NP-MRD: Showing NP-Card for 8-C-beta-D-boivinopyranosylapigenin (NP0036496)

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Record Information

Version

2.0

Created at

2021-06-20 19:39:17 UTC

Updated at

2021-06-30 00:08:10 UTC

NP-MRD ID

NP0036496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-C-beta-D-boivinopyranosylapigenin

Provided By

JEOL Database JEOL Logo

Description

CHEMBL2011651 belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. 8-C-beta-D-boivinopyranosylapigenin is found in Chrysopogon aciculatis. 8-C-beta-D-boivinopyranosylapigenin was first documented in 2012 (Shen, C. -C., et al.). Based on a literature review very few articles have been published on CHEMBL2011651.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121393D          

 49 52  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652306202121393D          

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 18 19  2  0  0  0  0
 11 12  1  0  0  0  0
 19 21  1  0  0  0  0
 12 14  1  0  0  0  0
 21 22  2  0  0  0  0
 22 16  1  0  0  0  0
  4  3  1  0  0  0  0
 14 15  2  0  0  0  0
 15 23  1  0  0  0  0
 24 11  1  0  0  0  0
 12 13  2  0  0  0  0
  4 25  1  0  0  0  0
  3  2  1  0  0  0  0
  2 28  1  0  0  0  0
 28 26  1  0  0  0  0
 26 25  1  0  0  0  0
  9 10  1  0  0  0  0
  2  1  1  0  0  0  0
  8  9  1  0  0  0  0
 26 27  1  0  0  0  0
  6  7  1  0  0  0  0
 28 29  1  0  0  0  0
  9 11  2  0  0  0  0
 19 20  1  0  0  0  0
  4  5  1  0  0  0  0
  8 36  1  0  0  0  0
 14 38  1  0  0  0  0
 10 37  1  0  0  0  0
  7 35  1  0  0  0  0
  4 34  1  6  0  0  0
 17 39  1  0  0  0  0
 18 40  1  0  0  0  0
 21 42  1  0  0  0  0
 22 43  1  0  0  0  0
  2 33  1  6  0  0  0
 28 48  1  1  0  0  0
 26 46  1  1  0  0  0
 25 44  1  0  0  0  0
 25 45  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 27 47  1  0  0  0  0
 29 49  1  0  0  0  0
 20 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)C2=C(O[H])C([H])=C(O[H])C(=C2O1)[C@]1([H])O[C@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O8/c1-9-20(27)15(26)8-17(28-9)19-13(24)6-12(23)18-14(25)7-16(29-21(18)19)10-2-4-11(22)5-3-10/h2-7,9,15,17,20,22-24,26-27H,8H2,1H3/t9-,15+,17-,20+/m1/s1

> <INCHI_KEY>
BZHMTPJDQAFTNF-MXKBHJLWSA-N

> <FORMULA>
C21H20O8

> <MOLECULAR_WEIGHT>
400.383

> <EXACT_MASS>
400.115817604

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.33521197507089

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.686572876333333

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.003824617194951

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.194956503170942

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2227236002346187

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
103.39140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -1.1907   -1.8443    4.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802   -1.3797    2.9938 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8702   -1.3151    1.7313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378   -1.0366    0.6432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6954   -1.1407   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909   -1.0296   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9070   -0.8721    0.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7288   -1.0809   -2.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9786   -1.2617   -3.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638   -1.3116   -4.3857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5906   -1.3840   -3.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2312   -1.5768   -4.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2749   -1.6474   -5.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6842   -1.6748   -4.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864   -1.5799   -2.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6382   -1.6622   -2.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5817   -1.0694   -3.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9512   -1.1440   -3.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3830   -1.8070   -2.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7065   -1.9034   -1.7543 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4706   -2.3906   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1035   -2.3155   -1.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139   -1.4202   -1.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0459   -1.3190   -1.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386    0.3619    0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276    0.4784    2.1928 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5200   -0.3079    2.1629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4084    0.0042    3.3287 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6332    0.9674    3.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -2.8419    3.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7415   -1.8875    5.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0666   -1.1875    4.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -2.1305    2.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8164   -1.8103    0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3786   -1.1175    1.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8100   -0.9889   -2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160   -1.4507   -5.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -1.8265   -5.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -0.5276   -4.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6565   -0.6764   -3.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2226   -1.4581   -2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8190   -2.9016   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056   -2.7778   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571    1.1158    0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3573    0.5813    0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6173    1.5247    2.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979    0.0155    2.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745   -0.0591    4.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098    0.8081    2.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  2  0
 15 16  1  0
 24  5  2  0
 16 17  2  0
  5  6  1  0
 17 18  1  0
 24 23  1  0
 18 19  2  0
 11 12  1  0
 19 21  1  0
 12 14  1  0
 21 22  2  0
 22 16  1  0
  4  3  1  0
 14 15  2  0
 15 23  1  0
 24 11  1  0
 12 13  2  0
  4 25  1  0
  3  2  1  0
  2 28  1  0
 28 26  1  0
 26 25  1  0
  9 10  1  0
  2  1  1  0
  8  9  1  0
 26 27  1  0
  6  7  1  0
 28 29  1  0
  9 11  2  0
 19 20  1  0
  4  5  1  0
  8 36  1  0
 14 38  1  0
 10 37  1  0
  7 35  1  0
  4 34  1  6
 17 39  1  0
 18 40  1  0
 21 42  1  0
 22 43  1  0
  2 33  1  6
 28 48  1  1
 26 46  1  1
 25 44  1  0
 25 45  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 27 47  1  0
 29 49  1  0
 20 41  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      -1.191  -1.844   4.036  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.180  -1.380   2.994  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.870  -1.315   1.731  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.038  -1.037   0.643  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.695  -1.141  -0.687  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.091  -1.030  -0.808  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.907  -0.872   0.278  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.729  -1.081  -2.048  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.979  -1.262  -3.202  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.664  -1.312  -4.386  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.591  -1.384  -3.118  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.231  -1.577  -4.319  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.275  -1.647  -5.434  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.684  -1.675  -4.133  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.186  -1.580  -2.894  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.638  -1.662  -2.627  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.582  -1.069  -3.484  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.951  -1.144  -3.207  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.383  -1.807  -2.064  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.707  -1.903  -1.754  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.471  -2.391  -1.196  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.104  -2.316  -1.474  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.414  -1.420  -1.756  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.046  -1.319  -1.875  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.639   0.362   0.833  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.328   0.478   2.193  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.520  -0.308   2.163  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.408   0.004   3.329  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.633   0.967   3.521  0.00  0.00           O+0
HETATM   30  H   UNK     0      -1.564  -2.842   3.779  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.742  -1.888   5.033  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.067  -1.188   4.069  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.617  -2.131   2.926  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.816  -1.810   0.665  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.379  -1.117   1.067  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.810  -0.989  -2.108  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.016  -1.451  -5.113  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.280  -1.827  -5.023  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.264  -0.528  -4.372  0.00  0.00           H+0
HETATM   40  H   UNK     0       6.657  -0.676  -3.886  0.00  0.00           H+0
HETATM   41  H   UNK     0       8.223  -1.458  -2.446  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.819  -2.902  -0.303  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.406  -2.778  -0.779  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.157   1.116   0.774  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.357   0.581   0.035  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.617   1.525   2.346  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.098   0.016   2.878  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.975  -0.059   4.265  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.310   0.808   2.836  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3   28    1   33                                             
CONECT    3    4    2                                                       
CONECT    4    3   25    5   34                                             
CONECT    5   24    6    4                                                  
CONECT    6    8    5    7                                                  
CONECT    7    6   35                                                       
CONECT    8    6    9   36                                                  
CONECT    9   10    8   11                                                  
CONECT   10    9   37                                                       
CONECT   11   12   24    9                                                  
CONECT   12   11   14   13                                                  
CONECT   13   12                                                            
CONECT   14   12   15   38                                                  
CONECT   15   16   14   23                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   39                                                  
CONECT   18   17   19   40                                                  
CONECT   19   18   21   20                                                  
CONECT   20   19   41                                                       
CONECT   21   19   22   42                                                  
CONECT   22   21   16   43                                                  
CONECT   23   24   15                                                       
CONECT   24    5   23   11                                                  
CONECT   25    4   26   44   45                                             
CONECT   26   28   25   27   46                                             
CONECT   27   26   47                                                       
CONECT   28    2   26   29   48                                             
CONECT   29   28   49                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    4                                                            
CONECT   35    7                                                            
CONECT   36    8                                                            
CONECT   37   10                                                            
CONECT   38   14                                                            
CONECT   39   17                                                            
CONECT   40   18                                                            
CONECT   41   20                                                            
CONECT   42   21                                                            
CONECT   43   22                                                            
CONECT   44   25                                                            
CONECT   45   25                                                            
CONECT   46   26                                                            
CONECT   47   27                                                            
CONECT   48   28                                                            
CONECT   49   29                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  104    0
END

RDKit          3D

49 52  0  0  0  0  0  0  0  0999 V2000
   -1.1907   -1.8443    4.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802   -1.3797    2.9938 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8702   -1.3151    1.7313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378   -1.0366    0.6432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6954   -1.1407   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909   -1.0296   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9070   -0.8721    0.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7288   -1.0809   -2.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9786   -1.2617   -3.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638   -1.3116   -4.3857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5906   -1.3840   -3.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2312   -1.5768   -4.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2749   -1.6474   -5.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6842   -1.6748   -4.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864   -1.5799   -2.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6382   -1.6622   -2.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5817   -1.0694   -3.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9512   -1.1440   -3.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3830   -1.8070   -2.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7065   -1.9034   -1.7543 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4706   -2.3906   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1035   -2.3155   -1.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139   -1.4202   -1.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0459   -1.3190   -1.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386    0.3619    0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276    0.4784    2.1928 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5200   -0.3079    2.1629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4084    0.0042    3.3287 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6332    0.9674    3.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -2.8419    3.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7415   -1.8875    5.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0666   -1.1875    4.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -2.1305    2.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8164   -1.8103    0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3786   -1.1175    1.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8100   -0.9889   -2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160   -1.4507   -5.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -1.8265   -5.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -0.5276   -4.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6565   -0.6764   -3.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2226   -1.4581   -2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8190   -2.9016   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056   -2.7778   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571    1.1158    0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3573    0.5813    0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6173    1.5247    2.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979    0.0155    2.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745   -0.0591    4.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098    0.8081    2.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  2  0
 15 16  1  0
 24  5  2  0
 16 17  2  0
  5  6  1  0
 17 18  1  0
 24 23  1  0
 18 19  2  0
 11 12  1  0
 19 21  1  0
 12 14  1  0
 21 22  2  0
 22 16  1  0
  4  3  1  0
 14 15  2  0
 15 23  1  0
 24 11  1  0
 12 13  2  0
  4 25  1  0
  3  2  1  0
  2 28  1  0
 28 26  1  0
 26 25  1  0
  9 10  1  0
  2  1  1  0
  8  9  1  0
 26 27  1  0
  6  7  1  0
 28 29  1  0
  9 11  2  0
 19 20  1  0
  4  5  1  0
  8 36  1  0
 14 38  1  0
 10 37  1  0
  7 35  1  0
  4 34  1  6
 17 39  1  0
 18 40  1  0
 21 42  1  0
 22 43  1  0
  2 33  1  6
 28 48  1  1
 26 46  1  1
 25 44  1  0
 25 45  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 27 47  1  0
 29 49  1  0
 20 41  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₈

Average Mass

400.3830 Da

Monoisotopic Mass

400.11582 Da

IUPAC Name

8-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

8-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)C2=C(O[H])C([H])=C(O[H])C(=C2O1)[C@]1([H])O[C@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])C1([H])[H]

InChI Identifier

InChI=1S/C21H20O8/c1-9-20(27)15(26)8-17(28-9)19-13(24)6-12(23)18-14(25)7-16(29-21(18)19)10-2-4-11(22)5-3-10/h2-7,9,15,17,20,22-24,26-27H,8H2,1H3/t9-,15+,17-,20+/m1/s1

InChI Key

BZHMTPJDQAFTNF-MXKBHJLWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, 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
Chrysopogon aciculatis	JEOL database	Shen, C. -C., et al, J. Nat. Prod. 75, 198 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Benzenoid
Oxane
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
1,2-diol
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.41	ALOGPS
logP	1.69	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.19	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.39 m³·mol⁻¹	ChemAxon
Polarizability	40.34 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

28503660

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57332513

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shen, C. -C., et al. (2012). Shen, C. -C., et al, J. Nat. Prod. 75, 198 (2012). J. Nat. Prod..

Showing NP-Card for 8-C-beta-D-boivinopyranosylapigenin (NP0036496)

MOL for NP0036496 (8-C-beta-D-boivinopyranosylapigenin)

3D MOL for NP0036496 (8-C-beta-D-boivinopyranosylapigenin)

3D SDF for NP0036496 (8-C-beta-D-boivinopyranosylapigenin)

3D-SDF for NP0036496 (8-C-beta-D-boivinopyranosylapigenin)

PDB for NP0036496 (8-C-beta-D-boivinopyranosylapigenin)

3D PDB for NP0036496 (8-C-beta-D-boivinopyranosylapigenin)

SMILES for NP0036496 (8-C-beta-D-boivinopyranosylapigenin)

INCHI for NP0036496 (8-C-beta-D-boivinopyranosylapigenin)

Structure for NP0036496 (8-C-beta-D-boivinopyranosylapigenin)

3D Structure for NP0036496 (8-C-beta-D-boivinopyranosylapigenin)