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Showing metabocard for 3,4-Dihydroxybenzeneacetic acid (HMDB0001336)

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enzymes (7) Show 7 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:37 UTC
HMDB IDHMDB0001336
Secondary Accession Numbers
  • HMDB01336
Metabolite Identification
Common Name3,4-Dihydroxybenzeneacetic acid
Description3,4-Dihydroxyphenylacetic acid (DOPAC) is a phenolic acid. DOPAC is a neuronal metabolite of dopamine (DA). DA undergoes monoamine oxidase-catalyzed oxidative deamination to 3,4-dihydroxyphenylacetaldehyde (DOPAL), which is metabolized primarily into DOPAC via aldehyde dehydrogenase (ALDH2). The biotransformation of DOPAL is critical as previous studies have demonstrated this DA-derived aldehyde to be a reactive electrophile and toxic to dopaminergic cells. Known inhibitors of mitochondrial ALDH2, such as 4-hydroxy-2-nonenal (4HNE) inhibit ALDH2-mediated oxidation of the endogenous neurotoxin DOPAL. 4HNE is one of the resulting products of oxidative stress, thus linking oxidative stress to the uncontrolled production of an endogenous neurotoxin relevant to Parkinson's disease. In early-onset Parkinson disease, there is markedly reduced activities of both monoamine oxidase (MAO) A and B. The amount of DOPAC, which is produced during dopamine oxidation by MAO, is greatly reduced as a result of increased parkin overexpression. Administration of methamphetamine to animals causes loss of DA terminals in the brain and significant decreases in dopamine and dihydroxyphenylacetic acid (DOPAC) in the striatum. Renal dopamine produced in the residual tubular units may be enhanced during a sodium challenge, thus behaving appropriately as a compensatory natriuretic hormone; however, the renal dopaminergic system in patients afflicted with renal parenchymal disorders should address parameters other than free urinary dopamine, namely the urinary excretion of L-DOPA and metabolites. DOPAC is one of the major phenolic acids formed during human microbial fermentation of tea, citrus, and soy flavonoid supplements. DOPAC exhibits a considerable antiproliferative effect in LNCaP prostate cancer and HCT116 colon cancer cells. The antiproliferative activity of DOPAC may be due to its catechol structure. A similar association of the catechol moiety in the B-ring with antiproliferative activity was demonstrated for flavanones (PMID:16956664 , 16455660 , 8561959 , 11369822 , 10443478 , 16365058 ). DOPAC can be found in Gram-positive bacteria (PMID:24752840 ).
Structure
Data?1676999737
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001336 (3,4-Dihydroxybenzeneacetic acid)

DHY
  Mrv1652305261923582D          

 12 12  0  0  0  0            999 V2000
    0.4407   -0.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4407   -0.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2737   -1.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9882   -0.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9882   -0.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2737    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552    1.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8697    1.5971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4407    1.5971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2737   -2.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -1.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for HMDB0001336 (3,4-Dihydroxybenzeneacetic acid)

HMDB0001336
     RDKit          3D
3,4-Dihydroxybenzeneacetic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.1683   -0.7619   -1.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6942   -0.4054   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0814   -0.3800   -0.6838 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9562   -0.0100    0.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5032   -0.0655    0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2568   -1.1873    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -1.1628    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2496   -0.0067    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6132    0.0581   -0.1643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5040    1.1152   -0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1483    2.2802   -0.7335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504    1.0660   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6048   -0.2910    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469   -0.7082    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2598    1.0231    0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -2.0884    0.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2132   -2.0351    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2469   -0.7079    0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1506    2.2901   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4109    1.9776   -0.3504 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12  5  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  9 18  1  0
 11 19  1  0
 12 20  1  0
M  END
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3D SDF for HMDB0001336 (3,4-Dihydroxybenzeneacetic acid)

DHY
  Mrv1652305261923582D          

 12 12  0  0  0  0            999 V2000
    0.4407   -0.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4407   -0.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2737   -1.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9882   -0.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9882   -0.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2737    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552    1.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8697    1.5971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4407    1.5971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2737   -2.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -1.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001336

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)

> <INCHI_KEY>
CFFZDZCDUFSOFZ-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.708406862574998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
1.0038634619999998

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.293556894434504

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6084358670447667

> <JCHEM_PKA_STRONGEST_BASIC>
-6.289422625216582

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
41.3274

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4 dihydroxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001336 (3,4-Dihydroxybenzeneacetic acid)

HMDB0001336
     RDKit          3D
3,4-Dihydroxybenzeneacetic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.1683   -0.7619   -1.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6942   -0.4054   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0814   -0.3800   -0.6838 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9562   -0.0100    0.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5032   -0.0655    0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2568   -1.1873    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -1.1628    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2496   -0.0067    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6132    0.0581   -0.1643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5040    1.1152   -0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1483    2.2802   -0.7335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504    1.0660   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6048   -0.2910    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469   -0.7082    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2598    1.0231    0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -2.0884    0.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2132   -2.0351    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2469   -0.7079    0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1506    2.2901   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4109    1.9776   -0.3504 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12  5  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  9 18  1  0
 11 19  1  0
 12 20  1  0
M  END
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PDB for HMDB0001336 (3,4-Dihydroxybenzeneacetic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: DHY                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       0.823  -0.099   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.823  -1.639   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.511  -2.409   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.845  -1.639   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.845  -0.099   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.511   0.671   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.156   0.671   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.156   2.211   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.490   2.981   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.823   2.981   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.511  -3.949   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.178  -2.409   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3                                                            
CONECT   12    4                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0001336 (3,4-Dihydroxybenzeneacetic acid)

COMPND    HMDB0001336
HETATM    1  O1  UNL     1       2.168  -0.762  -1.808  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.694  -0.405  -0.737  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.081  -0.380  -0.684  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.956  -0.010   0.475  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.503  -0.065   0.332  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.257  -1.187   0.617  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.625  -1.163   0.458  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.250  -0.007   0.008  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.613   0.058  -0.164  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.504   1.115  -0.279  1.00  0.00           C  
HETATM   11  O4  UNL     1      -2.148   2.280  -0.734  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.150   1.066  -0.112  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.605  -0.291   0.165  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.247  -0.708   1.291  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.260   1.023   0.769  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.232  -2.088   0.968  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.213  -2.035   0.680  1.00  0.00           H  
HETATM   18  H6  UNL     1      -4.247  -0.708   0.018  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.151   2.290  -0.848  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.411   1.978  -0.350  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6    6   12
CONECT    6    7   16
CONECT    7    8    8   17
CONECT    8    9   10
CONECT    9   18
CONECT   10   11   12   12
CONECT   11   19
CONECT   12   20
END
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SMILES for HMDB0001336 (3,4-Dihydroxybenzeneacetic acid)

OC(=O)CC1=CC(O)=C(O)C=C1
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INCHI for HMDB0001336 (3,4-Dihydroxybenzeneacetic acid)

InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-(3,4-DIHYDROXYPHENYL)acetIC ACIDChEBI
3,4-Dihydroxyphenyl acetic acidChEBI
3,4-Dihydroxyphenylacetic acidChEBI
Dopacetic acidChEBI
HomoprotocatechuateKegg
2-(3,4-DIHYDROXYPHENYL)acetateGenerator
3,4-Dihydroxyphenyl acetateGenerator
3,4-DihydroxyphenylacetateGenerator
DopacetateGenerator
3,4-DihydroxybenzeneacetateGenerator
3,4 Dihydroxyphenylacetic acidHMDB
3,4-Dihydroxyphenylacetic acid, monosodium saltHMDB
(3,4-Dihydroxyphenyl)-acetic acidHMDB
(3,4-Dihydroxyphenyl)acetateHMDB
(3,4-Dihydroxyphenyl)acetic acidHMDB
3,4-DHPOPHMDB
3,4-Dihydroxy-benzeneacetic acidHMDB
3,4-Dihydroxy-phenylacetic acidHMDB
DHYHMDB
DihydroxyphenylacetateHMDB
Dihydroxyphenylacetic acidHMDB
HAAHMDB
Homogentisic acidHMDB
3',4'-Dihydroxyphenylacetic acidHMDB
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-(3,4-dihydroxyphenyl)acetic acid
Traditional Name3,4 dihydroxyphenylacetic acid
CAS Registry Number102-32-9
SMILES
OC(=O)CC1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
InChI KeyCFFZDZCDUFSOFZ-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
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point168 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4 mg/mLNot Available
LogP0.98SANGSTER (1994)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.23 g/LALOGPS
logP0.93ALOGPS
logP1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability15.71 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]+136.53631661259
DarkChem[M-H]-132.93731661259
AllCCS[M+H]+135.94632859911
AllCCS[M-H]-132.44432859911
DeepCCS[M+H]+135.41830932474
DeepCCS[M-H]-132.67130932474
DeepCCS[M-2H]-168.83530932474
DeepCCS[M+Na]+144.03830932474
AllCCS[M+H]+135.932859911
AllCCS[M+H-H2O]+131.632859911
AllCCS[M+NH4]+140.032859911
AllCCS[M+Na]+141.232859911
AllCCS[M-H]-132.432859911
AllCCS[M+Na-2H]-133.432859911
AllCCS[M+HCOO]-134.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-Dihydroxybenzeneacetic acidOC(=O)CC1=CC(O)=C(O)C=C13277.7Standard polar33892256
3,4-Dihydroxybenzeneacetic acidOC(=O)CC1=CC(O)=C(O)C=C11711.7Standard non polar33892256
3,4-Dihydroxybenzeneacetic acidOC(=O)CC1=CC(O)=C(O)C=C11692.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dihydroxybenzeneacetic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=C(O)C(O)=C11837.6Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC(CC(=O)O)=CC=C1O1811.5Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1O1795.0Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C)C(O)=C11794.1Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CC1=CC=C(O)C(O[Si](C)(C)C)=C11784.7Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1O[Si](C)(C)C1814.4Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11844.9Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O)C(O)=C12070.1Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(CC(=O)O)=CC=C1O2075.8Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1O2052.1Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12274.0Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12257.0Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1O[Si](C)(C)C(C)(C)C2320.8Semi standard non polar33892256
3,4-Dihydroxybenzeneacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12511.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-004i-0942000000-54f714e694a7c3daeaf42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0931000000-c4bb79d921fb42cf1b402014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9310000000-9490bd0ec921894341f42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-MS (3 TMS)splash10-004i-0952000000-d45a1420d6ae61cb91692014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-EI-TOF (Non-derivatized)splash10-004i-0942000000-54f714e694a7c3daeaf42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-EI-TOF (Non-derivatized)splash10-004i-0931000000-c4bb79d921fb42cf1b402017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-EI-TOF (Non-derivatized)splash10-00di-9310000000-9490bd0ec921894341f42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-MS (Non-derivatized)splash10-004i-0952000000-d45a1420d6ae61cb91692017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-EI-TOF (Non-derivatized)splash10-004i-0931000000-3fab9c521f7f85372b942017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3900000000-9badffe195f5e0ba98e02017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-MS (3 TMS) - 70eV, Positivesplash10-014i-4093000000-178e6eeb94df071e6c152017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxybenzeneacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxybenzeneacetic 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-Dihydroxybenzeneacetic acid , negative-QTOFsplash10-014i-0900000000-709dd9faccdbbb3dc0882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 40V, Negative-QTOFsplash10-0a4l-9100000000-cf69597350b36ab341992021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 20V, Negative-QTOFsplash10-0a4i-9200000000-298c198dac69afd9b0a32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 35V, Negative-QTOFsplash10-014i-0900000000-ace1596cdfcf99646e9f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 35V, Negative-QTOFsplash10-00di-0900000000-e7f718ad00bdba6675832021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 35V, Negative-QTOFsplash10-00di-1900000000-d8334a99b44e227f0c592021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 10V, Negative-QTOFsplash10-01b9-1900000000-72071b19a4bfa3da409d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-0900000000-3e7377f36ca2547f48852012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00di-2900000000-60e1fc55d54131c2923e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0fi0-9400000000-c63542b296bac95866e22012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 10V, Negative-QTOFsplash10-01b9-0900000000-a59d2cab0d3d859760a72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 20V, Negative-QTOFsplash10-00xs-1900000000-6f630370c11294562cb72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 40V, Negative-QTOFsplash10-0a4l-9800000000-a45be46f3b52664dd4d12015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 10V, Negative-QTOFsplash10-01b9-0900000000-a59d2cab0d3d859760a72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 20V, Negative-QTOFsplash10-00xs-1900000000-6f630370c11294562cb72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 40V, Negative-QTOFsplash10-0a4l-9800000000-a45be46f3b52664dd4d12015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 10V, Negative-QTOFsplash10-00di-0900000000-aec26fe78ab78ddd40212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 20V, Negative-QTOFsplash10-00dj-2900000000-e59402b8b36f408fbe1c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 40V, Negative-QTOFsplash10-00r6-9400000000-f36bad25ade880ae2e1f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 10V, Positive-QTOFsplash10-0udi-0900000000-579796710abc38249c3a2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 20V, Positive-QTOFsplash10-0fk9-0900000000-22f8a4f4efd0f10804b52015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 40V, Positive-QTOFsplash10-0zmi-9700000000-42b3de6bccbc10ad7b482015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 10V, Positive-QTOFsplash10-0udi-0900000000-579796710abc38249c3a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 20V, Positive-QTOFsplash10-0fk9-0900000000-22f8a4f4efd0f10804b52015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxybenzeneacetic acid 40V, Positive-QTOFsplash10-0zmi-9700000000-42b3de6bccbc10ad7b482015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C 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 (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)2022-02-11FELIX 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+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
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Brain
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
BloodDetected and Quantified0.019 +/- 0.009 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.01 +/- 0.005 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.008 +/- 0.004 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.016 +/- 0.006 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.015 +/- 0.005 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.003 +/- 0.001 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.003 +/- 0.001 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.003 +/- 0.001 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.014 +/- 0.012 uMAdult (>18 years old)Male
Normal		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0001 +/- 0.00002 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.003 +/- 0.0015 (0.0013 - 0.0045) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.002 +/- 0.001 (0.001 - 0.003) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified13.56 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected and Quantified28.368 +/- 21.113 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected and Quantified39.549 +/- 48.529 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified40.857 +/- 59.710 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal		 details
FecesDetected and Quantified22.124 +/- 5.174 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
UrineDetected and Quantified1.16 +/- 0.50 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified0.05 (0.02-0.11) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified4.34 +/- 1.49 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.337 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.0340-3.310 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.48 +/- 0.4 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.9(0.6-1.3) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.044 +/- 0.006 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.01 +/- 0.003 uMAdult (>18 years old)Not SpecifiedEncephalitis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0001 (0.000070-0.00013) uMAdult (>18 years old)BothHypothyroidism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0001 +/- 0.00003 uMAdult (>18 years old)BothHypothyroidism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0023 (0.00051-0.0042) uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Encephalitis
  1. Kalita J, Kumar S, Vijaykumar K, Palit G, Misra UK: A study of CSF catecholamine and its metabolites in acute and convalescent period of encephalitis. J Neurol Sci. 2007 Jan 15;252(1):62-6. Epub 2006 Nov 28. [PubMed:17134724 ]
Hypothyroidism
  1. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
Alzheimer's disease
  1. Raskind MA, Peskind ER, Holmes C, Goldstein DS: Patterns of cerebrospinal fluid catechols support increased central noradrenergic responsiveness in aging and Alzheimer's disease. Biol Psychiatry. 1999 Sep 15;46(6):756-65. [PubMed:10494443 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB01702
Phenol Explorer Compound ID572
FooDB IDFDB000316
KNApSAcK IDC00040996
Chemspider ID532
KEGG Compound IDC01161
BioCyc IDCPD-782
BiGG ID36946
Wikipedia LinkDOPAC
METLIN ID6170
PubChem Compound547
PDB IDNot Available
ChEBI ID41941
Food Biomarker OntologyNot Available
VMH ID34DHPHA
MarkerDB IDMDB00029997
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. Panholzer TJ, Beyer J, Lichtwald K: Coupled-column liquid chromatographic analysis of catecholamines, serotonin, and metabolites in human urine. Clin Chem. 1999 Feb;45(2):262-8. [PubMed:9931050 ]
  3. Raskind MA, Peskind ER, Holmes C, Goldstein DS: Patterns of cerebrospinal fluid catechols support increased central noradrenergic responsiveness in aging and Alzheimer's disease. Biol Psychiatry. 1999 Sep 15;46(6):756-65. [PubMed:10494443 ]
  4. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
  5. Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. [PubMed:8884658 ]
  6. Ebinger G, Michotte Y, Herregodts P: The significance of homovanillic acid and 3,4-dihydroxyphenylacetic acid concentrations in human lumbar cerebrospinal fluid. J Neurochem. 1987 Jun;48(6):1725-9. [PubMed:3572399 ]
  7. Van Loon GR, De Souza EB, Kim C: Alterations in brain dopamine and serotonin metabolism during the development of tolerance to human beta-endorphin in rats. Can J Physiol Pharmacol. 1978 Dec;56(6):1067-71. [PubMed:743624 ]
  8. Braestrup C: Biochemical differentiation of amphetamine vs methylphenidate and nomifensine in rats. J Pharm Pharmacol. 1977 Aug;29(8):463-70. [PubMed:19594 ]
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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-Dihydroxybenzeneacetic acid → S-Adenosylhomocysteine + Homovanillic 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-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic 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-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Iondetails
Enzyme Details
4. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3,4-Dihydroxybenzeneacetic acid → 6-[4-(carboxymethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,4-Dihydroxybenzeneacetic acid → 6-[5-(carboxymethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,4-Dihydroxybenzeneacetic acid → 6-{[2-(3,4-dihydroxyphenyl)acetyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Enzyme Details
5. 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-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Iondetails
Enzyme Details
6. 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-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Iondetails
Enzyme Details
7. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
3,4-Dihydroxybenzeneacetic acid → 2-[4-hydroxy-3-(sulfooxy)phenyl]acetic aciddetails