NP-MRD: Showing NP-Card for saccharumoside B (NP0036376)

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Record Information

Version

2.0

Created at

2021-06-20 19:33:57 UTC

Updated at

2021-06-30 00:08:00 UTC

NP-MRD ID

NP0036376

Secondary Accession Numbers

None

Natural Product Identification

Common Name

saccharumoside B

Provided By

JEOL Database JEOL Logo

Description

Saccharumoside B belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. saccharumoside B is found in Acer saccharum. saccharumoside B was first documented in 2011 (Yuan, T., et al.). Based on a literature review very few articles have been published on Saccharumoside B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121333D          

 59 61  0  0  0  0            999 V2000
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    2.6045    0.2705   -2.7973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890    0.8099   -1.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149    0.8973   -0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    1.4338    0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325    1.4795    1.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726    1.6144    2.5734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9775    1.3386    0.5970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997    1.0271    1.2992 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5083   -0.4549    1.0531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4230   -1.2394    1.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540   -2.6285    1.2632 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4514   -3.3749    1.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774   -3.2064    1.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6576   -2.3398    1.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3406   -2.7055   -1.1470 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.8760   -3.9431   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0489   -4.5705    1.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6876    1.2613   -0.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8600    1.1718   -1.6747 O   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  2  0  0  0  0
  5  6  1  0  0  0  0
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  6  8  1  0  0  0  0
 12 24  1  0  0  0  0
 24 26  1  0  0  0  0
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  3 32  1  0  0  0  0
  6  7  2  0  0  0  0
 32 31  2  0  0  0  0
 15 14  2  0  0  0  0
  8  9  1  0  0  0  0
 14 21  1  0  0  0  0
 31 30  1  0  0  0  0
 21 20  2  0  0  0  0
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 20 17  1  0  0  0  0
  5  4  1  0  0  0  0
 17 16  2  0  0  0  0
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  3  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121333D          

 59 61  0  0  0  0            999 V2000
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   -4.9293   -0.1612    1.1634 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593    1.8800    1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337    1.7973    0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876    1.2613   -0.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8600    1.1718   -1.6747 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405   -0.3520   -4.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8606   -0.8544   -2.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7478    0.8574   -3.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3751    0.5241   -1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9840    1.6664    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6117   -2.7657    0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8002   -0.6809    2.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5916    2.2833    2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6772    2.1389    0.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241    0.8135   -2.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  6  1  0  0  0  0
 30  5  2  0  0  0  0
  6  8  1  0  0  0  0
 12 24  1  0  0  0  0
 24 26  1  0  0  0  0
 26 28  1  0  0  0  0
 28 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 28 29  1  0  0  0  0
 26 27  1  0  0  0  0
 24 25  1  0  0  0  0
  3 32  1  0  0  0  0
  6  7  2  0  0  0  0
 32 31  2  0  0  0  0
 15 14  2  0  0  0  0
  8  9  1  0  0  0  0
 14 21  1  0  0  0  0
 31 30  1  0  0  0  0
 21 20  2  0  0  0  0
 32 33  1  0  0  0  0
 20 17  1  0  0  0  0
  5  4  1  0  0  0  0
 17 16  2  0  0  0  0
 16 15  1  0  0  0  0
 17 18  1  0  0  0  0
  3  2  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 13  1  0  0  0  0
  2  1  1  0  0  0  0
 18 19  1  0  0  0  0
 10  9  1  0  0  0  0
 12 13  1  0  0  0  0
 31 58  1  0  0  0  0
 30 57  1  0  0  0  0
  4 37  1  0  0  0  0
 33 59  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  9 38  1  0  0  0  0
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 12 41  1  6  0  0  0
 28 55  1  1  0  0  0
 29 56  1  0  0  0  0
 26 53  1  6  0  0  0
 27 54  1  0  0  0  0
 24 51  1  1  0  0  0
 25 52  1  0  0  0  0
 10 40  1  6  0  0  0
 18 44  1  0  0  0  0
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 15 42  1  0  0  0  0
 20 47  1  0  0  0  0
 16 43  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 23 50  1  0  0  0  0
 19 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036376

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])C(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([H])C([H])=C(C([H])=C2OC([H])([H])[H])C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O11/c1-29-15-8-12(4-5-13(15)24)21(28)31-10-17-18(25)19(26)20(27)22(33-17)32-14-6-3-11(9-23)7-16(14)30-2/h3-8,17-20,22-27H,9-10H2,1-2H3/t17-,18-,19+,20-,22-/m1/s1

> <INCHI_KEY>
XDCJBRVCYFCQAN-OUUKCGNVSA-N

> <FORMULA>
C22H26O11

> <MOLECULAR_WEIGHT>
466.439

> <EXACT_MASS>
466.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.72692335723412

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
0.65

> <JCHEM_LOGP>
0.5106546293333336

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20102558510016

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.991473716237511

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8257256427161535

> <JCHEM_POLAR_SURFACE_AREA>
164.37

> <JCHEM_REFRACTIVITY>
111.72850000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
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   -2.8264   -3.1954    1.9205 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.2142   -2.8011    2.1948 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7337    1.7973    0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876    1.2613   -0.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  2  0
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 26 28  1  0
 28 10  1  0
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 31 30  1  0
 21 20  2  0
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 17 16  2  0
 16 15  1  0
 17 18  1  0
  3  2  1  0
 21 22  1  0
 22 23  1  0
 14 13  1  0
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 18 19  1  0
 10  9  1  0
 12 13  1  0
 31 58  1  0
 30 57  1  0
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 26 53  1  6
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 16 43  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 19 46  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       1.386  -0.029  -3.475  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.604   0.271  -2.797  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.489   0.810  -1.541  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.315   0.897  -0.794  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.347   1.434   0.505  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.133   1.480   1.362  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.173   1.614   2.573  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.978   1.339   0.597  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.200   1.027   1.299  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.508  -0.455   1.053  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.423  -1.239   1.573  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.554  -2.628   1.263  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.451  -3.375   1.808  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.677  -3.206   1.045  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.658  -2.340   1.527  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.843  -2.171   0.815  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.055  -2.870  -0.380  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.341  -2.705  -1.147  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.062  -2.336  -2.491  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.065  -3.759  -0.842  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.876  -3.943  -0.131  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.138  -4.794  -0.488  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.104  -5.657  -1.593  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.826  -3.195   1.921  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.049  -4.571   1.563  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.042  -2.382   1.478  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.214  -2.801   2.195  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.824  -0.883   1.709  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.929  -0.161   1.163  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.559   1.880   1.051  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.734   1.797   0.305  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.688   1.261  -0.976  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.860   1.172  -1.675  0.00  0.00           O+0
HETATM   34  H   UNK     0       1.641  -0.352  -4.489  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.861  -0.854  -2.984  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.748   0.857  -3.556  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.375   0.524  -1.186  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.984   1.666   0.882  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.121   1.241   2.371  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.551  -0.606  -0.034  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.612  -2.766   0.175  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.493  -1.795   2.454  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.599  -1.488   1.199  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.901  -3.646  -1.148  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.978  -1.931  -0.707  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.475  -1.560  -2.442  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.261  -4.296  -1.766  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.766  -6.311  -1.701  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.979  -6.292  -1.418  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.207  -5.085  -2.521  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.738  -3.170   3.014  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.181  -5.014   1.657  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.264  -2.572   0.420  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.198  -3.780   2.158  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.800  -0.681   2.787  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.726  -0.613   1.512  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.592   2.283   2.062  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.677   2.139   0.721  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.624   0.814  -2.552  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    3    1                                                       
CONECT    3    4   32    2                                                  
CONECT    4    3    5   37                                                  
CONECT    5    6   30    4                                                  
CONECT    6    5    8    7                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   38   39                                             
CONECT   10   28   11    9   40                                             
CONECT   11   10   12                                                       
CONECT   12   24   11   13   41                                             
CONECT   13   14   12                                                       
CONECT   14   15   21   13                                                  
CONECT   15   14   16   42                                                  
CONECT   16   17   15   43                                                  
CONECT   17   20   16   18                                                  
CONECT   18   17   19   44   45                                             
CONECT   19   18   46                                                       
CONECT   20   21   17   47                                                  
CONECT   21   14   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   48   49   50                                             
CONECT   24   12   26   25   51                                             
CONECT   25   24   52                                                       
CONECT   26   24   28   27   53                                             
CONECT   27   26   54                                                       
CONECT   28   26   10   29   55                                             
CONECT   29   28   56                                                       
CONECT   30    5   31   57                                                  
CONECT   31   32   30   58                                                  
CONECT   32    3   31   33                                                  
CONECT   33   32   59                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    4                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   12                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
CONECT   50   23                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   27                                                            
CONECT   55   28                                                            
CONECT   56   29                                                            
CONECT   57   30                                                            
CONECT   58   31                                                            
CONECT   59   33                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

RDKit          3D

59 61  0  0  0  0  0  0  0  0999 V2000
    1.3861   -0.0287   -3.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045    0.2705   -2.7973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890    0.8099   -1.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149    0.8973   -0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    1.4338    0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325    1.4795    1.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726    1.6144    2.5734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9775    1.3386    0.5970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997    1.0271    1.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083   -0.4549    1.0531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4230   -1.2394    1.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540   -2.6285    1.2632 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4514   -3.3749    1.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774   -3.2064    1.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6576   -2.3398    1.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8432   -2.1706    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0550   -2.8704   -0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3406   -2.7055   -1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0618   -2.3362   -2.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0650   -3.7587   -0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760   -3.9431   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376   -4.7941   -0.4878 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041   -5.6566   -1.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8264   -3.1954    1.9205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0489   -4.5705    1.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0419   -2.3819    1.4778 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2142   -2.8011    2.1948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8240   -0.8834    1.7092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9293   -0.1612    1.1634 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593    1.8800    1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337    1.7973    0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876    1.2613   -0.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8600    1.1718   -1.6747 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405   -0.3520   -4.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8606   -0.8544   -2.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7478    0.8574   -3.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3751    0.5241   -1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9840    1.6664    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1212    1.2414    2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512   -0.6063   -0.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6117   -2.7657    0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926   -1.7947    2.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5985   -1.4880    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9006   -3.6461   -1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9776   -1.9313   -0.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4749   -1.5595   -2.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614   -4.2964   -1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7659   -6.3115   -1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790   -6.2915   -1.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2071   -5.0851   -2.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7378   -3.1698    3.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1806   -5.0138    1.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2636   -2.5721    0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1980   -3.7796    2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8002   -0.6809    2.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7257   -0.6126    1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5916    2.2833    2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6772    2.1389    0.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241    0.8135   -2.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0
  5  6  1  0
 30  5  2  0
  6  8  1  0
 12 24  1  0
 24 26  1  0
 26 28  1  0
 28 10  1  0
 10 11  1  0
 11 12  1  0
 28 29  1  0
 26 27  1  0
 24 25  1  0
  3 32  1  0
  6  7  2  0
 32 31  2  0
 15 14  2  0
  8  9  1  0
 14 21  1  0
 31 30  1  0
 21 20  2  0
 32 33  1  0
 20 17  1  0
  5  4  1  0
 17 16  2  0
 16 15  1  0
 17 18  1  0
  3  2  1  0
 21 22  1  0
 22 23  1  0
 14 13  1  0
  2  1  1  0
 18 19  1  0
 10  9  1  0
 12 13  1  0
 31 58  1  0
 30 57  1  0
  4 37  1  0
 33 59  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  9 38  1  0
  9 39  1  0
 12 41  1  6
 28 55  1  1
 29 56  1  0
 26 53  1  6
 27 54  1  0
 24 51  1  1
 25 52  1  0
 10 40  1  6
 18 44  1  0
 18 45  1  0
 15 42  1  0
 20 47  1  0
 16 43  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 19 46  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₁₁

Average Mass

466.4390 Da

Monoisotopic Mass

466.14751 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])C(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([H])C([H])=C(C([H])=C2OC([H])([H])[H])C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C22H26O11/c1-29-15-8-12(4-5-13(15)24)21(28)31-10-17-18(25)19(26)20(27)22(33-17)32-14-6-3-11(9-23)7-16(14)30-2/h3-8,17-20,22-27H,9-10H2,1-2H3/t17-,18-,19+,20-,22-/m1/s1

InChI Key

XDCJBRVCYFCQAN-OUUKCGNVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Acer saccharum	JEOL database	Yuan, T., et al, J. Nat. Prod. 74, 2472 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Phenolic glycoside
M-methoxybenzoic acid or derivatives
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-glycosyl compound
Glycosyl compound
Methoxyphenol
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Anisole
Phenol ether
Benzyl alcohol
Benzoyl
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Aromatic alcohol
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tannin (CHEBI:68960 )

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	0.65	ALOGPS
logP	0.51	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	111.73 m³·mol⁻¹	ChemAxon
Polarizability	44.73 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

28478379

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56834590

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yuan, T., et al. (2011). Yuan, T., et al, J. Nat. Prod. 74, 2472 (2011). J. Nat. Prod..

Showing NP-Card for saccharumoside B (NP0036376)

MOL for NP0036376 (saccharumoside B)

3D MOL for NP0036376 (saccharumoside B)

3D SDF for NP0036376 (saccharumoside B)

3D-SDF for NP0036376 (saccharumoside B)

PDB for NP0036376 (saccharumoside B)

3D PDB for NP0036376 (saccharumoside B)

SMILES for NP0036376 (saccharumoside B)

INCHI for NP0036376 (saccharumoside B)

Structure for NP0036376 (saccharumoside B)

3D Structure for NP0036376 (saccharumoside B)