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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 22:28:08 UTC

Update Date

2021-09-23 22:28:09 UTC

HMDB ID

HMDB0302998

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Orsellinic acid 2-O-beta-D-glucoside

Description

Orsellinic acid 2-o-beta-d-glucoside 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. Orsellinic acid 2-o-beta-d-glucoside is soluble (in water) and a weakly acidic compound (based on its pKa). Orsellinic acid 2-o-beta-d-glucoside can be found in cloves, which makes orsellinic acid 2-o-beta-d-glucoside a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302998
     RDKit          3D
Orsellinic acid 2-O-beta-D-glucoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.1610   -0.7946    0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9795    0.0496   -0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654    1.3335   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0524    2.0734   -0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042    3.3733   -1.3779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7932    1.5362   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815    0.2606   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3805   -0.3467   -0.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9039    0.1697   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4383   -0.5591   -1.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7880   -0.3932   -1.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1642    1.0510   -1.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5277    1.2151   -1.9337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719   -1.0667   -0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874   -2.4527   -0.6785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9028   -0.7303    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9294   -0.0998    1.6389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    0.0884    0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8655   -0.3493    1.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7211   -0.4785   -0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -1.8569    0.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5583   -2.8404   -0.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4873   -2.0559    1.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0738   -0.1676    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0284   -1.1957    1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025   -1.6158   -0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763    1.7413   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2302    4.1365   -0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583    2.1409   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8404    1.2321   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809   -0.9293   -2.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8078    1.7133   -0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806    1.3976   -2.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952    2.1683   -2.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5766   -0.8435   -0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6276   -2.6847   -1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329   -1.6977    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5286    0.4149    1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9655    1.1407    1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6900   -1.3174    1.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9467   -2.7606    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  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
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20  2  1  0
 18  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 23 41  1  0
M  END


  Mrv0541 02241223322D          

 23 24  0  0  0  0            999 V2000
    0.1625   -3.0557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0770   -2.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3768   -0.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467   -0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467   -1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3768   -2.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3768   -3.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467   -1.7728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0770   -0.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8308   -0.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536    0.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4317    0.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0526    0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952    1.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1171    1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962    1.1668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5890   -0.7180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8308    0.3623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172    1.9778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9608    2.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5816    3.0557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302998

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=CC(OC2OC(CO)C(O)C(O)C2O)=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O9/c1-5-2-6(16)3-7(9(5)13(20)21)22-14-12(19)11(18)10(17)8(4-15)23-14/h2-3,8,10-12,14-19H,4H2,1H3,(H,20,21)

> <INCHI_KEY>
AQLSLUZPCXWYQZ-UHFFFAOYSA-N

> <FORMULA>
C14H18O9

> <MOLECULAR_WEIGHT>
330.2873

> <EXACT_MASS>
330.095082174

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
30.855629420747107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-2-methyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.7309486233333335

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.7993655269292

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8579145388678238

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923463070615

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
74.4616

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-2-methyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302998
     RDKit          3D
Orsellinic acid 2-O-beta-D-glucoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.1610   -0.7946    0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9795    0.0496   -0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654    1.3335   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0524    2.0734   -0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042    3.3733   -1.3779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7932    1.5362   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815    0.2606   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3805   -0.3467   -0.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9039    0.1697   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4383   -0.5591   -1.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7880   -0.3932   -1.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1642    1.0510   -1.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5277    1.2151   -1.9337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719   -1.0667   -0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874   -2.4527   -0.6785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9028   -0.7303    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9294   -0.0998    1.6389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    0.0884    0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8655   -0.3493    1.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7211   -0.4785   -0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -1.8569    0.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5583   -2.8404   -0.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4873   -2.0559    1.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0738   -0.1676    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0284   -1.1957    1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025   -1.6158   -0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763    1.7413   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2302    4.1365   -0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583    2.1409   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8404    1.2321   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809   -0.9293   -2.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8078    1.7133   -0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806    1.3976   -2.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952    2.1683   -2.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5766   -0.8435   -0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6276   -2.6847   -1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329   -1.6977    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5286    0.4149    1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9655    1.1407    1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6900   -1.3174    1.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9467   -2.7606    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  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
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20  2  1  0
 18  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 23 41  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  O   UNK     0       0.303  -5.704   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.144  -4.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.133  -3.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.133  -1.713   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.570  -0.914   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.007  -1.713   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.007  -3.309   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.570  -4.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.570  -5.704   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.580  -3.309   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.144  -0.914   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.284  -0.914   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.220   0.672   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.673   0.172   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.831   1.177   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.538   2.683   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.085   3.183   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.926   2.178   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.966  -1.340   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.284   0.676   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.699   3.692   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.793   4.693   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.952   5.704   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8                                                            
CONECT   10    2                                                            
CONECT   11    4   13                                                       
CONECT   12    6                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   22                                                  
CONECT   18   13   17                                                       
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   17   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0302998
HETATM    1  C1  UNL     1       5.161  -0.795   0.189  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.980   0.050  -0.154  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.165   1.334  -0.611  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.052   2.073  -0.915  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.204   3.373  -1.378  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.793   1.536  -0.763  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.581   0.261  -0.310  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.380  -0.347  -0.132  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.904   0.170  -0.361  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.438  -0.559  -1.413  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.788  -0.393  -1.591  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.164   1.051  -1.753  1.00  0.00           C  
HETATM   13  O4  UNL     1      -4.528   1.215  -1.934  1.00  0.00           O  
HETATM   14  C10 UNL     1      -3.472  -1.067  -0.435  1.00  0.00           C  
HETATM   15  O5  UNL     1      -3.387  -2.453  -0.679  1.00  0.00           O  
HETATM   16  C11 UNL     1      -2.903  -0.730   0.892  1.00  0.00           C  
HETATM   17  O6  UNL     1      -3.929  -0.100   1.639  1.00  0.00           O  
HETATM   18  C12 UNL     1      -1.681   0.088   0.904  1.00  0.00           C  
HETATM   19  O7  UNL     1      -0.866  -0.349   1.977  1.00  0.00           O  
HETATM   20  C13 UNL     1       2.721  -0.479  -0.006  1.00  0.00           C  
HETATM   21  C14 UNL     1       2.586  -1.857   0.486  1.00  0.00           C  
HETATM   22  O8  UNL     1       2.558  -2.840  -0.300  1.00  0.00           O  
HETATM   23  O9  UNL     1       2.487  -2.056   1.849  1.00  0.00           O  
HETATM   24  H1  UNL     1       6.074  -0.168   0.206  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.028  -1.196   1.214  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.202  -1.616  -0.540  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.176   1.741  -0.724  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.230   4.137  -0.706  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.958   2.141  -1.009  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.840   1.232  -0.741  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.081  -0.929  -2.516  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.808   1.713  -0.967  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.681   1.398  -2.705  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.695   2.168  -2.142  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.577  -0.844  -0.508  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.628  -2.685  -1.592  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.733  -1.698   1.452  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.529   0.415   1.057  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.966   1.141   1.205  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.690  -1.317   1.833  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.947  -2.761   2.296  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   20
CONECT    3    4   27
CONECT    4    5    6    6
CONECT    5   28
CONECT    6    7   29
CONECT    7    8   20   20
CONECT    8    9
CONECT    9   10   18   30
CONECT   10   11
CONECT   11   12   14   31
CONECT   12   13   32   33
CONECT   13   34
CONECT   14   15   16   35
CONECT   15   36
CONECT   16   17   18   37
CONECT   17   38
CONECT   18   19   39
CONECT   19   40
CONECT   20   21
CONECT   21   22   22   23
CONECT   23   41
END

HMDB0302998
     RDKit          3D
Orsellinic acid 2-O-beta-D-glucoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.1610   -0.7946    0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9795    0.0496   -0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654    1.3335   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0524    2.0734   -0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042    3.3733   -1.3779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7932    1.5362   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815    0.2606   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3805   -0.3467   -0.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9039    0.1697   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4383   -0.5591   -1.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7880   -0.3932   -1.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1642    1.0510   -1.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5277    1.2151   -1.9337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719   -1.0667   -0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874   -2.4527   -0.6785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9028   -0.7303    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9294   -0.0998    1.6389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    0.0884    0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8655   -0.3493    1.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7211   -0.4785   -0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -1.8569    0.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5583   -2.8404   -0.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4873   -2.0559    1.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0738   -0.1676    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0284   -1.1957    1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025   -1.6158   -0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763    1.7413   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2302    4.1365   -0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583    2.1409   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8404    1.2321   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809   -0.9293   -2.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8078    1.7133   -0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806    1.3976   -2.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952    2.1683   -2.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5766   -0.8435   -0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6276   -2.6847   -1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329   -1.6977    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5286    0.4149    1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9655    1.1407    1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6900   -1.3174    1.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9467   -2.7606    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  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
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20  2  1  0
 18  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-2-methyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate	Generator
Orsellinate 2-O-b-D-glucoside	Generator
Orsellinate 2-O-beta-D-glucoside	Generator
Orsellinate 2-O-β-D-glucoside	Generator
Orsellinic acid 2-O-b-D-glucoside	Generator
Orsellinic acid 2-O-β-D-glucoside	Generator

Chemical Formula

C₁₄H₁₈O₉

Average Molecular Weight

330.2873

Monoisotopic Molecular Weight

330.095082174

IUPAC Name

4-hydroxy-2-methyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

Traditional Name

4-hydroxy-2-methyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(OC2OC(CO)C(O)C(O)C2O)=C1C(O)=O

InChI Identifier

InChI=1S/C14H18O9/c1-5-2-6(16)3-7(9(5)13(20)21)22-14-12(19)11(18)10(17)8(4-15)23-14/h2-3,8,10-12,14-19H,4H2,1H3,(H,20,21)

InChI Key

AQLSLUZPCXWYQZ-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
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Benzoyl
M-cresol
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Toluene
Sugar acid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Cloves (FooDB: FOOD00179)

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	-0.65	ALOGPS
logP	-0.73	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.46 m³·mol⁻¹	ChemAxon
Polarizability	30.86 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	175.626	32859911
AllCCS	[M+H-H2O]+	172.522	32859911
AllCCS	[M+Na]+	179.32	32859911
AllCCS	[M+NH4]+	178.496	32859911
AllCCS	[M-H]-	171.495	32859911
AllCCS	[M+Na-2H]-	171.441	32859911
AllCCS	[M+HCOO]-	171.506	32859911
DeepCCS	[M+H]+	174.555	30932474
DeepCCS	[M-H]-	172.197	30932474
DeepCCS	[M-2H]-	205.083	30932474
DeepCCS	[M+Na]+	180.648	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Orsellinic acid 2-O-beta-D-glucoside,3TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O	3518.5	Semi standard non polar	33892256
Orsellinic acid 2-O-beta-D-glucoside,3TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O	3464.7	Standard non polar	33892256
Orsellinic acid 2-O-beta-D-glucoside,3TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O	3837.8	Standard polar	33892256
Orsellinic acid 2-O-beta-D-glucoside,4TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O	3718.3	Semi standard non polar	33892256
Orsellinic acid 2-O-beta-D-glucoside,4TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O	3606.8	Standard non polar	33892256
Orsellinic acid 2-O-beta-D-glucoside,4TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O	3630.8	Standard polar	33892256
Orsellinic acid 2-O-beta-D-glucoside,4TBDMS,isomer #4	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O	3701.8	Semi standard non polar	33892256
Orsellinic acid 2-O-beta-D-glucoside,4TBDMS,isomer #4	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O	3553.7	Standard non polar	33892256
Orsellinic acid 2-O-beta-D-glucoside,4TBDMS,isomer #4	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O	3608.4	Standard polar	33892256
Orsellinic acid 2-O-beta-D-glucoside,4TBDMS,isomer #6	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O[Si](C)(C)C(C)(C)C	3649.8	Semi standard non polar	33892256
Orsellinic acid 2-O-beta-D-glucoside,4TBDMS,isomer #6	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O[Si](C)(C)C(C)(C)C	3627.0	Standard non polar	33892256
Orsellinic acid 2-O-beta-D-glucoside,4TBDMS,isomer #6	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)=C1C(=O)O[Si](C)(C)C(C)(C)C	3728.5	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 10V, Positive-QTOF	splash10-0159-0936000000-ead1a93c37c5c94bff87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 20V, Positive-QTOF	splash10-0gb9-0910000000-0d11819b3543ba29935d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 40V, Positive-QTOF	splash10-0uxr-2900000000-58a90dad3b0b7dcfab5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 10V, Negative-QTOF	splash10-00or-1958000000-1ce80f0ed4eb96133f48	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 20V, Negative-QTOF	splash10-01b9-1941000000-ce8e1f502d1296657875	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 40V, Negative-QTOF	splash10-00xr-2900000000-9070dc8e4db233ba0970	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 10V, Positive-QTOF	splash10-0udi-0905000000-916f6a29d15d87818276	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 20V, Positive-QTOF	splash10-0udi-0900000000-901d54ddfdd420019c60	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 40V, Positive-QTOF	splash10-0udi-3900000000-156a05c10d178e092de4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 10V, Negative-QTOF	splash10-0200-0329000000-dc5529f9db9d62818eb1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 20V, Negative-QTOF	splash10-00di-0900000000-0f38739172ee17a290dd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orsellinic acid 2-O-beta-D-glucoside 40V, Negative-QTOF	splash10-00di-1900000000-1b074dfd25e45d1e5e35	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

FDB007220

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

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

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 Orsellinic acid 2-O-beta-D-glucoside (HMDB0302998)

MOL for HMDB0302998 (Orsellinic acid 2-O-beta-D-glucoside)

3D MOL for HMDB0302998 (Orsellinic acid 2-O-beta-D-glucoside)

3D SDF for HMDB0302998 (Orsellinic acid 2-O-beta-D-glucoside)

3D-SDF for HMDB0302998 (Orsellinic acid 2-O-beta-D-glucoside)

PDB for HMDB0302998 (Orsellinic acid 2-O-beta-D-glucoside)

3D PDB for HMDB0302998 (Orsellinic acid 2-O-beta-D-glucoside)

SMILES for HMDB0302998 (Orsellinic acid 2-O-beta-D-glucoside)

INCHI for HMDB0302998 (Orsellinic acid 2-O-beta-D-glucoside)

Structure for HMDB0302998 (Orsellinic acid 2-O-beta-D-glucoside)

3D Structure for HMDB0302998 (Orsellinic acid 2-O-beta-D-glucoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra