NP-MRD: Showing NP-Card for methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate (NP0314656)

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Record Information

Version

2.0

Created at

2022-09-11 12:51:53 UTC

Updated at

2022-09-11 12:51:53 UTC

NP-MRD ID

NP0314656

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate

Description

Methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-16-yl]acetate 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. methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate is found in Cipadessa baccifera. Based on a literature review very few articles have been published on methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-16-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112214512D          

 41 45  0  0  0  0            999 V2000
    0.8460   -3.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -3.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1221   -2.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9315   -2.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8554   -1.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3982   -1.1240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0459   -1.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2207   -0.8052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220   -0.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038   -0.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8430   -0.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067    0.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300    0.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2963   -0.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1197   -0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4860   -0.8828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767    0.5433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104    1.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674    1.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804    2.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0273    3.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7141    2.7978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917    2.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3871    1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8441    2.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0207    2.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1974    2.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    1.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587    1.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031    2.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7623    0.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    1.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194    1.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    1.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    2.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5382    2.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8638    3.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044    4.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443    0.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    0.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7579    0.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  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  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  2  0  0  0  0
 18 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 10 31  1  0  0  0  0
 31 32  2  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 33 39  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
M  END

     RDKit          3D

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    5.1479   -2.7666    0.9931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2060   -3.6538    2.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8801   -2.1683    0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8947   -2.3901    1.5613 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6019   -1.2986   -0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4031   -0.6355   -0.4125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    0.3185    0.5639 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0275   -0.0802    1.4040 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1543   -1.0083    0.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2067   -0.4760    0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2299   -1.3190    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0002   -2.7858    0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8682    0.5330    0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6257    1.2057    1.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5146    0.9923    0.2392 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3626    1.8495    0.6236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9518    3.1557    1.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633    1.1526    1.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587    1.5507    2.9295 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6768    2.1021   -0.4438 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2172    1.7864   -1.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442    2.3646   -2.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789    1.7465   -3.8164 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9122    3.7532   -3.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5626    4.4522   -4.1109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0449    1.6966   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6777    2.6990    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0349    1.7177   -1.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7018   -0.8490   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5750   -0.2066    2.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0939   -0.6324   -1.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8875   -0.4396   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9138    2.2717    1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3667    0.7604    2.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0972    3.8970    1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6941    3.6032    0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7544    3.2537   -0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2056    0.6670   -2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526    2.0508   -2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5040    4.8686   -3.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8509    3.8075   -4.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9519    5.3293   -4.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0284    2.9926    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6199    2.2048    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0283    3.5496    0.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0902    1.7207   -0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0363    2.6759   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0410    0.8051   -1.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
 38 37  1  0
 37 35  1  0
 35 36  2  0
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 33 39  1  0
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 39  9  1  0
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  8  7  1  0
  7  5  1  0
  5  6  2  0
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  3  4  1  0
  3  2  2  0
  2  1  1  0
  9 10  1  0
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  7 50  1  0
  4 46  1  0
  4 47  1  0
  4 48  1  0
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  1 42  1  0
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 26 65  1  0
 27 66  1  0
 27 67  1  0
 28 68  1  6
 30 69  1  0
 30 70  1  0
 30 71  1  0
M  END


  Mrv1652309112214512D          

 41 45  0  0  0  0            999 V2000
    0.8460   -3.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -3.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9315   -2.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8554   -1.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3982   -1.1240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0459   -1.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2207   -0.8052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220   -0.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1067    0.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300    0.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2963   -0.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1197   -0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4860   -0.8828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767    0.5433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104    1.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674    1.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804    2.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0273    3.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7141    2.7978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917    2.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3871    1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8441    2.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0207    2.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1974    2.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    1.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587    1.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031    2.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7623    0.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    1.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194    1.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    1.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    2.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5382    2.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8638    3.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044    4.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443    0.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    0.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7579    0.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  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  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  2  0  0  0  0
 18 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 10 31  1  0  0  0  0
 31 32  2  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 33 39  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314656

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1C(C)(C)C(OCC(=O)C(C)=CC)C2CC3=C4CC(=O)OC(C5=COC=C5)C4(C)CCC3C1(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O8/c1-8-18(2)24(34)17-40-30-21-13-20-22(33(6,28(21)37)25(31(30,3)4)15-26(35)38-7)9-11-32(5)23(20)14-27(36)41-29(32)19-10-12-39-16-19/h8,10,12,16,21-22,25,29-30H,9,11,13-15,17H2,1-7H3

> <INCHI_KEY>
AQGPNYISVMVMTQ-UHFFFAOYSA-N

> <FORMULA>
C33H42O8

> <MOLECULAR_WEIGHT>
566.691

> <EXACT_MASS>
566.287968312

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
61.28249120300109

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate

> <JCHEM_LOGP>
5.0264505753333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.90364550234844

> <JCHEM_PKA_STRONGEST_BASIC>
-2.866119431495923

> <JCHEM_POLAR_SURFACE_AREA>
109.11

> <JCHEM_REFRACTIVITY>
151.7285

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl [6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.579  -7.332   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.081  -5.875   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.095  -4.715   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.606  -5.013   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.597  -3.258   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.610  -2.098   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.086  -2.960   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.412  -1.503   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.601  -0.343   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.060  -0.835   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.440  -0.152   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.932   1.307   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.469   1.210   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.153  -0.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.690  -0.268   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.374  -1.648   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.543   1.014   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.859   2.394   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.713   3.676   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.177   5.120   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.384   6.076   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.666   5.222   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.251   3.739   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.322   2.492   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.176   3.774   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.639   3.872   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.102   3.969   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.249   2.687   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.789   3.180   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.686   4.716   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.423   1.138   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.119   1.957   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.410   2.496   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.750   3.509   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.453   5.020   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.005   5.518   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -1.612   6.033   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.315   7.544   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.083   1.037   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.507   1.623   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.415   0.264   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   39                                                  
CONECT   10    9   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19                                                       
CONECT   24   18   13   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   12   29                                                  
CONECT   29   28   30   31   33                                             
CONECT   30   29                                                            
CONECT   31   29   10   32                                                  
CONECT   32   31                                                            
CONECT   33   29   34   39                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37                                                            
CONECT   39   33    9   40   41                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0,.0,]heptadec-10-en-16-yl]acetic acid	Generator

Chemical Formula

C₃₃H₄₂O₈

Average Mass

566.6910 Da

Monoisotopic Mass

566.28797 Da

IUPAC Name

methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate

Traditional Name

methyl [6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)CC1C(C)(C)C(OCC(=O)C(C)=CC)C2CC3=C4CC(=O)OC(C5=COC=C5)C4(C)CCC3C1(C)C2=O

InChI Identifier

InChI=1S/C33H42O8/c1-8-18(2)24(34)17-40-30-21-13-20-22(33(6,28(21)37)25(31(30,3)4)15-26(35)38-7)9-11-32(5)23(20)14-27(36)41-29(32)19-10-12-39-16-19/h8,10,12,16,21-22,25,29-30H,9,11,13-15,17H2,1-7H3

InChI Key

AQGPNYISVMVMTQ-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
Cipadessa baccifera	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

Mexicanolide
Limonoid skeleton
Naphthopyran
Naphthalene
Delta_valerolactone
Delta valerolactone
Alpha-branched alpha,beta-unsaturated-ketone
Pyran
Oxane
Dicarboxylic acid or derivatives
Heteroaromatic compound
Alpha,beta-unsaturated ketone
Methyl ester
Furan
Enone
Acryloyl-group
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.03	ChemAxon
pKa (Strongest Acidic)	18.9	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	109.11 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	151.73 m³·mol⁻¹	ChemAxon
Polarizability	61.28 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

162820289

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate (NP0314656)

MOL for NP0314656 (methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate)

3D MOL for NP0314656 (methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate)

3D SDF for NP0314656 (methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate)

3D-SDF for NP0314656 (methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate)

PDB for NP0314656 (methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate)

3D PDB for NP0314656 (methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate)

SMILES for NP0314656 (methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate)

INCHI for NP0314656 (methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate)

Structure for NP0314656 (methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate)

3D Structure for NP0314656 (methyl 2-[6-(furan-3-yl)-1,5,15,15-tetramethyl-14-[(3-methyl-2-oxopent-3-en-1-yl)oxy]-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]acetate)