NP-MRD: Showing NP-Card for methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate (NP0319051)

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Record Information

Version

2.0

Created at

2022-09-11 19:53:23 UTC

Updated at

2022-09-11 19:53:23 UTC

NP-MRD ID

NP0319051

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate

Description

Methyl 11-({2,5,8,11,14,20-hexamethyl-7,17-dioxo-19-oxahexacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²¹.0¹⁸,²⁰]Tricosa-1(23),15,21-trien-18-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylate belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate is found in Monteverdia ilicifolia. Methyl 11-({2,5,8,11,14,20-hexamethyl-7,17-dioxo-19-oxahexacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²¹.0¹⁸,²⁰]Tricosa-1(23),15,21-trien-18-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191517502D          

 66 76  0  0  0  0            999 V2000
   -3.4543   -9.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790   -9.9836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5358  -10.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1678  -11.3264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605  -11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6173  -10.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730  -11.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605  -12.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355  -12.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480  -13.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230  -13.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020  -13.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270  -13.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395  -12.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520  -13.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770  -13.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895  -13.9362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895  -12.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145  -12.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270  -13.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270  -11.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520  -11.7927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145  -11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270  -10.3638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520  -10.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520  -11.1888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664  -10.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789  -11.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809  -10.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954  -10.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099  -10.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099   -9.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -9.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -8.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -8.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099   -7.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -8.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -7.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -7.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -7.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2533   -6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2533   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9677   -7.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6822   -6.6513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9677   -7.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2533   -8.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9677   -8.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2533   -9.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -9.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -9.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -9.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -9.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664   -9.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -9.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -9.1263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895  -11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770  -11.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520  -11.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645  -11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395  -11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020  -11.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105  -11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230  -11.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355  -11.0783    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 40 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 33 51  1  0  0  0  0
 38 51  1  0  0  0  0
 51 52  1  0  0  0  0
 34 53  1  0  0  0  0
 30 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 26 55  1  0  0  0  0
 55 56  2  0  0  0  0
 24 57  1  0  0  0  0
 57 58  2  0  0  0  0
 19 58  1  0  0  0  0
 58 59  1  0  0  0  0
 15 59  1  0  0  0  0
 59 60  1  0  0  0  0
 59 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 13 63  1  0  0  0  0
 63 64  1  0  0  0  0
 63 65  1  0  0  0  0
  9 65  1  0  0  0  0
 65 66  1  0  0  0  0
  5 66  1  0  0  0  0
M  END

     RDKit          3D

140150  0  0  0  0  0  0  0  0999 V2000
   11.2841   -0.4598    4.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7393    0.2195    3.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0757   -0.0946    1.9699 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8945   -1.0170    1.7685 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4952    0.6295    0.7931 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9591    2.0849    1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2043    0.2177   -0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5237   -0.7678   -1.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2095   -1.2735   -0.8330 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5050   -2.4427    0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5467   -1.9109   -2.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0635   -1.9039   -1.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6382   -0.4221   -2.0295 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9891   -0.0762   -3.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1463   -0.5002   -1.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5689   -1.2509   -2.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1169   -1.4343   -2.9169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890   -2.1410   -3.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2737   -0.7893   -1.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9053   -0.0303   -0.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1202    0.5293    0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417    0.3335    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0246    0.9217    1.0416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3589    0.9516    1.1859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6111    1.6357    2.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0975    0.3406    2.1331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5625   -0.8228    2.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5664    0.3311    1.9658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2956   -0.5720    2.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7227   -0.5798    2.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4624    0.2607    1.7394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7269    1.3485    1.0372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0088    2.6252    1.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3566    1.5591   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8024    1.7982   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6251    0.9049    0.7125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.4501    1.8681    1.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6992    0.2595   -0.1619 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.0682    0.2282    0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1141   -0.0690   -0.6028 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.3551   -0.5536    0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6172   -1.1838   -1.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0608   -1.4871   -2.5367 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4865   -1.9531   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2988   -0.9814   -0.8591 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.9521   -0.7619   -2.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1276   -1.6812   -0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0316   -1.4698    1.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9136   -0.0018    1.6356 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4860    0.0446    3.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2645    1.1978    1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5532    1.8896    0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0821    1.7874    0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    2.3690   -0.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1099   -0.4443   -0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444   -0.6192   -0.8650 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955   -1.0010   -1.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2631   -1.8281   -2.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3352    0.2602   -1.0258 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3453    1.7394   -1.5497 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0769    0.3138    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3690    1.0363    0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2892    0.4087   -0.9968 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9827    1.5832   -1.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3194   -0.3375   -0.1265 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0155    0.6461    0.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4008   -0.4085    4.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9742    0.0857    5.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0132   -1.5162    4.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8360    2.6144    0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0444    2.0357    1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4050    2.5185    1.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3914    1.1332   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004191517502D          

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> <DATABASE_ID>
NP0319051

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(C)CCC2(C)CCC3(C)C4=CC(=O)C5=C(C)C(O)=C(OC67OC6(C)C6=CC=C8C(C)(CCC9(C)C%10CC(C)C(=O)CC%10(C)CCC89C)C6=CC7=O)C=C5C4(C)CCC3(C)C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C58H74O8/c1-32-26-41-49(4,30-38(32)60)19-23-53(8)40-15-14-34-35(51(40,6)20-24-54(41,53)9)28-44(61)58(57(34,12)66-58)65-39-27-36-45(33(2)46(39)62)37(59)29-42-52(36,7)21-25-56(11)43-31-50(5,47(63)64-13)17-16-48(43,3)18-22-55(42,56)10/h14-15,27-29,32,41,43,62H,16-26,30-31H2,1-13H3

> <INCHI_KEY>
GXGZUOULORXKMU-UHFFFAOYSA-N

> <FORMULA>
C58H74O8

> <MOLECULAR_WEIGHT>
899.222

> <EXACT_MASS>
898.538369343

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
140

> <JCHEM_AVERAGE_POLARIZABILITY>
103.60982655368537

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 11-({2,5,8,11,14,20-hexamethyl-7,17-dioxo-19-oxahexacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²¹.0¹⁸,²⁰]tricosa-1(23),15,21-trien-18-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylate

> <ALOGPS_LOGP>
8.38

> <JCHEM_LOGP>
11.736922244333332

> <ALOGPS_LOGS>
-7.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.487363094873988

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.596141862922988

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4179999603778075

> <JCHEM_POLAR_SURFACE_AREA>
119.5

> <JCHEM_REFRACTIVITY>
258.52740000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.56e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 11-({2,5,8,11,14,20-hexamethyl-7,17-dioxo-19-oxahexacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²¹.0¹⁸,²⁰]tricosa-1(23),15,21-trien-18-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate

> <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      -6.448 -18.109   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.001 -18.636   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.733 -20.153   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.913 -21.143   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.286 -20.679   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.019 -19.163   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.056 -22.013   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.286 -23.347   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.746 -23.347   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.516 -24.680   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.976 -24.680   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.564 -24.680   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -23.347   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104 -24.680   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874 -23.347   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.644 -24.680   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.184 -24.680   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.954 -26.014   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.954 -23.347   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494 -23.347   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.264 -24.680   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.264 -22.013   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.804 -22.013   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.494 -20.679   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.264 -19.346   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.804 -19.346   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.804 -20.886   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.137 -20.116   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.907 -21.449   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.471 -19.346   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.805 -20.116   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.138 -19.346   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.138 -17.806   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.805 -17.036   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.471 -16.266   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.805 -15.496   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.138 -14.726   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.472 -15.496   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.472 -13.956   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      17.806 -14.726   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      17.806 -13.186   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.139 -12.416   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      19.139 -10.876   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      20.473 -13.186   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      21.807 -12.416   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      20.473 -14.726   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      19.139 -15.496   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      20.473 -16.266   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      19.139 -17.036   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      17.806 -17.806   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      16.472 -17.036   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      16.472 -18.576   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      12.471 -17.806   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      11.137 -17.036   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       9.804 -17.806   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       8.470 -17.036   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       5.954 -20.679   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       5.184 -22.013   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       3.644 -22.013   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       4.414 -20.679   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       2.874 -20.679   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       1.334 -20.679   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       0.564 -22.013   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -0.206 -20.679   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -0.976 -22.013   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      -1.746 -20.679   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    7   66                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   65                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   63                                             
CONECT   14   13                                                            
CONECT   15   13   16   59                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   58                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   57                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28   55                                             
CONECT   27   26   28                                                       
CONECT   28   27   26   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31   53                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   51                                                  
CONECT   34   33   35   36   53                                             
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40   51                                             
CONECT   39   38                                                            
CONECT   40   38   41   47                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   40   48   49                                             
CONECT   48   47                                                            
CONECT   49   47   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   33   38   52                                             
CONECT   52   51                                                            
CONECT   53   34   30   54                                                  
CONECT   54   53   55                                                       
CONECT   55   54   26   56                                                  
CONECT   56   55                                                            
CONECT   57   24   58                                                       
CONECT   58   57   19   59                                                  
CONECT   59   58   15   60   61                                             
CONECT   60   59                                                            
CONECT   61   59   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   13   64   65                                             
CONECT   64   63                                                            
CONECT   65   63    9   66                                                  
CONECT   66   65    5                                                       
MASTER        0    0    0    0    0    0    0    0   66    0  152    0
END

View in JSmol

Synonyms

Value	Source
Methyl 11-({2,5,8,11,14,20-hexamethyl-7,17-dioxo-19-oxahexacyclo[12.9.0.0,.0,.0,.0,]tricosa-1(23),15,21-trien-18-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid	Generator
Methyl 11-({2,5,8,11,14,20-hexamethyl-7,17-dioxo-19-oxahexacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²¹.0¹⁸,²⁰]tricosa-1(23),15,21-trien-18-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid	Generator

Chemical Formula

C₅₈H₇₄O₈

Average Mass

899.2220 Da

Monoisotopic Mass

898.53837 Da

IUPAC Name

methyl 11-({2,5,8,11,14,20-hexamethyl-7,17-dioxo-19-oxahexacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²¹.0¹⁸,²⁰]tricosa-1(23),15,21-trien-18-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C)CCC2(C)CCC3(C)C4=CC(=O)C5=C(C)C(O)=C(OC67OC6(C)C6=CC=C8C(C)(CCC9(C)C%10CC(C)C(=O)CC%10(C)CCC89C)C6=CC7=O)C=C5C4(C)CCC3(C)C2C1

InChI Identifier

InChI=1S/C58H74O8/c1-32-26-41-49(4,30-38(32)60)19-23-53(8)40-15-14-34-35(51(40,6)20-24-54(41,53)9)28-44(61)58(57(34,12)66-58)65-39-27-36-45(33(2)46(39)62)37(59)29-42-52(36,7)21-25-56(11)43-31-50(5,47(63)64-13)17-16-48(43,3)18-22-55(42,56)10/h14-15,27-29,32,41,43,62H,16-26,30-31H2,1-13H3

InChI Key

GXGZUOULORXKMU-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
Monteverdia ilicifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Naphthalene
Aryl ketone
Cyclohexenone
Methyl ester
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Oxirane
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	8.38	ALOGPS
logP	11.74	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	9.6	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	119.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	258.53 m³·mol⁻¹	ChemAxon
Polarizability	103.61 Å³	ChemAxon
Number of Rings	11	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

14734039

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate (NP0319051)

MOL for NP0319051 (methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate)

3D MOL for NP0319051 (methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate)

3D SDF for NP0319051 (methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate)

3D-SDF for NP0319051 (methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate)

PDB for NP0319051 (methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate)

3D PDB for NP0319051 (methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate)

SMILES for NP0319051 (methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate)

INCHI for NP0319051 (methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate)

Structure for NP0319051 (methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate)

3D Structure for NP0319051 (methyl 11-({1a,3b,5a,8,9b,11a-hexamethyl-7,13-dioxo-4h,5h,6h,8h,9h,9ah,10h,11h-piceno[3,4-b]oxiren-13a-yl}oxy)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate)