NP-MRD: Showing NP-Card for 8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one (NP0027191)

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Record Information

Version

2.0

Created at

2021-06-19 18:52:53 UTC

Updated at

2021-06-29 23:53:10 UTC

NP-MRD ID

NP0027191

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one

Provided By

JEOL Database JEOL Logo

Description

8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one is found in Rhododendron collettianum. 8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one was first documented in 2004 (Ahmad, V. U., et al.). Based on a literature review very few articles have been published on 2-Methyl-6-hydroxy-8-(beta-D-glucopyranosyloxy)-4H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120523D          

 43 45  0  0  0  0            999 V2000
    3.5367   -2.2935   -2.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9840   -0.9407   -2.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075   -0.6315   -3.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9769    0.7188   -4.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5371    1.0358   -5.2813 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028    1.6517   -3.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    2.9563   -3.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5638    3.8156   -2.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108    5.0981   -2.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    3.3932   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403    2.0843   -0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    1.6950    0.4534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981    1.0094    1.2573 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3608    1.9526    2.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3870    1.3130    2.8891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3993    2.4186    3.6006 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0072    3.2725    2.6279 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0759    0.3791    3.8909 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1200   -0.3136    4.6938 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6633   -1.4318    4.0853 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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    2.0028    1.6517   -3.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    2.9563   -3.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5638    3.8156   -2.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108    5.0981   -2.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    3.3932   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403    2.0843   -0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    1.6950    0.4534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981    1.0094    1.2573 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192120523D          

 43 45  0  0  0  0            999 V2000
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    2.9840   -0.9407   -2.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9769    0.7188   -4.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0796    3.3932   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0027191

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])=C2OC(=C([H])C(=O)C2=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O9/c1-6-2-9(19)8-3-7(18)4-10(15(8)23-6)24-16-14(22)13(21)12(20)11(5-17)25-16/h2-4,11-14,16-18,20-22H,5H2,1H3/t11-,12-,13+,14-,16-/m1/s1

> <INCHI_KEY>
IHKBMBAIVWTELS-XYFZXANASA-N

> <FORMULA>
C16H18O9

> <MOLECULAR_WEIGHT>
354.311

> <EXACT_MASS>
354.09508216

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.73523147454938

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxy-2-methyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-1.003645467333333

> <ALOGPS_LOGS>
-1.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200139094219859

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.12449094532678

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549591504

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
83.21340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-2-methyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
    3.5367   -2.2935   -2.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9840   -0.9407   -2.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075   -0.6315   -3.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9769    0.7188   -4.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5371    1.0358   -5.2813 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028    1.6517   -3.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    2.9563   -3.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5638    3.8156   -2.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108    5.0981   -2.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    3.3932   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403    2.0843   -0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    1.6950    0.4534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981    1.0094    1.2573 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3608    1.9526    2.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3870    1.3130    2.8891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3993    2.4186    3.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    3.2725    2.6279 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0759    0.3791    3.8909 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1200   -0.3136    4.6938 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9286   -0.6428    3.1359 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6633   -1.4318    4.0853 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860    0.0504    2.1698 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5782   -0.9596    1.4154 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5212    1.2100   -1.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0165   -0.0579   -1.6542 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.9723   -3.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5811   -2.2079   -2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   -2.7482   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867   -1.3267   -4.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1153    3.2814   -4.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7764    5.2608   -3.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201    4.0781   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4099    0.4314    0.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3135    0.7579    2.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    2.0090    4.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606    3.0421    4.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2924    3.5202    2.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7175    0.9540    4.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315   -0.9971    5.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2859   -1.3520    2.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3012   -1.9476    3.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6529    0.5973    2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0782   -0.4828    0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 22  1  0
  8 10  2  0
 11 24  2  0
 22 20  1  0
  6  7  2  0
  7  8  1  0
  6 24  1  0
 20 18  1  0
 18 15  1  0
 15 14  1  0
 14 13  1  0
 18 19  1  0
  6  4  1  0
 24 25  1  0
 25  2  1  0
  2  3  2  0
  3  4  1  0
 11 10  1  0
 20 21  1  0
 22 23  1  0
 11 12  1  0
  2  1  1  0
  8  9  1  0
 16 17  1  0
  4  5  2  0
 15 16  1  0
 13 12  1  0
 13 33  1  6
 18 38  1  1
 19 39  1  0
 20 40  1  6
 21 41  1  0
 22 42  1  1
 23 43  1  0
 16 35  1  0
 16 36  1  0
 15 34  1  6
 17 37  1  0
  7 30  1  0
  3 29  1  0
 10 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  9 31  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.537  -2.293  -2.396  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.984  -0.941  -2.721  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.507  -0.632  -3.936  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.977   0.719  -4.185  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.537   1.036  -5.281  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.003   1.652  -3.050  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.516   2.956  -3.192  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.564   3.816  -2.099  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.111   5.098  -2.185  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.080   3.393  -0.877  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.540   2.084  -0.745  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.077   1.695   0.453  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.098   1.009   1.257  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.361   1.953   2.041  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.387   1.313   2.889  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.399   2.419   3.601  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.007   3.272   2.628  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.076   0.379   3.891  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.120  -0.314   4.694  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.929  -0.643   3.136  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.663  -1.432   4.085  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.886   0.050   2.170  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.578  -0.960   1.415  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.521   1.210  -1.835  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.017  -0.058  -1.654  0.00  0.00           O+0
HETATM   26  H   UNK     0       3.499  -2.972  -3.254  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.581  -2.208  -2.079  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.965  -2.748  -1.580  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.487  -1.327  -4.765  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.115   3.281  -4.148  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.776   5.261  -3.083  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.120   4.078  -0.035  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.410   0.431   0.623  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.314   0.758   2.251  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.190   2.009   4.235  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.261   3.042   4.213  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.292   3.520   2.010  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.718   0.954   4.571  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.632  -0.997   5.174  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.286  -1.352   2.599  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.301  -1.948   3.551  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.653   0.597   2.732  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.078  -0.483   0.723  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2   25    3    1                                                  
CONECT    3    2    4   29                                                  
CONECT    4    6    3    5                                                  
CONECT    5    4                                                            
CONECT    6    7   24    4                                                  
CONECT    7    6    8   30                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8   31                                                       
CONECT   10    8   11   32                                                  
CONECT   11   24   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   22   14   12   33                                             
CONECT   14   15   13                                                       
CONECT   15   18   14   16   34                                             
CONECT   16   17   15   35   36                                             
CONECT   17   16   37                                                       
CONECT   18   20   15   19   38                                             
CONECT   19   18   39                                                       
CONECT   20   22   18   21   40                                             
CONECT   21   20   41                                                       
CONECT   22   13   20   23   42                                             
CONECT   23   22   43                                                       
CONECT   24   11    6   25                                                  
CONECT   25   24    2                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    7                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   13                                                            
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   16                                                            
CONECT   37   17                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

RDKit          3D

43 45  0  0  0  0  0  0  0  0999 V2000
    3.5367   -2.2935   -2.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9840   -0.9407   -2.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075   -0.6315   -3.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9769    0.7188   -4.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5371    1.0358   -5.2813 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028    1.6517   -3.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    2.9563   -3.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5638    3.8156   -2.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108    5.0981   -2.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    3.3932   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403    2.0843   -0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    1.6950    0.4534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981    1.0094    1.2573 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3608    1.9526    2.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3870    1.3130    2.8891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3993    2.4186    3.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    3.2725    2.6279 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0759    0.3791    3.8909 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1200   -0.3136    4.6938 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9286   -0.6428    3.1359 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6633   -1.4318    4.0853 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860    0.0504    2.1698 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5782   -0.9596    1.4154 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5212    1.2100   -1.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0165   -0.0579   -1.6542 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.9723   -3.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5811   -2.2079   -2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   -2.7482   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867   -1.3267   -4.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1153    3.2814   -4.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7764    5.2608   -3.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201    4.0781   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4099    0.4314    0.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3135    0.7579    2.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    2.0090    4.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606    3.0421    4.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2924    3.5202    2.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7175    0.9540    4.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315   -0.9971    5.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2859   -1.3520    2.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3012   -1.9476    3.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6529    0.5973    2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0782   -0.4828    0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 22  1  0
  8 10  2  0
 11 24  2  0
 22 20  1  0
  6  7  2  0
  7  8  1  0
  6 24  1  0
 20 18  1  0
 18 15  1  0
 15 14  1  0
 14 13  1  0
 18 19  1  0
  6  4  1  0
 24 25  1  0
 25  2  1  0
  2  3  2  0
  3  4  1  0
 11 10  1  0
 20 21  1  0
 22 23  1  0
 11 12  1  0
  2  1  1  0
  8  9  1  0
 16 17  1  0
  4  5  2  0
 15 16  1  0
 13 12  1  0
 13 33  1  6
 18 38  1  1
 19 39  1  0
 20 40  1  6
 21 41  1  0
 22 42  1  1
 23 43  1  0
 16 35  1  0
 16 36  1  0
 15 34  1  6
 17 37  1  0
  7 30  1  0
  3 29  1  0
 10 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  9 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-Methyl-6-hydroxy-8-(b-D-glucopyranosyloxy)-4H-1-benzopyran-4-one	Generator
2-Methyl-6-hydroxy-8-(β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one	Generator

Chemical Formula

C₁₆H₁₈O₉

Average Mass

354.3110 Da

Monoisotopic Mass

354.09508 Da

IUPAC Name

6-hydroxy-2-methyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

6-hydroxy-2-methyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])=C2OC(=C([H])C(=O)C2=C1[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C16H18O9/c1-6-2-9(19)8-3-7(18)4-10(15(8)23-6)24-16-14(22)13(21)12(20)11(5-17)25-16/h2-4,11-14,16-18,20-22H,5H2,1H3/t11-,12-,13+,14-,16-/m1/s1

InChI Key

IHKBMBAIVWTELS-XYFZXANASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OH, 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
Rhododendron collettianum	JEOL database	Ahmad, V. U., et al, Chem. Pharm. Bull. 52, 1458 (2004)

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
Hexose monosaccharide
Chromone
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Oxane
Monosaccharide
Benzenoid
Heteroaromatic compound
Secondary alcohol
Oxacycle
Polyol
Acetal
Organoheterocyclic compound
Alcohol
Primary alcohol
Hydrocarbon derivative
Organic oxide
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	-0.65	ALOGPS
logP	-1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.21 m³·mol⁻¹	ChemAxon
Polarizability	33.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

9385474

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11210412

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ahmad, V. U., et al. (2004). Ahmad, V. U., et al, Chem. Pharm. Bull. 52, 1458 (2004). Chem. Pharm. Bull..

Showing NP-Card for 8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one (NP0027191)

MOL for NP0027191 (8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one)

3D MOL for NP0027191 (8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one)

3D SDF for NP0027191 (8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one)

3D-SDF for NP0027191 (8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one)

PDB for NP0027191 (8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one)

3D PDB for NP0027191 (8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one)

SMILES for NP0027191 (8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one)

INCHI for NP0027191 (8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one)

Structure for NP0027191 (8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one)

3D Structure for NP0027191 (8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one)