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Showing NP-Card for 3,4-Dihydroxymandelic acid (NP0001443)

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Record Information
Version1.0
Created at2006-02-23 11:07:11 UTC
Updated at2021-06-29 00:47:14 UTC
NP-MRD IDNP0001443
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001443 (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 NP0001443 (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
Download

3D SDF for NP0001443 (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>
NP0001443

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0001443 (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 NP0001443 (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 NP0001443 (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 NP0001443 (3,4-Dihydroxymandelic acid)

OC(C(O)=O)C1=CC=C(O)C(O)=C1
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INCHI for NP0001443 (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 JSmol
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 Mass184.1461 Da
Monoisotopic Mass184.03717 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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
Not Available
Chemical Shift Submissions
Not Available
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
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
HMDB IDHMDB0001866
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]