NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0190470)

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Record Information

Version

2.0

Created at

2022-09-04 07:08:32 UTC

Updated at

2022-09-04 07:08:32 UTC

NP-MRD ID

NP0190470

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(2S,3R,4S,5S,6R)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol 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. (2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Tragopogon orientalis. Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042209082D          

 31 33  0  0  1  0            999 V2000
   -2.1434   -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
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  0  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
   -3.5724  -11.1375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -11.5500    0.0000 C   0  0  1  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
   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  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
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  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  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  2  0  0  0  0
  9 27  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    9.1923    0.1136    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0987   -0.3511    0.8149 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7860   -0.2636    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4401    0.2932   -0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1338    0.3861   -1.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1319   -0.1001   -0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175   -0.0124   -0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0925    1.3095   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6638    1.3437   -0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3339    1.8771   -2.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578    1.9258   -2.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2783    2.4724   -3.8391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9493    1.4025   -1.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6920    0.8556   -0.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6480    0.3319    0.3167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0263    0.2520    0.0964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6506    0.9064    1.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9282    0.5007    1.4050 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0179   -0.2709    2.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5793    0.6135    3.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6093   -0.2309    0.2974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9440    0.6532   -0.7137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8436   -1.4231   -0.1964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2507   -2.5702    0.4898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3822   -1.2176    0.0379 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7100   -1.7310   -1.0959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.8438   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4791   -0.6561    0.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7911   -0.7530    1.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -1.3244    2.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0437   -1.8037    3.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0135    1.1246   -0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0968    0.0745    0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3606   -0.6457   -0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2271    0.6857   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9118    0.8349   -2.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587   -0.8726   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6641   -0.0882   -1.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654    1.2866    0.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6809    2.1404   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1240    2.2757   -2.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2626    1.7938   -4.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618    1.4443   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3086    0.6735   -0.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5369    1.4353    1.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0633   -0.5147    2.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4452   -1.2050    2.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6137    0.4907    3.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5913   -0.6015    0.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5268    1.5239   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0553   -1.5048   -1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6604   -3.2112   -0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9750   -1.7883    0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2537   -2.3775   -1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1278    0.4204    0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7010   -1.0467    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3841   -2.1358    4.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3071   -0.9633    3.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899   -2.6218    2.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14 27  2  0
  6 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 29  3  1  0
 27  9  1  0
 25 16  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 10 41  1  0
 12 42  1  0
 13 43  1  0
 16 44  1  6
 18 45  1  1
 19 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  1
 22 50  1  0
 23 51  1  6
 24 52  1  0
 25 53  1  1
 26 54  1  0
 27 55  1  0
 28 56  1  0
 31 57  1  0
 31 58  1  0
 31 59  1  0
M  END


  Mrv1652309042209082D          

 31 33  0  0  1  0            999 V2000
   -2.1434   -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
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  0  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
   -3.5724  -11.1375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -11.5500    0.0000 C   0  0  1  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
   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  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
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  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  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  2  0  0  0  0
  9 27  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190470

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CCC2=CC(O)=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O9/c1-28-16-6-5-12(9-17(16)29-2)3-4-13-7-14(24)10-15(8-13)30-22-21(27)20(26)19(25)18(11-23)31-22/h5-10,18-27H,3-4,11H2,1-2H3/t18-,19-,20+,21-,22-/m1/s1

> <INCHI_KEY>
GMRCECHKJFTTSK-QMCAAQAGSA-N

> <FORMULA>
C22H28O9

> <MOLECULAR_WEIGHT>
436.457

> <EXACT_MASS>
436.173332482

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.27469372260329

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
1.3190672399999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200958219354535

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.5197885000008

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343726333

> <JCHEM_POLAR_SURFACE_AREA>
138.07

> <JCHEM_REFRACTIVITY>
109.42880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <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  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334 -19.250   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.668 -19.250   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.335 -21.560   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667 -23.100   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.668 -23.870   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.668 -25.410   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -9.336 -23.870   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -9.336 -20.790   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   14    9                                                       
CONECT   28    6   29                                                       
CONECT   29   28    3   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₉

Average Mass

436.4570 Da

Monoisotopic Mass

436.17333 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5S,6R)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CCC2=CC(O)=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2)C=C1OC

InChI Identifier

InChI=1S/C22H28O9/c1-28-16-6-5-12(9-17(16)29-2)3-4-13-7-14(24)10-15(8-13)30-22-21(27)20(26)19(25)18(11-23)31-22/h5-10,18-27H,3-4,11H2,1-2H3/t18-,19-,20+,21-,22-/m1/s1

InChI Key

GMRCECHKJFTTSK-QMCAAQAGSA-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
Tragopogon orientalis	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
Dimethoxybenzene
O-dimethoxybenzene
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Oxacycle
Acetal
Organoheterocyclic compound
Ether
Polyol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Organooxygen compound
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	1.32	ChemAxon
pKa (Strongest Acidic)	9.52	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	138.07 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	109.43 m³·mol⁻¹	ChemAxon
Polarizability	45.27 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

101418770

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0190470)

MOL for NP0190470 ((2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0190470 ((2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0190470 ((2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0190470 ((2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0190470 ((2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0190470 ((2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0190470 ((2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0190470 ((2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0190470 ((2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0190470 ((2s,3r,4s,5s,6r)-2-{3-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)