NP-MRD: Showing NP-Card for {6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate (NP0198319)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-04 16:45:03 UTC

Updated at

2022-09-04 16:45:03 UTC

NP-MRD ID

NP0198319

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate

Description

{6-[(4-{1,5-Dimethyl-3-oxo-6-oxabicyclo[3.2.1]Octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. {6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate is found in Macaranga tanarius. {6-[(4-{1,5-Dimethyl-3-oxo-6-oxabicyclo[3.2.1]Octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171523052D          

 38 41  0  0  0  0            999 V2000
    2.1524   -2.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9130   -1.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5699   -2.2650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4662   -3.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231   -3.5826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0193   -4.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6762   -4.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724   -5.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2293   -6.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9900   -5.8983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1255   -7.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7824   -7.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786   -8.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3355   -8.8528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9179   -8.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8141   -9.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2610   -8.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003   -8.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3648   -7.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2586   -4.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1548   -5.5388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017   -4.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410   -4.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7055   -3.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486   -2.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168   -0.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189   -0.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871    1.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174   -0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -0.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9063   -1.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714    0.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.7432    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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 11 19  1  0  0  0  0
  6 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
 22 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26  2  1  4  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 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
 29 38  1  0  0  0  0
M  END

     RDKit          3D

 72 75  0  0  0  0  0  0  0  0999 V2000
   -2.0887    3.5976    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8520    2.2071   -0.0348 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8265    1.2982    0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7352    0.6179   -0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7073   -0.2852    0.5716 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1267    0.2085    0.2584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2959    1.6475    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1482   -0.6262    0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8937   -2.0787    0.8011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8241   -2.8632    0.7740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5014   -2.5995    0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7378   -1.6145   -0.1945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3772   -2.0804   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6139   -1.2426   -1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1919   -0.0284   -1.1012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5559    1.8427    0.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2146    1.5884   -0.9015 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5818    0.2820   -0.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7575   -0.0609   -0.2888 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7238   -0.5790   -1.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9655   -1.0175   -0.9420 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1231   -0.4506   -0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2231    0.7878   -0.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3190   -1.2521   -0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2951   -2.6287   -0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4126   -3.3380    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4715   -4.7315   -0.0542 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5651   -2.6860    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7143   -3.4349    0.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6195   -1.3112    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7641   -0.6375    0.9119 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4636   -0.6042    0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2427    0.9870    0.6102 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3926    1.0478    1.7929 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222    2.3579    0.0249 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0198    3.3263    1.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238    2.5686   -1.0927 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8202    3.8680   -1.0792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699    3.7117    1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7701    4.3816   -0.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1672    3.7387    0.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9892    2.2147   -1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7528    1.2218    1.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7450    0.7471   -1.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5517   -0.4323    1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8386    2.3531   -0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9217    1.7792    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3923    1.8634    0.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1434   -0.4034    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1887   -0.3419    2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0133   -2.7575    1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4762   -3.5738    0.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5655   -1.4083   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1879   -3.0797   -0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3813   -2.2579   -1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4184   -2.0115   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9901   -1.2187   -2.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    1.7679   -1.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4503   -0.9412    0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2029   -1.4245   -1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7815    0.2472   -2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981   -3.1065   -0.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7152   -5.3177   -0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5632   -2.9921    1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7626    0.3549    0.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4865    0.4839    0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2028    0.7186    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1370    0.0935    1.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3072    2.6256   -0.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6820    4.0548    1.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718    2.4140   -2.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2408    4.4127   -0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 19 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 37 17  1  0
  6  5  1  0
 32 24  1  0
 11 12  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  6
 17 58  1  6
 19 59  1  1
 20 60  1  0
 20 61  1  0
 25 62  1  0
 27 63  1  0
 29 64  1  0
 31 65  1  0
 32 66  1  0
 33 67  1  1
 34 68  1  0
 35 69  1  6
 36 70  1  0
 37 71  1  6
 38 72  1  0
  3 43  1  0
  4 44  1  0
  5 45  1  1
 13 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
  7 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
 11 51  1  0
 11 52  1  0
M  END


  Mrv1533004171523052D          

 38 41  0  0  0  0            999 V2000
    2.1524   -2.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9130   -1.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5699   -2.2650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4662   -3.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231   -3.5826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0193   -4.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6762   -4.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724   -5.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2293   -6.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9900   -5.8983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1255   -7.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7824   -7.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786   -8.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3355   -8.8528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9179   -8.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8141   -9.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2610   -8.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003   -8.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3648   -7.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2586   -4.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1548   -5.5388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017   -4.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410   -4.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7055   -3.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486   -2.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168   -0.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189   -0.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871    1.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174   -0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -0.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9063   -1.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714    0.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.7432    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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 11 19  1  0  0  0  0
  6 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
 22 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26  2  1  4  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 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
 29 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198319

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(OC1OC(COC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O)C=CC1C2(C)COC1(C)CC(=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O12/c1-12(4-5-18-25(2)8-14(27)9-26(18,3)36-11-25)37-24-22(33)21(32)20(31)17(38-24)10-35-23(34)13-6-15(28)19(30)16(29)7-13/h4-7,12,17-18,20-22,24,28-33H,8-11H2,1-3H3

> <INCHI_KEY>
LQVNYRWMNGPIEB-UHFFFAOYSA-N

> <FORMULA>
C26H34O12

> <MOLECULAR_WEIGHT>
538.546

> <EXACT_MASS>
538.205026535

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.067149772348685

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
0.8477191036666664

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.2370668925297

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.107866484644903

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490929202777753

> <JCHEM_POLAR_SURFACE_AREA>
192.44

> <JCHEM_REFRACTIVITY>
130.85110000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.018  -3.892   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.438  -3.296   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.664  -4.228   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.470  -5.756   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.696  -6.687   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.503  -8.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.729  -9.147   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.535 -10.675   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.761 -11.606   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.181 -11.010   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.568 -13.134   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.794 -14.066   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.600 -15.593   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.826 -16.525   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.180 -16.190   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.986 -17.717   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.954 -15.258   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.534 -15.854   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.148 -13.730   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.083  -8.811   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.889 -10.339   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.856  -7.880   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.437  -8.476   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.050  -6.352   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.824  -5.420   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.631  -1.769   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.329  -0.779   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.602  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.170   1.730   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.656   3.221   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.966   0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.966  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.170  -1.730   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.692  -3.247   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.671  -1.388   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.339  -0.000   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.920   0.394   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.671   1.387   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11                                                       
CONECT   20    6   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    4   25                                                  
CONECT   25   24                                                            
CONECT   26    2   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31   38                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   29                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
{6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₆H₃₄O₁₂

Average Mass

538.5460 Da

Monoisotopic Mass

538.20503 Da

IUPAC Name

{6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate

Traditional Name

{6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

CC(OC1OC(COC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O)C=CC1C2(C)COC1(C)CC(=O)C2

InChI Identifier

InChI=1S/C26H34O12/c1-12(4-5-18-25(2)8-14(27)9-26(18,3)36-11-25)37-24-22(33)21(32)20(31)17(38-24)10-35-23(34)13-6-15(28)19(30)16(29)7-13/h4-7,12,17-18,20-22,24,28-33H,8-11H2,1-3H3

InChI Key

LQVNYRWMNGPIEB-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
Macaranga tanarius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Galloyl ester
Alkyl glycoside
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
O-glycosyl compound
Glycosyl compound
Benzoate ester
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Oxepane
Monocyclic benzene moiety
Oxane
Monosaccharide
Benzenoid
Tetrahydrofuran
Secondary alcohol
Ketone
Cyclic ketone
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen 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	1.05	ALOGPS
logP	0.85	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.85 m³·mol⁻¹	ChemAxon
Polarizability	54.07 Å³	ChemAxon
Number of Rings	4	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 {6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate (NP0198319)

MOL for NP0198319 ({6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D MOL for NP0198319 ({6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D SDF for NP0198319 ({6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0198319 ({6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

PDB for NP0198319 ({6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D PDB for NP0198319 ({6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

SMILES for NP0198319 ({6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

INCHI for NP0198319 ({6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

Structure for NP0198319 ({6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D Structure for NP0198319 ({6-[(4-{1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl}but-3-en-2-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3,4,5-trihydroxybenzoate)