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Showing NP-Card for 3,4-Dihydroxybenzeneacetic acid (NP0000956)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:18:54 UTC
NP-MRD IDNP0000956
Natural Product DOIhttps://doi.org/10.57994/1557
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000956 (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 NP0000956 (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 NP0000956 (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>
NP0000956

> <DATABASE_NAME>
NP-MRD

> <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 NP0000956 (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 NP0000956 (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 NP0000956 (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 NP0000956 (3,4-Dihydroxybenzeneacetic acid)

OC(=O)CC1=CC(O)=C(O)C=C1
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INCHI for NP0000956 (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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Synonyms
ValueSource
2-(3,4-DIHYDROXYPHENYL)acetIC ACIDChEBI
3,4-Dihydroxyphenyl acetic acidChEBI
3,4-Dihydroxyphenylacetic acidChEBI
Dopacetic acidChEBI
Homoprotocatechuic 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
DOPACHMDB, MeSH
3,4-Dihydroxyphenylethanoic acid
Chemical FormulaC8H8O4
Average Mass168.1467 Da
Monoisotopic Mass168.04226 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
Olea europaeaFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Rubus idaeusFooDB
Secamone afzeliiLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tamarindus indicaFooDB
Taxus baccataKNApSAcK Database
Tragopogon pratensisLOTUS Database
Vaccinium myrtillusFooDB
Vanilla planifolia Jacks.LOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point168 °CNot Available
Boiling Point418.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility4 mg/mLNot Available
LogP0.98Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted 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
HMDB IDHMDB0001336
DrugBank IDDB01702
Phenol Explorer Compound ID572
FoodDB IDFDB030384
KNApSAcK IDC00040996
Chemspider ID532
KEGG Compound IDC01161
BioCyc IDCPD-782
BiGG ID36946
Wikipedia LinkDOPAC
METLIN ID6170
PubChem Compound547
PDB IDNot Available
ChEBI ID41941
Good Scents IDrw1183451
References
General References
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  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 ]
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  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 ]
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  9. Nakao N, Shintani-Mizushima A, Kakishita K, Itakura T: The ability of grafted human sympathetic neurons to synthesize and store dopamine: a potential mechanism for the clinical effect of sympathetic neuron autografts in patients with Parkinson's disease. Exp Neurol. 2004 Jul;188(1):65-73. [PubMed:15191803 ]
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  11. De Simoni MG, Guardabasso V, Misterek K, Algeri S: Similarities and differences between D-ALA2 MET5 enkephalin amide and morphine in the induction of tolerance to their effects on catalepsy and on dopamine metabolism in the rat brain. Naunyn Schmiedebergs Arch Pharmacol. 1982 Nov;321(2):105-11. [PubMed:6891440 ]
  12. Gramsch C, Blasig J, Herz A: Changes in striatal dopamine metabolism during precipitated morphine withdrawal. Eur J Pharmacol. 1977 Aug 1;44(3):231-40. [PubMed:560969 ]
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  14. Garrett MC, Soares-da-Silva P: Increased cerebrospinal fluid dopamine and 3,4-dihydroxyphenylacetic acid levels in Huntington's disease: evidence for an overactive dopaminergic brain transmission. J Neurochem. 1992 Jan;58(1):101-6. [PubMed:1309230 ]
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  22. Jiang H, Jiang Q, Liu W, Feng J: Parkin suppresses the expression of monoamine oxidases. J Biol Chem. 2006 Mar 31;281(13):8591-9. Epub 2006 Feb 2. [PubMed:16455660 ]
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  24. Pestana M, Jardim H, Correia F, Vieira-Coelho MA, Soares-da-Silva P: Renal dopaminergic mechanisms in renal parenchymal diseases and hypertension. Nephrol Dial Transplant. 2001;16 Suppl 1:53-9. [PubMed:11369822 ]
  25. Kim DH, Kim SY, Park SY, Han MJ: Metabolism of quercitrin by human intestinal bacteria and its relation to some biological activities. Biol Pharm Bull. 1999 Jul;22(7):749-51. [PubMed:10443478 ]
  26. Gao K, Xu A, Krul C, Venema K, Liu Y, Niu Y, Lu J, Bensoussan L, Seeram NP, Heber D, Henning SM: Of the major phenolic acids formed during human microbial fermentation of tea, citrus, and soy flavonoid supplements, only 3,4-dihydroxyphenylacetic acid has antiproliferative activity. J Nutr. 2006 Jan;136(1):52-7. [PubMed:16365058 ]