NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate (NP0154643)

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Record Information

Version

2.0

Created at

2022-09-02 11:35:25 UTC

Updated at

2022-09-02 11:35:25 UTC

NP-MRD ID

NP0154643

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate

Description

Itoside J belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate is found in Itoa orientalis. Based on a literature review very few articles have been published on Itoside J.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022213352D          

 59 64  0  0  1  0            999 V2000
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3289   -5.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1413   -4.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9538   -4.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4841   -5.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2019   -5.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7322   -6.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5447   -6.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8269   -5.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6393   -5.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9215   -4.6462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1696   -6.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8875   -6.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0750   -6.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7928   -7.7472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3231   -8.3792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1356   -8.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6659   -8.8679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.4784   -8.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0087   -9.3566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3837   -9.6431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9140  -10.2751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5713   -9.7864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2891  -10.5617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0410   -9.1544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2285   -9.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3895   -5.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1073   -6.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 37 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 35 44  1  0  0  0  0
 44 45  1  1  0  0  0
 25 46  1  0  0  0  0
 20 46  1  0  0  0  0
 46 47  2  0  0  0  0
  7 48  1  0  0  0  0
 48 49  1  6  0  0  0
 48 50  1  0  0  0  0
 50 51  1  1  0  0  0
 50 52  1  0  0  0  0
  5 52  1  0  0  0  0
 52 53  1  6  0  0  0
  2 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 54 59  1  0  0  0  0
M  END

     RDKit          3D

101106  0  0  0  0  0  0  0  0999 V2000
    9.4730    1.8564    3.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9406    1.4147    2.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0866    0.9441    1.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6617    0.9305    1.8136 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0229    0.3524    0.5673 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6524    0.2946    0.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0395    0.2218   -0.6067 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7326   -0.2261   -0.5105 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3231   -1.4613   -0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1243   -2.4562   -1.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632   -3.6640   -1.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2171   -3.9133   -1.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6907   -5.1321   -2.1341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -2.9292   -1.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9513   -1.7300   -0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724   -0.6614   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2278   -1.1577   -0.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3791   -0.5347    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678    0.6325    0.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7163   -1.1309    0.1236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5419   -2.4191   -0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3783   -1.3383    1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6335   -1.7846    1.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3843   -2.0802    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9776   -1.0756   -0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7900   -0.8369   -1.8890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1022   -1.4723   -2.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0835   -2.5160   -3.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1839   -3.2708   -3.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1402   -4.2949   -4.2468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3693   -2.9912   -2.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3861   -1.9829   -1.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2384   -1.1934   -1.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3589   -0.2244   -0.5215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7046    0.7976    0.0687 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5421    0.5375    1.4040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4100    1.5534    2.2825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5583    1.5238    3.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4975    0.2817    3.9514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1516    2.9187    1.7627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7790    3.2031    1.8782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6656    3.2120    0.3918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2612    4.4619    0.2906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5495    2.0844   -0.0542 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.9443    2.2550   -1.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575   -0.4089   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4676    0.6419   -1.3703 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2037    1.5231   -1.3725 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9356    1.2387   -2.7156 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6703    3.1530   -0.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8417   -0.0005   -1.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3741    1.4099    2.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9556    0.9371    1.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.1838    1.4160    2.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5980    1.8881    3.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2277    1.8784    3.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4592    0.2872    2.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2806    1.9413    2.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3563   -0.7285    0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422   -0.5155   -1.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846   -2.2813   -1.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -4.4001   -2.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3661   -5.2571   -3.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -3.0856   -1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918    0.2911   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3440   -0.4292    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9643   -2.3884   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8250   -1.1198    2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1379   -1.9422    2.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4423   -1.8967    0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1527   -3.0979   -0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4960   -0.0995   -2.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1645   -2.7542   -3.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.2212   -3.6145   -2.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3087   -1.7680   -1.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5042    1.2900    2.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2886   -0.2837    3.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6651    3.6366    2.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5592    3.6486    2.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7658    3.1901   -0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2604    4.3273    0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4669    1.9594    0.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7679    1.7359   -1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5269    2.3164   -1.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3309    1.9740   -3.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9931    2.2984   -2.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2674    3.8476   -0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
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   13.7794    0.5775    0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022213352D          

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   12.9140  -10.2751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2285   -9.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
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 31 32  1  0  0  0  0
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 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 37 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 35 44  1  0  0  0  0
 44 45  1  1  0  0  0
 25 46  1  0  0  0  0
 20 46  1  0  0  0  0
 46 47  2  0  0  0  0
  7 48  1  0  0  0  0
 48 49  1  6  0  0  0
 48 50  1  0  0  0  0
 50 51  1  1  0  0  0
 50 52  1  0  0  0  0
  5 52  1  0  0  0  0
 52 53  1  6  0  0  0
  2 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 54 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154643

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(O)C=C2\C=C2/CC=CC(O)(C(=O)OCC3=CC(O)=CC=C3O[C@@H]3O[C@H](COC(=O)C4=CC=CC=C4)[C@@H](O)[C@H](O)[C@H]3O)C2=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C40H42O19/c41-16-27-29(44)31(46)33(48)37(58-27)56-25-10-8-23(42)14-21(25)13-20-7-4-12-40(53,35(20)50)39(52)55-17-22-15-24(43)9-11-26(22)57-38-34(49)32(47)30(45)28(59-38)18-54-36(51)19-5-2-1-3-6-19/h1-6,8-15,27-34,37-38,41-49,53H,7,16-18H2/b20-13+/t27-,28-,29-,30-,31+,32+,33-,34-,37-,38-,40?/m1/s1

> <INCHI_KEY>
VJDJBHKKFHYOAP-BQQHIGENSA-N

> <FORMULA>
C40H42O19

> <MOLECULAR_WEIGHT>
826.757

> <EXACT_MASS>
826.232029132

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
101

> <JCHEM_AVERAGE_POLARIZABILITY>
81.61310296467019

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5E)-1-hydroxy-5-[(5-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.939149987666667

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.882940513584504

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.355007589398117

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649110483481084

> <JCHEM_POLAR_SURFACE_AREA>
308.89

> <JCHEM_REFRACTIVITY>
198.4642

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5E)-1-hydroxy-5-[(5-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.681 -11.190   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      15.197  -8.563   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.714  -8.295   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.704  -9.475   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.177 -10.922   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.167 -12.102   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.683 -11.835   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.210 -10.387   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.727 -10.120   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      22.253  -8.673   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      22.717 -11.300   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.190 -12.747   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      20.673 -13.014   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      20.147 -14.461   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      21.137 -15.641   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      22.653 -15.374   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      23.643 -16.553   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      25.160 -16.286   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      26.150 -17.466   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      23.116 -18.001   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      24.106 -19.180   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      21.600 -18.268   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      21.073 -19.715   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      20.610 -17.088   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      19.093 -17.356   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      15.660 -11.190   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      15.134 -12.637   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   54                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   52                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   48                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   46                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   46                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   27   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   44                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   35   45                                                  
CONECT   45   44                                                            
CONECT   46   25   20   47                                                  
CONECT   47   46                                                            
CONECT   48    7   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50    5   53                                                  
CONECT   53   52                                                            
CONECT   54    2   55   59                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   54                                                       
MASTER        0    0    0    0    0    0    0    0   59    0  128    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₄₂O₁₉

Average Mass

826.7570 Da

Monoisotopic Mass

826.23203 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5E)-1-hydroxy-5-[(5-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(O)C=C2\C=C2/CC=CC(O)(C(=O)OCC3=CC(O)=CC=C3O[C@@H]3O[C@H](COC(=O)C4=CC=CC=C4)[C@@H](O)[C@H](O)[C@H]3O)C2=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C40H42O19/c41-16-27-29(44)31(46)33(48)37(58-27)56-25-10-8-23(42)14-21(25)13-20-7-4-12-40(53,35(20)50)39(52)55-17-22-15-24(43)9-11-26(22)57-38-34(49)32(47)30(45)28(59-38)18-54-36(51)19-5-2-1-3-6-19/h1-6,8-15,27-34,37-38,41-49,53H,7,16-18H2/b20-13+/t27-,28-,29-,30-,31+,32+,33-,34-,37-,38-,40?/m1/s1

InChI Key

VJDJBHKKFHYOAP-BQQHIGENSA-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
Itoa orientalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Benzoate ester
Benzyloxycarbonyl
4-alkoxyphenol
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Phenol
Acyloin
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Benzenoid
Oxane
Tertiary alcohol
Secondary alcohol
Cyclic ketone
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Primary alcohol
Alcohol
Aldehyde
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.17	ALOGPS
logP	0.94	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.36	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	308.89 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	198.46 m³·mol⁻¹	ChemAxon
Polarizability	81.61 Å³	ChemAxon
Number of Rings	6	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

C00039469

Chemspider ID

24708184

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24879103

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate (NP0154643)

MOL for NP0154643 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

3D MOL for NP0154643 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

3D SDF for NP0154643 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

3D-SDF for NP0154643 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

PDB for NP0154643 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

3D PDB for NP0154643 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

SMILES for NP0154643 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

INCHI for NP0154643 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

Structure for NP0154643 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

3D Structure for NP0154643 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(5e)-1-hydroxy-5-[(5-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)