NP-MRD: Showing NP-Card for 3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside (NP0036066)

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Record Information

Version

2.0

Created at

2021-06-20 19:20:22 UTC

Updated at

2021-06-30 00:07:31 UTC

NP-MRD ID

NP0036066

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside

Provided By

JEOL Database JEOL Logo

Description

3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside is found in Scorzonera judaica. 3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside was first documented in 2011 (Bader, A., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121203D          

 72 76  0  0  0  0            999 V2000
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   -2.3273    4.7970    0.4720 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8571    3.5552    0.9566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758    2.4074    0.5617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8516    1.6197   -0.5098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8435    2.3207   -1.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0690   -0.6305   -1.6607 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
   -0.5950    6.1819   -1.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 44  1  6
 35 67  1  1
 37 69  1  1
 38 70  1  0
 13 53  1  6
  7 47  1  1
  8 48  1  0
  6 46  1  6
 33 65  1  1
 34 66  1  0
 10 50  1  0
 10 51  1  0
  9 49  1  6
 11 52  1  0
 19 56  1  1
 17 55  1  0
 16 54  1  0
 32 64  1  0
 31 63  1  0
 26 62  1  0
 23 60  1  0
 24 61  1  0
 22 59  1  0
 20 57  1  0
 20 58  1  0
M  END


  Mrv1652306202121203D          

 72 76  0  0  0  0            999 V2000
   -0.5950    6.1819   -1.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1183    6.1144   -1.5231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5391    4.8721   -0.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3273    4.7970    0.4720 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8571    3.5552    0.9566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758    2.4074    0.5617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8516    1.6197   -0.5098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8435    2.3207   -1.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2290    0.2329   -0.7134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0690   -0.6305   -1.6607 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4863   -1.9350   -1.7501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1316   -0.4740    0.5337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2553    0.1873    1.4461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1375   -0.5496    2.6720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -1.6986    2.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1977   -2.2811    3.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5440   -3.4586    4.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1096   -4.0851    2.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944   -5.3767    3.1070 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6655   -5.9599    1.9185 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8642   -5.1039    1.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789   -4.9938    0.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5011   -4.2005    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   -3.5278    1.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6286   -3.6515    2.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3141   -2.9801    3.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4947   -4.4344    2.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819   -4.5917    4.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6360   -4.1799    5.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958   -5.2303    4.2308 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8837   -3.5011    1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -2.3180    1.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412    1.5612    1.8193 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9540    2.2720    2.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0835    5.9116    1.2140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8029    5.8613    2.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714    7.2856    0.6864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3448    7.5965    1.1275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7614    7.3432   -0.8412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1473    7.3887   -1.2159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1168    6.2022   -0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744    7.0698   -2.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2087    5.2947   -2.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926    6.0720   -2.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2600    4.8348    0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086    2.7369    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982    1.5250   -0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0128    3.2686   -1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2213    0.3151   -1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134   -0.2045   -2.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0890   -0.7569   -1.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3972   -2.2377   -0.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558    0.3266    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199   -1.8181    4.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826   -3.8846    5.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1572   -6.1329    3.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -6.9592    2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212   -6.0652    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107   -5.5196   -0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8977   -4.1094   -0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0023   -2.9155    0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9239   -3.2142    4.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -3.9441    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020   -1.9191    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7859    1.4364    2.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7786    1.6687    3.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1643    5.7734    1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9043    4.9195    2.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263    8.0445    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429    7.3802    2.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2900    8.2557   -1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871    8.2681   -0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
 33 34  1  0  0  0  0
 10 11  1  0  0  0  0
 37 38  1  0  0  0  0
 19 18  1  0  0  0  0
 39 37  1  0  0  0  0
 18 17  1  0  0  0  0
 37 35  1  0  0  0  0
 17 16  2  0  0  0  0
 35  4  1  0  0  0  0
 16 15  1  0  0  0  0
  4  3  1  0  0  0  0
 15 32  2  0  0  0  0
  3  2  1  0  0  0  0
 32 31  1  0  0  0  0
 31 18  2  0  0  0  0
 15 14  1  0  0  0  0
  2 39  1  0  0  0  0
  4  5  1  0  0  0  0
 23 24  2  0  0  0  0
 13 33  1  0  0  0  0
 24 25  1  0  0  0  0
 25 27  2  0  0  0  0
 33  6  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7  8  1  0  0  0  0
 21 20  1  0  0  0  0
 27 28  1  0  0  0  0
 28 30  1  0  0  0  0
 30 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6  5  1  0  0  0  0
 28 29  2  0  0  0  0
 13 14  1  0  0  0  0
 39 40  1  0  0  0  0
  2  1  1  0  0  0  0
 35 36  1  0  0  0  0
  9 10  1  0  0  0  0
 36 68  1  0  0  0  0
 40 72  1  0  0  0  0
 39 71  1  6  0  0  0
  4 45  1  6  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  1 43  1  0  0  0  0
  2 44  1  6  0  0  0
 35 67  1  1  0  0  0
 37 69  1  1  0  0  0
 38 70  1  0  0  0  0
 13 53  1  6  0  0  0
  7 47  1  1  0  0  0
  8 48  1  0  0  0  0
  6 46  1  6  0  0  0
 33 65  1  1  0  0  0
 34 66  1  0  0  0  0
 10 50  1  0  0  0  0
 10 51  1  0  0  0  0
  9 49  1  6  0  0  0
 11 52  1  0  0  0  0
 19 56  1  1  0  0  0
 17 55  1  0  0  0  0
 16 54  1  0  0  0  0
 32 64  1  0  0  0  0
 31 63  1  0  0  0  0
 26 62  1  0  0  0  0
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 22 59  1  0  0  0  0
 20 57  1  0  0  0  0
 20 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036066

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)O[C@@]([H])(C3=C([H])C([H])=C(O[C@@]4([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[C@@]5([H])O[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@]5([H])O[H])[C@]4([H])O[H])C([H])=C3[H])C([H])([H])C2=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O13/c1-11-19(30)21(32)22(33)26(36-11)40-24-20(31)17(10-28)39-27(23(24)34)37-14-7-5-12(6-8-14)16-9-13-3-2-4-15(29)18(13)25(35)38-16/h2-8,11,16-17,19-24,26-34H,9-10H2,1H3/t11-,16-,17+,19-,20+,21+,22+,23+,24-,26-,27+/m1/s1

> <INCHI_KEY>
KAWWUODRABPWGU-JWSNHHPASA-N

> <FORMULA>
C27H32O13

> <MOLECULAR_WEIGHT>
564.54

> <EXACT_MASS>
564.18429109

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.80983248450265

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-(4-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}phenyl)-8-hydroxy-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
-0.07

> <JCHEM_LOGP>
0.6517270579999999

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.943068229507785

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.645004539201734

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981099567710814

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
132.65150000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-(4-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}phenyl)-8-hydroxy-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
   -0.5950    6.1819   -1.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1183    6.1144   -1.5231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5391    4.8721   -0.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3273    4.7970    0.4720 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8571    3.5552    0.9566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758    2.4074    0.5617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8516    1.6197   -0.5098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8435    2.3207   -1.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2290    0.2329   -0.7134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0690   -0.6305   -1.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4863   -1.9350   -1.7501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1316   -0.4740    0.5337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2553    0.1873    1.4461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1375   -0.5496    2.6720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -1.6986    2.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1977   -2.2811    3.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5440   -3.4586    4.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1096   -4.0851    2.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944   -5.3767    3.1070 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6655   -5.9599    1.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642   -5.1039    1.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789   -4.9938    0.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5011   -4.2005    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   -3.5278    1.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6286   -3.6515    2.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3141   -2.9801    3.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4947   -4.4344    2.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819   -4.5917    4.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6360   -4.1799    5.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8837   -3.5011    1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -2.3180    1.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412    1.5612    1.8193 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.8029    5.8613    2.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714    7.2856    0.6864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3448    7.5965    1.1275 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1473    7.3887   -1.2159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1168    6.2022   -0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744    7.0698   -2.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2600    4.8348    0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0128    3.2686   -1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2213    0.3151   -1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134   -0.2045   -2.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3972   -2.2377   -0.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558    0.3266    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199   -1.8181    4.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826   -3.8846    5.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1572   -6.1329    3.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -6.9592    2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212   -6.0652    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107   -5.5196   -0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8977   -4.1094   -0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0023   -2.9155    0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9239   -3.2142    4.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -3.9441    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020   -1.9191    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7859    1.4364    2.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7786    1.6687    3.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1643    5.7734    1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9043    4.9195    2.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263    8.0445    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429    7.3802    2.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2900    8.2557   -1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871    8.2681   -0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
 33 34  1  0
 10 11  1  0
 37 38  1  0
 19 18  1  0
 39 37  1  0
 18 17  1  0
 37 35  1  0
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 35  4  1  0
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  3  2  1  0
 32 31  1  0
 31 18  2  0
 15 14  1  0
  2 39  1  0
  4  5  1  0
 23 24  2  0
 13 33  1  0
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 25 27  2  0
 33  6  1  0
 21 22  2  0
 22 23  1  0
 25 26  1  0
 21 27  1  0
  6  7  1  0
  7  9  1  0
  9 12  1  0
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  7  8  1  0
 21 20  1  0
 27 28  1  0
 28 30  1  0
 30 19  1  0
 19 20  1  0
  6  5  1  0
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 35 36  1  0
  9 10  1  0
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 40 72  1  0
 39 71  1  6
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 17 55  1  0
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 22 59  1  0
 20 57  1  0
 20 58  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.595   6.182  -1.609  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.118   6.114  -1.523  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.539   4.872  -0.932  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.327   4.797   0.472  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.857   3.555   0.957  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.076   2.407   0.562  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.852   1.620  -0.510  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.844   2.321  -1.755  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.229   0.233  -0.713  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.069  -0.631  -1.661  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.486  -1.935  -1.750  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.132  -0.474   0.534  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.255   0.187   1.446  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.137  -0.550   2.672  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.398  -1.699   2.656  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.198  -2.281   3.906  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.544  -3.459   4.033  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.110  -4.085   2.910  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.894  -5.377   3.107  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.666  -5.960   1.919  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.864  -5.104   1.627  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.379  -4.994   0.329  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.501  -4.200   0.087  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.124  -3.528   1.139  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.629  -3.652   2.435  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.314  -2.980   3.412  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.495  -4.434   2.687  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.982  -4.592   4.070  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.636  -4.180   5.023  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.796  -5.230   4.231  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.884  -3.501   1.656  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.142  -2.318   1.531  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.841   1.561   1.819  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.954   2.272   2.703  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.083   5.912   1.214  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.803   5.861   2.626  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.671   7.286   0.686  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.345   7.596   1.127  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.761   7.343  -0.841  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.147   7.389  -1.216  0.00  0.00           O+0
HETATM   41  H   UNK     0      -0.117   6.202  -0.627  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.274   7.070  -2.163  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.209   5.295  -2.123  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.493   6.072  -2.554  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.260   4.835   0.721  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.109   2.737   0.158  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.898   1.525  -0.195  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.013   3.269  -1.555  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.221   0.315  -1.143  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.113  -0.205  -2.667  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.089  -0.757  -1.283  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.397  -2.238  -0.826  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.256   0.327   1.010  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.620  -1.818   4.795  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.683  -3.885   5.027  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.157  -6.133   3.407  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.038  -6.959   2.179  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.021  -6.065   1.039  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.911  -5.520  -0.501  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.898  -4.109  -0.921  0.00  0.00           H+0
HETATM   61  H   UNK     0       7.002  -2.916   0.952  0.00  0.00           H+0
HETATM   62  H   UNK     0       5.924  -3.214   4.283  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.275  -3.944   0.744  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.002  -1.919   0.531  0.00  0.00           H+0
HETATM   65  H   UNK     0      -2.786   1.436   2.364  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.779   1.669   3.451  0.00  0.00           H+0
HETATM   67  H   UNK     0      -4.164   5.773   1.088  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.904   4.920   2.875  0.00  0.00           H+0
HETATM   69  H   UNK     0      -3.326   8.044   1.132  0.00  0.00           H+0
HETATM   70  H   UNK     0      -1.343   7.380   2.084  0.00  0.00           H+0
HETATM   71  H   UNK     0      -2.290   8.256  -1.225  0.00  0.00           H+0
HETATM   72  H   UNK     0      -4.487   8.268  -0.972  0.00  0.00           H+0
CONECT    1    2   41   42   43                                             
CONECT    2    3   39    1   44                                             
CONECT    3    4    2                                                       
CONECT    4   35    3    5   45                                             
CONECT    5    4    6                                                       
CONECT    6   33    7    5   46                                             
CONECT    7    6    9    8   47                                             
CONECT    8    7   48                                                       
CONECT    9    7   12   10   49                                             
CONECT   10   11    9   50   51                                             
CONECT   11   10   52                                                       
CONECT   12    9   13                                                       
CONECT   13   33   12   14   53                                             
CONECT   14   15   13                                                       
CONECT   15   16   32   14                                                  
CONECT   16   17   15   54                                                  
CONECT   17   18   16   55                                                  
CONECT   18   19   17   31                                                  
CONECT   19   18   30   20   56                                             
CONECT   20   21   19   57   58                                             
CONECT   21   22   27   20                                                  
CONECT   22   21   23   59                                                  
CONECT   23   24   22   60                                                  
CONECT   24   23   25   61                                                  
CONECT   25   24   27   26                                                  
CONECT   26   25   62                                                       
CONECT   27   25   21   28                                                  
CONECT   28   27   30   29                                                  
CONECT   29   28                                                            
CONECT   30   28   19                                                       
CONECT   31   32   18   63                                                  
CONECT   32   15   31   64                                                  
CONECT   33   34   13    6   65                                             
CONECT   34   33   66                                                       
CONECT   35   37    4   36   67                                             
CONECT   36   35   68                                                       
CONECT   37   38   39   35   69                                             
CONECT   38   37   70                                                       
CONECT   39   37    2   40   71                                             
CONECT   40   39   72                                                       
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    2                                                            
CONECT   45    4                                                            
CONECT   46    6                                                            
CONECT   47    7                                                            
CONECT   48    8                                                            
CONECT   49    9                                                            
CONECT   50   10                                                            
CONECT   51   10                                                            
CONECT   52   11                                                            
CONECT   53   13                                                            
CONECT   54   16                                                            
CONECT   55   17                                                            
CONECT   56   19                                                            
CONECT   57   20                                                            
CONECT   58   20                                                            
CONECT   59   22                                                            
CONECT   60   23                                                            
CONECT   61   24                                                            
CONECT   62   26                                                            
CONECT   63   31                                                            
CONECT   64   32                                                            
CONECT   65   33                                                            
CONECT   66   34                                                            
CONECT   67   35                                                            
CONECT   68   36                                                            
CONECT   69   37                                                            
CONECT   70   38                                                            
CONECT   71   39                                                            
CONECT   72   40                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  152    0
END

RDKit          3D

72 76  0  0  0  0  0  0  0  0999 V2000
   -0.5950    6.1819   -1.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8571    3.5552    0.9566 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8516    1.6197   -0.5098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8435    2.3207   -1.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2290    0.2329   -0.7134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0690   -0.6305   -1.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4863   -1.9350   -1.7501 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2553    0.1873    1.4461 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.8412    1.5612    1.8193 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.1473    7.3887   -1.2159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1168    6.2022   -0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8977   -4.1094   -0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9239   -3.2142    4.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -3.9441    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020   -1.9191    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7859    1.4364    2.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7786    1.6687    3.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1643    5.7734    1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9043    4.9195    2.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263    8.0445    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429    7.3802    2.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2900    8.2557   -1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871    8.2681   -0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
 33 34  1  0
 10 11  1  0
 37 38  1  0
 19 18  1  0
 39 37  1  0
 18 17  1  0
 37 35  1  0
 17 16  2  0
 35  4  1  0
 16 15  1  0
  4  3  1  0
 15 32  2  0
  3  2  1  0
 32 31  1  0
 31 18  2  0
 15 14  1  0
  2 39  1  0
  4  5  1  0
 23 24  2  0
 13 33  1  0
 24 25  1  0
 25 27  2  0
 33  6  1  0
 21 22  2  0
 22 23  1  0
 25 26  1  0
 21 27  1  0
  6  7  1  0
  7  9  1  0
  9 12  1  0
 12 13  1  0
  7  8  1  0
 21 20  1  0
 27 28  1  0
 28 30  1  0
 30 19  1  0
 19 20  1  0
  6  5  1  0
 28 29  2  0
 13 14  1  0
 39 40  1  0
  2  1  1  0
 35 36  1  0
  9 10  1  0
 36 68  1  0
 40 72  1  0
 39 71  1  6
  4 45  1  6
  1 41  1  0
  1 42  1  0
  1 43  1  0
  2 44  1  6
 35 67  1  1
 37 69  1  1
 38 70  1  0
 13 53  1  6
  7 47  1  1
  8 48  1  0
  6 46  1  6
 33 65  1  1
 34 66  1  0
 10 50  1  0
 10 51  1  0
  9 49  1  6
 11 52  1  0
 19 56  1  1
 17 55  1  0
 16 54  1  0
 32 64  1  0
 31 63  1  0
 26 62  1  0
 23 60  1  0
 24 61  1  0
 22 59  1  0
 20 57  1  0
 20 58  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₁₃

Average Mass

564.5400 Da

Monoisotopic Mass

564.18429 Da

IUPAC Name

(3R)-3-(4-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}phenyl)-8-hydroxy-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

(3R)-3-(4-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}phenyl)-8-hydroxy-3,4-dihydro-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(=O)O[C@@]([H])(C3=C([H])C([H])=C(O[C@@]4([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[C@@]5([H])O[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@]5([H])O[H])[C@]4([H])O[H])C([H])=C3[H])C([H])([H])C2=C([H])C([H])=C1[H]

InChI Identifier

InChI=1S/C27H32O13/c1-11-19(30)21(32)22(33)26(36-11)40-24-20(31)17(10-28)39-27(23(24)34)37-14-7-5-12(6-8-14)16-9-13-3-2-4-15(29)18(13)25(35)38-16/h2-8,11,16-17,19-24,26-34H,9-10H2,1H3/t11-,16-,17+,19-,20+,21+,22+,23+,24-,26-,27+/m1/s1

InChI Key

KAWWUODRABPWGU-JWSNHHPASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Scorzonera judaica	JEOL database	Bader, A., et al, J. Nat. Prod. 74, 1421 (2011)

Chemical Taxonomy

Classification

Not classified

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	-0.07	ALOGPS
logP	0.65	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.65	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	132.65 m³·mol⁻¹	ChemAxon
Polarizability	55.81 Å³	ChemAxon
Number of Rings	5	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

Not Available

References

General References

Bader, A., et al. (2011). Bader, A., et al, J. Nat. Prod. 74, 1421 (2011). J. Nat. Prod..

Showing NP-Card for 3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside (NP0036066)

MOL for NP0036066 (3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside)

3D MOL for NP0036066 (3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside)

3D SDF for NP0036066 (3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside)

3D-SDF for NP0036066 (3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside)

PDB for NP0036066 (3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside)

3D PDB for NP0036066 (3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside)

SMILES for NP0036066 (3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside)

INCHI for NP0036066 (3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside)

Structure for NP0036066 (3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside)

3D Structure for NP0036066 (3S-hydrangenol 4'-O-alpha-L-rhamnopyranoysl-(1-3)-beta-D-glucopyranoside)