NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate (NP0155413)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 12:27:58 UTC

Updated at

2022-09-02 12:27:58 UTC

NP-MRD ID

NP0155413

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

ZINC38143594 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-{[(1r)-1-hydroxy-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 ZINC38143594.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022214272D          

 39 42  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  1  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
    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
 20 18  1  1  0  0  0
 20 21  1  6  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  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  2  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  6  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
M  END

     RDKit          3D

 67 70  0  0  0  0  0  0  0  0999 V2000
    5.6794   -1.6872   -2.2430 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0320   -0.9256   -1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0377   -0.5639   -0.4084 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6935   -1.0602   -0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9123   -0.4390    0.5503 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5635   -0.8109    0.5668 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403    0.0765    1.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4354    0.1080    1.2727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1646    1.1748    0.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250    2.3843    0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    3.4070   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8272    3.2008   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7170    4.1686   -0.5682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3310    1.9731    0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5544    0.9314    0.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0443   -0.3776    1.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085   -0.5198    0.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0637   -0.4914   -0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4006   -0.3328   -1.3158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5632   -0.6485   -0.3605 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0906   -0.8210    0.9348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0760    0.5926   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1905    0.5855   -1.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9960   -0.6289   -1.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2023   -1.8961   -1.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9212   -1.7758   -1.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1187   -2.7113   -1.3792 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2678   -0.4388    2.8718 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3301    0.6048    3.8002 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4935   -1.2758    2.8539 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2271   -2.6077    2.4537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5651   -0.7853    1.8762 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3018    0.2704    2.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4058   -0.4727   -1.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3190   -0.8768   -2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6202   -0.4963   -2.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0864    0.3094   -1.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1731    0.7209   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8538    0.3352   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840   -0.6931   -1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6760   -2.1609   -0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326    0.6587    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500    1.0990    1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252    2.5789    0.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0738    4.3775   -0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9822    4.2874   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4105    1.8345    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5445   -1.2190    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039   -0.5855    2.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9956   -1.1893    0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5316    1.5130   -0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5885    1.5154   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6689   -0.5205   -2.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7079   -0.6926   -1.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7854   -2.6857   -1.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0296   -2.1908   -3.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4150   -1.1224    3.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6630    1.4440    3.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -1.3743    3.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3075   -2.6827    2.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2666   -1.6303    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2873    0.9783    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9935   -1.5227   -3.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2762   -0.8568   -2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1218    0.6124   -1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5737    1.3543    0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1473    0.6731    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 32  1  0
 32 33  1  0
 32  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
  7 28  1  0
 28 29  1  0
 28 30  1  0
 39 34  1  0
 15  9  1  0
 26 20  1  0
 31 60  1  0
 30 59  1  1
 32 61  1  6
 33 62  1  0
  5 42  1  6
  4 40  1  0
  4 41  1  0
 35 63  1  0
 36 64  1  0
 37 65  1  0
 38 66  1  0
 39 67  1  0
  7 43  1  1
 10 44  1  0
 11 45  1  0
 13 46  1  0
 14 47  1  0
 16 48  1  0
 16 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 25 56  1  0
 28 57  1  1
 29 58  1  0
M  END


  Mrv1652309022214272D          

 39 42  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  1  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
    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
 20 18  1  1  0  0  0
 20 21  1  6  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  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  2  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  6  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155413

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](O)[C@@H](COC(=O)C2=CC=CC=C2)O[C@@H](OC2=CC=C(O)C=C2COC(=O)[C@@]2(O)C=CCCC2=O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O12/c28-17-9-10-18(16(12-17)13-37-26(34)27(35)11-5-4-8-20(27)29)38-25-23(32)22(31)21(30)19(39-25)14-36-24(33)15-6-2-1-3-7-15/h1-3,5-7,9-12,19,21-23,25,28,30-32,35H,4,8,13-14H2/t19-,21-,22+,23-,25-,27-/m1/s1

> <INCHI_KEY>
WVZFLDUSZYAGPC-OJSSCUGGSA-N

> <FORMULA>
C27H28O12

> <MOLECULAR_WEIGHT>
544.509

> <EXACT_MASS>
544.158076342

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.0271628969652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.30

> <JCHEM_LOGP>
1.759902107666666

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.405618470552389

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.586726534715448

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649110483481084

> <JCHEM_POLAR_SURFACE_AREA>
189.28

> <JCHEM_REFRACTIVITY>
132.2116

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1R)-1-hydroxy-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      15.660 -11.190   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.134 -12.637   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   28                                                  
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   26                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   20   27                                                  
CONECT   27   26                                                            
CONECT   28    7   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    5   33                                                  
CONECT   33   32                                                            
CONECT   34    2   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈O₁₂

Average Mass

544.5090 Da

Monoisotopic Mass

544.15808 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](O)[C@@H](COC(=O)C2=CC=CC=C2)O[C@@H](OC2=CC=C(O)C=C2COC(=O)[C@@]2(O)C=CCCC2=O)[C@@H]1O

InChI Identifier

InChI=1S/C27H28O12/c28-17-9-10-18(16(12-17)13-37-26(34)27(35)11-5-4-8-20(27)29)38-25-23(32)22(31)21(30)19(39-25)14-36-24(33)15-6-2-1-3-7-15/h1-3,5-7,9-12,19,21-23,25,28,30-32,35H,4,8,13-14H2/t19-,21-,22+,23-,25-,27-/m1/s1

InChI Key

WVZFLDUSZYAGPC-OJSSCUGGSA-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
Ketone
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Aldehyde
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	1.3	ALOGPS
logP	1.76	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.59	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	132.21 m³·mol⁻¹	ChemAxon
Polarizability	53.03 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

93473134

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-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate (NP0155413)

MOL for NP0155413 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

3D MOL for NP0155413 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

3D SDF for NP0155413 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

3D-SDF for NP0155413 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

PDB for NP0155413 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

3D PDB for NP0155413 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

SMILES for NP0155413 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

INCHI for NP0155413 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

Structure for NP0155413 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)

3D Structure for NP0155413 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-2-{[(1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)oxan-2-yl]methyl benzoate)