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Showing metabocard for 3,4-Dihydroxymandelic acid (HMDB0001866)

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enzymes (5) Show 5 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-23 11:07:11 UTC
Update Date2023-02-21 17:15:52 UTC
HMDB IDHMDB0001866
Secondary Accession Numbers
  • HMDB01866
Metabolite Identification
Common Name3,4-Dihydroxymandelic acid
Description3,4-Dihydroxymandelic acid, also known as DOMA or 3,4-dihydroxyphenylglycolate, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxymandelic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 3,4-dihydroxymandelic acid participates in a number of enzymatic reactions. In particular, 3,4-dihydroxymandelic acid can be biosynthesized from 3,4-dihydroxymandelaldehyde through its interaction with the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, 3,4-dihydroxymandelic acid and guaiacol can be converted into vanillylmandelic acid and pyrocatechol through the action of the enzyme catechol O-methyltransferase. In humans, 3,4-dihydroxymandelic acid is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, 3,4-Dihydroxymandelic acid has been detected, but not quantified in several different foods, such as yellow wax beans, soy beans, pomegranates, cucurbita (gourd), and daikon radish.
Structure
Data?1676999752
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001866 (3,4-Dihydroxymandelic acid)

3-chlorotyrosine.mol
  Mrv1652305261923582D          

 13 13  0  0  0  0            999 V2000
    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
    0.7145   -1.2375    0.0000 O   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   -0.4125    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
   -0.7145    1.2375    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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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
   -2.1434   -0.4125    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
  2  4  1  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
  8  9  1  0  0  0  0
  4  9  2  0  0  0  0
  1 10  2  0  0  0  0
  1 11  1  0  0  0  0
  7 12  1  0  0  0  0
  6 13  1  0  0  0  0
M  END
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3D MOL for HMDB0001866 (3,4-Dihydroxymandelic acid)

HMDB0001866
     RDKit          3D
3,4-Dihydroxymandelic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    2.6170    1.8356    0.4464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6440    0.7086   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255    0.6327   -1.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226   -0.4397    0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415   -1.5110   -0.5978 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3632   -0.2205    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4697   -1.3377    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.2156    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    0.0291   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7860    0.1512   -0.1534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6096    1.1332   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793    2.3905   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    0.9970    0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5324    0.5472   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1266   -0.7674    1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4557   -2.2965   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0153   -2.3115    0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4900   -2.0950    0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3715   -0.6676   -0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538    2.5561   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460    1.8813   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
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3D SDF for HMDB0001866 (3,4-Dihydroxymandelic acid)

3-chlorotyrosine.mol
  Mrv1652305261923582D          

 13 13  0  0  0  0            999 V2000
    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
    0.7145   -1.2375    0.0000 O   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   -0.4125    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
   -0.7145    1.2375    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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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
   -2.1434   -0.4125    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
  2  4  1  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
  8  9  1  0  0  0  0
  4  9  2  0  0  0  0
  1 10  2  0  0  0  0
  1 11  1  0  0  0  0
  7 12  1  0  0  0  0
  6 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001866

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)

> <INCHI_KEY>
RGHMISIYKIHAJW-UHFFFAOYSA-N

> <FORMULA>
C8H8O5

> <MOLECULAR_WEIGHT>
184.1461

> <EXACT_MASS>
184.037173366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.515506363683954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
0.28870500133333327

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.219357318675643

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9769258542306654

> <JCHEM_PKA_STRONGEST_BASIC>
-4.126018555289758

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
42.6656

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydroxymandelic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001866 (3,4-Dihydroxymandelic acid)

HMDB0001866
     RDKit          3D
3,4-Dihydroxymandelic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    2.6170    1.8356    0.4464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6440    0.7086   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255    0.6327   -1.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226   -0.4397    0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415   -1.5110   -0.5978 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3632   -0.2205    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4697   -1.3377    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.2156    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    0.0291   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7860    0.1512   -0.1534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6096    1.1332   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793    2.3905   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    0.9970    0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5324    0.5472   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1266   -0.7674    1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4557   -2.2965   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0153   -2.3115    0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4900   -2.0950    0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3715   -0.6676   -0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538    2.5561   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460    1.8813   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
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PDB for HMDB0001866 (3,4-Dihydroxymandelic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3-chlorotyrosine.mol                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   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  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2   10   11                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    1                                                            
CONECT   11    1                                                            
CONECT   12    7                                                            
CONECT   13    6                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0001866 (3,4-Dihydroxymandelic acid)

COMPND    HMDB0001866
HETATM    1  O1  UNL     1       2.617   1.836   0.446  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.644   0.709  -0.140  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.525   0.633  -1.210  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.823  -0.440   0.259  1.00  0.00           C  
HETATM    5  O3  UNL     1       2.141  -1.511  -0.598  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.363  -0.221   0.147  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.470  -1.338   0.181  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.839  -1.216   0.082  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.418   0.029  -0.054  1.00  0.00           C  
HETATM   10  O4  UNL     1      -3.786   0.151  -0.153  1.00  0.00           O  
HETATM   11  C7  UNL     1      -1.610   1.133  -0.090  1.00  0.00           C  
HETATM   12  O5  UNL     1      -2.179   2.391  -0.227  1.00  0.00           O  
HETATM   13  C8  UNL     1      -0.242   0.997   0.010  1.00  0.00           C  
HETATM   14  H1  UNL     1       4.532   0.547  -1.105  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.127  -0.767   1.276  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.456  -2.297  -0.123  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.015  -2.312   0.289  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.490  -2.095   0.110  1.00  0.00           H  
HETATM   19  H6  UNL     1      -4.371  -0.668  -0.126  1.00  0.00           H  
HETATM   20  H7  UNL     1      -3.154   2.556  -0.304  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.346   1.881  -0.022  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    6   15
CONECT    5   16
CONECT    6    7    7   13
CONECT    7    8   17
CONECT    8    9    9   18
CONECT    9   10   11
CONECT   10   19
CONECT   11   12   13   13
CONECT   12   20
CONECT   13   21
END
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SMILES for HMDB0001866 (3,4-Dihydroxymandelic acid)

OC(C(O)=O)C1=CC=C(O)C(O)=C1
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INCHI for HMDB0001866 (3,4-Dihydroxymandelic acid)

InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(3,4-Dihydroxyphenyl)(hydroxy)acetic acidChEBI
3,4-DihydroxymandelateChEBI
3,4-Dihydroxyphenylglycolic acidChEBI
Dihydroxymandelic acidChEBI
DOMAChEBI
(3,4-Dihydroxyphenyl)(hydroxy)acetateGenerator
3,4-DihydroxyphenylglycolateGenerator
DihydroxymandelateGenerator
3,4 DihydroxymandelateHMDB
3,4 Dihydroxymandelic acidHMDB
3,4-Dihydroxymandelic acid, (S)-isomerHMDB
3,4-Dihydroxymandelic acid, ion(1-)HMDB
3,4-Dihydroxymandelic acid, monosodium saltHMDB
DHMAHMDB
3,4-Dihydroxymandelic acid, (+-)-isomerHMDB
Chemical FormulaC8H8O5
Average Molecular Weight184.1461
Monoisotopic Molecular Weight184.037173366
IUPAC Name2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid
Traditional Namedihydroxymandelic acid
CAS Registry Number775-01-9
SMILES
OC(C(O)=O)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)
InChI KeyRGHMISIYKIHAJW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg135.00130932474
[M-H]-Not Available137.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00000299
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.7 g/LALOGPS
logP0.72ALOGPS
logP0.29ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.67 m³·mol⁻¹ChemAxon
Polarizability16.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.0331661259
DarkChem[M-H]-135.96131661259
AllCCS[M+H]+140.36332859911
AllCCS[M-H]-135.0432859911
DeepCCS[M+H]+134.62730932474
DeepCCS[M-H]-132.00530932474
DeepCCS[M-2H]-167.80830932474
DeepCCS[M+Na]+142.80330932474
AllCCS[M+H]+140.432859911
AllCCS[M+H-H2O]+136.132859911
AllCCS[M+NH4]+144.332859911
AllCCS[M+Na]+145.432859911
AllCCS[M-H]-135.032859911
AllCCS[M+Na-2H]-135.832859911
AllCCS[M+HCOO]-136.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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. 1.77 minutes32390414
Predicted by Siyang on May 30, 20229.4182 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.35 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid197.5 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid678.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid299.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid64.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid164.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid47.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid261.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid238.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)594.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid588.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid54.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid813.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid171.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid178.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate598.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA369.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water378.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-Dihydroxymandelic acidOC(C(O)=O)C1=CC=C(O)C(O)=C13487.5Standard polar33892256
3,4-Dihydroxymandelic acidOC(C(O)=O)C1=CC=C(O)C(O)=C11843.0Standard non polar33892256
3,4-Dihydroxymandelic acidOC(C(O)=O)C1=CC=C(O)C(O)=C11712.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dihydroxymandelic acid,1TMS,isomer #1C[Si](C)(C)OC(C(=O)O)C1=CC=C(O)C(O)=C11949.0Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C(O)C1=CC=C(O)C(O)=C11952.2Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(C(O)C(=O)O)C=C1O1860.5Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TMS,isomer #4C[Si](C)(C)OC1=CC(C(O)C(=O)O)=CC=C1O1868.2Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=C(O)C(O)=C11926.7Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(C(O[Si](C)(C)C)C(=O)O)C=C1O1882.1Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC(C(O[Si](C)(C)C)C(=O)O)=CC=C1O1899.3Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #4C[Si](C)(C)OC(=O)C(O)C1=CC=C(O[Si](C)(C)C)C(O)=C11864.7Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #5C[Si](C)(C)OC(=O)C(O)C1=CC=C(O)C(O[Si](C)(C)C)=C11849.5Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #6C[Si](C)(C)OC1=CC=C(C(O)C(=O)O)C=C1O[Si](C)(C)C1864.6Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C11903.1Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C11903.5Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TMS,isomer #3C[Si](C)(C)OC1=CC=C(C(O[Si](C)(C)C)C(=O)O)C=C1O[Si](C)(C)C1900.4Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TMS,isomer #4C[Si](C)(C)OC(=O)C(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11905.2Semi standard non polar33892256
3,4-Dihydroxymandelic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11941.3Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C(=O)O)C1=CC=C(O)C(O)=C12215.3Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=C(O)C(O)=C12202.2Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)C(=O)O)C=C1O2143.9Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(C(O)C(=O)O)=CC=C1O2133.4Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C12396.9Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1O2400.0Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(C(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O2406.2Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12370.8Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12345.9Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2387.9Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12565.3Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12567.3Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2595.9Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12609.6Semi standard non polar33892256
3,4-Dihydroxymandelic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12774.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0629000000-ae329bc0399bdead30ee2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-MS (4 TMS)splash10-0a4i-1679200000-30b0a470753b8a534ffb2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-EI-TOF (Non-derivatized)splash10-0a4i-0629000000-ae329bc0399bdead30ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-MS (Non-derivatized)splash10-0a4i-1679200000-30b0a470753b8a534ffb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-EI-TOF (Non-derivatized)splash10-0a4i-0938000000-048f9a7dbf493cb105d02017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-06rl-2900000000-45a24bed7c390b0517a92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-1009100000-2a01ecfd802a6d86fff72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-01qi-1900000000-54c118704077cc354da72012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-03k9-5900000000-ef520e550b3f5cce89d42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4l-7900000000-2c2914429bf7b73d4a332012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-001i-0900000000-80a2a015caa693fb0bdb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-000i-0900000000-5d651845e3e03edc63dc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-000i-0900000000-5ed666462a4d020d9bad2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-000i-1900000000-f785c36e33914dd6cfa02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-052r-3900000000-15fd25c25c09bb8789122012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0002-9400000000-42f34c3c13cd670ff16f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-0900000000-e0e14e382ffa485ebcfc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ , negative-QTOFsplash10-001i-0900000000-80a2a015caa693fb0bdb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-717de91658e43f0217e42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-5ed666462a4d020d9bad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ , negative-QTOFsplash10-000i-1900000000-f7a0f4c346c5c2d4669f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ , negative-QTOFsplash10-052r-3900000000-15fd25c25c09bb8789122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QTOF , negative-QTOFsplash10-000i-0900000000-e0e14e382ffa485ebcfc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid , negative-QTOFsplash10-00kr-0900000000-bd002360ad3147f32bdb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QTOF , positive-QTOFsplash10-0002-9400000000-42f34c3c13cd670ff16f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 20V, Negative-QTOFsplash10-000i-0900000000-1b8bb3963db8dbdf68b72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 10V, Positive-QTOFsplash10-00kr-0900000000-adc00447f61ba09ff2b92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 20V, Positive-QTOFsplash10-000i-0900000000-c3215810f102f9a6bcd52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 40V, Positive-QTOFsplash10-0r7i-7900000000-d9fef758451d2742cf582017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 10V, Negative-QTOFsplash10-001r-0900000000-6ac7602cc5f3af7016622017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 20V, Negative-QTOFsplash10-0apr-0900000000-b6bce5b5e83f1dd663a72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 40V, Negative-QTOFsplash10-0a4i-2900000000-dfbd957390c0796149632017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.011 +/- 0.004 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.12 +/- 0.05 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030383
KNApSAcK IDNot Available
Chemspider ID77371
KEGG Compound IDC05580
BioCyc IDCPD-11879
BiGG ID46062
Wikipedia Link3,4-Dihydroxymandelic_acid
METLIN ID696
PubChem Compound85782
PDB IDNot Available
ChEBI ID27637
Food Biomarker OntologyNot Available
VMH ID34DHOXMAND
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceJoray, Marcel; Breuninger, Manfred. Process for the preparation of phenolic compounds. PCT Int. Appl. (2007), 15pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]
  2. Zambotti F, Blau K, King GS, Campbell S, Sandler M: Monoamine metabolites and related compounds in human amniotic fluid: assay by gas chromatography and gas chromatography-mass spectrometry. Clin Chim Acta. 1975 Jun 20;61(3):247-56. [PubMed:1149252 ]
  3. Eisenhofer G, Kopin IJ, Goldstein DS: Catecholamine metabolism: a contemporary view with implications for physiology and medicine. Pharmacol Rev. 2004 Sep;56(3):331-49. [PubMed:15317907 ]
  4. O'Meara A, Tormey W, FitzGerald RJ, Fitzgibbon M, Kenny D: Interpretation of random urinary catecholamines and their metabolites in neuroblastoma. Acta Paediatr. 1994 Jan;83(1):88-92. [PubMed:8193481 ]
  5. Nohta H, Yamaguchi E, Ohkura Y, Watanabe H: Measurement of catecholamines, their precursor and metabolites in human urine and plasma by solid-phase extraction followed by high-performance liquid chromatography with fluorescence derivatization. J Chromatogr. 1989 Aug 25;493(1):15-26. [PubMed:2778005 ]
  6. Odink J, Korthals H, Knijff JH: Simultaneous determination of the major acidic metabolites of catecholamines and serotonin in urine by liquid chromatography with electrochemical detection after a one-step sample clean-up on Sephadex G-10; influence of vanilla and banana ingestion. J Chromatogr. 1988 Feb 26;424(2):273-83. [PubMed:2453525 ]

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
S-Adenosylmethionine + 3,4-Dihydroxymandelic acid → S-Adenosylhomocysteine + Vanillylmandelic aciddetails
Enzyme Details
2. Aldehyde dehydrogenase, dimeric NADP-preferring
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails
Enzyme Details
3. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails
Enzyme Details
4. Aldehyde dehydrogenase family 3 member B2
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails
Enzyme Details
5. Aldehyde dehydrogenase family 3 member B1
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails