NP-MRD: Showing NP-Card for Toonacilin (NP0052214)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 23:21:19 UTC

Updated at

2022-04-27 23:21:19 UTC

NP-MRD ID

NP0052214

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Toonacilin

Description

Toonacilin belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Toonacilin is found in Toona ciliata . Toonacilin was first documented in 2015 (PMID: 26320684). Based on a literature review very few articles have been published on Toonacilin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201212D          

 40 44  0  0  1  0            999 V2000
    3.3258    0.0332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8343    0.6958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0147    0.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4389    1.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6866   -0.1556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1782   -0.8182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9977   -0.7238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8408   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7234   -0.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1837   -0.1178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6013   -1.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999   -1.4904    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9128   -1.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9046   -0.4183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0681    0.3903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9626   -2.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -2.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9759   -3.6073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7580   -3.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7497   -2.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008   -1.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1623    1.4527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7295    2.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942    2.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    3.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7299    3.9017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1246    2.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3599    1.6444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8001    1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8949    1.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297    0.4081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5374    1.8330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2852    1.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7638    3.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    2.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0572    1.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2831   -0.2433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -0.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1155   -0.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0425   -1.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  1  0  0  0
  5 15  1  1  0  0  0
 12 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 16 20  1  0  0  0  0
  6 21  1  6  0  0  0
  2 22  1  1  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 27 34  1  0  0  0  0
 27 35  1  0  0  0  0
 22 36  1  1  0  0  0
  1 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END

     RDKit          3D

 78 82  0  0  0  0  0  0  0  0999 V2000
   -0.7041    0.2866    2.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0483   -0.2330    1.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460    0.0969    0.1688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8708    0.5150   -0.0718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1507    1.9179    0.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0102    0.5901   -1.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1929   -0.4901   -2.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2578   -1.7510   -1.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6284   -2.7555   -1.9367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1433   -1.6804   -0.3603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9156   -2.9373    0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5769   -1.8081   -0.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8510   -0.4619    0.4702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0614    0.0816    1.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1985    0.5689    0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3762    0.1602    0.5432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1017    1.5844   -0.5003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1753    2.1105   -1.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268    0.9639   -0.3827 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7769    0.7490   -1.7575 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7494    1.7267   -2.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137    1.4456   -4.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5768    2.9050   -2.3839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9293    0.7155    0.3683 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9896    1.4759   -0.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471    2.4954    0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7740    3.1769   -0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2279    2.7771    1.6610 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2115   -0.7132    0.6639 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0884   -1.6962   -0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3807   -0.9892    1.4951 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7221   -0.7547    1.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3994   -0.8653   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7009   -0.4748    0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8143   -0.1451    1.3133 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7128   -0.2789    1.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0458   -2.4288    1.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5362   -2.2480    2.2306 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5548   -1.0494    3.1107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1114   -1.1205    1.6930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3196   -0.0300    3.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209    0.9446    2.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3679   -0.8777   -0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9558    2.0196    1.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241    2.5285   -0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2548    2.4387    0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9778    1.5683   -2.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2794   -0.4545   -3.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8281   -3.0997    1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0951   -2.7546    1.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7820   -3.8276   -0.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5407   -2.6739   -1.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2567   -2.2147   -0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -0.9846   -1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2877   -0.9289    1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8171    0.6398    2.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4532   -0.9003    1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9450    3.1138   -1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0080    2.2955   -0.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5409    1.4288   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358    2.0420   -0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    1.9572   -4.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9147    1.8636   -4.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9118    0.3668   -4.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453    1.1552    1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2319    2.5407   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4928    4.1842   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5884    3.3573    0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9940   -2.3153   -0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3142   -2.5041   -0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8231   -1.2997   -1.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1981   -0.4228    2.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9377   -1.2003   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4301   -0.4766   -0.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5969   -0.0563    3.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6043   -2.5841    2.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2435   -3.1779    1.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328   -3.1226    2.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  1  0
 13 10  1  0
 10 11  1  1
 10 12  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  1
  4  3  1  0
  3 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 24 29  1  0
 29 30  1  6
 29 31  1  0
 31 37  1  0
 37 38  1  0
 38 39  1  0
 40 39  1  1
 40  2  1  0
  2  1  2  3
 31 32  1  0
 32 36  2  0
 36 35  1  0
 35 34  1  0
 34 33  2  0
  4 13  1  0
  2  3  1  0
 33 32  1  0
 40 29  1  0
 40 38  1  0
 18 58  1  0
 18 59  1  0
 18 60  1  0
 14 56  1  0
 14 57  1  0
 13 55  1  1
 11 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 12 54  1  0
  7 48  1  0
  6 47  1  0
  5 44  1  0
  5 45  1  0
  5 46  1  0
  3 43  1  6
 19 61  1  6
 22 62  1  0
 22 63  1  0
 22 64  1  0
 24 65  1  1
 27 66  1  0
 27 67  1  0
 27 68  1  0
 30 69  1  0
 30 70  1  0
 30 71  1  0
 31 72  1  1
 37 76  1  0
 37 77  1  0
 38 78  1  1
  1 41  1  0
  1 42  1  0
 36 75  1  0
 34 74  1  0
 33 73  1  0
M  END


  Mrv1652304282201212D          

 40 44  0  0  1  0            999 V2000
    3.3258    0.0332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8343    0.6958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0147    0.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4389    1.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6866   -0.1556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1782   -0.8182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9977   -0.7238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8408   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7234   -0.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1837   -0.1178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6013   -1.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999   -1.4904    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9128   -1.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9046   -0.4183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0681    0.3903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9626   -2.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -2.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9759   -3.6073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7580   -3.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7497   -2.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008   -1.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1623    1.4527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7295    2.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942    2.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    3.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7299    3.9017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1246    2.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3599    1.6444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8001    1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8949    1.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297    0.4081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5374    1.8330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2852    1.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7638    3.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    2.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0572    1.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2831   -0.2433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -0.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1155   -0.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0425   -1.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  1  0  0  0
  5 15  1  1  0  0  0
 12 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 16 20  1  0  0  0  0
  6 21  1  6  0  0  0
  2 22  1  1  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 27 34  1  0  0  0  0
 27 35  1  0  0  0  0
 22 36  1  1  0  0  0
  1 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052214

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1C(C)(C)C(=O)C=C[C@]1(C)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@]2(C)[C@@H](C[C@H]3O[C@@]23C1=C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O9/c1-16-25(29(6)11-9-22(34)28(4,5)21(29)14-24(35)36-8)26(38-17(2)32)27(39-18(3)33)30(7)20(19-10-12-37-15-19)13-23-31(16,30)40-23/h9-12,15,20-21,23,25-27H,1,13-14H2,2-8H3/t20-,21-,23+,25+,26-,27-,29-,30+,31+/m0/s1

> <INCHI_KEY>
RRBQYKQIAKFGIS-AMVRVENBSA-N

> <FORMULA>
C31H38O9

> <MOLECULAR_WEIGHT>
554.636

> <EXACT_MASS>
554.251582804

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.81783442422726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1R,2S)-2-[(R,1bR,2R,3S,4R,5aS,5bR)-2,3-bis(acetyloxy)--(furan-3-yl)-1b-methyl-5-methylidene-octahydroindeno[1,7a-b]oxiren-4-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
3.4241599436666683

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8574138430403346

> <JCHEM_POLAR_SURFACE_AREA>
121.63999999999999

> <JCHEM_REFRACTIVITY>
142.3571

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,2S)-2-[(R,1bR,2R,3S,4R,5aS,5bR)-2,3-bis(acetyloxy)--(furan-3-yl)-1b-methyl-5-methylidene-hexahydroindeno[1,7a-b]oxiren-4-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.208   0.062   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.291   1.299   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.761   1.123   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.686   2.660   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.148  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.066  -1.527   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.596  -1.351   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.170  -1.925   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.817  -1.796   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.676  -0.220   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.456  -2.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.173  -2.782   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.704  -2.321   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.689  -0.781   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.994   0.729   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.664  -4.242   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.771  -5.497   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.688  -6.734   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.148  -6.243   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.133  -4.703   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.415  -2.376   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.903   2.712   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.962   3.830   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.522   5.306   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.025   5.664   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.096   7.283   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.966   4.546   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.405   3.069   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.360   1.906   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.671   2.034   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.802   0.762   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.003   3.422   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.532   3.538   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.292   6.100   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.309   4.896   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.573   2.491   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       7.995  -0.454   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.696  -1.399   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      11.416  -1.186   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       9.413  -3.201   0.000  0.00  0.00           C+0
CONECT    1    2    7   37                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14   15                                             
CONECT    6    5    7   12   21                                             
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    5   15                                                  
CONECT   15   14    5                                                       
CONECT   16   12   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21    6                                                            
CONECT   22    2   23   28   36                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   34   35                                             
CONECT   28   27   22   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   27                                                            
CONECT   35   27                                                            
CONECT   36   22                                                            
CONECT   37    1   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₈O₉

Average Mass

554.6360 Da

Monoisotopic Mass

554.25158 Da

IUPAC Name

methyl 2-[(1R,2S)-2-[(R,1bR,2R,3S,4R,5aS,5bR)-2,3-bis(acetyloxy)--(furan-3-yl)-1b-methyl-5-methylidene-octahydroindeno[1,7a-b]oxiren-4-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

Traditional Name

methyl [(1R,2S)-2-[(R,1bR,2R,3S,4R,5aS,5bR)-2,3-bis(acetyloxy)--(furan-3-yl)-1b-methyl-5-methylidene-hexahydroindeno[1,7a-b]oxiren-4-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1C(C)(C)C(=O)C=C[C@]1(C)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@]2(C)[C@@H](C[C@H]3O[C@@]23C1=C)C1=COC=C1

InChI Identifier

InChI=1S/C31H38O9/c1-16-25(29(6)11-9-22(34)28(4,5)21(29)14-24(35)36-8)26(38-17(2)32)27(39-18(3)33)30(7)20(19-10-12-37-15-19)13-23-31(16,30)40-23/h9-12,15,20-21,23,25-27H,1,13-14H2,2-8H3/t20-,21-,23+,25+,26-,27-,29-,30+,31+/m0/s1

InChI Key

RRBQYKQIAKFGIS-AMVRVENBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Toona ciliata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Tricarboxylic acid or derivatives
Cyclohexenone
Oxane
Furan
Heteroaromatic compound
Methyl ester
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:9632 )
Limonoids (C08785 )

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	4.26	ALOGPS
logP	3.42	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	121.64 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	142.36 m³·mol⁻¹	ChemAxon
Polarizability	56.82 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

C00003733

Chemspider ID

158137

KEGG Compound ID

C08785

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

181814

PDB ID

Not Available

ChEBI ID

9632

Good Scents ID

Not Available

References

General References

Irungu BN, Adipo N, Orwa JA, Kimani F, Heydenreich M, Midiwo JO, Martin Bjoremark P, Hakansson M, Yenesew A, Erdelyi M: Antiplasmodial and cytotoxic activities of the constituents of Turraea robusta and Turraea nilotica. J Ethnopharmacol. 2015 Nov 4;174:419-25. doi: 10.1016/j.jep.2015.08.039. Epub 2015 Aug 28. [PubMed:26320684 ]

Showing NP-Card for Toonacilin (NP0052214)

MOL for NP0052214 (Toonacilin)

3D MOL for NP0052214 (Toonacilin)

3D SDF for NP0052214 (Toonacilin)

3D-SDF for NP0052214 (Toonacilin)

PDB for NP0052214 (Toonacilin)

3D PDB for NP0052214 (Toonacilin)

SMILES for NP0052214 (Toonacilin)

INCHI for NP0052214 (Toonacilin)

Structure for NP0052214 (Toonacilin)

3D Structure for NP0052214 (Toonacilin)