4                                                            
CONECT   58    5                                                            
CONECT   59    5                                                            
CONECT   60    6                                                            
CONECT   61   11                                                            
CONECT   62   13                                                            
CONECT   63   15                                                            
CONECT   64   17                                                            
CONECT   65   18                                                            
CONECT   66   18                                                            
CONECT   67   19                                                            
CONECT   68   20                                                            
CONECT   69   21                                                            
CONECT   70   22                                                            
CONECT   71   23                                                            
CONECT   72   24                                                            
CONECT   73   25                                                            
CONECT   74   26                                                            
CONECT   75   27                                                            
CONECT   76   28                                                            
CONECT   77   28                                                            
CONECT   78   29                                                            
CONECT   79   31                                                            
CONECT   80   33                                                            
CONECT   81   35                                                            
CONECT   82   36                                                            
CONECT   83   36                                                            
CONECT   84   37                                                            
CONECT   85   38                                                            
CONECT   86   39                                                            
CONECT   87   40                                                            
CONECT   88   41                                                            
CONECT   89   42                                                            
CONECT   90   43                                                            
CONECT   91   45                                                            
CONECT   92   50                                                            
CONECT   93   50                                                            
CONECT   94   50                                                            
CONECT   95   51                                                            
CONECT   96   52                                                            
CONECT   97   52                                                            
CONECT   98   52                                                            
MASTER        0    0    0    0    0    0    0    0   98    0  204    0
END

RDKit          3D

98102  0  0  0  0  0  0  0  0999 V2000
   -0.1172   -6.9016   -3.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0526   -5.6965   -4.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -4.3342   -3.4137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6824   -4.2387   -1.9321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9326   -3.3552   -2.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6404   -2.4609   -3.2310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8021   -1.7384   -3.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -0.6376   -2.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4057   -0.2958   -2.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2216    0.1541   -2.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817    0.6409   -2.9363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    1.3776   -2.4240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013    1.8466   -1.0804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0156    3.0938   -1.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2362    4.1699   -1.5707 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7485    4.5818   -0.6147 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2359    5.1519    0.6051 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1971    4.0755    1.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3945    3.2938    1.6929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1168    5.8653    0.4576 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2535    6.9330    1.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1975    6.4474   -0.9488 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4016    7.2134   -1.1052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752    5.3273   -1.9902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7617    5.9003   -3.2437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0305    0.8572   -0.1492 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4113    0.4936   -0.7836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2122   -0.5178    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7989    0.1647    1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524    0.1645    2.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0878   -0.3254    0.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4273   -0.7502    1.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984   -0.2672    2.5186 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7107   -1.0074    2.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7083   -0.6474    3.3593 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9535   -1.4894    3.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6189   -2.8774    2.9752 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1963   -0.8914    4.7842 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1487   -0.4350    5.7495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8896   -0.1273    4.9920 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3605   -0.4421    6.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -0.4637    3.9092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2620    0.4006    4.1148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311   -1.4110   -0.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662   -2.4968   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4058   -3.7304   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628   -4.7879   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0835   -5.9762   -0.4823 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -4.2511   -0.1891 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5249   -5.2077    0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1703   -3.4975   -4.2505 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5650   -2.8543   -5.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385   -7.0479   -2.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0872   -7.8034   -4.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4053   -5.6836   -5.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193   -3.8329   -3.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0351   -5.2020   -1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8152   -3.9750   -2.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795   -2.8188   -1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003   -1.7901   -3.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    0.4592   -3.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081    2.0210   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052    3.8287   -2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972    5.8809    0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849    4.5285    2.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386    3.3891    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8891    3.5531    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    5.1859    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673    6.5447    2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    7.1550   -1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4390    7.7892   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    4.9376   -2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3799    6.6388   -3.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2486    1.3951    0.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0078    1.4200   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6127   -1.3612    0.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0607   -0.9395   -0.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7310    0.7303    1.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580    0.0095    0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828    0.7994    2.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758    0.4095    3.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7398   -1.3546    3.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3576   -1.2111    2.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371   -2.9290    2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0276   -1.9600    4.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875   -0.5023    6.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0838    0.9530    5.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5446   -0.0681    6.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4922   -1.4925    4.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9431    0.1562    3.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703   -2.2655    0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1674   -5.7066    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479   -4.6728    0.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7411   -5.9373   -0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0213   -4.1147   -4.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256   -3.6143   -6.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925   -2.2220   -5.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3043   -2.2275   -6.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 27 26  1  0
 17 16  1  0
 16 15  1  0
 20 21  1  0
 22 23  1  0
 24 25  1  0
 27 10  1  0
 26 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 10  8  1  0
 33 42  1  0
  8  9  2  0
 42 40  1  0
  8  7  1  0
 40 38  1  0
 27 28  1  0
 38 35  1  0
 28 29  1  0
 35 34  1  0
 29 30  2  0
 34 33  1  0
 29 78  1  0
 26 31  1  0
 38 39  1  0
 31 44  1  0
 40 41  1  0
 44 45  1  0
 42 43  1  0
 45 46  2  0
 46  4  1  0
 46 47  1  0
 47 48  2  0
 36 37  1  0
 47 49  1  0
 31 32  1  0
  4  5  1  0
 26 74  1  1
 13 14  1  0
 18 19  1  0
 49 50  1  0
  7  6  1  0
 15 24  1  0
 51 52  1  0
 24 22  1  0
  3  2  1  0
 22 20  1  0
  2  1  2  3
 20 17  1  0
  4 57  1  1
  5  6  1  0
  6 60  1  1
  6 51  1  0
  3 56  1  1
 51  3  1  0
 27 75  1  6
 17 18  1  0
 15 14  1  0
 35 36  1  0
 33 32  1  0
 15 63  1  6
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 21 69  1  0
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 24 72  1  6
 25 73  1  0
 18 65  1  0
 18 66  1  0
 17 64  1  1
 19 67  1  0
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 38 85  1  1
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 40 87  1  1
 41 88  1  0
 42 89  1  1
 43 90  1  0
 36 82  1  0
 36 83  1  0
 35 81  1  1
 37 84  1  0
  5 58  1  0
  5 59  1  0
 51 95  1  6
 13 62  1  1
 11 61  1  0
 28 76  1  0
 28 77  1  0
 31 79  1  1
 45 91  1  0
 50 92  1  0
 50 93  1  0
 50 94  1  0
 52 96  1  0
 52 97  1  0
 52 98  1  0
  2 55  1  0
  1 53  1  0
  1 54  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl (4S,5S,6R,7S,8E,11R,12R,13S,16S)-6-ethenyl-5-methyl-2-oxo-16-(2-oxoethyl)-11,13-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-3,10,14-trioxatricyclo[10.3.1.1,]heptadeca-1(15),8-diene-8-carboxylic acid	Generator

Chemical Formula

C₃₃H₄₆O₁₉

Average Mass

746.7120 Da

Monoisotopic Mass

746.26333 Da

IUPAC Name

methyl (4S,5S,6R,7S,8E,11R,12R,13S,16S)-6-ethenyl-5-methyl-2-oxo-16-(2-oxoethyl)-11,13-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-3,10,14-trioxatricyclo[10.3.1.1^{4,7}]heptadeca-1(15),8-diene-8-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C3C(=O)O[C@@]4([H])C([H])([H])[C@]([H])(\C(=C([H])/O[C@]([H])(O[C@]5([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]5([H])O[H])[C@]2([H])[C@]3([H])C([H])([H])C([H])=O)C(=O)OC([H])([H])[H])[C@@]([H])(C([H])=C([H])[H])[C@]4([H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C33H46O19/c1-4-13-12(2)18-7-15(13)17(28(43)45-3)11-47-31(52-33-27(42)25(40)23(38)20(9-36)50-33)21-14(5-6-34)16(29(44)48-18)10-46-30(21)51-32-26(41)24(39)22(37)19(8-35)49-32/h4,6,10-15,18-27,30-33,35-42H,1,5,7-9H2,2-3H3/b17-11+/t12-,13-,14+,15-,18-,19+,20+,21+,22+,23+,24-,25-,26+,27+,30-,31+,32-,33-/m0/s1

InChI Key

QMDDOXYGVQQWAK-HQBCCELPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Heracleum rapula	JEOL database	Xiao, W., et al, Tetrahedron Letts. 46, 5743 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Alpha-hydrogen aldehyde
Vinylogous ester
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
Aldehyde
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.88	ALOGPS
logP	-3.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	286.89 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	167.39 m³·mol⁻¹	ChemAxon
Polarizability	72.63 Å³	ChemAxon
Number of Rings	5	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

9541105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23232130

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiao, W., et al. (2005). Xiao, W., et al, Tetrahedron Letts. 46, 5743 (2005). Tetrahedron Lett.

Showing NP-Card for rapulaside A (NP0028590)

MOL for NP0028590 (rapulaside A)

3D MOL for NP0028590 (rapulaside A)

3D SDF for NP0028590 (rapulaside A)

3D-SDF for NP0028590 (rapulaside A)

PDB for NP0028590 (rapulaside A)

3D PDB for NP0028590 (rapulaside A)

SMILES for NP0028590 (rapulaside A)

INCHI for NP0028590 (rapulaside A)

Structure for NP0028590 (rapulaside A)

3D Structure for NP0028590 (rapulaside A)