NP-MRD: Showing NP-Card for bisdehydrostemoninine A (NP0032298)

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Record Information

Version

2.0

Created at

2021-06-19 23:08:07 UTC

Updated at

2021-06-30 00:01:23 UTC

NP-MRD ID

NP0032298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bisdehydrostemoninine A

Provided By

JEOL Database JEOL Logo

Description

(2S)-4-[(2R,2'R,3'S,6'R)-3'-ethyl-4-methyl-5-oxo-5H-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]Tridecane]-1'(13'),11'-dien-11'-yl]-2-methyl-4-oxobutanoic acid belongs to the class of organic compounds known as pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom. bisdehydrostemoninine A is found in Stemona tuberosa. bisdehydrostemoninine A was first documented in 2006 (Lin, L. -G., et al.). Based on a literature review very few articles have been published on (2S)-4-[(2R,2'R,3'S,6'R)-3'-ethyl-4-methyl-5-oxo-5H-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]Tridecane]-1'(13'),11'-dien-11'-yl]-2-methyl-4-oxobutanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101083D          

 56 59  0  0  0  0            999 V2000
    2.9990   -2.6539    1.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5498   -1.3118    1.2921 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3153   -1.3210   -0.2289 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7014   -0.0135   -0.7353 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2344    0.1846   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -0.6033    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    0.0363    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    1.2069   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    2.1348   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229    3.0143   -1.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2103    1.9593   -0.5624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1399    3.1195   -0.9430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2907    3.2304    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6975    2.9012   -2.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8219    2.4870   -2.5800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8218    3.1976   -3.3267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4210    1.3140   -0.9431 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2784    2.4227   -1.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8144    2.0633   -2.9702 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1033    1.2336   -2.9440 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9750   -0.1182   -2.2421 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1991   -0.8531   -2.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -1.3853   -1.1184 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1534   -2.7224   -1.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401   -2.7371   -0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4414   -3.8211   -1.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7516   -1.3889   -0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8348   -1.0279   -0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -0.6147   -0.5738 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3209   -3.4561    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108   -2.9091    1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0053   -2.6197    2.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6186   -1.0405    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2780   -0.5415    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6456   -2.1544   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2625    0.8252   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233   -1.5564    0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955   -0.3536    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6192    1.0033   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021    1.9226    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6160    4.0834   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9126    3.4685    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8574    2.2948    0.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9891    4.0221   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202    3.4417   -3.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0861    2.7332   -0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3929    3.2795   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0476    1.5357   -3.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321    2.9948   -3.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9094    1.8146   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4346    1.0649   -3.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1981   -0.7103   -2.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -3.5558   -1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2780   -3.5381   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8332   -4.0368   -0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0064   -4.7440   -1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0  0  0  0
 24 25  2  0  0  0  0
 17  8  1  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
 18 19  1  0  0  0  0
 27 28  2  0  0  0  0
 20 19  1  0  0  0  0
 21 52  1  6  0  0  0
 21  4  1  0  0  0  0
  4 36  1  1  0  0  0
 25 27  1  0  0  0  0
 25 26  1  0  0  0  0
 27 29  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  4  5  1  0  0  0  0
  8  9  1  0  0  0  0
  4  3  1  0  0  0  0
  9 11  1  0  0  0  0
  3 23  1  0  0  0  0
 11 12  1  0  0  0  0
 23 22  1  6  0  0  0
 12 14  1  0  0  0  0
 22 21  1  0  0  0  0
 14 16  1  0  0  0  0
  5 17  1  0  0  0  0
  9 10  2  0  0  0  0
 23 24  1  0  0  0  0
 12 13  1  0  0  0  0
 17 18  1  0  0  0  0
 14 15  2  0  0  0  0
 23 29  1  0  0  0  0
 24 53  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
  3 35  1  1  0  0  0
  7 38  1  0  0  0  0
  6 37  1  0  0  0  0
 26 54  1  0  0  0  0
 26 55  1  0  0  0  0
 26 56  1  0  0  0  0
  2 33  1  0  0  0  0
  2 34  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 12 41  1  6  0  0  0
 16 45  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    2.9990   -2.6539    1.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5498   -1.3118    1.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3153   -1.3210   -0.2289 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7014   -0.0135   -0.7353 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2344    0.1846   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -0.6033    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    0.0363    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    1.2069   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    2.1348   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229    3.0143   -1.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2103    1.9593   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1399    3.1195   -0.9430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2907    3.2304    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6975    2.9012   -2.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8219    2.4870   -2.5800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8218    3.1976   -3.3267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4210    1.3140   -0.9431 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2784    2.4227   -1.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8144    2.0633   -2.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    1.2336   -2.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -0.1182   -2.2421 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1991   -0.8531   -2.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -1.3853   -1.1184 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1534   -2.7224   -1.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401   -2.7371   -0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4414   -3.8211   -1.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7516   -1.3889   -0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8348   -1.0279   -0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -0.6147   -0.5738 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3209   -3.4561    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108   -2.9091    1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0053   -2.6197    2.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6186   -1.0405    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2780   -0.5415    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6456   -2.1544   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2625    0.8252   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233   -1.5564    0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955   -0.3536    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6192    1.0033   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021    1.9226    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6160    4.0834   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9126    3.4685    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8574    2.2948    0.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9891    4.0221   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202    3.4417   -3.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0861    2.7332   -0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3929    3.2795   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0476    1.5357   -3.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321    2.9948   -3.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9094    1.8146   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4346    1.0649   -3.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1981   -0.7103   -2.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -3.5558   -1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2780   -3.5381   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8332   -4.0368   -0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0064   -4.7440   -1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 24 25  2  0
 17  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
 18 19  1  0
 27 28  2  0
 20 19  1  0
 21 52  1  6
 21  4  1  0
  4 36  1  1
 25 27  1  0
 25 26  1  0
 27 29  1  0
  3  2  1  0
  2  1  1  0
  4  5  1  0
  8  9  1  0
  4  3  1  0
  9 11  1  0
  3 23  1  0
 11 12  1  0
 23 22  1  6
 12 14  1  0
 22 21  1  0
 14 16  1  0
  5 17  1  0
  9 10  2  0
 23 24  1  0
 12 13  1  0
 17 18  1  0
 14 15  2  0
 23 29  1  0
 24 53  1  0
 18 46  1  0
 18 47  1  0
 20 50  1  0
 20 51  1  0
 19 48  1  0
 19 49  1  0
  3 35  1  1
  7 38  1  0
  6 37  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  6
 16 45  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
M  END


  Mrv1652306202101083D          

 56 59  0  0  0  0            999 V2000
    2.9990   -2.6539    1.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5498   -1.3118    1.2921 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3153   -1.3210   -0.2289 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7014   -0.0135   -0.7353 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2344    0.1846   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -0.6033    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    0.0363    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    1.2069   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    2.1348   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229    3.0143   -1.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2103    1.9593   -0.5624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1399    3.1195   -0.9430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2907    3.2304    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6975    2.9012   -2.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8219    2.4870   -2.5800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8218    3.1976   -3.3267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4210    1.3140   -0.9431 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2784    2.4227   -1.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8144    2.0633   -2.9702 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1033    1.2336   -2.9440 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9750   -0.1182   -2.2421 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1991   -0.8531   -2.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -1.3853   -1.1184 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1534   -2.7224   -1.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401   -2.7371   -0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4414   -3.8211   -1.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7516   -1.3889   -0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8348   -1.0279   -0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -0.6147   -0.5738 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3209   -3.4561    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108   -2.9091    1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0053   -2.6197    2.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6186   -1.0405    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2780   -0.5415    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6456   -2.1544   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2625    0.8252   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233   -1.5564    0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955   -0.3536    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6192    1.0033   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021    1.9226    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6160    4.0834   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9126    3.4685    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8574    2.2948    0.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9891    4.0221   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202    3.4417   -3.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0861    2.7332   -0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3929    3.2795   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0476    1.5357   -3.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321    2.9948   -3.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9094    1.8146   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4346    1.0649   -3.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1981   -0.7103   -2.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -3.5558   -1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2780   -3.5381   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8332   -4.0368   -0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0064   -4.7440   -1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0  0  0  0
 24 25  2  0  0  0  0
 17  8  1  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
 18 19  1  0  0  0  0
 27 28  2  0  0  0  0
 20 19  1  0  0  0  0
 21 52  1  6  0  0  0
 21  4  1  0  0  0  0
  4 36  1  1  0  0  0
 25 27  1  0  0  0  0
 25 26  1  0  0  0  0
 27 29  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  4  5  1  0  0  0  0
  8  9  1  0  0  0  0
  4  3  1  0  0  0  0
  9 11  1  0  0  0  0
  3 23  1  0  0  0  0
 11 12  1  0  0  0  0
 23 22  1  6  0  0  0
 12 14  1  0  0  0  0
 22 21  1  0  0  0  0
 14 16  1  0  0  0  0
  5 17  1  0  0  0  0
  9 10  2  0  0  0  0
 23 24  1  0  0  0  0
 12 13  1  0  0  0  0
 17 18  1  0  0  0  0
 14 15  2  0  0  0  0
 23 29  1  0  0  0  0
 24 53  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
  3 35  1  1  0  0  0
  7 38  1  0  0  0  0
  6 37  1  0  0  0  0
 26 54  1  0  0  0  0
 26 55  1  0  0  0  0
 26 56  1  0  0  0  0
  2 33  1  0  0  0  0
  2 34  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 12 41  1  6  0  0  0
 16 45  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032298

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(C([H])([H])[H])C([H])([H])C(=O)C1=C([H])C([H])=C2N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])O[C@@]3(OC(=O)C(=C3[H])C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[H])[C@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO6/c1-4-14-19-16-8-7-15(17(24)10-12(2)20(25)26)23(16)9-5-6-18(19)28-22(14)11-13(3)21(27)29-22/h7-8,11-12,14,18-19H,4-6,9-10H2,1-3H3,(H,25,26)/t12-,14-,18+,19+,22-/m0/s1

> <INCHI_KEY>
KABGIFKEGLAKQV-YUXICHDRSA-N

> <FORMULA>
C22H27NO6

> <MOLECULAR_WEIGHT>
401.459

> <EXACT_MASS>
401.183837593

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.772306448102995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-4-[(2R,2'R,3'S,6'R)-3'-ethyl-4-methyl-5-oxo-5H-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-1'(13'),11'-dien-11'-yl]-2-methyl-4-oxobutanoic acid

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
3.4654134073333323

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.999805266274628

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.092119246205927

> <JCHEM_PKA_STRONGEST_BASIC>
-4.390353737750537

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
105.2761

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-4-[(2R,2'R,3'S,6'R)-3'-ethyl-4-methyl-5-oxo-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-1'(13'),11'-dien-11'-yl]-2-methyl-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    2.9990   -2.6539    1.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5498   -1.3118    1.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3153   -1.3210   -0.2289 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7014   -0.0135   -0.7353 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2344    0.1846   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -0.6033    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    0.0363    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    1.2069   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    2.1348   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229    3.0143   -1.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2103    1.9593   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1399    3.1195   -0.9430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2907    3.2304    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6975    2.9012   -2.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8219    2.4870   -2.5800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8218    3.1976   -3.3267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4210    1.3140   -0.9431 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2784    2.4227   -1.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8144    2.0633   -2.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    1.2336   -2.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -0.1182   -2.2421 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1991   -0.8531   -2.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -1.3853   -1.1184 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1534   -2.7224   -1.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401   -2.7371   -0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4414   -3.8211   -1.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7516   -1.3889   -0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8348   -1.0279   -0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -0.6147   -0.5738 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3209   -3.4561    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108   -2.9091    1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0053   -2.6197    2.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6186   -1.0405    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2780   -0.5415    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6456   -2.1544   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2625    0.8252   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233   -1.5564    0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955   -0.3536    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6192    1.0033   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021    1.9226    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6160    4.0834   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9126    3.4685    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8574    2.2948    0.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9891    4.0221   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202    3.4417   -3.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0861    2.7332   -0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3929    3.2795   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0476    1.5357   -3.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321    2.9948   -3.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9094    1.8146   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4346    1.0649   -3.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1981   -0.7103   -2.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -3.5558   -1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2780   -3.5381   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8332   -4.0368   -0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0064   -4.7440   -1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 24 25  2  0
 17  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
 18 19  1  0
 27 28  2  0
 20 19  1  0
 21 52  1  6
 21  4  1  0
  4 36  1  1
 25 27  1  0
 25 26  1  0
 27 29  1  0
  3  2  1  0
  2  1  1  0
  4  5  1  0
  8  9  1  0
  4  3  1  0
  9 11  1  0
  3 23  1  0
 11 12  1  0
 23 22  1  6
 12 14  1  0
 22 21  1  0
 14 16  1  0
  5 17  1  0
  9 10  2  0
 23 24  1  0
 12 13  1  0
 17 18  1  0
 14 15  2  0
 23 29  1  0
 24 53  1  0
 18 46  1  0
 18 47  1  0
 20 50  1  0
 20 51  1  0
 19 48  1  0
 19 49  1  0
  3 35  1  1
  7 38  1  0
  6 37  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  6
 16 45  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       2.999  -2.654   1.849  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.550  -1.312   1.292  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.315  -1.321  -0.229  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.701  -0.014  -0.735  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.234   0.185  -0.479  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.704  -0.603   0.152  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.954   0.036   0.021  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.782   1.207  -0.706  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.815   2.135  -1.153  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.623   3.014  -1.997  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.210   1.959  -0.562  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.140   3.119  -0.943  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.291   3.230   0.060  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.697   2.901  -2.341  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.822   2.487  -2.580  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.822   3.198  -3.327  0.00  0.00           O+0
HETATM   17  N   UNK     0      -0.421   1.314  -0.943  0.00  0.00           N+0
HETATM   18  C   UNK     0       0.278   2.423  -1.585  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.814   2.063  -2.970  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.103   1.234  -2.944  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.975  -0.118  -2.242  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.199  -0.853  -2.394  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.569  -1.385  -1.118  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.153  -2.722  -1.335  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.440  -2.737  -0.995  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.441  -3.821  -1.053  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.752  -1.389  -0.508  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.835  -1.028  -0.085  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.636  -0.615  -0.574  0.00  0.00           O+0
HETATM   30  H   UNK     0       2.321  -3.456   1.542  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.011  -2.909   1.528  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.005  -2.620   2.944  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.619  -1.040   1.802  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.278  -0.542   1.571  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.646  -2.154  -0.487  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.263   0.825  -0.300  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.523  -1.556   0.633  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.896  -0.354   0.388  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.619   1.003  -0.910  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.102   1.923   0.529  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.616   4.083  -0.932  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.913   3.469   1.060  0.00  0.00           H+0
HETATM   43  H   UNK     0      -6.857   2.295   0.126  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.989   4.022  -0.233  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.920   3.442  -3.004  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.086   2.733  -0.912  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.393   3.280  -1.649  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.048   1.536  -3.551  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.032   2.995  -3.507  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.909   1.815  -2.477  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.435   1.065  -3.977  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.198  -0.710  -2.744  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.608  -3.556  -1.751  0.00  0.00           H+0
HETATM   54  H   UNK     0       7.278  -3.538  -1.700  0.00  0.00           H+0
HETATM   55  H   UNK     0       6.833  -4.037  -0.054  0.00  0.00           H+0
HETATM   56  H   UNK     0       6.006  -4.744  -1.450  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1   33   34                                             
CONECT    3    2    4   23   35                                             
CONECT    4   21   36    5    3                                             
CONECT    5    6    4   17                                                  
CONECT    6    7    5   37                                                  
CONECT    7    8    6   38                                                  
CONECT    8   17    7    9                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9                                                            
CONECT   11    9   12   39   40                                             
CONECT   12   11   14   13   41                                             
CONECT   13   12   42   43   44                                             
CONECT   14   12   16   15                                                  
CONECT   15   14                                                            
CONECT   16   14   45                                                       
CONECT   17    8    5   18                                                  
CONECT   18   19   17   46   47                                             
CONECT   19   18   20   48   49                                             
CONECT   20   21   19   50   51                                             
CONECT   21   20   52    4   22                                             
CONECT   22   23   21                                                       
CONECT   23    3   22   24   29                                             
CONECT   24   25   23   53                                                  
CONECT   25   24   27   26                                                  
CONECT   26   25   54   55   56                                             
CONECT   27   28   25   29                                                  
CONECT   28   27                                                            
CONECT   29   27   23                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    6                                                            
CONECT   38    7                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   16                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   24                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  118    0
END

RDKit          3D

56 59  0  0  0  0  0  0  0  0999 V2000
    2.9990   -2.6539    1.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5498   -1.3118    1.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3153   -1.3210   -0.2289 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7014   -0.0135   -0.7353 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2344    0.1846   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -0.6033    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    0.0363    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    1.2069   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    2.1348   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229    3.0143   -1.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2103    1.9593   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1399    3.1195   -0.9430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2907    3.2304    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6975    2.9012   -2.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8219    2.4870   -2.5800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8218    3.1976   -3.3267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4210    1.3140   -0.9431 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2784    2.4227   -1.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8144    2.0633   -2.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    1.2336   -2.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -0.1182   -2.2421 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1991   -0.8531   -2.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -1.3853   -1.1184 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1534   -2.7224   -1.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401   -2.7371   -0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4414   -3.8211   -1.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7516   -1.3889   -0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8348   -1.0279   -0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -0.6147   -0.5738 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3209   -3.4561    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108   -2.9091    1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0053   -2.6197    2.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6186   -1.0405    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2780   -0.5415    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6456   -2.1544   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2625    0.8252   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233   -1.5564    0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955   -0.3536    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6192    1.0033   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021    1.9226    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6160    4.0834   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9126    3.4685    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8574    2.2948    0.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9891    4.0221   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202    3.4417   -3.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0861    2.7332   -0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3929    3.2795   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0476    1.5357   -3.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321    2.9948   -3.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9094    1.8146   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4346    1.0649   -3.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1981   -0.7103   -2.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -3.5558   -1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2780   -3.5381   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8332   -4.0368   -0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0064   -4.7440   -1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 24 25  2  0
 17  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
 18 19  1  0
 27 28  2  0
 20 19  1  0
 21 52  1  6
 21  4  1  0
  4 36  1  1
 25 27  1  0
 25 26  1  0
 27 29  1  0
  3  2  1  0
  2  1  1  0
  4  5  1  0
  8  9  1  0
  4  3  1  0
  9 11  1  0
  3 23  1  0
 11 12  1  0
 23 22  1  6
 12 14  1  0
 22 21  1  0
 14 16  1  0
  5 17  1  0
  9 10  2  0
 23 24  1  0
 12 13  1  0
 17 18  1  0
 14 15  2  0
 23 29  1  0
 24 53  1  0
 18 46  1  0
 18 47  1  0
 20 50  1  0
 20 51  1  0
 19 48  1  0
 19 49  1  0
  3 35  1  1
  7 38  1  0
  6 37  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  6
 16 45  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2S)-4-[(2R,2'r,3's,6'r)-3'-Ethyl-4-methyl-5-oxo-5H-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0,]tridecane]-1'(13'),11'-dien-11'-yl]-2-methyl-4-oxobutanoate	Generator

Chemical Formula

C₂₂H₂₇NO₆

Average Mass

401.4590 Da

Monoisotopic Mass

401.18384 Da

IUPAC Name

(2S)-4-[(2R,2'R,3'S,6'R)-3'-ethyl-4-methyl-5-oxo-5H-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-1'(13'),11'-dien-11'-yl]-2-methyl-4-oxobutanoic acid

Traditional Name

(2S)-4-[(2R,2'R,3'S,6'R)-3'-ethyl-4-methyl-5-oxo-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-1'(13'),11'-dien-11'-yl]-2-methyl-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]([H])(C([H])([H])[H])C([H])([H])C(=O)C1=C([H])C([H])=C2N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])O[C@@]3(OC(=O)C(=C3[H])C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[H])[C@]21[H]

InChI Identifier

InChI=1S/C22H27NO6/c1-4-14-19-16-8-7-15(17(24)10-12(2)20(25)26)23(16)9-5-6-18(19)28-22(14)11-13(3)21(27)29-22/h7-8,11-12,14,18-19H,4-6,9-10H2,1-3H3,(H,25,26)/t12-,14-,18+,19+,22-/m0/s1

InChI Key

KABGIFKEGLAKQV-YUXICHDRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stemona tuberosa	JEOL database	Lin, L. -G., et al, J. Nat. Prod. 69, 1051 (2006)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroloazepines

Sub Class

Not Available

Direct Parent

Pyrroloazepines

Alternative Parents

Substituents

Pyrroloazepine
Aryl ketone
Aryl alkyl ketone
Gamma-keto acid
Azepine
Ketal
Dicarboxylic acid or derivatives
Keto acid
Substituted pyrrole
2-furanone
Dihydrofuran
Heteroaromatic compound
Oxolane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrole
Ketone
Lactone
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Organic oxide
Organopnictogen compound
Aldehyde
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
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	3.07	ALOGPS
logP	3.47	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	105.28 m³·mol⁻¹	ChemAxon
Polarizability	43.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

10017491

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11843014

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin, L. -G., et al. (2006). Lin, L. -G., et al, J. Nat. Prod. 69, 1051 (2006) . J. Nat. Prod..

Showing NP-Card for bisdehydrostemoninine A (NP0032298)

MOL for NP0032298 (bisdehydrostemoninine A)

3D MOL for NP0032298 (bisdehydrostemoninine A)

3D SDF for NP0032298 (bisdehydrostemoninine A)

3D-SDF for NP0032298 (bisdehydrostemoninine A)

PDB for NP0032298 (bisdehydrostemoninine A)

3D PDB for NP0032298 (bisdehydrostemoninine A)

SMILES for NP0032298 (bisdehydrostemoninine A)

INCHI for NP0032298 (bisdehydrostemoninine A)

Structure for NP0032298 (bisdehydrostemoninine A)

3D Structure for NP0032298 (bisdehydrostemoninine A)