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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:52 UTC

Update Date

2022-03-07 02:53:28 UTC

HMDB ID

HMDB0032796

Secondary Accession Numbers

HMDB32796

Metabolite Identification

Common Name

Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate

Description

Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate, also known as hostmaniane, belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group. Based on a literature review very few articles have been published on Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate.

Structure

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

HMDB0032796
     RDKit          3D
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate
 36 36  0  0  0  0  0  0  0  0999 V2000
    6.1782   -0.4758    1.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0935   -0.1653    0.5150 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7952   -0.0555    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5860   -0.2369    2.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727    0.2575    0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8971    0.4616   -1.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954    0.7583   -2.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131    0.8569   -1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077    1.1593   -2.5228 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3252    0.6666   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    0.7931    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8918   -0.4202   -0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3476   -1.5528    0.3545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3052   -0.2680    0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1445   -1.4697   -0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9789    0.9576   -0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3606   -0.1259    1.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3825    0.3689    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2699    0.3929    2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1201   -0.5158    0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0116   -1.4303    1.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226    0.3720   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397    0.9035   -3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382    1.3063   -3.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    0.8300    1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5295    1.7328   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8893   -0.6024   -1.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955   -2.1725    0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4889   -2.0350    0.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018   -2.1681   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0765   -1.1709   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6689    1.1357   -1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070    1.8435    0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0675    0.7529   -0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0115   -0.9051    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1569    0.2206    1.5800 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 10 18  2  0
 18  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END


  Mrv0541 05061306422D          

 18 18  0  0  0  0            999 V2000
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  2  0  0  0  0
 17 13  1  0  0  0  0
 18  3  1  0  0  0  0
 18 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032796

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1=CC(CC(O)C(C)(C)O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O5/c1-13(2,17)11(15)7-9-6-8(12(16)18-3)4-5-10(9)14/h4-6,11,14-15,17H,7H2,1-3H3

> <INCHI_KEY>
ABFHVQPVDSMGNR-UHFFFAOYSA-N

> <FORMULA>
C13H18O5

> <MOLECULAR_WEIGHT>
254.279

> <EXACT_MASS>
254.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.618155513889405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
1.2612856470000002

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.769787559801923

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.651130468107686

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0940531055586433

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
66.6546

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032796
     RDKit          3D
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate
 36 36  0  0  0  0  0  0  0  0999 V2000
    6.1782   -0.4758    1.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0935   -0.1653    0.5150 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7952   -0.0555    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5860   -0.2369    2.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727    0.2575    0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8971    0.4616   -1.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954    0.7583   -2.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131    0.8569   -1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077    1.1593   -2.5228 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3252    0.6666   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    0.7931    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8918   -0.4202   -0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3476   -1.5528    0.3545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3052   -0.2680    0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1445   -1.4697   -0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9789    0.9576   -0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3606   -0.1259    1.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3825    0.3689    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2699    0.3929    2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1201   -0.5158    0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0116   -1.4303    1.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226    0.3720   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397    0.9035   -3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382    1.3063   -3.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    0.8300    1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5295    1.7328   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8893   -0.6024   -1.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955   -2.1725    0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4889   -2.0350    0.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018   -2.1681   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0765   -1.1709   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6689    1.1357   -1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070    1.8435    0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0675    0.7529   -0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0115   -0.9051    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1569    0.2206    1.5800 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 10 18  2  0
 18  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.437   3.286   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.897   5.954   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   18                                                            
CONECT    4    5    8                                                       
CONECT    5    4   10                                                       
CONECT    6    8    9                                                       
CONECT    7    9   11                                                       
CONECT    8    4    6   12                                                  
CONECT    9    6    7   10                                                  
CONECT   10    5    9   14                                                  
CONECT   11    7   13   15                                                  
CONECT   12    8   16   18                                                  
CONECT   13    1    2   11   17                                             
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18    3   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0032796
HETATM    1  C1  UNL     1       6.178  -0.476   1.397  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.094  -0.165   0.515  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.795  -0.055   0.971  1.00  0.00           C  
HETATM    4  O2  UNL     1       3.586  -0.237   2.194  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.673   0.257   0.106  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.897   0.462  -1.255  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.895   0.758  -2.130  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.613   0.857  -1.631  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.408   1.159  -2.523  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.325   0.667  -0.297  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.082   0.793   0.141  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.892  -0.420  -0.243  1.00  0.00           C  
HETATM   13  O4  UNL     1      -1.348  -1.553   0.354  1.00  0.00           O  
HETATM   14  C10 UNL     1      -3.305  -0.268   0.231  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.145  -1.470  -0.146  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.979   0.958  -0.353  1.00  0.00           C  
HETATM   17  O5  UNL     1      -3.361  -0.126   1.619  1.00  0.00           O  
HETATM   18  C13 UNL     1       1.383   0.369   0.537  1.00  0.00           C  
HETATM   19  H1  UNL     1       6.270   0.393   2.080  1.00  0.00           H  
HETATM   20  H2  UNL     1       7.120  -0.516   0.812  1.00  0.00           H  
HETATM   21  H3  UNL     1       6.012  -1.430   1.925  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.923   0.372  -1.591  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.140   0.904  -3.169  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.238   1.306  -3.509  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.067   0.830   1.256  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.529   1.733  -0.199  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.889  -0.602  -1.336  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.095  -2.172   0.541  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.489  -2.035   0.755  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.602  -2.168  -0.831  1.00  0.00           H  
HETATM   31  H13 UNL     1      -5.076  -1.171  -0.691  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.669   1.136  -1.385  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.807   1.844   0.306  1.00  0.00           H  
HETATM   34  H16 UNL     1      -5.067   0.753  -0.366  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.011  -0.905   2.101  1.00  0.00           H  
HETATM   36  H18 UNL     1       1.157   0.221   1.580  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   18
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   10
CONECT    9   24
CONECT   10   11   18   18
CONECT   11   12   25   26
CONECT   12   13   14   27
CONECT   13   28
CONECT   14   15   16   17
CONECT   15   29   30   31
CONECT   16   32   33   34
CONECT   17   35
CONECT   18   36
END

HMDB0032796
     RDKit          3D
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate
 36 36  0  0  0  0  0  0  0  0999 V2000
    6.1782   -0.4758    1.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0935   -0.1653    0.5150 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7952   -0.0555    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5860   -0.2369    2.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727    0.2575    0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8971    0.4616   -1.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954    0.7583   -2.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131    0.8569   -1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077    1.1593   -2.5228 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3252    0.6666   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    0.7931    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8918   -0.4202   -0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3476   -1.5528    0.3545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3052   -0.2680    0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1445   -1.4697   -0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9789    0.9576   -0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3606   -0.1259    1.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3825    0.3689    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2699    0.3929    2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1201   -0.5158    0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0116   -1.4303    1.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226    0.3720   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397    0.9035   -3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382    1.3063   -3.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    0.8300    1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5295    1.7328   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8893   -0.6024   -1.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955   -2.1725    0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4889   -2.0350    0.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018   -2.1681   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0765   -1.1709   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6689    1.1357   -1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070    1.8435    0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0675    0.7529   -0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0115   -0.9051    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1569    0.2206    1.5800 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 10 18  2  0
 18  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoic acid	Generator
Hostmaniane	HMDB

Chemical Formula

C₁₃H₁₈O₅

Average Molecular Weight

254.279

Monoisotopic Molecular Weight

254.115423686

IUPAC Name

methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate

Traditional Name

methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate

CAS Registry Number

117176-70-2

SMILES

COC(=O)C1=CC(CC(O)C(C)(C)O)=C(O)C=C1

InChI Identifier

InChI=1S/C13H18O5/c1-13(2,17)11(15)7-9-6-8(12(16)18-3)4-5-10(9)14/h4-6,11,14-15,17H,7H2,1-3H3

InChI Key

ABFHVQPVDSMGNR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

p-Hydroxybenzoic acid alkyl esters

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Methyl ester
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Alcohol
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032796)
Cytoplasm (HMDB: HMDB0032796)

Source

Exogenous

Exogenous (HMDB: HMDB0032796)

Food

Food (HMDB: HMDB0032796)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032796)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	143 - 144 °C	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
Water Solubility	1.67 g/L	ALOGPS
logP	0.82	ALOGPS
logP	1.26	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	8.65	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	66.65 m³·mol⁻¹	ChemAxon
Polarizability	26.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	160.576	31661259
DarkChem	[M-H]-	159.694	31661259
DeepCCS	[M+H]+	164.098	30932474
DeepCCS	[M-H]-	161.74	30932474
DeepCCS	[M-2H]-	194.631	30932474
DeepCCS	[M+Na]+	170.191	30932474
AllCCS	[M+H]+	158.8	32859911
AllCCS	[M+H-H2O]+	155.2	32859911
AllCCS	[M+NH4]+	162.1	32859911
AllCCS	[M+Na]+	163.0	32859911
AllCCS	[M-H]-	160.0	32859911
AllCCS	[M+Na-2H]-	160.5	32859911
AllCCS	[M+HCOO]-	161.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	3.92 minutes	32390414
Predicted by Siyang on May 30, 2022	10.07 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.12 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	60.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1635.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	213.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	125.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	153.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	59.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	398.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	358.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	704.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	327.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	987.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	231.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	290.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	241.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	68.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate	COC(=O)C1=CC(CC(O)C(C)(C)O)=C(O)C=C1	3536.8	Standard polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate	COC(=O)C1=CC(CC(O)C(C)(C)O)=C(O)C=C1	2098.1	Standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate	COC(=O)C1=CC(CC(O)C(C)(C)O)=C(O)C=C1	2182.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,1TMS,isomer #1	COC(=O)C1=CC=C(O)C(CC(O[Si](C)(C)C)C(C)(C)O)=C1	2155.7	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,1TMS,isomer #2	COC(=O)C1=CC=C(O)C(CC(O)C(C)(C)O[Si](C)(C)C)=C1	2211.2	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,1TMS,isomer #3	COC(=O)C1=CC=C(O[Si](C)(C)C)C(CC(O)C(C)(C)O)=C1	2146.4	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,2TMS,isomer #1	COC(=O)C1=CC=C(O[Si](C)(C)C)C(CC(O[Si](C)(C)C)C(C)(C)O)=C1	2155.9	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,2TMS,isomer #2	COC(=O)C1=CC=C(O)C(CC(O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C)=C1	2197.8	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,2TMS,isomer #3	COC(=O)C1=CC=C(O[Si](C)(C)C)C(CC(O)C(C)(C)O[Si](C)(C)C)=C1	2195.6	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,3TMS,isomer #1	COC(=O)C1=CC=C(O[Si](C)(C)C)C(CC(O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C)=C1	2229.0	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,1TBDMS,isomer #1	COC(=O)C1=CC=C(O)C(CC(O[Si](C)(C)C(C)(C)C)C(C)(C)O)=C1	2418.4	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,1TBDMS,isomer #2	COC(=O)C1=CC=C(O)C(CC(O)C(C)(C)O[Si](C)(C)C(C)(C)C)=C1	2471.8	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,1TBDMS,isomer #3	COC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC(O)C(C)(C)O)=C1	2429.5	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,2TBDMS,isomer #1	COC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC(O[Si](C)(C)C(C)(C)C)C(C)(C)O)=C1	2627.9	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,2TBDMS,isomer #2	COC(=O)C1=CC=C(O)C(CC(O[Si](C)(C)C(C)(C)C)C(C)(C)O[Si](C)(C)C(C)(C)C)=C1	2705.6	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,2TBDMS,isomer #3	COC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC(O)C(C)(C)O[Si](C)(C)C(C)(C)C)=C1	2675.0	Semi standard non polar	33892256
Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate,3TBDMS,isomer #1	COC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC(O[Si](C)(C)C(C)(C)C)C(C)(C)O[Si](C)(C)C(C)(C)C)=C1	2873.5	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB010768

KNApSAcK ID

C00056545

Chemspider ID

9359446

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11184361

PDB ID

Not Available

ChEBI ID

138773

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate (HMDB0032796)

MOL for HMDB0032796 (Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate)

3D MOL for HMDB0032796 (Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate)

3D SDF for HMDB0032796 (Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate)

3D-SDF for HMDB0032796 (Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate)

PDB for HMDB0032796 (Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate)

3D PDB for HMDB0032796 (Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate)

SMILES for HMDB0032796 (Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate)

INCHI for HMDB0032796 (Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate)

Structure for HMDB0032796 (Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate)

3D Structure for HMDB0032796 (Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized