NP-MRD: Showing NP-Card for methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate (NP0152166)

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Record Information

Version

2.0

Created at

2022-09-02 08:35:30 UTC

Updated at

2022-09-02 08:35:30 UTC

NP-MRD ID

NP0152166

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate

Description

Methyl (1R,4S,5S,6S,10R,11R,13R,16R,17S,18R)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]Octadecane-4-carboxylate belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate is found in Brucea javanica. Based on a literature review very few articles have been published on methyl (1R,4S,5S,6S,10R,11R,13R,16R,17S,18R)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]Octadecane-4-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210352D          

 36 40  0  0  1  0            999 V2000
    1.2936   -2.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1349   -2.1565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3544   -1.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2674   -2.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958   -1.0795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5119   -1.4047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7876   -0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    0.1710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3706   -0.3030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2843   -0.2985    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7244   -0.9963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5488   -0.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -1.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9330   -0.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347    0.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559    0.5048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1410    1.0873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129    0.9775    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0706    1.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911    1.7385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2828    2.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499    3.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    2.4884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247    1.0350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7079    1.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1684    1.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6099    0.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4343    0.4106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2252   -0.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -0.3814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0233   -1.1157    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4449   -1.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2698   -1.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6732   -1.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6914   -2.5234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009    0.3049    0.0000 C   0  0  1  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  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  9  8  1  6  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18 17  1  6  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 30 29  1  6  0  0  0
 30 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 30 36  1  0  0  0  0
 24 36  1  0  0  0  0
 36  8  1  1  0  0  0
M  END

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
   -4.9373    1.4211   -2.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5468    1.0816   -2.2859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342    0.9415   -1.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4721    1.1281   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4103    0.5958   -1.0207 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9227    0.4453   -2.3459 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2905   -0.2331   -2.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3874   -0.7959   -0.8429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0891   -0.7511   -0.5232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5076   -1.1844    0.7906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6462   -2.0366    0.7449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7722   -1.8465    1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8855   -2.7945    1.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7481   -0.8707    2.3037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4461   -2.1141    1.3433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3494   -2.1999    2.5838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181   -2.7822    0.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070   -2.2175   -0.7767 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2811   -2.4271   -0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9486   -1.5732    0.2596 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3922   -1.8812    0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4511   -1.4040    1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250   -2.6099   -0.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722   -0.1112   -0.0164 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4087    0.2680   -1.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2487    0.7016    1.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607    2.0073    1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2028    2.9056    1.9295 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2953    2.3101    0.8715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997    1.5578   -0.2374 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6714    1.7496   -0.4281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3400    2.3798    0.6210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142    3.6160    0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6066    4.2259    1.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8066    4.2243   -0.4337 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2078    0.1229   -0.0082 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5230    0.7110   -2.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3419    1.4902   -1.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9776    2.4551   -2.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676    0.4849   -2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -1.0442   -3.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287   -1.4639   -1.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570   -0.4082    1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9973   -3.1526    0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8528   -2.4127    1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6698   -3.7196    1.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3208   -2.7835   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625   -3.4900   -0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527   -2.3526   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5099   -1.8527    1.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0612   -0.6501    0.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1935   -2.2580    1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921   -1.0424    2.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2969    1.3396   -1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497   -0.4120   -2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4934    0.1717   -1.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248    0.8894    0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0444    0.1096    2.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085    1.9108   -1.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7413    2.5375   -1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6790    4.4130    1.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362    3.5741    2.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250    5.1892    2.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9139   -0.0828    1.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  6
  5  6  1  0
  6  7  1  0
  8  7  1  6
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 10 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 30 36  1  0
  9  5  1  0
 36 24  1  0
 31  5  1  0
 18  8  1  0
 36  8  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  7 40  1  0
  7 41  1  0
  9 42  1  6
 10 43  1  1
 13 44  1  0
 13 45  1  0
 13 46  1  0
 18 47  1  6
 19 48  1  0
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 20 50  1  1
 22 51  1  0
 22 52  1  0
 22 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 30 59  1  6
 31 60  1  6
 34 61  1  0
 34 62  1  0
 34 63  1  0
 36 64  1  1
M  END


  Mrv1652309022210352D          

 36 40  0  0  1  0            999 V2000
    1.2936   -2.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1349   -2.1565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3544   -1.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2674   -2.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958   -1.0795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5119   -1.4047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7876   -0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    0.1710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3706   -0.3030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2843   -0.2985    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7244   -0.9963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5488   -0.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -1.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9330   -0.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347    0.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559    0.5048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1410    1.0873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129    0.9775    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0706    1.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911    1.7385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2828    2.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499    3.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    2.4884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247    1.0350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7079    1.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1684    1.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6099    0.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2252   -0.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0233   -1.1157    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4449   -1.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2698   -1.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6732   -1.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6914   -2.5234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009    0.3049    0.0000 C   0  0  1  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  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  9  8  1  6  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18 17  1  6  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 30 29  1  6  0  0  0
 30 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 30 36  1  0  0  0  0
 24 36  1  0  0  0  0
 36  8  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0152166

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]12OC[C@@]34[C@H]1[C@@H](OC(C)=O)C(=O)O[C@@H]3C[C@@H](C(C)=O)[C@]1(C)CC(=O)O[C@H]([C@@H]2OC(C)=O)[C@@H]41

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O12/c1-9(25)12-6-13-23-8-32-24(21(30)31-5,18(23)16(20(29)35-13)33-10(2)26)19(34-11(3)27)15-17(23)22(12,4)7-14(28)36-15/h12-13,15-19H,6-8H2,1-5H3/t12-,13+,15-,16+,17+,18+,19-,22-,23+,24-/m0/s1

> <INCHI_KEY>
WHUAIEAFPHHTPO-DVCOBEPXSA-N

> <FORMULA>
C24H28O12

> <MOLECULAR_WEIGHT>
508.476

> <EXACT_MASS>
508.158076342

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.28487608375001

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,4S,5S,6S,10R,11R,13R,16R,17S,18R)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0^{1,13}.0^{4,17}.0^{6,18}]octadecane-4-carboxylate

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
-0.8547706639999999

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.045436304325687

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.14764001246447

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2611347586116075

> <JCHEM_POLAR_SURFACE_AREA>
157.79999999999998

> <JCHEM_REFRACTIVITY>
112.09829999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4S,5S,6S,10R,11R,13R,16R,17S,18R)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0^{1,13}.0^{4,17}.0^{6,18}]octadecane-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.415  -5.537   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.118  -4.025   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.662  -3.526   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.499  -4.538   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.365  -2.015   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.956  -2.622   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.470  -1.133   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000   0.319   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.692  -0.566   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.397  -0.557   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.219  -1.860   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.758  -1.800   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.579  -3.102   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.475  -0.437   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.051   0.795   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.584   0.942   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.130   2.030   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.584   1.825   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.132   3.201   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.663   3.245   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.395   4.601   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.587   5.911   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.934   4.645   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.473   1.932   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.188   3.296   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.048   2.014   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.872   0.706   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.411   0.766   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.154  -0.663   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.580  -0.712   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.910  -2.083   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.697  -3.406   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.237  -3.387   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.990  -2.043   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.024  -4.710   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.682   0.569   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9   31                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   18   36                                             
CONECT    9    8    5   10                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    8   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25   26   36                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30    5   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   30   24    8                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,4S,5S,6S,10R,11R,13R,16R,17S,18R)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0,.0,.0,]octadecane-4-carboxylic acid	Generator

Chemical Formula

C₂₄H₂₈O₁₂

Average Mass

508.4760 Da

Monoisotopic Mass

508.15808 Da

IUPAC Name

methyl (1R,4S,5S,6S,10R,11R,13R,16R,17S,18R)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0^{1,13}.0^{4,17}.0^{6,18}]octadecane-4-carboxylate

Traditional Name

methyl (1R,4S,5S,6S,10R,11R,13R,16R,17S,18R)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0^{1,13}.0^{4,17}.0^{6,18}]octadecane-4-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]12OC[C@@]34[C@H]1[C@@H](OC(C)=O)C(=O)O[C@@H]3C[C@@H](C(C)=O)[C@]1(C)CC(=O)O[C@H]([C@@H]2OC(C)=O)[C@@H]41

InChI Identifier

InChI=1S/C24H28O12/c1-9(25)12-6-13-23-8-32-24(21(30)31-5,18(23)16(20(29)35-13)33-10(2)26)19(34-11(3)27)15-17(23)22(12,4)7-14(28)36-15/h12-13,15-19H,6-8H2,1-5H3/t12-,13+,15-,16+,17+,18+,19-,22-,23+,24-/m0/s1

InChI Key

WHUAIEAFPHHTPO-DVCOBEPXSA-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
Brucea javanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Furopyran
Delta valerolactone
Oxepane
Delta_valerolactone
Pyran
Oxane
Furan
Methyl ester
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.19	ALOGPS
logP	-0.85	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	16.15	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	157.8 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.1 m³·mol⁻¹	ChemAxon
Polarizability	48.28 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

162999175

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate (NP0152166)

MOL for NP0152166 (methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate)

3D MOL for NP0152166 (methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate)

3D SDF for NP0152166 (methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate)

3D-SDF for NP0152166 (methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate)

PDB for NP0152166 (methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate)

3D PDB for NP0152166 (methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate)

SMILES for NP0152166 (methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate)

INCHI for NP0152166 (methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate)

Structure for NP0152166 (methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate)

3D Structure for NP0152166 (methyl (1r,4s,5s,6s,10r,11r,13r,16r,17s,18r)-11-acetyl-5,16-bis(acetyloxy)-10-methyl-8,15-dioxo-3,7,14-trioxapentacyclo[8.7.1.0¹,¹³.0⁴,¹⁷.0⁶,¹⁸]octadecane-4-carboxylate)