NP-MRD: Showing NP-Card for 2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol (NP0236391)

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Record Information

Version

2.0

Created at

2022-09-06 19:16:56 UTC

Updated at

2022-09-06 19:16:56 UTC

NP-MRD ID

NP0236391

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol

Description

Isolariciresinol 4'-O-beta-D-glucoside belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. Isolariciresinol 4'-O-beta-D-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isolariciresinol 4'-O-beta-D-glucoside has been detected, but not quantified in, alcoholic beverages. 2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol is found in Hovenia dulcis. This could make isolariciresinol 4'-O-beta-D-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241215512D          

 55 62  0  0  0  0            999 V2000
   -1.9047   -1.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9047   -1.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1905   -2.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -1.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -1.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1905   -0.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2354   -2.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9496   -1.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9496   -1.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2354   -0.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6584   -0.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6584    0.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9496    0.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2354    0.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388   -0.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9136   -0.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388    0.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7187   -0.1321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0503    0.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5742    1.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    1.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6203   -2.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -2.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7790   -2.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -0.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9496   -0.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    2.0025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9721    1.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7659    1.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4830    0.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2000    1.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4830   -0.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0713   -1.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1282   -1.0101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374   -2.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503   -2.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701   -2.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701   -3.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503   -3.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374   -3.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6203   -3.9264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503   -4.7619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4872   -3.9264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    2.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1508    2.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7371    2.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5251    3.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7269    3.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1407    3.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    1.5703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5339    2.7346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1100    4.3324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5136    4.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4872   -2.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2000   -2.6878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 22  1  0  0  0  0
  3  4  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 25  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 26  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 33  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  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
 16 34  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 29  1  0  0  0  0
 20 21  1  0  0  0  0
 21 27  1  0  0  0  0
 21 28  1  0  0  0  0
 22 35  1  0  0  0  0
 27 44  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 33 34  1  0  0  0  0
 35 36  1  0  0  0  0
 35 40  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 54  1  0  0  0  0
 38 39  1  0  0  0  0
 38 43  1  0  0  0  0
 39 40  1  0  0  0  0
 39 42  1  0  0  0  0
 40 41  1  0  0  0  0
 44 45  1  0  0  0  0
 44 49  1  0  0  0  0
 45 46  1  0  0  0  0
 45 50  1  0  0  0  0
 46 47  1  0  0  0  0
 46 51  1  0  0  0  0
 47 48  1  0  0  0  0
 47 52  1  0  0  0  0
 48 49  1  0  0  0  0
 48 53  1  0  0  0  0
 54 55  1  0  0  0  0
M  END

     RDKit          3D

123130  0  0  0  0  0  0  0  0999 V2000
   -6.6997    4.8200   -1.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8020    4.3654   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5716    5.1594    0.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1831    3.2313    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4146    2.4312   -0.9068 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5362    0.9699   -0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    0.4614    0.4626 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2551    0.5200    1.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2880   -0.8465    0.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3947   -1.6549    0.1330 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2647   -2.6601    1.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4115   -3.3949    1.2911 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4423   -2.7205    2.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0733   -3.7959   -0.0208 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5334   -5.1115    0.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9847   -3.7530   -1.0657 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8770   -4.4821   -0.6246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5485   -2.3154   -1.2395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3329   -2.3468   -1.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3855    1.3601    0.4925 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0719    0.6183    0.6493 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3973    1.2351    1.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0124    0.6343    1.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8562    1.1297    0.7390 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2555    0.6516    0.9541 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4575    0.7022    2.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3043    1.5699    0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1507    0.9901   -0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7664   -0.2741   -0.2343 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0426   -0.1482    0.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0547   -0.7046   -0.4141 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8418   -1.5938    0.2835 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8885   -1.0079    0.9617 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5462   -1.9938    1.9276 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5969   -1.3691    2.5963 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9807   -0.5178    0.0372 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5878    0.5840    0.5920 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3118   -0.0879   -1.2546 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0285    0.8721   -1.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9405    0.4316   -0.8816 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0160    1.4797    0.0313 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883   -1.2079    0.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4602   -1.6618    1.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8988   -2.5379   -0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4778   -0.7846    0.5724 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7120   -1.2559   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3026   -0.7805   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1746    0.7496   -0.5201 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7632    1.3473   -1.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730    0.9689   -0.5828 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9704    0.2240   -1.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137    0.8647   -1.8537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2566    1.9000   -0.9301 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7870    2.3573   -0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1360    2.8779   -1.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3281    4.1974   -2.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0906    5.8546   -1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6144    4.7683   -1.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0644    5.1264    1.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5783    6.2099    0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6257    4.8202    0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2551    2.9059    1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9570    2.5615   -1.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5617    0.8025   -0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4789    0.3831   -1.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768   -0.3812    2.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3694    0.5948    1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9384    1.3975    2.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3566   -1.1497    0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1125   -4.3448    1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0158   -1.9321    1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0110   -2.2811    3.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1785   -3.4872    2.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8895   -3.1087   -0.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7300   -5.6967   -0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3208   -4.1552   -2.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2586   -4.6107   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3197   -1.8296   -1.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5204   -2.3668   -2.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5093    2.1965    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1695   -0.4544    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963    2.3224    1.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9438    0.8153    2.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146   -0.4527    1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3672    0.9367    2.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630    2.2370    0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5744    0.6638    2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0407   -0.1405    3.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2062    1.7173    2.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0490    1.8389    1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9622    2.5665    0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9019    1.7529   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5187    0.8203   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0270   -0.7919   -1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0236391

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2(C)CC(OC34CC5(CO3)C(CCC3C6(C)CCC(OC7OC(CO)C(O)C(O)C7O)C(C)(C)C6CCC53C)C24)C=C(C)C)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C42H68O13/c1-20(2)15-22-16-40(8,55-36-33(49)30(46)28(44)21(3)51-36)34-23-9-10-26-38(6)13-12-27(53-35-32(48)31(47)29(45)24(17-43)52-35)37(4,5)25(38)11-14-39(26,7)41(23)18-42(34,54-22)50-19-41/h15,21-36,43-49H,9-14,16-19H2,1-8H3

> <INCHI_KEY>
AIQVSZGMSMEENK-UHFFFAOYSA-N

> <FORMULA>
C42H68O13

> <MOLECULAR_WEIGHT>
780.9815

> <EXACT_MASS>
780.465992262

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
87.26359282520062

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
2.4265965756666654

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.441916283420912

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.91616646233841

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835440417778

> <JCHEM_POLAR_SURFACE_AREA>
196.98999999999998

> <JCHEM_REFRACTIVITY>
198.09430000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.555  -1.934   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.555  -3.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.222  -4.246   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.891  -3.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.891  -1.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.222  -1.169   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.439  -4.246   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.773  -3.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.773  -1.934   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.439  -1.169   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.096  -1.169   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.096   0.365   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.773   1.123   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.439   0.365   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.552  -1.637   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.439  -0.398   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.552   0.827   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.942  -0.247   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.561   1.123   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.672   2.356   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.169   2.196   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.891  -4.246   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.993  -5.582   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.454  -5.582   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.891  -0.398   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.773  -0.398   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.169   3.738   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.681   2.597   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.896   1.906   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.235   1.123   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.573   1.906   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.235  -0.398   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.866  -2.507   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.839  -1.886   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -6.230  -5.017   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -7.561  -4.246   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -8.904  -5.017   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -8.904  -6.564   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -7.561  -7.347   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -6.230  -6.564   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.891  -7.329   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -7.561  -8.889   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -10.243  -7.329   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       6.258   4.827   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.748   4.421   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       8.843   5.508   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       8.447   6.998   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.957   7.399   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       5.863   6.307   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       8.141   2.931   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      10.330   5.105   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       9.539   8.087   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       6.559   8.889   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -10.243  -4.246   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0     -11.573  -5.017   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4   23   24                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   25                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   26                                             
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   33                                             
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17   18   34                                             
CONECT   17   12   16   21                                                  
CONECT   18   16   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   17   20   27   28                                             
CONECT   22    2   35                                                       
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    5                                                            
CONECT   26    9                                                            
CONECT   27   21   44                                                       
CONECT   28   21                                                            
CONECT   29   19   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   11   34                                                       
CONECT   34   16   33                                                       
CONECT   35   22   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   54                                                  
CONECT   38   37   39   43                                                  
CONECT   39   38   40   42                                                  
CONECT   40   35   39   41                                                  
CONECT   41   40                                                            
CONECT   42   39                                                            
CONECT   43   38                                                            
CONECT   44   27   45   49                                                  
CONECT   45   44   46   50                                                  
CONECT   46   45   47   51                                                  
CONECT   47   46   48   52                                                  
CONECT   48   47   49   53                                                  
CONECT   49   44   48                                                       
CONECT   50   45                                                            
CONECT   51   46                                                            
CONECT   52   47                                                            
CONECT   53   48                                                            
CONECT   54   37   55                                                       
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  124    0
END

View in JSmol

Synonyms

Value	Source
Isolariciresinol 4'-O-b-D-glucoside	Generator
Isolariciresinol 4'-O-β-D-glucoside	Generator

Chemical Formula

C₄₂H₆₈O₁₃

Average Mass

780.9815 Da

Monoisotopic Mass

780.46599 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1OC(OC2(C)CC(OC34CC5(CO3)C(CCC3C6(C)CCC(OC7OC(CO)C(O)C(O)C7O)C(C)(C)C6CCC53C)C24)C=C(C)C)C(O)C(O)C1O

InChI Identifier

InChI=1S/C42H68O13/c1-20(2)15-22-16-40(8,55-36-33(49)30(46)28(44)21(3)51-36)34-23-9-10-26-38(6)13-12-27(53-35-32(48)31(47)29(45)24(17-43)52-35)37(4,5)25(38)11-14-39(26,7)41(23)18-42(34,54-22)50-19-41/h15,21-36,43-49H,9-14,16-19H2,1-8H3

InChI Key

AIQVSZGMSMEENK-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
Hovenia dulcis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
9,9p-dihydroxyaryltetralin lignan
1-aryltetralin lignan
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Oxane
Benzenoid
Fatty acyl
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Organooxygen compound
Alcohol
Primary alcohol
Organic oxygen compound
Hydrocarbon derivative
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	2.04	ALOGPS
logP	2.43	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.92	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	196.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	198.09 m³·mol⁻¹	ChemAxon
Polarizability	87.26 Å³	ChemAxon
Number of Rings	8	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

HMDB0040471

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020225

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

74407576

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol (NP0236391)

MOL for NP0236391 (2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol)

3D MOL for NP0236391 (2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol)

3D SDF for NP0236391 (2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol)

3D-SDF for NP0236391 (2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol)

PDB for NP0236391 (2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol)

3D PDB for NP0236391 (2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol)

SMILES for NP0236391 (2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol)

INCHI for NP0236391 (2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol)

Structure for NP0236391 (2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol)

3D Structure for NP0236391 (2-methyl-6-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}oxane-3,4,5-triol)