NP-MRD: Showing NP-Card for [(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate (NP0269478)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 14:58:58 UTC

Updated at

2022-09-08 14:58:58 UTC

NP-MRD ID

NP0269478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate

Description

CHEMBL450708 belongs to the class of organic compounds known as benzazocines. These are organic compounds containing the benzazocine ring system, which consists of a benzene ring bound to an azocine ring. [(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate is found in Jorunna funebris. Based on a literature review very few articles have been published on CHEMBL450708.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082216582D          

 43 47  0  0  1  0            999 V2000
    7.2464   -5.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8242   -4.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6031   -3.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1810   -3.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8043   -3.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2265   -4.3591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5832   -2.9754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7844   -2.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633   -1.9746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1411   -1.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9201   -0.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1212   -0.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5434   -0.9738    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8251   -0.5680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0302   -0.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167    0.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860   -0.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3668    0.6242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5418    0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803   -0.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5553   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938   -2.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455   -2.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1958   -2.8107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5639   -2.7080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3587   -2.4869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8671   -3.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755   -3.7864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -1.7686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9620   -1.6707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5657   -2.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -0.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2769    0.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2968   -0.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8746    0.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5178   -1.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3167   -1.2089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8945   -0.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9400   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1611   -2.3866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
 14 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  3  0  0  0  0
 29 32  1  0  0  0  0
 13 32  1  6  0  0  0
  9 32  1  0  0  0  0
 28 33  1  1  0  0  0
 14 33  1  1  0  0  0
 33 34  1  0  0  0  0
 11 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 39 42  1  0  0  0  0
 10 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END

     RDKit          3D

 76 80  0  0  0  0  0  0  0  0999 V2000
   -6.2689   -0.5437    1.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7707   -1.0745    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9755   -1.5994   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6204   -2.0993   -1.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5540   -1.7165   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8976   -2.2536   -1.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7407   -1.3166    0.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3763   -1.4644    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4777   -0.8811   -0.1188 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3533    0.6171   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2482    1.1986   -0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871    0.4646   -1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280   -1.0117   -1.0826 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9338   -1.7030   -1.2856 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0972   -0.9965   -0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9588   -0.1879   -1.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7781    0.0183   -2.7364 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0105    0.4244   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8720    1.2379   -1.4646 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5849    2.6213   -1.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2363    0.2531    0.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3596    0.8995    1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -0.5579    1.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5141   -0.7965    2.6698 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3077   -1.1806    0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3701   -2.0534    1.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2793   -1.9995    2.6148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5515   -2.9827    0.6010 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0578   -2.6180    0.6142 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5556   -3.6219   -0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684   -4.4189   -0.9125 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0632   -1.2767    0.1437 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9400   -3.0836   -0.7964 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736   -3.6042   -0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0699    2.6636   -0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9726    3.2076   -1.0248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    3.5229   -0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8600    5.0105   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1732    2.9888    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1520    3.8091    1.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1483    4.4286    0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3473    1.5148    0.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083    1.0941    0.9542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5157   -1.2301    2.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9408    0.4998    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1089   -0.4891    2.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8627   -1.0170    0.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4065   -1.4637   -2.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7035   -2.2886   -1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1677   -3.0939   -1.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0969   -0.9390    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1675   -2.5308    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6542   -1.1405   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0256    0.7530   -2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8255    0.6779   -0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0509   -1.2698   -1.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1022   -1.7802   -2.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3909    0.5989   -3.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105    2.8002   -2.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5450    3.0481   -0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3548    3.1308   -2.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0496    1.3479    0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8997    1.6565    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9308    0.1957    1.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2670   -0.3732    3.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -4.0092    1.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2191   -2.6631    1.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6567   -3.9293    0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0064   -2.8284   -1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3743   -4.4527   -1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1357    5.2244    0.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8150    5.3896   -1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6154    5.4837    0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116    5.0315    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7240    5.1019   -0.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7051    3.6257   -0.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  3  0
 29 32  1  0
 32 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  2  1  1  0
 10 42  1  0
 42 43  2  0
 42 39  1  0
 39 40  1  0
 40 41  1  0
 39 37  2  0
 37 38  1  0
 37 35  1  0
 35 36  2  0
 13 14  1  0
 14 33  1  0
 33 34  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 15 25  1  0
 33 28  1  0
  9 32  1  0
 35 11  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 22 62  1  0
 22 63  1  0
 22 64  1  0
 24 65  1  0
 28 66  1  1
 29 67  1  1
 13 56  1  6
 12 54  1  0
 12 55  1  0
  9 53  1  6
  8 51  1  0
  8 52  1  0
  4 48  1  0
  4 49  1  0
  4 50  1  0
  2 47  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
 41 74  1  0
 41 75  1  0
 41 76  1  0
 38 71  1  0
 38 72  1  0
 38 73  1  0
 14 57  1  6
 34 68  1  0
 34 69  1  0
 34 70  1  0
 17 58  1  0
M  END


  Mrv1652309082216582D          

 43 47  0  0  1  0            999 V2000
    7.2464   -5.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8242   -4.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6031   -3.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1810   -3.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8043   -3.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2265   -4.3591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5832   -2.9754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7844   -2.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633   -1.9746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1411   -1.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9201   -0.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1212   -0.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5434   -0.9738    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8251   -0.5680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0302   -0.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167    0.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860   -0.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3668    0.6242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5418    0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803   -0.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5553   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938   -2.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455   -2.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1958   -2.8107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5639   -2.7080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3587   -2.4869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8671   -3.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755   -3.7864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -1.7686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9620   -1.6707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5657   -2.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -0.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2769    0.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2968   -0.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8746    0.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5178   -1.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3167   -1.2089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8945   -0.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9400   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1611   -2.3866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
 14 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  3  0  0  0  0
 29 32  1  0  0  0  0
 13 32  1  6  0  0  0
  9 32  1  0  0  0  0
 28 33  1  1  0  0  0
 14 33  1  1  0  0  0
 33 34  1  0  0  0  0
 11 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 39 42  1  0  0  0  0
 10 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0269478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(O)=C2C(=O)[C@H]3[C@H](C#N)N4[C@@H](CC5=C([C@@H]4COC(=O)C(\C)=C/C)C(=O)C(OC)=C(C)C5=O)[C@H](N3C)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C31H33N3O9/c1-8-12(2)31(40)43-11-18-19-15(24(35)13(3)29(41-6)27(19)38)9-16-22-20-21(25(36)14(4)30(42-7)28(20)39)26(37)23(33(22)5)17(10-32)34(16)18/h8,16-18,22-23,36,39H,9,11H2,1-7H3/b12-8-/t16-,17-,18-,22-,23+/m0/s1

> <INCHI_KEY>
TXQHLRYOWKLEFP-YIRKZLORSA-N

> <FORMULA>
C31H33N3O9

> <MOLECULAR_WEIGHT>
591.617

> <EXACT_MASS>
591.221679655

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
59.08878215407314

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,10R,12R,13R)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.650547383000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.807421317145335

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.990073094480596

> <JCHEM_PKA_STRONGEST_BASIC>
1.2699362545439048

> <JCHEM_POLAR_SURFACE_AREA>
166.69999999999996

> <JCHEM_REFRACTIVITY>
156.24839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,10R,12R,13R)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      13.527 -10.005   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.605  -8.906   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.193  -7.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.271  -6.323   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.701  -7.038   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.623  -8.137   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      12.289  -5.554   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.797  -5.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.385  -3.686   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.463  -2.587   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.051  -1.103   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.560  -0.719   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.481  -1.818   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.140  -1.060   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.656  -1.473   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.874  -0.147   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.631   1.194   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.334  -0.161   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.551   1.165   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.011   1.151   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.577  -1.502   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.037  -1.517   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.359  -2.828   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.602  -4.169   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.899  -2.814   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.312  -4.298   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.099  -5.247   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.653  -5.055   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.136  -4.642   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.085  -5.855   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      10.034  -7.068   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       8.894  -3.301   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0       7.396  -3.119   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       8.523  -4.168   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.129  -0.004   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.717   1.480   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      13.621  -0.388   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.699   0.711   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      14.033  -1.872   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      15.525  -2.257   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      16.603  -1.157   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.955  -2.971   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      13.367  -4.455   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    9   11   42                                                  
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13   15   33                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   15   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   13    9                                                  
CONECT   33   28   14   34                                                  
CONECT   34   33                                                            
CONECT   35   11   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   39   10   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₃N₃O₉

Average Mass

591.6170 Da

Monoisotopic Mass

591.22168 Da

IUPAC Name

[(1R,2S,10R,12R,13R)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2Z)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(O)=C2C(=O)[C@H]3[C@H](C#N)N4[C@@H](CC5=C([C@@H]4COC(=O)C(\C)=C/C)C(=O)C(OC)=C(C)C5=O)[C@H](N3C)C2=C1O

InChI Identifier

InChI=1S/C31H33N3O9/c1-8-12(2)31(40)43-11-18-19-15(24(35)13(3)29(41-6)27(19)38)9-16-22-20-21(25(36)14(4)30(42-7)28(20)39)26(37)23(33(22)5)17(10-32)34(16)18/h8,16-18,22-23,36,39H,9,11H2,1-7H3/b12-8-/t16-,17-,18-,22-,23+/m0/s1

InChI Key

TXQHLRYOWKLEFP-YIRKZLORSA-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
Jorunna funebris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzazocines. These are organic compounds containing the benzazocine ring system, which consists of a benzene ring bound to an azocine ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzazocines

Direct Parent

Benzazocines

Alternative Parents

Substituents

Isoquinoline quinone
Benzazocine
Isoquinolone
Tetrahydroisoquinoline
Anisole
Aryl ketone
Aryl alkyl ketone
Phenol ether
Alkyl aryl ether
N-methylpiperazine
N-alkylpiperazine
Fatty acid ester
Phenol
Aralkylamine
1,4-diazinane
Piperazine
Fatty acyl
Vinylogous acid
Vinylogous ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Alpha-aminonitrile
Ketone
Tertiary aliphatic amine
Tertiary amine
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Ether
Carbonyl group
Organic nitrogen compound
Cyanide
Amine
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen 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	3.65	ChemAxon
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	1.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	166.7 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	156.25 m³·mol⁻¹	ChemAxon
Polarizability	59.09 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8252692

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10077154

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate (NP0269478)

MOL for NP0269478 ([(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate)

3D MOL for NP0269478 ([(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate)

3D SDF for NP0269478 ([(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0269478 ([(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate)

PDB for NP0269478 ([(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate)

3D PDB for NP0269478 ([(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate)

SMILES for NP0269478 ([(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate)

INCHI for NP0269478 ([(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate)

Structure for NP0269478 ([(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate)

3D Structure for NP0269478 ([(1r,2s,10r,12r,13r)-12-cyano-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl (2z)-2-methylbut-2-enoate)