NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate (NP0196105)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 14:06:52 UTC

Updated at

2022-09-04 14:06:52 UTC

NP-MRD ID

NP0196105

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate

Description

Chiritoside C 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,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate is found in Primulina sinensis. Based on a literature review very few articles have been published on Chiritoside C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042216062D          

 45 48  0  0  1  0            999 V2000
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  6  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
  5 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 32 39  1  0  0  0  0
 28 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 26 44  1  0  0  0  0
 44 45  1  6  0  0  0
M  END

     RDKit          3D

 81 84  0  0  0  0  0  0  0  0999 V2000
    2.3384    1.6728   -1.8896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3805    2.1510   -1.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1442    1.3470   -1.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9142    1.7774   -0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1745    1.0773   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4295   -0.1697   -0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6414   -0.7890   -0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7001   -0.1914   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8599   -0.8940    0.0691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0629   -0.6521    0.6628 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3749   -1.5476    1.6957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7226   -2.7992    1.2755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5845   -3.6136    0.7053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5876   -3.7856    1.6560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9298   -2.8052    0.3720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.9833   -2.2332    1.0855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6387   -1.9426   -0.8137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7792   -2.5556   -1.7098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1897   -0.5985   -0.3602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2435    0.1790    0.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4509    1.0487    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4361    1.7248    1.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169    1.6411    0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5140    3.3716   -0.6971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5986    4.2440   -0.6816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8248    3.7248    0.0223 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2840    2.5988   -0.5853 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4570    2.0653   -0.1092 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0553    1.3839   -1.1589 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3414    0.0584   -0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0814   -0.7018   -0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3490   -2.1396   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3900   -3.0019   -1.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6331   -4.3487   -1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8258   -4.7835    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0662   -6.1173    0.2683 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7825   -3.8994    1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9766   -4.3345    2.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5409   -2.5611    0.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4574    3.1164    0.3381 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3537    3.3545    1.7086 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1862    4.3706   -0.4618 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0518    3.9898   -1.7999 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8229    4.8746    0.0299 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0227    5.2445    1.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899    0.3794   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227    2.7632   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6165   -0.6409   -1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7997   -1.7823   -1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0876    0.3373    1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0477   -3.3558    2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0154   -4.6065    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1268   -3.1938   -0.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5039   -4.7695    1.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1783   -3.8536    0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8556   -2.3409    0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6058   -1.7862   -1.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8099   -2.0305   -2.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7587   -0.0684   -1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1494    0.3649    1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1982    2.6272    1.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358    2.6399    0.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8787    4.5771   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2822    5.2281   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4894    3.4895    1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3225    1.3963    0.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7542   -0.3411   -1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0799   -0.0825   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4464   -0.2624    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4890   -0.6548   -1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2337   -2.6372   -2.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6704   -5.0434   -2.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2094   -6.4396    1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9391   -3.6770    3.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5005   -1.8604    1.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4690    2.6978    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2495    3.7409    1.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9617    5.1309   -0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9378    3.7190   -2.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5106    5.7225   -0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5399    6.0617    1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  2  0
 28 40  1  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
  5 23  1  0
 23 21  2  0
 21 22  1  0
 10 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 12  1  0
 21  8  1  0
 44 26  1  0
 39 32  1  0
 14 54  1  0
 13 52  1  0
 13 53  1  0
 12 51  1  1
 10 50  1  1
  7 49  1  0
  6 48  1  0
  4 47  1  0
  3 46  1  0
 25 63  1  0
 25 64  1  0
 26 65  1  1
 28 66  1  1
 30 67  1  0
 30 68  1  0
 31 69  1  0
 31 70  1  0
 33 71  1  0
 34 72  1  0
 36 73  1  0
 38 74  1  0
 39 75  1  0
 40 76  1  1
 41 77  1  0
 42 78  1  6
 43 79  1  0
 44 80  1  6
 45 81  1  0
 23 62  1  0
 22 61  1  0
 19 59  1  6
 20 60  1  0
 17 57  1  6
 18 58  1  0
 15 55  1  6
 16 56  1  0
M  END


  Mrv1652309042216062D          

 45 48  0  0  1  0            999 V2000
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  6  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
  5 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 32 39  1  0  0  0  0
 28 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 26 44  1  0  0  0  0
 44 45  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0196105

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(\C=C\C(=O)OC[C@H]3O[C@@H](OCCC4=CC=C(O)C(O)=C4)[C@H](O)[C@@H](O)[C@@H]3O)C=C2O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O16/c30-11-19-22(35)24(37)27(40)29(44-19)43-18-5-2-13(10-17(18)33)3-6-21(34)42-12-20-23(36)25(38)26(39)28(45-20)41-8-7-14-1-4-15(31)16(32)9-14/h1-6,9-10,19-20,22-33,35-40H,7-8,11-12H2/b6-3+/t19-,20-,22-,23-,24+,25+,26-,27-,28-,29-/m1/s1

> <INCHI_KEY>
RUOZCMRVSFOEKD-YBFWZAHASA-N

> <FORMULA>
C29H36O16

> <MOLECULAR_WEIGHT>
640.591

> <EXACT_MASS>
640.200335079

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
62.7476520293827

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate

> <JCHEM_LOGP>
-0.7247170539999993

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.870069512263065

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.242171885309329

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490922422252465

> <JCHEM_POLAR_SURFACE_AREA>
265.5199999999999

> <JCHEM_REFRACTIVITY>
149.6779

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668 -19.250   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336 -20.790   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.003 -19.250   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.005   3.850   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      21.339   4.620   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      21.339   1.540   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      17.338  -2.310   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      17.338  -5.390   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    5                                                       
CONECT   24    2   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   44                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   40                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32                                                       
CONECT   40   28   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   26   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₁₆

Average Mass

640.5910 Da

Monoisotopic Mass

640.20034 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(\C=C\C(=O)OC[C@H]3O[C@@H](OCCC4=CC=C(O)C(O)=C4)[C@H](O)[C@@H](O)[C@@H]3O)C=C2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C29H36O16/c30-11-19-22(35)24(37)27(40)29(44-19)43-18-5-2-13(10-17(18)33)3-6-21(34)42-12-20-23(36)25(38)26(39)28(45-20)41-8-7-14-1-4-15(31)16(32)9-14/h1-6,9-10,19-20,22-33,35-40H,7-8,11-12H2/b6-3+/t19-,20-,22-,23-,24+,25+,26-,27-,28-,29-/m1/s1

InChI Key

RUOZCMRVSFOEKD-YBFWZAHASA-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
Primulina sinensis	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
Coumaric acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Tyrosol derivative
Phenol ether
Phenoxy compound
Styrene
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Oxane
Monosaccharide
Benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Primary alcohol
Carbonyl group
Alcohol
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	-0.72	ChemAxon
pKa (Strongest Acidic)	9.24	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	265.52 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	149.68 m³·mol⁻¹	ChemAxon
Polarizability	62.75 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101673669

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,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate (NP0196105)

MOL for NP0196105 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

3D MOL for NP0196105 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

3D SDF for NP0196105 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

3D-SDF for NP0196105 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

PDB for NP0196105 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

3D PDB for NP0196105 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

SMILES for NP0196105 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

INCHI for NP0196105 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

Structure for NP0196105 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

3D Structure for NP0196105 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)