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Showing metabocard for Methoxyhydroxymandelic Acid (HMDB0254548)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 13:54:26 UTC
Update Date2021-09-26 23:08:37 UTC
HMDB IDHMDB0254548
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethoxyhydroxymandelic Acid
DescriptionMethoxyhydroxymandelic Acid, also known as acid, vanillylmandelic or vanillylmandelic acid, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Based on a literature review very few articles have been published on Methoxyhydroxymandelic Acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Methoxyhydroxymandelic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Methoxyhydroxymandelic Acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0254548 (Methoxyhydroxymandelic Acid)

  Mrv1652309112115542D          

 14 14  0  0  0  0            999 V2000
    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
    0.7145    1.2375    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
    1.4289   -0.0000    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    0.0000    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
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
M  END
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3D MOL for HMDB0254548 (Methoxyhydroxymandelic Acid)

HMDB0254548
     RDKit          3D
Methoxyhydroxymandelic Acid
 24 24  0  0  0  0  0  0  0  0999 V2000
   -1.6030    1.9885   -1.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355    1.3091   -1.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8608    0.3207   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1524   -0.0437    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3961   -1.0580    0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3343   -1.6987    1.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -1.3384    1.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1912   -0.3334    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5606    0.0568   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8316    1.3875    0.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670   -0.0177   -1.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -0.8770    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5258   -2.1147    0.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925   -0.3631    1.3036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788    2.5571   -1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444    2.7230   -2.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136    1.2735   -2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9489    0.4908   -0.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4115   -1.2924    1.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5506   -2.4792    2.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7670   -1.8681    1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6221    1.6412   -0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3570   -0.8641   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785    0.6005    1.2199 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  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
 12 13  2  0
 12 14  1  0
  8  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  0
  7 21  1  0
 10 22  1  0
 11 23  1  0
 14 24  1  0
M  END
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3D SDF for HMDB0254548 (Methoxyhydroxymandelic Acid)

  Mrv1652309112115542D          

 14 14  0  0  0  0            999 V2000
    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
    0.7145    1.2375    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
    1.4289   -0.0000    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    0.0000    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
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254548

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC=C1C(O)(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O5/c1-14-7-5-3-2-4-6(7)9(12,13)8(10)11/h2-5,12-13H,1H3,(H,10,11)

> <INCHI_KEY>
UEXOOCQHGZGWFB-UHFFFAOYSA-N

> <FORMULA>
C9H10O5

> <MOLECULAR_WEIGHT>
198.174

> <EXACT_MASS>
198.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.229215565544898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-dihydroxy-2-(2-methoxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
0.7006695550000003

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.196237988411784

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7404224592034754

> <JCHEM_PKA_STRONGEST_BASIC>
-4.85941618438694

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
46.7094

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydroxy(2-methoxyphenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0254548 (Methoxyhydroxymandelic Acid)

HMDB0254548
     RDKit          3D
Methoxyhydroxymandelic Acid
 24 24  0  0  0  0  0  0  0  0999 V2000
   -1.6030    1.9885   -1.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355    1.3091   -1.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8608    0.3207   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1524   -0.0437    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3961   -1.0580    0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3343   -1.6987    1.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -1.3384    1.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1912   -0.3334    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5606    0.0568   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8316    1.3875    0.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670   -0.0177   -1.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -0.8770    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5258   -2.1147    0.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925   -0.3631    1.3036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788    2.5571   -1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444    2.7230   -2.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136    1.2735   -2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9489    0.4908   -0.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4115   -1.2924    1.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5506   -2.4792    2.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7670   -1.8681    1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6221    1.6412   -0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3570   -0.8641   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785    0.6005    1.2199 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  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
 12 13  2  0
 12 14  1  0
  8  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  0
  7 21  1  0
 10 22  1  0
 11 23  1  0
 14 24  1  0
M  END
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PDB for HMDB0254548 (Methoxyhydroxymandelic Acid)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.564   3.644   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.104   0.976   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   13   14                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for HMDB0254548 (Methoxyhydroxymandelic Acid)

COMPND    HMDB0254548
HETATM    1  C1  UNL     1      -1.603   1.988  -1.819  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.536   1.309  -1.184  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.861   0.321  -0.278  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.152  -0.044   0.045  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.396  -1.058   0.976  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.334  -1.699   1.575  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.019  -1.338   1.257  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.191  -0.333   0.334  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.561   0.057  -0.001  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.832   1.387   0.300  1.00  0.00           O  
HETATM   11  O3  UNL     1       1.667  -0.018  -1.413  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.555  -0.877   0.524  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.526  -2.115   0.311  1.00  0.00           O  
HETATM   14  O5  UNL     1       3.592  -0.363   1.304  1.00  0.00           O  
HETATM   15  H1  UNL     1      -2.179   2.557  -1.043  1.00  0.00           H  
HETATM   16  H2  UNL     1      -1.244   2.723  -2.571  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.314   1.273  -2.278  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.949   0.491  -0.454  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.412  -1.292   1.182  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.551  -2.479   2.291  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.767  -1.868   1.758  1.00  0.00           H  
HETATM   22  H8  UNL     1       2.622   1.641  -0.272  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.357  -0.864  -1.765  1.00  0.00           H  
HETATM   24  H10 UNL     1       3.878   0.601   1.220  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   18
CONECT    5    6    6   19
CONECT    6    7   20
CONECT    7    8    8   21
CONECT    8    9
CONECT    9   10   11   12
CONECT   10   22
CONECT   11   23
CONECT   12   13   13   14
CONECT   14   24
END
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SMILES for HMDB0254548 (Methoxyhydroxymandelic Acid)

COC1=CC=CC=C1C(O)(O)C(O)=O
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INCHI for HMDB0254548 (Methoxyhydroxymandelic Acid)

InChI=1S/C9H10O5/c1-14-7-5-3-2-4-6(7)9(12,13)8(10)11/h2-5,12-13H,1H3,(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
MethoxyhydroxymandelateGenerator
Acid, vanillylmandelicHMDB
Acid, 4-hydroxy-3-methoxymandelicHMDB
Acid, methoxyhydroxymandelicHMDB
Acid, vanilmandelicHMDB
Vanillylmandelic acidHMDB
4 Hydroxy 3 methoxymandelic acidHMDB
4-Hydroxy-3-methoxymandelic acidHMDB
Vanilmandelic acidHMDB
Chemical FormulaC9H10O5
Average Molecular Weight198.174
Monoisotopic Molecular Weight198.052823422
IUPAC Name2,2-dihydroxy-2-(2-methoxyphenyl)acetic acid
Traditional Namedihydroxy(2-methoxyphenyl)acetic acid
CAS Registry NumberNot Available
SMILES
COC1=CC=CC=C1C(O)(O)C(O)=O
InChI Identifier
InChI=1S/C9H10O5/c1-14-7-5-3-2-4-6(7)9(12,13)8(10)11/h2-5,12-13H,1H3,(H,10,11)
InChI KeyUEXOOCQHGZGWFB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Alkyl aryl ether
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID67492456
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54349796
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]