NP-MRD: Showing NP-Card for 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside (NP0137964)

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Record Information

Version

2.0

Created at

2022-05-31 16:40:57 UTC

Updated at

2022-05-31 16:40:57 UTC

NP-MRD ID

NP0137964

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside

Description

(E)-2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside, also known as tetrahydroxystilbene glucoside or THSG CPD, belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside is found in Hopea reticulata. 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside was first documented in 2003 (PMID: 15015285). Based on a literature review a small amount of articles have been published on (E)-2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside (PMID: 16201354) (PMID: 17613621) (PMID: 17701557) (PMID: 17963744).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218402D          

 36 38  0  0  1  0            999 V2000
    1.4289   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  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
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  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
   -0.7145   -2.8875    0.0000 C   0  0  0  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
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    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
   -3.5724   -4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    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   -3.3000    0.0000 H   0  0  0  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
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   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
   -2.8579   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  6  0  0  0
 24 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  6  0  0  0
  2 30  1  0  0  0  0
 30 31  2  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
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 30 36  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -1.6462    3.0949    1.3793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768    3.0733    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2827    1.7988   -0.5484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5068    0.7378   -0.1002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7963   -0.4542   -0.7102 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1618   -1.5037   -0.0479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2666   -2.4031   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7628   -3.5570   -1.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429   -3.8113   -1.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -4.4688   -1.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4906   -4.2838   -1.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3762   -5.2365   -2.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9769   -3.1133   -1.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0894   -2.1789   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6304   -0.9475    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839   -0.6246    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3867    0.6014    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434    0.8420    0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3172    1.9559    1.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4938    2.9049    1.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0622    4.0587    2.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290    2.7233    1.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5815    1.5661    1.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3080   -0.5806   -0.7463 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7431    0.0209   -1.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9129    0.2606    0.3868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2402    0.0906    1.5738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060    1.7181   -0.0457 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6428    2.0009   -1.0250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4493    3.5188    1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2746    3.9672   -0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6553    3.2506   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3014    1.8551   -1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4336   -0.4136   -1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4306   -4.6764   -1.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300   -5.3951   -2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9861   -6.0634   -2.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0546   -2.9931   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9124   -0.2570    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -1.3107   -0.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4307    0.1022    0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3922    2.1362    1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0647    4.1807    2.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4883    3.4908    2.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    1.4496    1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6826   -1.5994   -0.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2065   -0.2443   -2.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879    0.0133    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7548   -0.5786    2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8795    2.3482    0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6736    2.9343   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  1  0
 11 10  2  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 28  1  0
 28 29  1  0
 28 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
  7 14  1  0
 24  5  1  0
 23 17  1  0
 16 40  1  0
 15 39  1  0
 13 38  1  0
 12 37  1  0
 10 36  1  0
  9 35  1  0
  5 34  1  6
  3 33  1  6
  2 31  1  0
  2 32  1  0
  1 30  1  0
 28 50  1  1
 29 51  1  0
 26 48  1  1
 27 49  1  0
 24 46  1  1
 25 47  1  0
 18 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
M  END


  Mrv1652305312218402D          

 36 38  0  0  1  0            999 V2000
    1.4289   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  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
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  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
   -0.7145   -2.8875    0.0000 C   0  0  0  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
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    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
   -3.5724   -4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    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   -3.3000    0.0000 H   0  0  0  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
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   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
   -2.8579   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  6  0  0  0
 24 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  6  0  0  0
  2 30  1  0  0  0  0
 30 31  2  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
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 30 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137964

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C1=CC(O)=CC(O)=C1O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O9/c21-9-15-16(25)17(26)18(27)20(28-15)29-19-11(7-13(23)8-14(19)24)4-1-10-2-5-12(22)6-3-10/h1-8,15-18,20-27H,9H2/b4-1+/t15-,16-,17+,18-,20+/m1/s1

> <INCHI_KEY>
JAYVHSBYKLLDJC-DSNJPTTOSA-N

> <FORMULA>
C20H22O9

> <MOLECULAR_WEIGHT>
406.387

> <EXACT_MASS>
406.126382288

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
40.44115995400174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
0.8307574713333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.280032275096458

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.696037146093989

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092357419066

> <JCHEM_POLAR_SURFACE_AREA>
160.07

> <JCHEM_REFRACTIVITY>
101.58080000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0       2.667  -3.080   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      -1.334  -2.310   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      -4.001  -3.850   0.000  0.00  0.00           H+0
HETATM   16  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      -6.668  -8.470   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      -8.002  -6.160   0.000  0.00  0.00           H+0
HETATM   23  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      -6.668  -3.850   0.000  0.00  0.00           H+0
HETATM   26  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      -5.335  -6.160   0.000  0.00  0.00           H+0
HETATM   29  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   27                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19   21                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   17   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   14   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    2   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   30                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
2,3,5,4'-Tetrahydroxystilbene-2-O-beta-D-glucoside	ChEBI
Tetrahydroxystilbene glucoside	ChEBI
trans-2,3,5,4'-Tetrahydroxystilbene-2-O-beta-D-glucoside	ChEBI
2,3,5,4'-Tetrahydroxystilbene-2-O-b-D-glucoside	Generator
2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucoside	Generator
trans-2,3,5,4'-Tetrahydroxystilbene-2-O-b-D-glucoside	Generator
trans-2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucoside	Generator
(e)-2,3,5,4'-Tetrahydroxystilbene-2-O-b-D-glucoside	Generator
(e)-2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucoside	Generator
2,3,5,4'-Tetrahydroxystilbene 2-O-beta-D-glucoside	MeSH
THSG CPD	MeSH
2,3,5,4'-Tetrahydroxystilbene-2-O-D-glucoside	MeSH
2,3,5,4'-Tetrahydroxystilbene-2-O-glucoside	MeSH
4oh-Stil-2-O-glu	MeSH
(e)-2,3,4',5-beta-Tetrahydroxystilbene-2-beta-D-glucopyranoside	MeSH
2,3,4',5-Tetrahydroxystilbene-2-O-beta-D-glucoside	MeSH
2,3,5,4'-Tetrahydroxystilbene 2-O-glucopyranoside	MeSH

Chemical Formula

C₂₀H₂₂O₉

Average Mass

406.3870 Da

Monoisotopic Mass

406.12638 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

82373-94-2

SMILES

[H]\C(=C(\[H])C1=CC(O)=CC(O)=C1O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C20H22O9/c21-9-15-16(25)17(26)18(27)20(28-15)29-19-11(7-13(23)8-14(19)24)4-1-10-2-5-12(22)6-3-10/h1-8,15-18,20-27H,9H2/b4-1+/t15-,16-,17+,18-,20+/m1/s1

InChI Key

JAYVHSBYKLLDJC-DSNJPTTOSA-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
Hopea reticulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Stilbene glycosides

Direct Parent

Stilbene glycosides

Alternative Parents

Substituents

Stilbene glycoside
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Phenol ether
Resorcinol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Acetal
Polyol
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Organooxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015893

Chemspider ID

19026512

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321884

PDB ID

Not Available

ChEBI ID

140850

Good Scents ID

Not Available

References

General References

Zhao HP, Sun YK, Zhang XQ: [Determination of 2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside in yangan oral liquid by HPLC]. Zhongguo Zhong Yao Za Zhi. 2003 Feb;28(2):133-4, 176. [PubMed:15015285 ]
Wei HQ, Liu EB, Ren RF, Zhao XL, Li XX, Jiang FX: [Determination of 2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside in the traditional Chinese preparation by high performance liquid chromatography with chemiluminescence detection]. Guang Pu Xue Yu Guang Pu Fen Xi. 2005 Jun;25(6):844-7. [PubMed:16201354 ]
Zhang YZ, Shen JF, Xu JY, Xiao JH, Wang JL: Inhibitory effects of 2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside on experimental inflammation and cyclooxygenase 2 activity. J Asian Nat Prod Res. 2007 Apr-Aug;9(3-5):355-63. doi: 10.1080/10286020600727772. [PubMed:17613621 ]
Liu QL, Xiao JH, Ma R, Ban Y, Wang JL: Effect of 2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside on lipoprotein oxidation and proliferation of coronary arterial smooth cells. J Asian Nat Prod Res. 2007 Sep-Dec;9(6-8):689-97. doi: 10.1080/17415990500209064. [PubMed:17701557 ]
Wang X, Zhao L, Han T, Chen S, Wang J: Protective effects of 2,3,5,4'-tetrahydroxystilbene-2-O-beta-d-glucoside, an active component of Polygonum multiflorum Thunb, on experimental colitis in mice. Eur J Pharmacol. 2008 Jan 14;578(2-3):339-48. doi: 10.1016/j.ejphar.2007.09.013. Epub 2007 Oct 25. [PubMed:17963744 ]

Showing NP-Card for 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside (NP0137964)

MOL for NP0137964 (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside)

3D MOL for NP0137964 (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside)

3D SDF for NP0137964 (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside)

3D-SDF for NP0137964 (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside)

PDB for NP0137964 (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside)

3D PDB for NP0137964 (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside)

SMILES for NP0137964 (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside)

INCHI for NP0137964 (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside)

Structure for NP0137964 (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside)

3D Structure for NP0137964 (2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside)