NP-MRD: Showing NP-Card for methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate (NP0231302)

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Record Information

Version

2.0

Created at

2022-09-06 12:06:00 UTC

Updated at

2022-09-06 12:06:00 UTC

NP-MRD ID

NP0231302

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate

Description

Methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-8,12,14-trimethyl-5-(propan-2-yl)-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]Octadecan-13-yl]acetate belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate is found in Chukrasia tabularis. Methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-8,12,14-trimethyl-5-(propan-2-yl)-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]Octadecan-13-yl]acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191515192D          

 58 64  0  0  0  0            999 V2000
    7.1059    0.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2827   -0.0499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8234    0.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1872    1.3759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0002    0.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6364   -0.1601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0957   -0.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9189   -0.7903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7319   -1.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5409    1.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7872    2.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6048    2.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6345    2.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7989    2.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    1.9496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7003    1.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7632    0.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8527    1.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4910    0.6081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8006    0.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4884   -0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4378   -1.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1256   -1.4559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993   -1.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0631   -0.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0076   -0.9115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2669   -1.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114   -2.0981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819   -0.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787    0.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0486   -0.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    0.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3333    1.3506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4706    1.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0331    0.9324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121    2.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0123   -0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1700   -0.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5515   -1.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1550   -0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8066    0.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4140    1.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7418    1.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0562    2.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145    3.1028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020    2.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3712    2.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1381    3.5532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155    3.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975    3.8196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3099    3.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919    4.7383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8404    3.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690    1.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656    2.1976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198    3.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5561    3.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    2.8732    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 20 25  1  0  0  0  0
 25 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
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 32 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 37 41  1  0  0  0  0
 30 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 14 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 11 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
 46 54  1  0  0  0  0
 18 54  1  0  0  0  0
 42 54  1  0  0  0  0
 54 55  1  0  0  0  0
 44 55  1  0  0  0  0
 44 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 58  1  0  0  0  0
M  END

     RDKit          3D

110116  0  0  0  0  0  0  0  0999 V2000
    1.9082   -4.8123   -1.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3394   -3.4810   -1.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9564   -3.0704   -0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1035   -3.9798    0.5779 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4625   -1.7051    0.0348 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1300   -1.9284    1.2973 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4997   -2.1445    1.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1517   -2.3693    2.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1432   -2.1412    0.2778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5354   -0.5882    0.0587 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2123    0.7109    0.4214 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4178    0.6905    1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3926    1.3363   -0.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028    1.2100   -1.2942 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8650    1.6820   -2.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428    2.0243   -0.1977 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5951    3.3594   -0.4645 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1547    1.6754    1.0295 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8896    2.7637    1.5305 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8716    3.1344    2.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6214    4.2611    3.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482    2.4366    3.6405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1086    1.7455    0.1342 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7973    2.9377   -0.1856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3647    2.6589   -1.4265 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6114    3.8104   -2.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5555    4.7772   -1.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872    4.5722   -2.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409    1.8748   -1.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0401    0.5143   -0.9927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7107   -0.5675   -0.3119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9653   -0.8890   -1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1524   -0.5020    1.0756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0711    0.5727    1.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9582    1.4700    2.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9477    2.5500    2.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9936    1.2858    3.1148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0150   -1.7144    1.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3541   -1.8706    1.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7424   -3.1032    1.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7151   -3.6718    2.1409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6782   -2.8732    2.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267   -1.8070   -0.5893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9136   -2.1656   -1.9501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123   -3.3843   -2.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4825   -3.7135   -3.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -4.1935   -1.4680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3641   -1.5368   -0.1881 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4507   -1.3405    1.1725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0766   -2.1944    2.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612   -1.7636    3.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4029   -3.2968    1.8672 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2170   -0.4677   -1.0428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2392   -0.8541   -2.3542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992    0.7912   -0.8560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5379    1.6668   -1.9885 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6751   -0.2978   -1.1365 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1804   -0.8847   -2.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852   -5.5238   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8094   -4.9096   -1.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2482   -5.1120   -2.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -1.5828   -0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4570   -2.0910    3.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4372   -3.4269    2.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0554   -1.7275    2.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8845   -0.7183    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5596    1.8027    1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3637    0.1928    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3366    0.5140    0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6193    2.4100   -0.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    0.8397   -1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6070    2.2550   -2.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9794    3.4977   -1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643    1.1452    1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3154    4.6682    2.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2311    3.8615    4.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101    5.0303    3.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659    1.4800    1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1214    3.4312   -3.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9771    5.6129   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0805    4.2420   -0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463    5.1409   -2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0011    5.1310   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4230    3.9532   -3.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6961    5.2992   -3.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3135    2.0337   -1.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1061    2.2969   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0989    0.1643   -2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896   -1.9190   -1.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7458   -0.1503   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004191515192D          

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M  END
> <DATABASE_ID>
NP0231302

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(OC(C)=O)C1C2(C)CC3(O)C(O)(C2OC(C)=O)C2OC4(CC5C2(O4)C(O)(C(OC(C)=O)C(OC(C)=O)C5(C)C(OC(C)=O)C2=COC=C2)C13C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H52O18/c1-17(2)36-14-24-34(9,27(53-19(4)42)23-12-13-51-15-23)28(54-20(5)43)29(55-21(6)44)40(49)35(10)26(25(30(46)50-11)52-18(3)41)33(8)16-37(35,47)38(48,31(33)56-22(7)45)32(57-36)39(24,40)58-36/h12-13,15,17,24-29,31-32,47-49H,14,16H2,1-11H3

> <INCHI_KEY>
YYQILFDODHPZSJ-UHFFFAOYSA-N

> <FORMULA>
C40H52O18

> <MOLECULAR_WEIGHT>
820.838

> <EXACT_MASS>
820.315364834

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
80.39332296649907

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-8,12,14-trimethyl-5-(propan-2-yl)-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
0.1543514073333307

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.338444657767457

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.61969938439231

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8635518033458442

> <JCHEM_POLAR_SURFACE_AREA>
250.08999999999992

> <JCHEM_REFRACTIVITY>
187.65740000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      13.264   0.010   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.728  -0.093   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.870   1.186   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.549   2.568   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.334   1.083   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.655  -0.299   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.512  -1.578   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.049  -1.475   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.833  -2.960   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.476   2.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.936   3.943   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.462   4.148   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.651   4.998   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.091   4.009   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.596   3.639   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.907   2.531   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.025   0.995   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.325   2.111   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.517   1.135   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.228   0.520   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.512  -0.330   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.417  -1.867   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.701  -2.718   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.039  -2.554   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.851  -0.165   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.747  -1.701   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.365  -2.380   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.261  -3.916   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.086  -1.522   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.574   0.703   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.957  -0.709   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.073   1.049   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.622   2.521   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.878   2.867   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.928   1.740   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.329   4.340   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.023  -0.078   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.317  -1.590   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.029  -2.337   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -2.156  -1.287   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.506   0.109   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.639   2.286   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.385   3.360   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.972   4.922   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       3.387   5.792   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       4.670   4.741   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.293   5.155   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       5.858   6.633   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       7.869   5.683   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       8.395   7.130   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       9.912   7.398   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      10.438   8.845   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      10.902   6.218   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       4.049   3.172   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       2.922   4.102   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       0.784   5.902   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       1.038   7.421   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -0.659   5.363   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   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   16                                                  
CONECT   11   10   12   13   49                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   47                                             
CONECT   15   14                                                            
CONECT   16   14   10   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19   20   54                                             
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31   32   42                                             
CONECT   31   30                                                            
CONECT   32   30   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32   38   41                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   37                                                       
CONECT   42   30   43   54                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   55   56                                             
CONECT   45   44   46                                                       
CONECT   46   45   47   54                                                  
CONECT   47   46   14   48   49                                             
CONECT   48   47                                                            
CONECT   49   47   11   50                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54   46   18   42   55                                             
CONECT   55   54   44                                                       
CONECT   56   44   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-8,12,14-trimethyl-5-(propan-2-yl)-4,18-dioxahexacyclo[12.2.1.1,.0,.0,.0,]octadecan-13-yl]acetic acid	Generator
Methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-8,12,14-trimethyl-5-(propan-2-yl)-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetic acid	Generator

Chemical Formula

C₄₀H₅₂O₁₈

Average Mass

820.8380 Da

Monoisotopic Mass

820.31536 Da

IUPAC Name

methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-8,12,14-trimethyl-5-(propan-2-yl)-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C(OC(C)=O)C1C2(C)CC3(O)C(O)(C2OC(C)=O)C2OC4(CC5C2(O4)C(O)(C(OC(C)=O)C(OC(C)=O)C5(C)C(OC(C)=O)C2=COC=C2)C13C)C(C)C

InChI Identifier

InChI=1S/C40H52O18/c1-17(2)36-14-24-34(9,27(53-19(4)42)23-12-13-51-15-23)28(54-20(5)43)29(55-21(6)44)40(49)35(10)26(25(30(46)50-11)52-18(3)41)33(8)16-37(35,47)38(48,31(33)56-22(7)45)32(57-36)39(24,40)58-36/h12-13,15,17,24-29,31-32,47-49H,14,16H2,1-11H3

InChI Key

YYQILFDODHPZSJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chukrasia tabularis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Diterpenoid
Hexacarboxylic acid or derivatives
Ketal
Oxane
Meta-dioxolane
Cyclic alcohol
Heteroaromatic compound
Furan
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.03	ALOGPS
logP	0.15	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.62	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	250.09 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	187.66 m³·mol⁻¹	ChemAxon
Polarizability	80.39 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate (NP0231302)

MOL for NP0231302 (methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate)

3D MOL for NP0231302 (methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate)

3D SDF for NP0231302 (methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate)

3D-SDF for NP0231302 (methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate)

PDB for NP0231302 (methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate)

3D PDB for NP0231302 (methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate)

SMILES for NP0231302 (methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate)

INCHI for NP0231302 (methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate)

Structure for NP0231302 (methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate)

3D Structure for NP0231302 (methyl 2-(acetyloxy)-2-[9,10,17-tris(acetyloxy)-8-[(acetyloxy)(furan-3-yl)methyl]-1,11,16-trihydroxy-5-isopropyl-8,12,14-trimethyl-4,18-dioxahexacyclo[12.2.1.1²,⁵.0³,⁷.0³,¹¹.0¹²,¹⁶]octadecan-13-yl]acetate)