MiMeDB: Showing metabocard for Arbutin (MMDBc0049980)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:47:31 UTC

Update Date

2024-10-09 23:00:59 UTC

Metabolite ID

MMDBc0049980

Metabolite Identification

Common Name

Arbutin

Description

Arbutin is found in apple. Glucoside in pear leaves (Pyrus communis

Structure

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

HMDB0029943
     RDKit          3D
Arbutin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.3947   -1.6621    0.5452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0263   -1.8044    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3396   -0.5350    1.0596 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0217   -0.7324    1.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -0.0489    0.1404 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8319   -0.8009   -0.3435 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749   -0.5972   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896   -1.4959   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4505   -1.3293   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9713   -0.2396   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3550   -0.0641    0.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937    0.6548    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7035    0.4835    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0391    0.5648   -1.0163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1693    1.2127   -1.8758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9632    1.5438   -0.3066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6038    2.3867   -1.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9296    0.6653    0.4494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6197    1.4714    1.3658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7502   -1.8687    1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7521   -2.6362    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512   -2.0860   -0.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6454   -0.5314    2.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1546    0.8349    0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575   -2.3426   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1143   -2.0641   -1.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7534    0.7242    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4779    1.5303    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0706    1.2221    0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6198   -0.2129   -1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186    0.8045   -2.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3968    2.1220    0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    3.3258   -0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7091    0.3560   -0.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5521    1.1489    1.4954 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
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  3  1  0
 13  7  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  1
  5 24  1  1
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  6
 15 31  1  0
 16 32  1  1
 17 33  1  0
 18 34  1  6
 19 35  1  0
M  END


  Mrv1652309272007412D          

 19 20  0  0  0  0            999 V2000
 9999.0831 9998.0678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.9435 9999.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.656010000.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.941410000.9556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6560 9997.2426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2247 9998.0678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2247 9999.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2282 9999.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5139 9999.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7994 9999.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7994 9998.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5138 9998.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2282 9998.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6547 9999.7175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.9402 9999.3050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.9402 9998.4800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.6547 9998.0676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.3691 9998.4800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.3691 9999.3050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
  8  2  1  0  0  0  0
  1 11  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
 18 19  1  0  0  0  0
 17  5  1  6  0  0  0
 16  6  1  1  0  0  0
 15  7  1  6  0  0  0
 14  3  1  1  0  0  0
 18  1  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049980

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1

> <INCHI_KEY>
BJRNKVDFDLYUGJ-RMPHRYRLSA-N

> <FORMULA>
C12H16O7

> <MOLECULAR_WEIGHT>
272.2512

> <EXACT_MASS>
272.089602866

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.87568345161489

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.36

> <JCHEM_LOGP>
-0.9019529206666663

> <ALOGPS_LOGS>
-0.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.201773728176159

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.820455894002922

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923436865826

> <JCHEM_POLAR_SURFACE_AREA>
119.61000000000001

> <JCHEM_REFRACTIVITY>
62.164199999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.91e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-arbutin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029943
     RDKit          3D
Arbutin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.3947   -1.6621    0.5452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0263   -1.8044    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3396   -0.5350    1.0596 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0217   -0.7324    1.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -0.0489    0.1404 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8319   -0.8009   -0.3435 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749   -0.5972   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896   -1.4959   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4505   -1.3293   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9713   -0.2396   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3550   -0.0641    0.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937    0.6548    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7035    0.4835    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0391    0.5648   -1.0163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1693    1.2127   -1.8758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9632    1.5438   -0.3066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6038    2.3867   -1.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9296    0.6653    0.4494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6197    1.4714    1.3658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7502   -1.8687    1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7521   -2.6362    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512   -2.0860   -0.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6454   -0.5314    2.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1546    0.8349    0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575   -2.3426   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1143   -2.0641   -1.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7534    0.7242    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4779    1.5303    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0706    1.2221    0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6198   -0.2129   -1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186    0.8045   -2.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3968    2.1220    0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    3.3258   -0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7091    0.3560   -0.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5521    1.1489    1.4954 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
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  3  1  0
 13  7  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  1
  5 24  1  1
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  6
 15 31  1  0
 16 32  1  1
 17 33  1  0
 18 34  1  6
 19 35  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8664.9558663.060   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8670.2948666.140   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8662.2918667.680   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8660.9578668.450   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8662.2918661.520   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8659.6198663.060   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8659.6198666.140   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8668.9598665.369   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.6268666.139   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.2928665.369   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.2928663.829   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.6268663.059   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.9598663.829   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.2898666.139   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.9558665.369   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.9558663.829   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.2898663.060   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.6228663.829   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8663.6228665.369   0.000  0.00  0.00           O+0
CONECT    1   11   18                                                       
CONECT    2    8                                                            
CONECT    3    4   14                                                       
CONECT    4    3                                                            
CONECT    5   17                                                            
CONECT    6   16                                                            
CONECT    7   15                                                            
CONECT    8    9   13    2                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    1                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   15   19    3                                                  
CONECT   15   14   16    7                                                  
CONECT   16   15   17    6                                                  
CONECT   17   16   18    5                                                  
CONECT   18   17   19    1                                                  
CONECT   19   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0029943
HETATM    1  O1  UNL     1      -4.395  -1.662   0.545  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.026  -1.804   0.525  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.340  -0.535   1.060  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.022  -0.732   1.015  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.232  -0.049   0.140  1.00  0.00           C  
HETATM    6  O3  UNL     1       0.832  -0.801  -0.343  1.00  0.00           O  
HETATM    7  C4  UNL     1       2.175  -0.597  -0.241  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.090  -1.496  -0.813  1.00  0.00           C  
HETATM    9  C6  UNL     1       4.450  -1.329  -0.734  1.00  0.00           C  
HETATM   10  C7  UNL     1       4.971  -0.240  -0.070  1.00  0.00           C  
HETATM   11  O4  UNL     1       6.355  -0.064   0.014  1.00  0.00           O  
HETATM   12  C8  UNL     1       4.094   0.655   0.499  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.703   0.483   0.418  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.039   0.565  -1.016  1.00  0.00           C  
HETATM   15  O5  UNL     1      -0.169   1.213  -1.876  1.00  0.00           O  
HETATM   16  C11 UNL     1      -1.963   1.544  -0.307  1.00  0.00           C  
HETATM   17  O6  UNL     1      -2.604   2.387  -1.197  1.00  0.00           O  
HETATM   18  C12 UNL     1      -2.930   0.665   0.449  1.00  0.00           C  
HETATM   19  O7  UNL     1      -3.620   1.471   1.366  1.00  0.00           O  
HETATM   20  H1  UNL     1      -4.750  -1.869   1.466  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.752  -2.636   1.228  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.651  -2.086  -0.458  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.645  -0.531   2.153  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.155   0.835   0.680  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.658  -2.343  -1.329  1.00  0.00           H  
HETATM   26  H7  UNL     1       5.114  -2.064  -1.201  1.00  0.00           H  
HETATM   27  H8  UNL     1       6.753   0.724   0.495  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.478   1.530   1.033  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.071   1.222   0.886  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.620  -0.213  -1.543  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.119   0.804  -2.760  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.397   2.122   0.449  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.364   3.326  -0.993  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.709   0.356  -0.308  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.552   1.149   1.495  1.00  0.00           H  
CONECT    1    2   20
CONECT    2    3   21   22
CONECT    3    4   18   23
CONECT    4    5
CONECT    5    6   14   24
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11   12
CONECT   11   27
CONECT   12   13   13   28
CONECT   13   29
CONECT   14   15   16   30
CONECT   15   31
CONECT   16   17   18   32
CONECT   17   33
CONECT   18   19   34
CONECT   19   35
END

HMDB0029943
     RDKit          3D
Arbutin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.3947   -1.6621    0.5452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0263   -1.8044    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3396   -0.5350    1.0596 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0217   -0.7324    1.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -0.0489    0.1404 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8319   -0.8009   -0.3435 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749   -0.5972   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896   -1.4959   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4505   -1.3293   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9713   -0.2396   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3550   -0.0641    0.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937    0.6548    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7035    0.4835    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0391    0.5648   -1.0163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1693    1.2127   -1.8758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9632    1.5438   -0.3066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6038    2.3867   -1.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9296    0.6653    0.4494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6197    1.4714    1.3658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7502   -1.8687    1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7521   -2.6362    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512   -2.0860   -0.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6454   -0.5314    2.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1546    0.8349    0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575   -2.3426   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1143   -2.0641   -1.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7534    0.7242    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4779    1.5303    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0706    1.2221    0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6198   -0.2129   -1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186    0.8045   -2.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3968    2.1220    0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    3.3258   -0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7091    0.3560   -0.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5521    1.1489    1.4954 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
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  3  1  0
 13  7  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  1
  5 24  1  1
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  6
 15 31  1  0
 16 32  1  1
 17 33  1  0
 18 34  1  6
 19 35  1  0
M  END

Synonyms

Value	Source
Hydroquinone-O-beta-D-glucopyranoside	ChEBI
p-Hydroxyphenyl beta-D-glucopyranoside	ChEBI
p-Hydroxyphenyl beta-D-glucoside	ChEBI
Ursin	ChEBI
Uvasol	ChEBI
Hydroquinone-O-b-D-glucopyranoside	Generator
Hydroquinone-O-β-D-glucopyranoside	Generator
p-Hydroxyphenyl b-D-glucopyranoside	Generator
p-Hydroxyphenyl β-D-glucopyranoside	Generator
p-Hydroxyphenyl b-D-glucoside	Generator
p-Hydroxyphenyl β-D-glucoside	Generator
4-Hydroxyphenyl-b-glucopyranoside	HMDB
4-Hydroxyphenyl-β-glucopyranoside	HMDB
4-Hydroxyphenyl beta-D-glucopyranoside	HMDB
4-Hydroxyphenyl β-D-glucopyranoside	HMDB
Arbutine	HMDB
Arbutoside	HMDB
Arbutyne	HMDB
Hydroquinone beta-D-glucopyranoside	HMDB
Hydroquinone glucose	HMDB
Hydroquinone β-D-glucopyranoside	HMDB
beta-Arbutin	HMDB
p-Arbutin	HMDB
Β-arbutin	HMDB
Arbutin	ChEBI

Molecular Formula

C₁₂H₁₆O₇

Average Mass

272.2512

Monoisotopic Mass

272.089602866

IUPAC Name

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

Traditional Name

β-arbutin

CAS Registry Number

497-76-7

SMILES

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

InChI Identifier

InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1

InChI Key

BJRNKVDFDLYUGJ-RMPHRYRLSA-N

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
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Primary alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:18305 )
monosaccharide derivative (CHEBI:18305 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	39.1 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-0.9	ChemAxon
logS	-0.84	ALOGPS
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.16 m³·mol⁻¹	ChemAxon
Polarizability	25.88 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

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	125	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	308	Pig ; Human feces; Human ; Human supragingival plaque; Human saliva; Cattle ; Human stool; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	10	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	84	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	3	Human feces; Human appendix biopsy	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	9	Human feces; Human	Metabolic reconstruction
Bacteria	Firmicutes	23	Pig ; Human feces; Human ; Human supragingival plaque; Human saliva; Cattle ; Human stool; Human subgingival plaque	Metabolic reconstruction
Bacteria	Proteobacteria	5	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	3	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0029943

DrugBank ID

DB11217

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

HYDROQUINONE-O-BETA-D-GLUCOPYRANOSIDE

BiGG ID

Not Available

Wikipedia Link

Arbutin

METLIN ID

Not Available

PubChem Compound

440936

PDB ID

Not Available

ChEBI ID

18305

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Siegers C, Bodinet C, Ali SS, Siegers CP: Bacterial deconjugation of arbutin by Escherichia coli. Phytomedicine. 2003;10 Suppl 4:58-60. doi: 10.1078/1433-187x-00301. [PubMed:12807345 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Arbutin (MMDBc0049980)

MOL for #<Metabolite:0x00007f91ec8ee218>

3D MOL for #<Metabolite:0x00007f91ec8ee218>

3D SDF for #<Metabolite:0x00007f91ec8ee218>

3D-SDF for #<Metabolite:0x00007f91ec8ee218>

PDB for #<Metabolite:0x00007f91ec8ee218>

3D PDB for #<Metabolite:0x00007f91ec8ee218>

SMILES for #<Metabolite:0x00007f91ec8ee218>

INCHI for #<Metabolite:0x00007f91ec8ee218>

Structure for #<Metabolite:0x00007f91ec8ee218>

3D Structure for #<Metabolite:0x00007f91ec8ee218>