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Showing NP-Card for 3,4-Dihydroxyphenylglycol (NP0000365)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:32 UTC
NP-MRD IDNP0000365
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,4-Dihydroxyphenylglycol
Description3,4-Dihydroxyphenylglycol, also known as DHPG or DOPEG, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxyphenylglycol is an extremely weak basic (essentially neutral) compound. 3,4-Dihydroxyphenylglycol exists in all living organisms, ranging from bacteria to plants to humans. It is a potent antioxidant (PMID: 30007612 ). In mammals, 3,4-Dihydroxyphenylglycol is the primary metabolite of norepinephrine and is generated through the action of the enzyme monoamine oxidase (MAO). DHPG is then further metabolized by the enzyme Catechol-O-methyltransferase (COMT) to 3-methoxy-4-hydroxyphenylglycol (MHPG). Within humans, 3,4-dihydroxyphenylglycol participates in a number of enzymatic reactions. In particular, 3,4-dihydroxyphenylglycol can be biosynthesized from 3,4-dihydroxymandelaldehyde; which is mediated by the enzyme alcohol dehydrogenase 1A. In addition, 3,4-dihydroxyphenylglycol and guaiacol can be converted into vanylglycol and pyrocatechol through its interaction with the enzyme catechol O-methyltransferase. Outside of the human body, 3,4-dihydroxyphenylglycol is found, on average, in the highest concentration in olives. High levels of DHPG (up to 368 mg/kg of dry weight) have been found in the pulp of natural black olives. This could make 3,4-dihydroxyphenylglycol a potential biomarker for the consumption of olives and olive oil. 3,4-Dihydroxyphenylglycol has been linked to Menkes disease (PMID: 19234788 ). DHPG level are lower in Menkes patients (3.57 ± 0.40 NM) than healthy infants 8.91 ± 0.77 NM). Menkes disease (also called “kinky hair disease”) is an X-linked recessive neurodevelopmental disorder caused by defects in a gene that encodes a copper-transporting ATPase (ATP7A). Affected infants typically appear healthy at birth and show normal neurodevelopment for 2-3 months. Subsequently there is loss of milestones (e.G., Smiling, visual tracking, head control) and death in late infancy or childhood (PMID: 19234788 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000365 (3,4-Dihydroxyphenylglycol)

3,4-Dihydroxyphenylglycol
  Mrv1652305261923582D          

 12 12  0  0  1  0            999 V2000
    2.8075    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  7  1  0  0  0  0
  3 10  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
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3D MOL for NP0000365 (3,4-Dihydroxyphenylglycol)

HMDB0000318
     RDKit          3D
3,4-Dihydroxyphenylglycol
 22 22  0  0  0  0  0  0  0  0999 V2000
   -1.9680    1.5600   -0.9772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5907    0.4590   -0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7473    0.0040    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3139   -1.1023    1.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3560   -0.2157    0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0715   -1.3672   -0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -1.5089   -0.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -0.5200   -0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6510   -0.6888   -0.7462 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9149    0.6285    0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7828    1.6620    0.5312 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5746    0.7729    0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6200    2.0789   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5984    0.7601   -0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6841   -0.3243   -1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7762    0.8242    1.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176   -1.8294    0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582   -2.1420   -0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6816   -2.4385   -1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3713   -0.0036   -0.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592    1.6959    0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2888    1.6951    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  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
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  9 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for NP0000365 (3,4-Dihydroxyphenylglycol)

3,4-Dihydroxyphenylglycol
  Mrv1652305261923582D          

 12 12  0  0  1  0            999 V2000
    2.8075    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  7  1  0  0  0  0
  3 10  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000365

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2

> <INCHI_KEY>
MTVWFVDWRVYDOR-UHFFFAOYSA-N

> <FORMULA>
C8H10O4

> <MOLECULAR_WEIGHT>
170.1626

> <EXACT_MASS>
170.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.570604001863305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(1,2-dihydroxyethyl)benzene-1,2-diol

> <ALOGPS_LOGP>
-0.72

> <JCHEM_LOGP>
-0.031569536666667

> <ALOGPS_LOGS>
-1.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.628439948439574

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.20999409215474

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9774649407240963

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
42.79820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxyphenylglycol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000365 (3,4-Dihydroxyphenylglycol)

HMDB0000318
     RDKit          3D
3,4-Dihydroxyphenylglycol
 22 22  0  0  0  0  0  0  0  0999 V2000
   -1.9680    1.5600   -0.9772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5907    0.4590   -0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7473    0.0040    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3139   -1.1023    1.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3560   -0.2157    0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0715   -1.3672   -0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -1.5089   -0.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -0.5200   -0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6510   -0.6888   -0.7462 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9149    0.6285    0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7828    1.6620    0.5312 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5746    0.7729    0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6200    2.0789   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5984    0.7601   -0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6841   -0.3243   -1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7762    0.8242    1.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176   -1.8294    0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582   -2.1420   -0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6816   -2.4385   -1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3713   -0.0036   -0.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592    1.6959    0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2888    1.6951    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  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
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  9 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

PDB for NP0000365 (3,4-Dihydroxyphenylglycol)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3,4-Dihydroxyphenylglycol                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0       5.241   2.695   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.908   4.235   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907  -2.695   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.574  -4.235   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.574   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.908   2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.241  -1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908  -1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -2.695   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    7                                                            
CONECT    3   10                                                            
CONECT    4   12                                                            
CONECT    5    1    6    7                                                  
CONECT    6    5    8    9                                                  
CONECT    7    2    5                                                       
CONECT    8    6   10                                                       
CONECT    9    6   11                                                       
CONECT   10    3    8   12                                                  
CONECT   11    9   12                                                       
CONECT   12    4   10   11                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0000365 (3,4-Dihydroxyphenylglycol)

COMPND    HMDB0000318
HETATM    1  O1  UNL     1      -1.968   1.560  -0.977  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.591   0.459  -0.403  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.747   0.004   0.779  1.00  0.00           C  
HETATM    4  O2  UNL     1      -2.314  -1.102   1.406  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.356  -0.216   0.368  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.071  -1.367  -0.258  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.404  -1.509  -0.622  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.331  -0.520  -0.373  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.651  -0.689  -0.746  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.915   0.628   0.249  1.00  0.00           C  
HETATM   11  O4  UNL     1       2.783   1.662   0.531  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.575   0.773   0.615  1.00  0.00           C  
HETATM   13  H1  UNL     1      -2.620   2.079  -1.521  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.598   0.760  -0.081  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.684  -0.324  -1.174  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.776   0.824   1.524  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.518  -1.829   0.763  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.658  -2.142  -0.452  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.682  -2.438  -1.112  1.00  0.00           H  
HETATM   20  H8  UNL     1       4.371  -0.004  -0.592  1.00  0.00           H  
HETATM   21  H9  UNL     1       3.759   1.696   0.328  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.289   1.695   1.104  1.00  0.00           H  
CONECT    1    2   13
CONECT    2    3   14   15
CONECT    3    4    5   16
CONECT    4   17
CONECT    5    6    6   12
CONECT    6    7   18
CONECT    7    8    8   19
CONECT    8    9   10
CONECT    9   20
CONECT   10   11   12   12
CONECT   11   21
CONECT   12   22
END
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SMILES for NP0000365 (3,4-Dihydroxyphenylglycol)

OCC(O)C1=CC(O)=C(O)C=C1
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INCHI for NP0000365 (3,4-Dihydroxyphenylglycol)

InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2
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View in JSmol
Synonyms
ValueSource
(3,4-Dihydroxyphenyl)ethylene glycolChEBI
1-(3,4-Dihydroxyphenyl)-1,2-ethanediolChEBI
2-Hydroxy-2-(3,4-dihydroxy)phenylethanolChEBI
3,4-Dihydroxyphenethyl glycolChEBI
3,4-Dihydroxyphenylethyl glycolChEBI
beta,3,4-Trihydroxy phenethyl alcoholChEBI
DHPGChEBI
Dihydroxyphenylethylene glycolChEBI
DOPEGChEBI
b,3,4-Trihydroxy phenethyl alcoholGenerator
Β,3,4-trihydroxy phenethyl alcoholGenerator
3,4-DihydroxyphenylethyleneglycolHMDB
4-(1,2-Dihydroxyethyl)-1,2-benzenediolHMDB
DL-3,4-DihydroxyphenylglycolHMDB
Dihydroxyphenylethylene glycol, (+-)-isomerHMDB
Dihydroxyphenylethylene glycol, (S)-isomerHMDB
DihydroxyphenylglycineHMDB
Chemical FormulaC8H10O4
Average Mass170.1626 Da
Monoisotopic Mass170.05791 Da
IUPAC Name4-(1,2-dihydroxyethyl)benzene-1,2-diol
Traditional Name3,4-dihydroxyphenylglycol
CAS Registry Number28822-73-3
SMILES
OCC(O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2
InChI KeyMTVWFVDWRVYDOR-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 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
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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
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point130 - 132 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.01Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility16.7 g/LALOGPS
logP-0.72ALOGPS
logP-0.032ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.8 m³·mol⁻¹ChemAxon
Polarizability16.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000318
DrugBank IDNot Available
Phenol Explorer Compound ID661
FoodDB IDFDB030385
KNApSAcK IDNot Available
Chemspider ID82648
KEGG Compound IDC05576
BioCyc IDCPD-11878
BiGG ID46054
Wikipedia LinkNot Available
METLIN ID5307
PubChem Compound91528
PDB IDNot Available
ChEBI ID1387
Good Scents IDNot Available
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Julien C, Rodriguez C, Sacquet J, Cuisinaud G, Sassard J: Liquid-chromatographic determination of free and total 3,4-dihydroxyphenylglycol and 3-methoxy-4-hydroxyphenylglycol in urine. Clin Chem. 1988 May;34(5):966-9. [PubMed:3370800 ]
  3. Nakada T, Sasagawa I, Kubota Y, Suzuki H, Ishigooka M, Watanabe M: Dihydroxyphenylglycol in pheochromocytoma: its diagnostic use for norepinephrine dominant tumor. J Urol. 1996 Jan;155(1):14-8. [PubMed:7490813 ]
  4. Eisenhofer G, Brush JE, Cannon RO 3rd, Stull R, Kopin IJ, Goldstein DS: Plasma dihydroxyphenylalanine and total body and regional noradrenergic activity in humans. J Clin Endocrinol Metab. 1989 Feb;68(2):247-55. [PubMed:2563731 ]
  5. Divers WA Jr, Wilkes MM, Babaknia A, Yen SS: Maternal smoking and elevation of catecholamines and metabolites in the amniotic fluid. Am J Obstet Gynecol. 1981 Nov 15;141(6):625-8. [PubMed:7315891 ]
  6. Graham PE, Smythe GA, Edwards GA, Lazarus L: Laboratory diagnosis of phaeochromocytoma: which analytes should we measure? Ann Clin Biochem. 1993 Mar;30 ( Pt 2):129-34. [PubMed:8466142 ]
  7. Machida M, Sakaguchi A, Kamada S, Fujimoto T, Takechi S, Kakinoki S, Nomura A: Simultaneous analysis of human plasma catecholamines by high-performance liquid chromatography with a reversed-phase triacontylsilyl silica column. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jan 18;830(2):249-54. Epub 2005 Nov 21. [PubMed:16301006 ]
  8. 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 ]
  9. Baskys A, Fang L, Bayazitov I: Activation of neuroprotective pathways by metabotropic group I glutamate receptors: a potential target for drug discovery? Ann N Y Acad Sci. 2005 Aug;1053:55-73. [PubMed:16179509 ]
  10. Esler MD, Lambert GW, Ferrier C, Kaye DM, Wallin BG, Kalff V, Kelly MJ, Jennings GL: Central nervous system noradrenergic control of sympathetic outflow in normotensive and hypertensive humans. Clin Exp Hypertens. 1995 Jan-Feb;17(1-2):409-23. [PubMed:7735286 ]
  11. Divers WA, Wilkes MM, Babaknia A, Hill LM, Quilligan EJ, Yen SS: Amniotic fluid catecholamines and metabolites in intrauterine growth retardation. Am J Obstet Gynecol. 1981 Nov 15;141(6):608-10. [PubMed:7315888 ]
  12. Elsworth JD, Roth RH, Redmond DE Jr: Relative importance of 3-methoxy-4-hydroxyphenylglycol and 3,4-dihydroxyphenylglycol as norepinephrine metabolites in rat, monkey, and humans. J Neurochem. 1983 Sep;41(3):786-93. [PubMed:6875564 ]
  13. Loo H, Scatton B, Dennis T, Benkelfat C, Gay C, Poirier-Littre MF, Garreau M, Vanelle JM, Olie JP, Deniker P: [Study of noradrenaline metabolism in depressed patients by the determination of plasma dihydroxyphenylethylene glycol]. Encephale. 1983;9(4):297-316. [PubMed:6671452 ]
  14. Bermudez-Oria A, Rodriguez-Gutierrez G, Rodriguez-Juan E, Gonzalez-Benjumea A, Fernandez-Bolanos J: Molecular interactions between 3,4-dihydroxyphenylglycol and pectin and antioxidant capacity of this complex in vitro. Carbohydr Polym. 2018 Oct 1;197:260-268. doi: 10.1016/j.carbpol.2018.05.089. Epub 2018 May 31. [PubMed:30007612 ]
  15. Goldstein DS, Holmes CS, Kaler SG: Relative efficiencies of plasma catechol levels and ratios for neonatal diagnosis of menkes disease. Neurochem Res. 2009 Aug;34(8):1464-8. doi: 10.1007/s11064-009-9933-8. Epub 2009 Feb 21. [PubMed:19234788 ]