NP-MRD: Showing NP-Card for shomaside F (NP0035222)

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Record Information

Version

2.0

Created at

2021-06-20 18:43:41 UTC

Updated at

2021-06-30 00:06:05 UTC

NP-MRD ID

NP0035222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

shomaside F

Provided By

JEOL Database JEOL Logo

Description

Shomaside F belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. shomaside F is found in Cimicifuga japonica, Meehania urticifolia and Trifolium lupinaster. shomaside F was first documented in 2010 (PMID: 20184336). Based on a literature review very few articles have been published on Shomaside F.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120433D          

 50 52  0  0  0  0            999 V2000
    1.7242   -1.2244   -1.5038 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147   -1.0968   -0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -1.6469    0.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -2.4319    0.4287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0647   -1.5968    0.6938 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1135   -0.5122   -0.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    0.3708   -0.0299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2423    1.4274   -1.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2524    2.3692   -0.9672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685    3.3662   -1.9409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4268    4.3921   -2.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412    4.4265   -1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    5.4610   -1.2951 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202120433D          

 50 52  0  0  0  0            999 V2000
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 12 11  1  0  0  0  0
 11 10  2  0  0  0  0
  9  8  1  0  0  0  0
  6  7  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 23 24  1  0  0  0  0
 15 16  2  0  0  0  0
 21 22  1  0  0  0  0
 15 17  1  0  0  0  0
 19 20  1  0  0  0  0
  4  3  1  0  0  0  0
 28 27  1  0  0  0  0
  7 19  1  0  0  0  0
 27 26  2  0  0  0  0
 10  9  1  0  0  0  0
 26 25  1  0  0  0  0
 19 21  1  0  0  0  0
 25 30  2  0  0  0  0
  9 18  2  0  0  0  0
 30 29  1  0  0  0  0
 29 28  2  0  0  0  0
 21 23  1  0  0  0  0
 25  2  1  0  0  0  0
 18 14  1  0  0  0  0
  2  1  2  0  0  0  0
  2  3  1  0  0  0  0
  7  8  1  0  0  0  0
  5  4  1  0  0  0  0
  7 34  1  1  0  0  0
 23 44  1  6  0  0  0
 24 45  1  0  0  0  0
 21 42  1  1  0  0  0
 22 43  1  0  0  0  0
 19 40  1  6  0  0  0
 20 41  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  5 33  1  1  0  0  0
 10 35  1  0  0  0  0
 18 39  1  0  0  0  0
 11 36  1  0  0  0  0
 13 37  1  0  0  0  0
 17 38  1  0  0  0  0
 28 48  1  0  0  0  0
 27 47  1  0  0  0  0
 26 46  1  0  0  0  0
 30 50  1  0  0  0  0
 29 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(O[H])C([H])=C([H])C(O[C@]2([H])O[C@]([H])(C([H])([H])OC(=O)C3=C([H])C([H])=C([H])C([H])=C3[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O10/c21-13-7-6-11(8-12(13)18(25)26)29-20-17(24)16(23)15(22)14(30-20)9-28-19(27)10-4-2-1-3-5-10/h1-8,14-17,20-24H,9H2,(H,25,26)/t14-,15-,16+,17-,20-/m1/s1

> <INCHI_KEY>
WPXSPUCEGBJXAA-ISIBIEBGSA-N

> <FORMULA>
C20H20O10

> <MOLECULAR_WEIGHT>
420.37

> <EXACT_MASS>
420.105646844

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.67720978325064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{[(2S,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxybenzoic acid

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
1.9009298360000002

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.195092001659527

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.512085276422396

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649110481310685

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
99.24240000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[(2S,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    1.7242   -1.2244   -1.5038 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147   -1.0968   -0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -1.6469    0.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -2.4319    0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0647   -1.5968    0.6938 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1135   -0.5122   -0.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    0.3708   -0.0299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2423    1.4274   -1.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2524    2.3692   -0.9672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685    3.3662   -1.9409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4268    4.3921   -2.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412    4.4265   -1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    5.4610   -1.2951 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702    3.4386   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9153    3.4926    0.7802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8214    4.3066    0.7101 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743    2.5530    1.7382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1805    2.4070   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5402   -0.3947   -0.2006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6799    0.4354    0.0799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5690   -1.5877    0.7502 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7399   -2.3866    0.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262   -2.4608    0.5697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3405   -3.4962    1.5548 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1565   -0.2704    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320    0.6400   -0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8051    1.4379   -0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3140    1.3247    0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7529    0.4142    1.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -0.3819    1.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311   -3.3022    1.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2192   -2.8020   -0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9820   -1.1728    1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735    0.8111    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1960    3.3410   -2.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    5.1585   -2.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2515    5.3588   -0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262    2.6498    2.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538    1.6369    0.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6553   -0.7403   -1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5835    1.2228   -0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6482   -1.2488    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4809   -1.7479    0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3628   -2.9459   -0.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -3.8811    1.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3429    0.7328   -1.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    2.1471   -1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1548    1.9433    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1600    0.3173    2.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543   -1.0917    2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  5  1  0
 14 12  2  0
  5  6  1  0
 12 11  1  0
 11 10  2  0
  9  8  1  0
  6  7  1  0
 12 13  1  0
 14 15  1  0
 23 24  1  0
 15 16  2  0
 21 22  1  0
 15 17  1  0
 19 20  1  0
  4  3  1  0
 28 27  1  0
  7 19  1  0
 27 26  2  0
 10  9  1  0
 26 25  1  0
 19 21  1  0
 25 30  2  0
  9 18  2  0
 30 29  1  0
 29 28  2  0
 21 23  1  0
 25  2  1  0
 18 14  1  0
  2  1  2  0
  2  3  1  0
  7  8  1  0
  5  4  1  0
  7 34  1  1
 23 44  1  6
 24 45  1  0
 21 42  1  1
 22 43  1  0
 19 40  1  6
 20 41  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  1
 10 35  1  0
 18 39  1  0
 11 36  1  0
 13 37  1  0
 17 38  1  0
 28 48  1  0
 27 47  1  0
 26 46  1  0
 30 50  1  0
 29 49  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  O   UNK     0       1.724  -1.224  -1.504  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.015  -1.097  -0.326  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.369  -1.647   0.732  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.197  -2.432   0.429  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.065  -1.597   0.694  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.113  -0.512  -0.247  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.214   0.371  -0.030  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.242   1.427  -1.002  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.252   2.369  -0.967  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.369   3.366  -1.941  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.427   4.392  -2.029  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.641   4.426  -1.139  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.525   5.461  -1.295  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.770   3.439  -0.154  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.915   3.493   0.780  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.821   4.307   0.710  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.874   2.553   1.738  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.181   2.407  -0.074  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.540  -0.395  -0.201  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.680   0.435   0.080  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.569  -1.588   0.750  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.740  -2.387   0.516  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.326  -2.461   0.570  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.341  -3.496   1.555  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.156  -0.270   0.148  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.732   0.640  -0.748  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.805   1.438  -0.347  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.314   1.325   0.947  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.753   0.414   1.842  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.675  -0.382   1.446  0.00  0.00           C+0
HETATM   31  H   UNK     0       0.231  -3.302   1.092  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.219  -2.802  -0.603  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.982  -1.173   1.704  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.174   0.811   0.976  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.196   3.341  -2.646  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.523   5.159  -2.793  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.252   5.359  -0.643  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.726   2.650   2.214  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.054   1.637   0.679  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.655  -0.740  -1.236  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.583   1.223  -0.492  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.648  -1.249   1.791  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.481  -1.748   0.475  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.363  -2.946  -0.414  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.240  -3.881   1.508  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.343   0.733  -1.761  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.244   2.147  -1.045  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.155   1.943   1.253  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.160   0.317   2.846  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.254  -1.092   2.154  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   25    1    3                                                  
CONECT    3    4    2                                                       
CONECT    4    3    5   31   32                                             
CONECT    5   23    6    4   33                                             
CONECT    6    5    7                                                       
CONECT    7    6   19    8   34                                             
CONECT    8    9    7                                                       
CONECT    9    8   10   18                                                  
CONECT   10   11    9   35                                                  
CONECT   11   12   10   36                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12   37                                                       
CONECT   14   12   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   38                                                       
CONECT   18    9   14   39                                                  
CONECT   19   20    7   21   40                                             
CONECT   20   19   41                                                       
CONECT   21   22   19   23   42                                             
CONECT   22   21   43                                                       
CONECT   23    5   24   21   44                                             
CONECT   24   23   45                                                       
CONECT   25   26   30    2                                                  
CONECT   26   27   25   46                                                  
CONECT   27   28   26   47                                                  
CONECT   28   27   29   48                                                  
CONECT   29   30   28   49                                                  
CONECT   30   25   29   50                                                  
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    7                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   13                                                            
CONECT   38   17                                                            
CONECT   39   18                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
CONECT   42   21                                                            
CONECT   43   22                                                            
CONECT   44   23                                                            
CONECT   45   24                                                            
CONECT   46   26                                                            
CONECT   47   27                                                            
CONECT   48   28                                                            
CONECT   49   29                                                            
CONECT   50   30                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
    1.7242   -1.2244   -1.5038 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147   -1.0968   -0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -1.6469    0.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -2.4319    0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0647   -1.5968    0.6938 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1135   -0.5122   -0.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    0.3708   -0.0299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2423    1.4274   -1.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2524    2.3692   -0.9672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685    3.3662   -1.9409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4268    4.3921   -2.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412    4.4265   -1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    5.4610   -1.2951 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702    3.4386   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9153    3.4926    0.7802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8214    4.3066    0.7101 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743    2.5530    1.7382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1805    2.4070   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5402   -0.3947   -0.2006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6799    0.4354    0.0799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5690   -1.5877    0.7502 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7399   -2.3866    0.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262   -2.4608    0.5697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3405   -3.4962    1.5548 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1565   -0.2704    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320    0.6400   -0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8051    1.4379   -0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3140    1.3247    0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7529    0.4142    1.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -0.3819    1.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311   -3.3022    1.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2192   -2.8020   -0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9820   -1.1728    1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735    0.8111    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1960    3.3410   -2.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    5.1585   -2.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2515    5.3588   -0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262    2.6498    2.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538    1.6369    0.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6553   -0.7403   -1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5835    1.2228   -0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6482   -1.2488    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4809   -1.7479    0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3628   -2.9459   -0.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -3.8811    1.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3429    0.7328   -1.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    2.1471   -1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1548    1.9433    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1600    0.3173    2.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543   -1.0917    2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  5  1  0
 14 12  2  0
  5  6  1  0
 12 11  1  0
 11 10  2  0
  9  8  1  0
  6  7  1  0
 12 13  1  0
 14 15  1  0
 23 24  1  0
 15 16  2  0
 21 22  1  0
 15 17  1  0
 19 20  1  0
  4  3  1  0
 28 27  1  0
  7 19  1  0
 27 26  2  0
 10  9  1  0
 26 25  1  0
 19 21  1  0
 25 30  2  0
  9 18  2  0
 30 29  1  0
 29 28  2  0
 21 23  1  0
 25  2  1  0
 18 14  1  0
  2  1  2  0
  2  3  1  0
  7  8  1  0
  5  4  1  0
  7 34  1  1
 23 44  1  6
 24 45  1  0
 21 42  1  1
 22 43  1  0
 19 40  1  6
 20 41  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  1
 10 35  1  0
 18 39  1  0
 11 36  1  0
 13 37  1  0
 17 38  1  0
 28 48  1  0
 27 47  1  0
 26 46  1  0
 30 50  1  0
 29 49  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₁₀

Average Mass

420.3700 Da

Monoisotopic Mass

420.10565 Da

IUPAC Name

5-{[(2S,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxybenzoic acid

Traditional Name

5-{[(2S,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C(O[H])C([H])=C([H])C(O[C@]2([H])O[C@]([H])(C([H])([H])OC(=O)C3=C([H])C([H])=C([H])C([H])=C3[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])=C1[H]

InChI Identifier

InChI=1S/C20H20O10/c21-13-7-6-11(8-12(13)18(25)26)29-20-17(24)16(23)15(22)14(30-20)9-28-19(27)10-4-2-1-3-5-10/h1-8,14-17,20-24H,9H2,(H,25,26)/t14-,15-,16+,17-,20-/m1/s1

InChI Key

WPXSPUCEGBJXAA-ISIBIEBGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD at 35C, 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
Actaea japonica	JEOL database	Iwanaga, A., et al, J. Nat. Prod. 73, 609 (2010)
Meehania urticifolia	LOTUS Database	35616633
Trifolium lupinaster	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Hydroxybenzoic acid
Salicylic acid or derivatives
Salicylic acid
Benzoate ester
Benzoic acid
Benzoic acid or derivatives
4-alkoxyphenol
Phenol ether
Benzoyl
Phenoxy compound
Sugar acid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.8	ALOGPS
logP	1.9	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.51	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	99.24 m³·mol⁻¹	ChemAxon
Polarizability	39.68 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

46210881

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Iwanaga A, Kusano G, Warashina T, Miyase T: Phenolic constituents of the aerial parts of Cimicifuga simplex and Cimicifuga japonica. J Nat Prod. 2010 Apr 23;73(4):609-12. doi: 10.1021/np900752t. [PubMed:20184336 ]
Iwanaga, A., et al. (2010). Iwanaga, A., et al, J. Nat. Prod. 73, 609 (2010). J. Nat. Prod..

Showing NP-Card for shomaside F (NP0035222)

MOL for NP0035222 (shomaside F)

3D MOL for NP0035222 (shomaside F)

3D SDF for NP0035222 (shomaside F)

3D-SDF for NP0035222 (shomaside F)

PDB for NP0035222 (shomaside F)

3D PDB for NP0035222 (shomaside F)

SMILES for NP0035222 (shomaside F)

INCHI for NP0035222 (shomaside F)

Structure for NP0035222 (shomaside F)

3D Structure for NP0035222 (shomaside F)