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

2022-09-01 02:17:42 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

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-0uxr-1971000000-e8260464bad4d4a7fa0c	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uxs-0940000000-9984522469f86670798f	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0r00-9750000000-b52a5d3b5fb7e98f0009	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0002-0090000000-a7028a3a9618849334b7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0229-0920000000-532b692f9942a62cc7c8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0229-0910000000-1cb0580496288b7004fc	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0950000000-4bafd0325d0163331c0a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0950000000-ffffdfe1cd448f0ea135	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-016r-0290000000-0ebc801fded534434aa5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-016r-0390000000-5831b5a141106482d24d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0a4i-0900000000-e517344bdabb66a133e9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0a4i-0900000000-315daa57d6f694ca71fb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4i-1900000000-df811a65eba1be7fd68d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0a4i-0900000000-4efe3ed1e7614387deb4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-014i-9000000000-6f8b05f1e0b20e00a25f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-014i-9100000000-7092290163d035871936	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-0900000000-a0b2ea306ed135900292	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0a4i-1900000000-26385cb99dd5b38d4f3c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0a4i-0900000000-0a4c12f1e9730c4685ea	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-0970000000-e87519bd2c30ca193e5e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-f812a22889a4e7871758	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-9600000000-9a8f2b8fb568a07413b4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-1890000000-cb67c77a9f0c57c986bd	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1910000000-52b74ad8f6f3181df26d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-45bf1851196d0254c239	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ab9-0950000000-597b2277ebb9d13fbb41	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-4940000000-6a46c2768079c1935cb9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-7900000000-56f28af9a02294ffb2fa	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0006905	Arbutin	Arbutin 6-phosphate	Not Available	Arbutin transport via PEP:Pyr PTS	VMH	30371894

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	Proteobacteria	130	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	Firmicutes	331	Pig ; Human feces; Human ; Human supragingival plaque; Human saliva; Cattle ; Human stool; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	94	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	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	3	Human feces; Human appendix biopsy	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	9	Human feces; Human	Metabolic reconstruction
Bacteria	Tenericutes	3	Human feces	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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:0x000055c79c666868>

3D MOL for #<Metabolite:0x000055c79c666868>

3D SDF for #<Metabolite:0x000055c79c666868>

3D-SDF for #<Metabolite:0x000055c79c666868>

PDB for #<Metabolite:0x000055c79c666868>

3D PDB for #<Metabolite:0x000055c79c666868>

SMILES for #<Metabolite:0x000055c79c666868>

INCHI for #<Metabolite:0x000055c79c666868>

Structure for #<Metabolite:0x000055c79c666868>

3D Structure for #<Metabolite:0x000055c79c666868>