NP-MRD: Showing NP-Card for 12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate (NP0249023)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 11:28:24 UTC

Updated at

2022-09-07 11:28:24 UTC

NP-MRD ID

NP0249023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate

Description

12-[(Butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]Pentadec-9-en-2-yl pyridine-3-carboxylate belongs to the class of organic compounds known as dolabellane and neodolabellane diterpenoids. These are diterpenoids with a structure based on the dolabellane skeleton (3a,6,10-trimethyl-1-(propan-2-yl)-cyclopenta[11]annulene) or the neodolabellane skeleton. 12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate is found in Nigella sativa. 12-[(Butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]Pentadec-9-en-2-yl pyridine-3-carboxylate is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161518372D          

 45 49  0  0  0  0            999 V2000
    6.6346    0.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8096    0.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3959    1.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5709    1.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4008    0.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1572    1.9391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3322    1.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9209    1.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7276    1.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1413    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903    0.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7632   -0.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511   -1.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483   -0.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361    0.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0830    0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3294    0.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5091    0.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5105   -0.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116    0.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1722    1.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7844    1.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9161    2.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692    3.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374    2.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0057    2.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0905    2.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4223    3.3476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8436    3.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9285    4.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6816    4.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3498    3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2650    3.0537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5119    2.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    3.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160   -0.7572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2704   -1.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5918   -0.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2034   -1.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4578   -2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908   -3.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -3.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8150   -3.2240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8820   -2.4018    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  4  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  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  2  0  0  0  0
 30 35  1  0  0  0  0
 24 36  1  0  0  0  0
 16 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 40 45  1  0  0  0  0
M  END

     RDKit          3D

 89 93  0  0  0  0  0  0  0  0999 V2000
    2.4669    6.2852    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622    5.2907    1.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3923    4.2524    2.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6420    3.4941    1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8227    3.9000   -0.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493    2.4727    1.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0466    1.5450    0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131    0.4652   -0.1725 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2211    1.2734   -1.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0498    0.3820   -2.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500   -0.1458   -2.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1726   -0.2203   -3.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5857    0.2466   -4.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5390   -0.7041   -3.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3306   -0.4415   -0.8408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6620   -0.6777   -0.1940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7233    0.1179   -0.5277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4977    0.8500    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2194    0.8141    1.5254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    1.6987   -0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3258    2.4089    0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4081    3.1621    0.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8321    3.2266   -0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1209    2.5106   -1.6687 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0549    1.7550   -1.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -2.1796   -0.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5293   -2.9420    0.9636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8003   -4.2172    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4922   -3.3971    1.9971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950   -2.3816    2.2075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3347   -2.4344    2.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0297   -1.0034    3.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4075   -0.6362    2.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3342   -0.6489    4.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9849   -0.3358    1.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8630   -0.1401    0.4667 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6527   -0.9002   -0.2551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4343   -1.6265   -0.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3724   -0.8967   -1.5040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5145   -3.0286   -1.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7158   -3.9671   -0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8005   -5.3136   -1.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7110   -5.6898   -2.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4918   -4.7488   -2.6338 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3856   -3.4583   -2.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6836    6.2673   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3879    6.0000    0.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959    7.3195    1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    5.8516    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0204    4.8518    0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9276    3.5588    2.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5806    4.7882    2.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7077    2.1608    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541    1.1687    1.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2397    1.5723   -1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949    2.1612   -1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0766    1.0202   -3.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7501   -0.4188   -2.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3703   -0.2357   -4.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462    0.0431   -5.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4932    1.3465   -4.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9222   -1.4010   -2.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333   -1.3620   -4.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2750    0.0758   -3.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528   -1.4965   -0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -0.5428    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9872    2.3598    1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9669    3.7345    1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6940    3.8251   -1.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5125    1.1894   -2.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0948   -2.3516   -0.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5404   -2.5407   -1.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224   -4.9274    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219   -4.7280    1.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1784   -4.0942   -0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1936   -1.4573    2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5079   -2.9727    2.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5639   -2.9890    3.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566   -0.3173    3.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0615   -0.9880    4.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486   -0.8158    5.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -1.4985    4.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068    0.2779    4.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1508   -0.1474    2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5081    0.9275    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0315   -3.6515    0.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1935   -6.0792   -0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7805   -6.7476   -2.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0577   -2.7529   -2.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 15  1  0
 15 16  1  0
 16 26  1  0
 26 27  1  0
 27 28  1  6
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 38 40  1  0
 40 41  2  0
 41 42  1  0
 42 43  2  0
 43 44  1  0
 44 45  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
 15  8  1  0
 30 27  1  0
 45 40  1  0
 25 20  1  0
 36  8  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  2 49  1  0
  2 50  1  0
  3 51  1  0
  3 52  1  0
  7 53  1  0
  7 54  1  0
  9 55  1  0
  9 56  1  0
 10 57  1  0
 10 58  1  0
 15 65  1  6
 16 66  1  1
 26 71  1  0
 26 72  1  0
 28 73  1  0
 28 74  1  0
 28 75  1  0
 30 76  1  6
 31 77  1  0
 31 78  1  0
 32 79  1  0
 32 80  1  0
 34 81  1  0
 34 82  1  0
 34 83  1  0
 35 84  1  0
 36 85  1  1
 41 86  1  0
 42 87  1  0
 43 88  1  0
 45 89  1  0
 21 67  1  0
 22 68  1  0
 23 69  1  0
 25 70  1  0
 13 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 14 64  1  0
M  END


  Mrv1533004161518372D          

 45 49  0  0  0  0            999 V2000
    6.6346    0.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8096    0.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3959    1.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5709    1.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4008    0.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1572    1.9391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3322    1.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9209    1.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7276    1.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1413    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903    0.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7632   -0.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511   -1.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483   -0.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361    0.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0830    0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3294    0.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5091    0.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5105   -0.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116    0.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1722    1.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7844    1.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9161    2.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692    3.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374    2.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0057    2.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0905    2.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4223    3.3476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8436    3.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9285    4.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6816    4.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3498    3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2650    3.0537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5119    2.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    3.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160   -0.7572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2704   -1.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5918   -0.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2034   -1.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4578   -2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908   -3.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -3.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8150   -3.2240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8820   -2.4018    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  4  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  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  2  0  0  0  0
 30 35  1  0  0  0  0
 24 36  1  0  0  0  0
 16 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 40 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)OCC12CCC(C1C(CC1(C)OC1CCC(C)=CC2OC(=O)C1=CC=CN=C1)OC(=O)C1=CC=CN=C1)=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C36H44N2O7/c1-6-9-31(39)42-22-36-15-14-27(23(2)3)32(36)28(43-33(40)25-10-7-16-37-20-25)19-35(5)29(45-35)13-12-24(4)18-30(36)44-34(41)26-11-8-17-38-21-26/h7-8,10-11,16-18,20-21,28-30,32H,6,9,12-15,19,22H2,1-5H3

> <INCHI_KEY>
JZFHYGAGQUMBJU-UHFFFAOYSA-N

> <FORMULA>
C36H44N2O7

> <MOLECULAR_WEIGHT>
616.755

> <EXACT_MASS>
616.314851765

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
66.59809266240256

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate

> <ALOGPS_LOGP>
4.69

> <JCHEM_LOGP>
5.580901862333331

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.5408182358380533

> <JCHEM_POLAR_SURFACE_AREA>
117.21

> <JCHEM_REFRACTIVITY>
169.21609999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      12.385   0.960   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.845   0.958   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.072   2.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.532   2.287   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.215   0.780   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       7.760   3.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.220   3.617   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.452   2.282   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.958   2.605   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.730   1.272   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.702   0.126   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.025  -1.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.882  -2.412   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.490  -1.853   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.294   0.750   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.888   0.121   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.482   1.049   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.950   0.886   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.953  -0.654   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.582   1.044   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.321   2.292   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.464   3.324   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.710   4.991   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.116   5.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.363   4.717   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.205   3.185   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.611   3.814   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.769   5.346   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.522   6.249   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.175   5.975   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.333   7.506   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.739   8.135   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.986   7.232   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       9.828   5.700   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       8.422   5.072   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.274   7.152   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.763  -1.413   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.371  -2.073   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.105  -1.197   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.246  -3.608   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.855  -4.267   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.730  -5.802   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.996  -6.677   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0       3.388  -6.018   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0       3.513  -4.483   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   15   26                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11    8   16                                                  
CONECT   16   15   17   37                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   18   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   36                                                  
CONECT   25   24   26                                                       
CONECT   26   25    8   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   24                                                            
CONECT   37   16   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   45                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   40                                                       
MASTER        0    0    0    0    0    0    0    0   45    0   98    0
END

View in JSmol

Synonyms

Value	Source
12-[(Butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0,]pentadec-9-en-2-yl pyridine-3-carboxylic acid	Generator
12-[(Butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₃₆H₄₄N₂O₇

Average Mass

616.7550 Da

Monoisotopic Mass

616.31485 Da

IUPAC Name

12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate

Traditional Name

12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate

CAS Registry Number

Not Available

SMILES

CCCC(=O)OCC12CCC(C1C(CC1(C)OC1CCC(C)=CC2OC(=O)C1=CC=CN=C1)OC(=O)C1=CC=CN=C1)=C(C)C

InChI Identifier

InChI=1S/C36H44N2O7/c1-6-9-31(39)42-22-36-15-14-27(23(2)3)32(36)28(43-33(40)25-10-7-16-37-20-25)19-35(5)29(45-35)13-12-24(4)18-30(36)44-34(41)26-11-8-17-38-21-26/h7-8,10-11,16-18,20-21,28-30,32H,6,9,12-15,19,22H2,1-5H3

InChI Key

JZFHYGAGQUMBJU-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
Nigella sativa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dolabellane and neodolabellane diterpenoids. These are diterpenoids with a structure based on the dolabellane skeleton (3a,6,10-trimethyl-1-(propan-2-yl)-cyclopenta[11]annulene) or the neodolabellane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Dolabellane and neodolabellane diterpenoids

Alternative Parents

Substituents

Dolabellane diterpenoid
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Tricarboxylic acid or derivatives
Fatty acid ester
Pyridine
Fatty acyl
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	4.69	ALOGPS
logP	5.58	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	3.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	117.21 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	169.22 m³·mol⁻¹	ChemAxon
Polarizability	66.6 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

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

85434652

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate (NP0249023)

MOL for NP0249023 (12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate)

3D MOL for NP0249023 (12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate)

3D SDF for NP0249023 (12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate)

3D-SDF for NP0249023 (12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate)

PDB for NP0249023 (12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate)

3D PDB for NP0249023 (12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate)

SMILES for NP0249023 (12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate)

INCHI for NP0249023 (12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate)

Structure for NP0249023 (12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate)

3D Structure for NP0249023 (12-[(butanoyloxy)methyl]-4,9-dimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylate)