NP-MRD: Showing NP-Card for 7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate (NP0194619)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 12:18:25 UTC

Updated at

2022-09-04 12:18:25 UTC

NP-MRD ID

NP0194619

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate

Description

7-(Furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]Nonadec-13-en-19-yl benzoate 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. 7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate is found in Azadirachta indica. 7-(Furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]Nonadec-13-en-19-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241508042D          

 40 46  0  0  0  0            999 V2000
    4.4709    1.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731    1.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    2.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    2.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    3.0630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    3.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    3.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    4.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    4.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644    1.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6463   -1.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1486   -2.4812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6310   -2.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150   -1.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.7243    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  6 16  1  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
 20 21  1  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
 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
 28 29  1  0  0  0  0
 16 29  1  0  0  0  0
 21 29  1  0  0  0  0
 27 29  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 30 34  1  0  0  0  0
 18 35  1  0  0  0  0
  4 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END

     RDKit          3D

 76 82  0  0  0  0  0  0  0  0999 V2000
   -3.5481   -3.5931    1.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6829   -3.2394   -0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -3.2950   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6582   -4.3078   -0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6536   -5.1681   -1.0644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6229   -4.2884    0.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1815   -3.1272    1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6865   -1.8473    0.6993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6825   -0.8949    1.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3699   -1.4619   -0.3172 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6884   -1.5410    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729   -0.7559   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4054    0.6756   -0.4029 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7889    1.4032    0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3631    1.2197   -1.4576 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7534    0.9093   -1.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5339    1.5916   -0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7501    0.9442   -0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7298   -0.0559   -0.8980 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5716   -0.1023   -1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2253    2.6266   -1.5922 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    3.0910   -1.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940    4.3132   -1.6758 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8204    2.1389   -1.4874 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125    2.0303   -0.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9782    0.9583   -0.7402 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1559   -0.2470   -1.1152 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6021   -0.5692   -2.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3215    0.0947   -1.1913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7161    0.9879   -0.2287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3279    2.1955   -0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5903    2.5789   -1.4979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6935    3.0615    0.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3201    4.2703    0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6839    5.1223    1.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4246    4.7813    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982    3.5732    3.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4357    2.7235    2.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909   -1.2150   -1.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0624   -1.8823    0.1593 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9178   -2.6825    1.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9091   -4.1269    1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3485   -4.2954    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4212   -2.5457   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0983   -4.3165   -1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0682   -3.1764   -2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2267   -5.2348    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6015   -3.1061    2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821    0.0127    1.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287   -1.3660    2.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7157   -0.5618    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867   -2.3469   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -1.1487    1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468   -2.5849    0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1820   -1.2259   -1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6538   -0.7883    0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571    1.2149    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6710    0.9093    1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043    2.4811    0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081    0.7094   -2.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2716    2.4505    0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6056    1.1972    0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2853   -0.8282   -2.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095    2.3032   -2.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9430    0.3388   -3.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2878   -1.4274   -2.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049   -0.8921   -3.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5369    0.5207   -2.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5160    4.5222   -0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1732    6.0610    1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7081    5.4471    3.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6035    3.3257    4.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9528    1.8030    2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969   -1.1090   -1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5402   -1.8847   -1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7828   -1.3480    0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2 40  1  0
 40 39  1  0
 39 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 29 27  1  0
 27 28  1  6
 27 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 26 25  1  1
 15 16  1  0
 16 20  2  0
 20 19  1  0
 19 18  1  0
 18 17  2  0
 10  8  1  0
  8  9  1  1
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  2  0
  4  2  1  0
  8 40  1  0
 38 33  1  0
 26 27  1  0
 17 16  1  0
 26 13  1  0
 26 24  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  3 44  1  0
  3 45  1  0
  3 46  1  0
 40 76  1  1
 39 74  1  0
 39 75  1  0
 29 68  1  6
 34 69  1  0
 35 70  1  0
 36 71  1  0
 37 72  1  0
 38 73  1  0
 28 65  1  0
 28 66  1  0
 28 67  1  0
 10 52  1  6
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 14 57  1  0
 14 58  1  0
 14 59  1  0
 15 60  1  6
 24 64  1  6
 20 63  1  0
 18 62  1  0
 17 61  1  0
  9 49  1  0
  9 50  1  0
  9 51  1  0
  7 48  1  0
  6 47  1  0
M  END


  Mrv1533004241508042D          

 40 46  0  0  0  0            999 V2000
    4.4709    1.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731    1.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    2.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    2.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    3.0630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    3.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    3.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    4.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    4.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644    1.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6463   -1.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1486   -2.4812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6310   -2.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150   -1.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.7243    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  6 16  1  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
 20 21  1  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
 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
 28 29  1  0  0  0  0
 16 29  1  0  0  0  0
 21 29  1  0  0  0  0
 27 29  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 30 34  1  0  0  0  0
 18 35  1  0  0  0  0
  4 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0194619

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CC(OC(=O)C3=CC=CC=C3)C3(C)C(CCC4(C)C(OC(=O)C5OC345)C3=COC=C3)C2(C)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H36O7/c1-29(2)22-17-24(38-27(35)19-9-7-6-8-10-19)32(5)21(30(22,3)14-12-23(29)34)11-15-31(4)25(20-13-16-37-18-20)39-28(36)26-33(31,32)40-26/h6-10,12-14,16,18,21-22,24-26H,11,15,17H2,1-5H3

> <INCHI_KEY>
FJGQKVDLYYRRKR-UHFFFAOYSA-N

> <FORMULA>
C33H36O7

> <MOLECULAR_WEIGHT>
544.644

> <EXACT_MASS>
544.246103499

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.38473263531587

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate

> <ALOGPS_LOGP>
5.56

> <JCHEM_LOGP>
6.354158751333333

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.869808689334488

> <JCHEM_POLAR_SURFACE_AREA>
95.34

> <JCHEM_REFRACTIVITY>
145.66350000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       8.346   3.664   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.216   3.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.854   3.971   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.358   5.427   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.870   5.718   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.350   6.591   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.838   6.300   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.830   7.464   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   8.919   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.846   9.210   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.854   8.046   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.227   2.886   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.838  -1.849   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.179   0.479   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.350   2.516   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.326  -2.140   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.206  -3.403   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.277  -4.632   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.178  -4.128   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.148  -2.588   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.375  -0.976   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   39                                             
CONECT    3    2                                                            
CONECT    4    2    5   35                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    6   17   18   29                                             
CONECT   17   16                                                            
CONECT   18   16   19   35                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   29                                             
CONECT   22   21                                                            
CONECT   23   21   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   16   21   27                                             
CONECT   30   23   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30                                                       
CONECT   35   18    4   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38    2   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Value	Source
7-(Furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0,.0,.0,]nonadec-13-en-19-yl benzoic acid	Generator
7-(Furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoic acid	Generator

Chemical Formula

C₃₃H₃₆O₇

Average Mass

544.6440 Da

Monoisotopic Mass

544.24610 Da

IUPAC Name

7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate

Traditional Name

7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate

CAS Registry Number

Not Available

SMILES

CC1(C)C2CC(OC(=O)C3=CC=CC=C3)C3(C)C(CCC4(C)C(OC(=O)C5OC345)C3=COC=C3)C2(C)C=CC1=O

InChI Identifier

InChI=1S/C33H36O7/c1-29(2)22-17-24(38-27(35)19-9-7-6-8-10-19)32(5)21(30(22,3)14-12-23(29)34)11-15-31(4)25(20-13-16-37-18-20)39-28(36)26-33(31,32)40-26/h6-10,12-14,16,18,21-22,24-26H,11,15,17H2,1-5H3

InChI Key

FJGQKVDLYYRRKR-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
Azadirachta indica	LOTUS Database	35616633

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
Naphthopyran
Naphthalene
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Delta_valerolactone
Dioxepane
1,4-dioxepane
Cyclohexenone
Delta valerolactone
Dicarboxylic acid or derivatives
Oxane
Pyran
Monocyclic benzene moiety
Benzenoid
Furan
Heteroaromatic compound
Carboxylic acid ester
Cyclic ketone
Lactone
Ketone
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Oxirane
Ether
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	5.56	ALOGPS
logP	6.35	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.34 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	145.66 m³·mol⁻¹	ChemAxon
Polarizability	57.38 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate (NP0194619)

MOL for NP0194619 (7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate)

3D MOL for NP0194619 (7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate)

3D SDF for NP0194619 (7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate)

3D-SDF for NP0194619 (7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate)

PDB for NP0194619 (7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate)

3D PDB for NP0194619 (7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate)

SMILES for NP0194619 (7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate)

INCHI for NP0194619 (7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate)

Structure for NP0194619 (7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate)

3D Structure for NP0194619 (7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl benzoate)