NP-MRD: Showing NP-Card for 3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate (NP0147954)

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Record Information

Version

2.0

Created at

2022-09-02 03:38:44 UTC

Updated at

2022-09-02 03:38:44 UTC

NP-MRD ID

NP0147954

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate

Description

3,22-Bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]Tricosan-15-yl 2-methylpropanoate 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. 3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate is found in Chukrasia tabularis. 3,22-Bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]Tricosan-15-yl 2-methylpropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241502582D          

 54 62  0  0  0  0            999 V2000
   -2.4720    0.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6486    1.0496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1920    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5588   -0.3765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687    0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879   -0.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2030   -1.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0225   -1.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0421   -1.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8013   -1.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185   -0.6727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504   -0.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8389    0.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695   -0.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7466    0.2288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2489   -0.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9819   -1.4450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -1.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -1.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5018   -2.5142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9434   -3.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1220   -3.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -3.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9953   -4.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6317   -4.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3827   -2.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1107   -2.8063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -2.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9718   -3.7390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2384   -2.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387   -0.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648   -0.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9904   -0.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8064   -0.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037   -0.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1990    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6836    1.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    2.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5272    2.2642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8323    2.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154    0.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069    1.4865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197   -0.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6224   -1.0235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090   -1.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4117   -2.4369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2931   -1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7797   -2.1936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8330    0.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6122    1.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3000    1.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9458    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6572    0.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  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
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 19 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  0  0  0  0
 16 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 37 42  1  0  0  0  0
 14 42  1  0  0  0  0
 42 43  1  0  0  0  0
 36 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 34 48  1  0  0  0  0
 48 49  1  0  0  0  0
 44 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 50 54  1  0  0  0  0
M  END

     RDKit          3D

 98106  0  0  0  0  0  0  0  0999 V2000
   -4.4352    5.4435   -1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2706    4.7297   -1.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6232    1.0674    0.8910 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9961    1.4334    1.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    0.3757    2.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    0.0503    1.1889 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3357   -0.5263    1.9048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3192    1.3728    0.5298 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3879    2.1531    1.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5069    1.1926   -0.7133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3321    1.6960   -1.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6117    0.6436   -2.5889 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0718    1.0615   -3.9490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3511   -0.3906   -2.0587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5316   -1.0043   -1.0658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3210   -0.8794    0.1884 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5318   -2.0785    0.8686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -3.2289    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291   -3.1951   -0.8565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2357   -4.4007    1.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8660   -4.8064    1.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -5.5968    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6697   -0.2038   -0.0029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7478   -0.9624    0.4478 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1838   -0.1132   -0.6532 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.5648   -1.6592    1.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4346   -1.6070    3.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7811   -0.5114    2.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5315   -2.1105   -0.6154 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6757   -3.8628   -1.8098 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894   -2.3414   -0.8198 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7933   -2.7946    0.4357 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287    1.3446   -0.3609 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.4409   -0.5716    2.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185    0.9645    2.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2953    1.6356    1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0125    0.1748   -4.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    1.8346   -4.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8583   -4.1743    2.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4534   -2.7999   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764   -3.7418    0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3109    1.5439    0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2082    3.0553   -2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1879    3.1527   -0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0206    4.4283   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7045    2.9776   -0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534    3.0199   -2.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 35 86  1  0
 48 93  1  1
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 53 97  1  1
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 37 87  1  6
 46 91  1  6
 47 92  1  0
 42 90  1  0
 40 89  1  0
 39 88  1  0
M  END


  Mrv1533004241502582D          

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    0.1107   -2.8063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -2.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9718   -3.7390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2384   -2.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387   -0.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648   -0.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9904   -0.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8064   -0.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037   -0.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1990    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6836    1.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    2.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5272    2.2642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8323    2.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154    0.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069    1.4865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197   -0.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6224   -1.0235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090   -1.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4117   -2.4369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2931   -1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7797   -2.1936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6122    1.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3000    1.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9458    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6572    0.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
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 20 21  1  0  0  0  0
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 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 19 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  0  0  0  0
 16 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 37 42  1  0  0  0  0
 14 42  1  0  0  0  0
 42 43  1  0  0  0  0
 36 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 34 48  1  0  0  0  0
 48 49  1  0  0  0  0
 44 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 50 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147954

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1C2(C)CC3(O)C1(C)C14OC5(C)OC(C3(OC(=O)C(C)C)C2OC(C)=O)C1(O5)C12CC1(C(OC(C)=O)C4O)C(OC(=O)C2O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C37H44O17/c1-15(2)25(43)51-35-27(49-17(4)39)29(5)13-34(35,45)30(6,19(29)11-20(40)46-8)36-21(41)24(48-16(3)38)32-14-33(32,37(36)28(35)52-31(7,53-36)54-37)22(42)26(44)50-23(32)18-9-10-47-12-18/h9-10,12,15,19,21-24,27-28,41-42,45H,11,13-14H2,1-8H3

> <INCHI_KEY>
JLSMPHIRZVGAOG-UHFFFAOYSA-N

> <FORMULA>
C37H44O17

> <MOLECULAR_WEIGHT>
760.742

> <EXACT_MASS>
760.257849957

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
73.84168465667634

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
0.299273621666666

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.74021737465928

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.033590396454061

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8624155651571628

> <JCHEM_POLAR_SURFACE_AREA>
233.01999999999998

> <JCHEM_REFRACTIVITY>
170.09559999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -4.614   1.863   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.077   1.959   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.225   0.677   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.910  -0.703   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.688   0.773   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.164  -0.509   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.379  -2.068   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.909  -2.246   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.079  -3.110   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.496  -2.120   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.221  -1.256   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.774  -0.610   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.566   0.916   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.490  -0.015   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.127   0.427   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.406  -1.200   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.931  -0.987   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.566  -2.697   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.068  -2.735   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.343  -3.224   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.803  -4.693   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.761  -5.827   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.228  -5.972   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.222  -7.296   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.725  -7.632   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.179  -8.430   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.714  -3.784   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.207  -5.238   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.306  -5.526   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.814  -6.979   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.312  -4.359   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.179  -1.228   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.721  -0.296   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.582  -1.457   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.105  -1.684   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.540  -0.251   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.971   1.413   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.876   2.660   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.249   4.066   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.717   4.227   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       7.154   5.313   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.322   1.437   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.560   2.775   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.063  -0.478   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       8.628  -1.911   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       7.670  -3.116   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       8.235  -4.549   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       6.147  -2.889   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       5.189  -4.095   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       9.022   0.728   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       8.609   2.211   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       9.893   3.062   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      11.099   2.104   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      10.560   0.661   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                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9   27                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   20                                             
CONECT   11   10                                                            
CONECT   12   10    6   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   32   42                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   18   33                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   10   21   27                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   20    7   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   19   14   33   34                                             
CONECT   33   32   16                                                       
CONECT   34   32   35   36   48                                             
CONECT   35   34   36                                                       
CONECT   36   35   34   37   44                                             
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   37   14   43                                                  
CONECT   43   42                                                            
CONECT   44   36   45   50                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   34   49                                                  
CONECT   49   48                                                            
CONECT   50   44   51   54                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   50                                                       
MASTER        0    0    0    0    0    0    0    0   54    0  124    0
END

View in JSmol

Synonyms

Value	Source
3,22-Bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1,.1,.0,.0,.0,.0,]tricosan-15-yl 2-methylpropanoic acid	Generator
3,22-Bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₃₇H₄₄O₁₇

Average Mass

760.7420 Da

Monoisotopic Mass

760.25785 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)CC1C2(C)CC3(O)C1(C)C14OC5(C)OC(C3(OC(=O)C(C)C)C2OC(C)=O)C1(O5)C12CC1(C(OC(C)=O)C4O)C(OC(=O)C2O)C1=COC=C1

InChI Identifier

InChI=1S/C37H44O17/c1-15(2)25(43)51-35-27(49-17(4)39)29(5)13-34(35,45)30(6,19(29)11-20(40)46-8)36-21(41)24(48-16(3)38)32-14-33(32,37(36)28(35)52-31(7,53-36)54-37)22(42)26(44)50-23(32)18-9-10-47-12-18/h9-10,12,15,19,21-24,27-28,41-42,45H,11,13-14H2,1-8H3

InChI Key

JLSMPHIRZVGAOG-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
Chukrasia tabularis	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
Mexicanolide
Prostaglandin skeleton
Eicosanoid
Pentacarboxylic acid or derivatives
Naphthopyran
Naphthalene
Caprolactone
Carboxylic acid orthoester
Delta_valerolactone
Ortho ester
Oxepane
Delta valerolactone
Fatty acyl
Meta-dioxane
Oxane
Pyran
Furan
Heteroaromatic compound
Cyclic alcohol
Methyl ester
Meta-dioxolane
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Orthocarboxylic acid derivative
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
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	1.35	ALOGPS
logP	0.3	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.03	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	233.02 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	170.1 m³·mol⁻¹	ChemAxon
Polarizability	73.84 Å³	ChemAxon
Number of Rings	9	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

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 3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate (NP0147954)

MOL for NP0147954 (3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate)

3D MOL for NP0147954 (3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate)

3D SDF for NP0147954 (3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate)

3D-SDF for NP0147954 (3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate)

PDB for NP0147954 (3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate)

3D PDB for NP0147954 (3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate)

SMILES for NP0147954 (3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate)

INCHI for NP0147954 (3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate)

Structure for NP0147954 (3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate)

3D Structure for NP0147954 (3,22-bis(acetyloxy)-5-(furan-3-yl)-2,8,16-trihydroxy-19-(2-methoxy-2-oxoethyl)-12,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaoctacyclo[10.8.1.1⁴,⁹.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]tricosan-15-yl 2-methylpropanoate)