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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 01:29:03 UTC

Update Date

2021-09-24 01:29:03 UTC

HMDB ID

HMDB0303383

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methylarbutin

Description

Methylarbutin is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides 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. Methylarbutin is soluble (in water) and a very weakly acidic compound (based on its pKa). Methylarbutin can be found in sweet marjoram, which makes methylarbutin a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303383
     RDKit          3D
Methylarbutin
 38 39  0  0  0  0  0  0  0  0999 V2000
    6.4412    0.0410    0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2247    0.0216    1.2782 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879   -0.0060    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8544   -0.0167   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017   -0.0444   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -0.0615   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2509   -0.0890   -1.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0139   -0.1101   -0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958    1.0233   -0.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    1.2452   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5629    2.0351    1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123    2.2936    1.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4688   -0.1040    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8239   -0.0401    0.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -1.0012   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136   -2.1025   -1.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154   -1.3656   -1.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -1.7185   -2.2623 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5835   -0.0514    0.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677   -0.0231    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7443   -0.9634    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3634    0.7340   -0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2695    0.4457    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7379   -0.0032   -1.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5320   -0.0522   -2.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -0.1034    0.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5825    1.7775   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    2.9808    0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168    1.3973    1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5777    3.1820    2.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -0.4998    0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0617   -0.6639    1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -0.3781   -2.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5169   -2.9494   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383   -2.1929   -0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903   -2.5581   -2.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7455   -0.0637    1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9403   -0.0152    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  2  0
 20  3  1  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

  Mrv0541 02241218032D          

 20 21  0  0  0  0            999 V2000
   -1.0737   -0.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8172   -0.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4776   -0.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4776    0.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8172    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737    0.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2211    0.8673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4776    1.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8165    0.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8165   -0.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5599   -0.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0737    1.1971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3302    0.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3302    1.1971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560   -1.2801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560   -0.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649   -0.7020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2211   -0.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2211   -1.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  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
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303383

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(OC2OC(CO)C(O)C(O)C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O7/c1-18-7-2-4-8(5-3-7)19-13-12(17)11(16)10(15)9(6-14)20-13/h2-5,9-17H,6H2,1H3

> <INCHI_KEY>
SIXFVXJMCGPTRB-UHFFFAOYSA-N

> <FORMULA>
C13H18O7

> <MOLECULAR_WEIGHT>
286.2778

> <EXACT_MASS>
286.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
28.068742246695084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.52

> <JCHEM_LOGP>
-0.7560588646666667

> <ALOGPS_LOGS>
-1.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19609144571097

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200141753492645

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923436865826

> <JCHEM_POLAR_SURFACE_AREA>
108.61000000000001

> <JCHEM_REFRACTIVITY>
66.6465

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.38e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303383
     RDKit          3D
Methylarbutin
 38 39  0  0  0  0  0  0  0  0999 V2000
    6.4412    0.0410    0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2247    0.0216    1.2782 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879   -0.0060    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8544   -0.0167   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017   -0.0444   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -0.0615   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2509   -0.0890   -1.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0139   -0.1101   -0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958    1.0233   -0.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    1.2452   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5629    2.0351    1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123    2.2936    1.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4688   -0.1040    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8239   -0.0401    0.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -1.0012   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136   -2.1025   -1.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154   -1.3656   -1.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -1.7185   -2.2623 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5835   -0.0514    0.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677   -0.0231    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7443   -0.9634    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3634    0.7340   -0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2695    0.4457    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7379   -0.0032   -1.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5320   -0.0522   -2.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -0.1034    0.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5825    1.7775   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    2.9808    0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168    1.3973    1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5777    3.1820    2.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -0.4998    0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0617   -0.6639    1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -0.3781   -2.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5169   -2.9494   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383   -2.1929   -0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903   -2.5581   -2.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7455   -0.0637    1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9403   -0.0152    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  2  0
 20  3  1  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.004  -0.076   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.392  -0.847   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.625  -0.076   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.625   1.464   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.392   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.004   1.464   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.013   1.619   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.625   2.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.391   1.464   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.391  -0.076   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.778  -0.847   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.004   2.235   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.616   1.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.616   2.235   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.158  -2.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.158  -0.847   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.770  -0.076   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.308  -1.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.013  -0.847   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -6.013  -2.390   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5   14                                                  
CONECT    7    8                                                            
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14    6   13                                                       
CONECT   15   16                                                            
CONECT   16   10   15   17                                                  
CONECT   17   13   16   18                                                  
CONECT   18   17                                                            
CONECT   19    3   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0303383
HETATM    1  C1  UNL     1       6.441   0.041   0.561  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.225   0.022   1.278  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.988  -0.006   0.683  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.854  -0.017  -0.701  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.602  -0.044  -1.265  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.475  -0.062  -0.450  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.251  -0.089  -1.060  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.014  -0.110  -0.479  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.696   1.023  -0.935  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.880   1.245  -0.246  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.563   2.035   1.012  1.00  0.00           C  
HETATM   12  O4  UNL     1      -3.712   2.294   1.753  1.00  0.00           O  
HETATM   13  C9  UNL     1      -3.469  -0.104   0.079  1.00  0.00           C  
HETATM   14  O5  UNL     1      -4.824  -0.040   0.370  1.00  0.00           O  
HETATM   15  C10 UNL     1      -3.184  -1.001  -1.109  1.00  0.00           C  
HETATM   16  O6  UNL     1      -4.014  -2.102  -1.090  1.00  0.00           O  
HETATM   17  C11 UNL     1      -1.715  -1.366  -1.024  1.00  0.00           C  
HETATM   18  O7  UNL     1      -1.189  -1.718  -2.262  1.00  0.00           O  
HETATM   19  C12 UNL     1       1.584  -0.051   0.920  1.00  0.00           C  
HETATM   20  C13 UNL     1       2.868  -0.023   1.481  1.00  0.00           C  
HETATM   21  H1  UNL     1       6.744  -0.963   0.216  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.363   0.734  -0.325  1.00  0.00           H  
HETATM   23  H3  UNL     1       7.269   0.446   1.170  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.738  -0.003  -1.312  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.532  -0.052  -2.352  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.001  -0.103   0.608  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.583   1.777  -0.905  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.079   2.981   0.719  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.917   1.397   1.641  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.578   3.182   2.175  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.966  -0.500   0.985  1.00  0.00           H  
HETATM   32  H12 UNL     1      -5.062  -0.664   1.113  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.330  -0.378  -2.037  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.517  -2.949  -0.937  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.638  -2.193  -0.282  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.690  -2.558  -2.162  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.745  -0.064   1.600  1.00  0.00           H  
HETATM   38  H18 UNL     1       2.940  -0.015   2.571  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   19
CONECT    7    8
CONECT    8    9   17   26
CONECT    9   10
CONECT   10   11   13   27
CONECT   11   12   28   29
CONECT   12   30
CONECT   13   14   15   31
CONECT   14   32
CONECT   15   16   17   33
CONECT   16   34
CONECT   17   18   35
CONECT   18   36
CONECT   19   20   20   37
CONECT   20   38
END

HMDB0303383
     RDKit          3D
Methylarbutin
 38 39  0  0  0  0  0  0  0  0999 V2000
    6.4412    0.0410    0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2247    0.0216    1.2782 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879   -0.0060    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8544   -0.0167   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017   -0.0444   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -0.0615   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2509   -0.0890   -1.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0139   -0.1101   -0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958    1.0233   -0.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    1.2452   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5629    2.0351    1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123    2.2936    1.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4688   -0.1040    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8239   -0.0401    0.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -1.0012   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136   -2.1025   -1.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154   -1.3656   -1.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -1.7185   -2.2623 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5835   -0.0514    0.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677   -0.0231    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7443   -0.9634    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3634    0.7340   -0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2695    0.4457    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7379   -0.0032   -1.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5320   -0.0522   -2.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -0.1034    0.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5825    1.7775   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    2.9808    0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168    1.3973    1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5777    3.1820    2.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -0.4998    0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0617   -0.6639    1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -0.3781   -2.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5169   -2.9494   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383   -2.1929   -0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903   -2.5581   -2.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7455   -0.0637    1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9403   -0.0152    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  2  0
 20  3  1  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈O₇

Average Molecular Weight

286.2778

Monoisotopic Molecular Weight

286.10525293

IUPAC Name

2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxane-3,4,5-triol

Traditional Name

2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(OC2OC(CO)C(O)C(O)C2O)C=C1

InChI Identifier

InChI=1S/C13H18O7/c1-18-7-2-4-8(5-3-7)19-13-12(17)11(16)10(15)9(6-14)20-13/h2-5,9-17H,6H2,1H3

InChI Key

SIXFVXJMCGPTRB-UHFFFAOYSA-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
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Organoheterocyclic compound
Ether
Acetal
Oxacycle
Polyol
Hydrocarbon derivative
Alcohol
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0303383)

Food

Herb and spice

Herb

Sweet marjoram (FooDB: FOOD00122)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.52	ALOGPS
logP	-0.76	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	108.61 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.65 m³·mol⁻¹	ChemAxon
Polarizability	28.07 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	168.422	32859911
AllCCS	[M+H-H2O]+	164.959	32859911
AllCCS	[M+Na]+	172.557	32859911
AllCCS	[M+NH4]+	171.634	32859911
AllCCS	[M-H]-	165.307	32859911
AllCCS	[M+Na-2H]-	165.392	32859911
AllCCS	[M+HCOO]-	165.603	32859911
DeepCCS	[M+H]+	167.013	30932474
DeepCCS	[M-H]-	164.655	30932474
DeepCCS	[M-2H]-	197.542	30932474
DeepCCS	[M+Na]+	173.106	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 10V, Positive-QTOF	splash10-004r-0970000000-59772d5496009e2425a8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 20V, Positive-QTOF	splash10-004i-1900000000-00de91e3feb41f52a953	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 40V, Positive-QTOF	splash10-056r-6900000000-5a8b6b75541f96526046	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 10V, Negative-QTOF	splash10-0079-1790000000-65dfe025877b37a3e65e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 20V, Negative-QTOF	splash10-05fr-2920000000-e4c1613ff12f695878fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 40V, Negative-QTOF	splash10-0ab9-4900000000-a125b859f09e5bdf419c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 10V, Positive-QTOF	splash10-004i-1920000000-fa401bd4fc13dbad8d10	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 20V, Positive-QTOF	splash10-002b-7930000000-9c581018280040d58e6a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 40V, Positive-QTOF	splash10-00fs-4920000000-a44ed2605e2f41c1f8c0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 10V, Negative-QTOF	splash10-05fr-0900000000-8e513fdf790330ef654b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 20V, Negative-QTOF	splash10-0a4i-8900000000-cd996c278fb21a6fedd5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylarbutin 40V, Negative-QTOF	splash10-0a6r-9600000000-9ea5dc3b23e3efacacf9	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012593

KNApSAcK ID

Not Available

Chemspider ID

337197

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

380510

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Methylarbutin (HMDB0303383)

MOL for HMDB0303383 (Methylarbutin)

3D MOL for HMDB0303383 (Methylarbutin)

3D SDF for HMDB0303383 (Methylarbutin)

3D-SDF for HMDB0303383 (Methylarbutin)

PDB for HMDB0303383 (Methylarbutin)

3D PDB for HMDB0303383 (Methylarbutin)

SMILES for HMDB0303383 (Methylarbutin)

INCHI for HMDB0303383 (Methylarbutin)

Structure for HMDB0303383 (Methylarbutin)

3D Structure for HMDB0303383 (Methylarbutin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra