NP-MRD: Showing NP-Card for 7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione (NP0261718)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 04:14:28 UTC

Updated at

2022-09-08 04:14:29 UTC

NP-MRD ID

NP0261718

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

Description

7-(5-Ethoxy-2-oxo-2,5-dihydrofuran-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icosane-5,15,20-trione 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-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione is found in Clausena excavata. 7-(5-Ethoxy-2-oxo-2,5-dihydrofuran-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icosane-5,15,20-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181501012D          

 39 44  0  0  0  0            999 V2000
    0.1246   -4.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1245   -3.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -3.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -2.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5997   -2.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5936   -1.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2574   -0.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1929   -1.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -1.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    0.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1670    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    1.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752    1.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7835    1.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0012   -0.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176   -0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1651   -1.2735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784    0.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6866    0.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -1.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9571   -0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5316    0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3143   -0.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    0.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7219    1.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2964    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725    2.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474    1.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3999    1.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917    1.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    0.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2508    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  8 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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 16 38  1  0  0  0  0
 22 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

 75 80  0  0  0  0  0  0  0  0999 V2000
    8.5666   -1.1354    0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9605   -1.5156   -0.8916 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7202   -2.1356   -0.7526 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8754   -1.2376   -0.1082 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6971   -0.8836   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562   -1.1305   -0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1648   -0.8798   -0.8002 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3450   -0.5511   -2.1896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    0.6863   -2.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5452    0.7747   -3.8438 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017    1.7172   -1.6760 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0372    2.4617   -0.9409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6923    1.1545   -0.8089 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3897    0.1082   -0.0192 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3771    0.8482    0.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3217   -0.4414    0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5172    0.7793    1.3135 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9665    0.5007    2.5517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4062    1.2934    0.2639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8559    0.9745    0.3679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6436    1.8298   -0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3095    1.5016    1.7016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3573    2.4677    1.5844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856    0.5119    2.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2798    0.2446    2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2484    0.4452    2.9062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4738   -0.2098    0.8492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5488   -0.9181    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1895   -1.0472   -1.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5988   -2.3567    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1533   -0.4353    0.0783 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5595   -0.8325   -1.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516   -0.2745   -1.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6177   -0.9610   -2.3436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7293    0.9972   -1.0961 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1492    2.0282   -2.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9514   -1.6777    1.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955   -2.0564    1.9497 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3562   -1.7275    1.0844 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3712   -0.0763    0.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2015   -1.7937    1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6680   -1.2926    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8265   -0.5547   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6735   -2.1210   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4076   -0.2680    0.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7669   -0.4646   -1.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635   -1.8791   -0.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8456    1.8149   -1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918    1.9512    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646    0.5268    1.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    0.7240    0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8054   -0.8060    1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2594   -1.2456    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857    1.5685    1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0472   -0.4767    2.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762    2.4313    0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7256    1.6200   -0.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617    1.5418   -1.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5672    2.9159   -0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318    2.1626    2.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5764    2.6874    2.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991    0.9667    3.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560   -0.5071    2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2733   -1.3066   -1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2476   -0.1409   -1.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8489   -1.9622   -1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656   -3.0810   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6348   -2.6043    0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   -2.5138    1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6071   -1.0451    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3089   -0.6801   -2.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835   -1.9628   -1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6193    2.9191   -1.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897    2.4502   -2.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276    1.5840   -3.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4 39  1  0
 39 37  1  0
 37 38  2  0
 37  6  1  0
  6  5  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 13 12  1  1
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  6
 20 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  6
 31 28  1  0
 28 29  1  0
 28 30  1  0
 28 27  1  0
 27 25  1  0
 25 26  2  0
 25 24  1  0
 24 22  1  0
 22 23  1  0
  5  4  1  0
 14  7  1  0
 35 19  1  0
 13 11  1  0
 35 13  1  0
 22 20  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  4 45  1  1
  5 46  1  0
  7 47  1  6
 11 48  1  1
 15 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  1
 18 55  1  0
 19 56  1  1
 21 57  1  0
 21 58  1  0
 21 59  1  0
 31 70  1  1
 32 71  1  0
 32 72  1  0
 36 73  1  0
 36 74  1  0
 36 75  1  0
 29 64  1  0
 29 65  1  0
 29 66  1  0
 30 67  1  0
 30 68  1  0
 30 69  1  0
 24 62  1  0
 24 63  1  0
 22 60  1  1
 23 61  1  0
M  END


  Mrv1533004181501012D          

 39 44  0  0  0  0            999 V2000
    0.1246   -4.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1245   -3.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -3.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -2.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5997   -2.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5936   -1.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2574   -0.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1929   -1.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -1.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    0.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1670    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    1.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752    1.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7835    1.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0012   -0.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176   -0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1651   -1.2735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784    0.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6866    0.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -1.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9571   -0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5316    0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3143   -0.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    0.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7219    1.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2964    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725    2.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474    1.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3999    1.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917    1.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    0.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2508    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  8 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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 16 38  1  0  0  0  0
 22 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261718

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC1OC(=O)C(=C1)C1OC(=O)C2OC22C1(C)CC(O)C1C3(C)C(CC(=O)C21C)C(C)(C)OC(=O)CC3O

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O11/c1-7-35-18-8-12(22(33)36-18)20-25(4)11-13(29)19-26(5)14(24(2,3)38-17(32)10-15(26)30)9-16(31)27(19,6)28(25)21(39-28)23(34)37-20/h8,13-15,18-21,29-30H,7,9-11H2,1-6H3

> <INCHI_KEY>
GHTNEXZFNIYRSE-UHFFFAOYSA-N

> <FORMULA>
C28H36O11

> <MOLECULAR_WEIGHT>
548.585

> <EXACT_MASS>
548.225761979

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.71895683069835

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-(5-ethoxy-2-oxo-2,5-dihydrofuran-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
1.2084577973333315

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.300701897883403

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.069497577964697

> <JCHEM_PKA_STRONGEST_BASIC>
-2.859332652666372

> <JCHEM_POLAR_SURFACE_AREA>
158.19

> <JCHEM_REFRACTIVITY>
130.56870000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(5-ethoxy-2-oxo-5H-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       0.233  -8.717   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.232  -7.249   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.807  -6.112   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.342  -4.644   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.119  -4.157   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.108  -2.617   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.347  -1.703   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.360  -2.152   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.256  -3.405   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.847  -0.691   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.175   0.461   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.312   1.922   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.710   3.074   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.820   2.231   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.329   2.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.842   1.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.356  -0.382   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.869  -1.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.378  -1.534   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.886  -1.225   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.908  -2.377   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.373   0.236   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.882   0.545   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.287  -0.876   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.720  -0.747   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.921  -2.063   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.253  -0.896   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.326   0.209   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.787  -0.278   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.130   1.737   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.814   2.536   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.887   3.641   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.975   3.828   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.368   2.006   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.346   3.158   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.838   2.849   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.816   4.001   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.351   1.388   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.201   2.921   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14   17   38                                             
CONECT   17   16   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   38                                                  
CONECT   23   22   24   25   34                                             
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   23   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   16   22   39                                             
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₁₁

Average Mass

548.5850 Da

Monoisotopic Mass

548.22576 Da

IUPAC Name

7-(5-ethoxy-2-oxo-2,5-dihydrofuran-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

Traditional Name

7-(5-ethoxy-2-oxo-5H-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

CAS Registry Number

Not Available

SMILES

CCOC1OC(=O)C(=C1)C1OC(=O)C2OC22C1(C)CC(O)C1C3(C)C(CC(=O)C21C)C(C)(C)OC(=O)CC3O

InChI Identifier

InChI=1S/C28H36O11/c1-7-35-18-8-12(22(33)36-18)20-25(4)11-13(29)19-26(5)14(24(2,3)38-17(32)10-15(26)30)9-16(31)27(19,6)28(25)21(39-28)23(34)37-20/h8,13-15,18-21,29-30H,7,9-11H2,1-6H3

InChI Key

GHTNEXZFNIYRSE-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
Clausena excavata	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
Tricarboxylic acid or derivatives
Caprolactone
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
Oxepane
2-furanone
Oxane
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Dihydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Ketone
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Dialkyl ether
Oxirane
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.54	ALOGPS
logP	1.21	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	158.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	130.57 m³·mol⁻¹	ChemAxon
Polarizability	55.72 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione (NP0261718)

MOL for NP0261718 (7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

3D MOL for NP0261718 (7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

3D SDF for NP0261718 (7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

3D-SDF for NP0261718 (7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

PDB for NP0261718 (7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

3D PDB for NP0261718 (7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

SMILES for NP0261718 (7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

INCHI for NP0261718 (7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

Structure for NP0261718 (7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)

3D Structure for NP0261718 (7-(5-ethoxy-2-oxo-5h-furan-3-yl)-10,13-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione)