NP-MRD: Showing NP-Card for (+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin (NP0077411)

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Record Information

Version

2.0

Created at

2022-04-28 22:34:15 UTC

Updated at

2022-04-28 22:34:15 UTC

NP-MRD ID

NP0077411

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin

Description

Methyl (1R,4S,5R,6S,7S,8R,11R,12R,14S,15S)-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]Dodec-3-en-9-yl]-6,11-dimethyl-14-{[(2E)-3-phenylprop-2-enoyl]oxy}-12-{[(2Z)-3-phenylprop-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.0¹,⁵.0¹¹,¹⁵]Pentadecane-4-carboxylate 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. (+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin is found in Melia azedarach . Based on a literature review very few articles have been published on methyl (1R,4S,5R,6S,7S,8R,11R,12R,14S,15S)-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]Dodec-3-en-9-yl]-6,11-dimethyl-14-{[(2E)-3-phenylprop-2-enoyl]oxy}-12-{[(2Z)-3-phenylprop-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.0¹,⁵.0¹¹,¹⁵]Pentadecane-4-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200342D          

 59 68  0  0  1  0            999 V2000
    2.8841    2.8453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3176    2.1434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9264    1.4170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1018    1.3926    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6683    2.0945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0595    2.8209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3472    3.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0063    3.6442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4261    4.3544    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1326    5.1254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3468    5.3767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6604    4.9189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5903    4.0969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1893    3.5296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4614    4.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0130    5.4303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2992    6.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235    6.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9404    5.9496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8312    3.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730    4.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668    1.8992    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8049    1.0765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011    0.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0567    2.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2133    2.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835    1.4317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2936    1.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806    2.6729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107    0.6662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1441   -0.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9688   -0.0113    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3599    0.7151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2398    1.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1293    1.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9405    0.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -0.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0111   -1.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1865   -1.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4446   -2.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0534   -2.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2288   -2.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376   -3.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0130   -3.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5795   -2.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9707   -2.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7953   -2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860    0.6418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4949   -0.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9283   -0.7865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3298   -0.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209   -0.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5456   -0.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9367   -1.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7614   -1.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1948   -0.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8037   -0.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9791   -0.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2753    3.5717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  6  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  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  6  0  0  0
 10 15  1  6  0  0  0
 12 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 11 19  1  6  0  0  0
  9 20  1  0  0  0  0
  8 20  1  6  0  0  0
  9 21  1  1  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  6  0  0  0
 22 25  1  6  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 29  1  1  0  0  0
  4 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  6  0  0  0
 33 36  1  1  0  0  0
 32 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
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 42 47  1  0  0  0  0
 30 48  1  6  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 53 58  1  0  0  0  0
  1 59  1  6  0  0  0
M  END

     RDKit          3D

107116  0  0  0  0  0  0  0  0999 V2000
   -4.0157    2.9312    1.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8923    2.2244    1.4320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4909    2.2497    0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1816    2.9436   -0.6761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3064    1.4980   -0.3755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2301    1.7405   -1.7269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341    2.0603    0.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3490    0.9885    1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3347   -0.0075   -0.0761 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3584    0.6382   -0.8725 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5008    2.0510   -0.8211 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608    2.8691   -1.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830    2.3228   -2.9930 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8827    4.3020   -1.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7553    4.8442   -0.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8633    6.2633   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7143    6.7358    1.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8117    8.0727    1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0624    8.9857    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2157    8.5619   -0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1153    7.2019   -1.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7047    0.2472   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1322   -1.1420   -0.6416 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3335   -1.5486   -0.1330 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5440   -1.6599   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4086   -1.3094   -1.9707 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8445   -2.0365   -0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5140   -2.6980    1.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2219   -3.0862    2.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310   -3.1640    3.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1796   -2.8393    4.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5020   -2.4433    4.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1408   -2.3774    3.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -1.9616   -0.6221 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6989   -2.5522   -1.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9461   -3.2149    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694   -3.5385    0.4112 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4743   -2.2154    0.1860 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2958   -1.7962    1.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9163   -1.0167   -0.6824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5915   -1.1474   -2.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4004   -0.9775   -0.4076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6664   -0.6815    0.9517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2713   -1.7428    0.2865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3434   -2.9380    1.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7116   -1.3028   -0.0939 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4387    0.0807   -0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1523   -1.3389   -1.9769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1288    0.1131   -0.1129 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7531   -1.3576    0.1077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6859    3.9673    2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3639    2.4083    2.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2796    1.3677    1.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3344    0.7192    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4882    0.3645   -1.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0845    4.9435   -2.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5530    4.1268    0.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5150    6.0596    1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6969    8.4522    2.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441   10.0531    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162    9.2960   -1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2420    6.9234   -2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6604   -3.4407    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1602   -2.8346   -1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421   -3.0638    0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2401   -2.6274    2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3473   -1.2695    0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2432    0.4409   -1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8150    0.6390   -1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3029   -2.9255   -1.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4326   -5.2064   -2.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2018   -3.9251   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9727   -1.4674    1.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
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 49100  1  0
 50101  1  6
 52102  1  1
 54103  1  0
 55104  1  0
 57105  1  0
M  END


  Mrv1652304292200342D          

 59 68  0  0  1  0            999 V2000
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    0.5795   -2.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9707   -2.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7953   -2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860    0.6418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9283   -0.7865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3298   -0.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209   -0.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5456   -0.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9367   -1.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7614   -1.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 11 12  1  0  0  0  0
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 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  6  0  0  0
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 16 17  1  0  0  0  0
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 22 23  1  0  0  0  0
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  4 24  1  6  0  0  0
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 27 28  1  0  0  0  0
 22 29  1  1  0  0  0
  4 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  6  0  0  0
 33 36  1  1  0  0  0
 32 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
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
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 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 42 47  1  0  0  0  0
 30 48  1  6  0  0  0
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 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 51 52  2  0  0  0  0
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 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
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 57 58  2  0  0  0  0
 53 58  1  0  0  0  0
  1 59  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0077411

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(O)OC[C@]23[C@H]4[C@@H](OC[C@]4(C)[C@@H](C[C@@H]2OC(=O)\C=C\C2=CC=CC=C2)OC(=O)\C=C/C2=CC=CC=C2)[C@@H](O)[C@](C)([C@H]13)[C@]12O[C@@]1(C)[C@H]1C[C@@H]2O[C@@H]2OC=C[C@@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C45H48O14/c1-39-23-54-33-34(39)42(29(57-32(47)18-16-26-13-9-6-10-14-26)22-28(39)56-31(46)17-15-25-11-7-5-8-12-25)24-55-44(51,37(49)52-4)36(42)40(2,35(33)48)45-30-21-27(41(45,3)59-45)43(50)19-20-53-38(43)58-30/h5-20,27-30,33-36,38,48,50-51H,21-24H2,1-4H3/b17-15-,18-16+/t27-,28-,29+,30+,33-,34+,35-,36+,38+,39-,40-,41+,42-,43-,44+,45+/m1/s1

> <INCHI_KEY>
PNGKXFPGBYNSCI-WOCVNPPKSA-N

> <FORMULA>
C45H48O14

> <MOLECULAR_WEIGHT>
812.865

> <EXACT_MASS>
812.304406226

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
107

> <JCHEM_AVERAGE_POLARIZABILITY>
82.36672166378506

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,4S,5R,6S,7S,8R,11R,12R,14S,15S)-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0^{2,6}.0^{9,11}]dodec-3-en-9-yl]-6,11-dimethyl-14-{[(2E)-3-phenylprop-2-enoyl]oxy}-12-{[(2Z)-3-phenylprop-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecane-4-carboxylate

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.9439712503333313

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.267862133804508

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.429178460606414

> <JCHEM_PKA_STRONGEST_BASIC>
-3.395750393233536

> <JCHEM_POLAR_SURFACE_AREA>
189.04

> <JCHEM_REFRACTIVITY>
205.90669999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4S,5R,6S,7S,8R,11R,12R,14S,15S)-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0^{2,6}.0^{9,11}]dodec-3-en-9-yl]-6,11-dimethyl-14-{[(2E)-3-phenylprop-2-enoyl]oxy}-12-{[(2Z)-3-phenylprop-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecane-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.384   5.311   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.193   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.463   2.645   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.923   2.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.114   3.910   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.844   5.266   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.515   6.043   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.745   6.802   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.529   8.128   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.981   9.567   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.514  10.036   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.233   9.182   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.102   7.648   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.220   6.589   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.728   8.298   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.024  10.137   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.559  11.581   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.097  11.519   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.622  11.106   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.285   6.787   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.923   8.782   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.618   3.545   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.502   2.009   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.802   1.842   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.106   3.836   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.398   5.292   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.903   2.672   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.415   2.964   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.084   4.989   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.193   1.244   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.002  -0.067   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.542  -0.021   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.272   1.335   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.914   2.199   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.708   3.726   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.356   0.241   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.351  -1.331   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.621  -2.687   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.081  -2.733   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       6.430  -3.998   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.700  -5.353   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.160  -5.399   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.430  -6.755   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.891  -6.801   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.082  -5.490   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       1.812  -4.134   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       3.351  -4.089   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       1.654   1.198   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       0.924  -0.158   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       1.733  -1.468   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -0.616  -0.204   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -1.346  -1.559   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -2.885  -1.605   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -3.615  -2.961   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -5.155  -3.007   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -5.964  -1.696   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -5.234  -0.340   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -3.694  -0.295   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       6.114   6.667   0.000  0.00  0.00           O+0
CONECT    1    2    6   59                                                  
CONECT    2    1    3   35                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3    5   24   30                                             
CONECT    5    4    6   22                                                  
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6    9   14   20                                             
CONECT    9    8   10   20   21                                             
CONECT   10    9   11   15                                                  
CONECT   11   10   12   18   19                                             
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   10                                                       
CONECT   16   12   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   11                                                       
CONECT   19   11                                                            
CONECT   20    9    8                                                       
CONECT   21    9                                                            
CONECT   22    5   23   25   29                                             
CONECT   23   22   24                                                       
CONECT   24   23    4                                                       
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   22                                                            
CONECT   30    4   31   48                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32    3   34   36                                             
CONECT   34   33   35                                                       
CONECT   35   34    2                                                       
CONECT   36   33                                                            
CONECT   37   32   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   47                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   42                                                       
CONECT   48   30   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   58                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   53                                                       
CONECT   59    1                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  136    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,4S,5R,6S,7S,8R,11R,12R,14S,15S)-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0,.0,]dodec-3-en-9-yl]-6,11-dimethyl-14-{[(2E)-3-phenylprop-2-enoyl]oxy}-12-{[(2Z)-3-phenylprop-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.0,.0,]pentadecane-4-carboxylic acid	Generator

Chemical Formula

C₄₅H₄₈O₁₄

Average Mass

812.8650 Da

Monoisotopic Mass

812.30441 Da

IUPAC Name

methyl (1R,4S,5R,6S,7S,8R,11R,12R,14S,15S)-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0^{2,6}.0^{9,11}]dodec-3-en-9-yl]-6,11-dimethyl-14-{[(2E)-3-phenylprop-2-enoyl]oxy}-12-{[(2Z)-3-phenylprop-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecane-4-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(O)OC[C@]23[C@H]4[C@@H](OC[C@]4(C)[C@@H](C[C@@H]2OC(=O)\C=C\C2=CC=CC=C2)OC(=O)\C=C/C2=CC=CC=C2)[C@@H](O)[C@](C)([C@H]13)[C@]12O[C@@]1(C)[C@H]1C[C@@H]2O[C@@H]2OC=C[C@@]12O

InChI Identifier

InChI=1S/C45H48O14/c1-39-23-54-33-34(39)42(29(57-32(47)18-16-26-13-9-6-10-14-26)22-28(39)56-31(46)17-15-25-11-7-5-8-12-25)24-55-44(51,37(49)52-4)36(42)40(2,35(33)48)45-30-21-27(41(45,3)59-45)43(50)19-20-53-38(43)58-30/h5-20,27-30,33-36,38,48,50-51H,21-24H2,1-4H3/b17-15-,18-16+/t27-,28-,29+,30+,33-,34+,35-,36+,38+,39-,40-,41+,42-,43-,44+,45+/m1/s1

InChI Key

PNGKXFPGBYNSCI-WOCVNPPKSA-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
Melia azedarach	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
Cinnamic acid ester
Cinnamic acid or derivatives
Tricarboxylic acid or derivatives
Furopyran
Styrene
Oxepane
Fatty acid ester
Fatty acyl
Benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Furan
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.18	ALOGPS
logP	3.94	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.43	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	189.04 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	205.91 m³·mol⁻¹	ChemAxon
Polarizability	82.37 Å³	ChemAxon
Number of Rings	10	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

162876537

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin (NP0077411)

MOL for NP0077411 ((+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin)

3D MOL for NP0077411 ((+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin)

3D SDF for NP0077411 ((+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin)

3D-SDF for NP0077411 ((+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin)

PDB for NP0077411 ((+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin)

3D PDB for NP0077411 ((+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin)

SMILES for NP0077411 ((+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin)

INCHI for NP0077411 ((+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin)

Structure for NP0077411 ((+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin)

3D Structure for NP0077411 ((+)-1,3-Dicinnamoyl-11-hydroxymeliacarpin)