NP-MRD: Showing NP-Card for Phenyl beta-D-glucoside (NP0002908)

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Record Information

Version

2.0

Created at

2020-11-23 19:43:22 UTC

Updated at

2021-08-12 19:52:29 UTC

NP-MRD ID

NP0002908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenyl beta-D-glucoside

Provided By

BMRB

Description

Phenyl beta-D-glucopyranoside, also known as phenylglucoside, 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. Phenyl beta-D-glucoside is found in Gymnadenia conopsea. Phenyl beta-D-glucoside was first documented in 2021 (PMID: 33843220). Based on a literature review very few articles have been published on Phenyl beta-D-glucopyranoside (PMID: 33477839).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
    1.9685   -4.0522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1896   -2.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4106   -1.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -1.1248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269    0.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474    1.0871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428    0.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6171    1.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0125    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2336   -0.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0593   -1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639   -0.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8421    1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0632    2.9559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3416    1.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7369    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258    0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3001   -0.6997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731   -4.6025    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6732   -2.7897    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7059   -2.3475    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8333   -1.5603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9961   -0.8406    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3960    2.9536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1868    1.8530    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6290   -1.1143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2804   -2.9808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896   -1.8802    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806    1.9477    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1111    3.8892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0419    2.9820    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9580    3.5462    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2489    1.2280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6955   -0.1494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 12 28  1  0
 13 29  1  1
 14 30  1  0
 15 31  1  6
 16 32  1  0
 17 33  1  1
 18 34  1  0
M  END

NP0002908
     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.6786    2.4019    1.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    1.1246    1.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3144    0.5654    0.1672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9997    0.5441    0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812    0.2281   -0.4032 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9779   -0.4719    0.1408 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149   -0.1370    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629    0.9811   -0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1170    1.2815   -0.5930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0257    0.4650    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.6676    0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2514   -0.9701    0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8234   -0.8421   -0.1267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6347   -0.8317   -1.2590 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2137    1.2223    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4682    1.2505   -0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0696    1.6562   -1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459    2.1804   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0886    0.6571    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8897   -1.8571    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8582   -2.6050   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892   -1.5867    1.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3224   -1.3007    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086   -1.6704   -1.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
    1.9685   -4.0522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1896   -2.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4106   -1.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -1.1248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269    0.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474    1.0871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428    0.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6171    1.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0125    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2336   -0.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0593   -1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639   -0.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8421    1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0632    2.9559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3416    1.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7369    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258    0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3001   -0.6997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6732   -2.7897    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7059   -2.3475    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8333   -1.5603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2804   -2.9808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2489    1.2280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6955   -0.1494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17  3  1  0
 12  7  1  0
  1 19  1  0
  2 20  1  6
  2 21  1  0
  3 22  1  6
  5 23  1  6
  8 24  1  0
  9 25  1  0
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 11 27  1  0
 12 28  1  0
 13 29  1  1
 14 30  1  0
 15 31  1  6
 16 32  1  0
 17 33  1  1
 18 34  1  0
M  END
> <DATABASE_ID>
NP0002908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9-,10+,11-,12-/m1/s1

> <INCHI_KEY>
NEZJDVYDSZTRFS-RMPHRYRLSA-N

> <FORMULA>
C12H16O6

> <MOLECULAR_WEIGHT>
256.254

> <EXACT_MASS>
256.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.99319773782993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-0.5983875990000002

> <ALOGPS_LOGS>
-0.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196091454684598

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200141777338832

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686484

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
60.18330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.72e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenyl β-D-glucoside

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002908
     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.6786    2.4019    1.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    1.1246    1.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3144    0.5654    0.1672 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7629    0.9811   -0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1170    1.2815   -0.5930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0257    0.4650    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.6676    0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2514   -0.9701    0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0886    0.6571    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3308   -1.3043    1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8897   -1.8571    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1125    0.7330   -2.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8582   -2.6050   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892   -1.5867    1.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3224   -1.3007    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086   -1.6704   -1.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 12  7  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  6
  5 23  1  6
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  6
 14 30  1  0
 15 31  1  6
 16 32  1  0
 17 33  1  1
 18 34  1  0
M  END

HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  O   UNK     0       6.574   0.239   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.574  -4.381   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907  -2.841   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.242   0.239   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.242  -2.841   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.907   1.779   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.574  -2.841   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241  -2.071   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908  -2.071   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.241  -0.531   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908  -0.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.907   0.239   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.242   1.779   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.576   2.549   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908   2.549   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.576   4.089   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.908   4.089   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.242   4.859   0.000  0.00  0.00           C+0
CONECT    1   10   11                                                       
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4   11   13                                                       
CONECT    5    9                                                            
CONECT    6   12                                                            
CONECT    7    2    8    9                                                  
CONECT    8    3    7   10                                                  
CONECT    9    5    7   11                                                  
CONECT   10    1    8   12                                                  
CONECT   11    1    4    9                                                  
CONECT   12    6   10                                                       
CONECT   13    4   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   18                                                       
CONECT   18   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    NP0002908
HETATM    1  O1  UNL     1      -2.679   2.402   1.581  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.147   1.125   1.306  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.314   0.565   0.167  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.000   0.544   0.604  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.081   0.228  -0.403  1.00  0.00           C  
HETATM    6  O3  UNL     1       0.978  -0.472   0.141  1.00  0.00           O  
HETATM    7  C4  UNL     1       2.315  -0.137   0.081  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.763   0.981  -0.556  1.00  0.00           C  
HETATM    9  C6  UNL     1       4.117   1.282  -0.593  1.00  0.00           C  
HETATM   10  C7  UNL     1       5.026   0.465   0.006  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.575  -0.668   0.651  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.251  -0.970   0.693  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.757  -0.756  -1.382  1.00  0.00           C  
HETATM   14  O4  UNL     1      -1.502  -0.104  -2.331  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.584  -1.670  -0.502  1.00  0.00           C  
HETATM   16  O5  UNL     1      -0.896  -1.880   0.702  1.00  0.00           O  
HETATM   17  C12 UNL     1      -2.823  -0.842  -0.127  1.00  0.00           C  
HETATM   18  O6  UNL     1      -3.635  -0.832  -1.259  1.00  0.00           O  
HETATM   19  H1  UNL     1      -2.803   3.042   0.854  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.214   1.222   0.989  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.044   0.523   2.228  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.468   1.250  -0.692  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.246   1.123  -0.916  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.070   1.656  -1.045  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.446   2.180  -1.108  1.00  0.00           H  
HETATM   26  H8  UNL     1       6.089   0.657   0.004  1.00  0.00           H  
HETATM   27  H9  UNL     1       5.331  -1.304   1.123  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.890  -1.857   1.197  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.043  -1.325  -1.918  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.113   0.733  -2.636  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.858  -2.605  -1.004  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.389  -1.587   1.488  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.322  -1.301   0.730  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.509  -1.670  -1.735  1.00  0.00           H  
CONECT    1    2   19
CONECT    2    3   20   21
CONECT    3    4   17   22
CONECT    4    5
CONECT    5    6   13   23
CONECT    6    7
CONECT    7    8    8   12
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   28
CONECT   13   14   15   29
CONECT   14   30
CONECT   15   16   17   31
CONECT   16   32
CONECT   17   18   33
CONECT   18   34
END

NP0002908
     RDKit          3D

34 35  0  0  0  0  0  0  0  0999 V2000
   -2.6786    2.4019    1.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    1.1246    1.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3144    0.5654    0.1672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9997    0.5441    0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812    0.2281   -0.4032 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9779   -0.4719    0.1408 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149   -0.1370    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629    0.9811   -0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1170    1.2815   -0.5930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0257    0.4650    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.6676    0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2514   -0.9701    0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7574   -0.7556   -1.3820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5018   -0.1044   -2.3314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5840   -1.6696   -0.5021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8956   -1.8798    0.7020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8234   -0.8421   -0.1267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6347   -0.8317   -1.2590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8028    3.0416    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137    1.2223    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444    0.5225    2.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4682    1.2505   -0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2459    1.1234   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0696    1.6562   -1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459    2.1804   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0886    0.6571    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3308   -1.3043    1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8897   -1.8571    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0426   -1.3250   -1.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    0.7330   -2.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8582   -2.6050   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892   -1.5867    1.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3224   -1.3007    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086   -1.6704   -1.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17  3  1  0
 12  7  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  6
  5 23  1  6
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  6
 14 30  1  0
 15 31  1  6
 16 32  1  0
 17 33  1  1
 18 34  1  0
M  END

View in JSmol

Synonyms

Value	Source
Phenylglucoside	Kegg
Phenyl b-D-glucopyranoside	Generator
Phenyl β-D-glucopyranoside	Generator
Phenyl-beta-glucoside	MeSH
Phenylglucoside, (alpha-(D))-isomer	MeSH
Phenylglucoside, (alpha-(L))-isomer	MeSH

Chemical Formula

C₁₂H₁₆O₆

Average Mass

256.2540 Da

Monoisotopic Mass

256.09469 Da

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol

Traditional Name

phenyl β-D-glucoside

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C12H16O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9-,10+,11-,12-/m1/s1

InChI Key

NEZJDVYDSZTRFS-RMPHRYRLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, methanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, methanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, methanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, methanol, experimental)	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
Gymnadenia conopsea	LOTUS Database	35616633
Gymnadenia conopsea R.BR.	KNApSAcK Database	22123792
Triticum aestivum	KNApSAcK Database	22123792

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

Not Available

Substituents

Not Available

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	-0.64	ALOGPS
logP	-0.6	ChemAxon
logS	-0.73	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.18 m³·mol⁻¹	ChemAxon
Polarizability	24.99 Å³	ChemAxon
Number of Rings	2	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

C00030988

Chemspider ID

58590

KEGG Compound ID

C11611

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen X, Fedrizzi B, Kilmartin PA, Quek SY: Free and Glycosidic Volatiles in Tamarillo (Solanum betaceum Cav. syn. Cyphomandra betacea Sendt.) Juices Prepared from Three Cultivars Grown in New Zealand. J Agric Food Chem. 2021 Apr 21;69(15):4518-4532. doi: 10.1021/acs.jafc.1c00837. Epub 2021 Apr 11. [PubMed:33843220 ]
Cebrian-Tarancon C, Oliva J, Camara MA, Alonso GL, Salinas MR: Analysis of Intact Glycosidic Aroma Precursors in Grapes by High-Performance Liquid Chromatography with a Diode Array Detector. Foods. 2021 Jan 19;10(1). pii: foods10010191. doi: 10.3390/foods10010191. [PubMed:33477839 ]

Showing NP-Card for Phenyl beta-D-glucoside (NP0002908)

MOL for NP0002908 (Phenyl beta-D-glucoside)

3D MOL for NP0002908 (Phenyl beta-D-glucoside)

3D SDF for NP0002908 (Phenyl beta-D-glucoside)

3D-SDF for NP0002908 (Phenyl beta-D-glucoside)

PDB for NP0002908 (Phenyl beta-D-glucoside)

3D PDB for NP0002908 (Phenyl beta-D-glucoside)

SMILES for NP0002908 (Phenyl beta-D-glucoside)

INCHI for NP0002908 (Phenyl beta-D-glucoside)

Structure for NP0002908 (Phenyl beta-D-glucoside)

3D Structure for NP0002908 (Phenyl beta-D-glucoside)