Np mrd loader

Showing NP-Card for 4-Hydroxy-3-methoxymandelic acid (NP0002861)

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Record Information
Version1.0
Created at2020-11-23 19:42:14 UTC
Updated at2021-08-12 19:52:21 UTC
NP-MRD IDNP0002861
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxy-3-methoxymandelic acid
Provided ByBMRBBMRB logo
Description It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on (2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid (PMID: 31100919) (PMID: 30391255) (PMID: 29875913) (PMID: 28426156).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002861 (4-Hydroxy-3-methoxymandelic acid)


     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    3.4784   -1.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0935    0.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    0.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5824   -0.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656   -0.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -1.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8705   -2.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9869   -0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8323    0.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4367   -0.5026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505    1.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1874    2.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2606    1.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3237    3.0521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9282   -0.9124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0286   -1.6822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8633   -2.7470    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673   -1.9639    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -2.2390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -3.6919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4949    0.5605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634    1.7392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5723    3.8352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7717    2.6605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13  3  1  0
  1 15  1  1
  1 16  1  0
  1 17  1  0
  4 18  1  0
  6 19  1  6
  7 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
M  END
Download

3D MOL for NP0002861 (4-Hydroxy-3-methoxymandelic acid)

NP0002861
     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
    2.1986    2.2554   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374    0.8934   -0.2537 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4877   -0.0617   -0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279    0.2101   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8156   -0.7683    0.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618   -0.5481    0.1377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8505   -1.2062    1.2308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037    0.8388    0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5103    1.2639    0.9507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.7502   -0.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3528   -2.0487    0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9764   -2.3819    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8935   -1.3597    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -1.7097    0.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1243    2.8044   -0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3842    2.6807    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0164    2.3868   -1.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1773    1.2113   -0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6826   -1.0799   -0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2843   -0.5570    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1006    2.6923   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0658   -2.8593    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2927   -3.4047    0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -1.0022    0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  6 19  1  6
  7 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
M  END
Download

3D SDF for NP0002861 (4-Hydroxy-3-methoxymandelic acid)


     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    3.4784   -1.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0935    0.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    0.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5824   -0.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656   -0.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -1.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8705   -2.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9869   -0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8323    0.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4367   -0.5026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505    1.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1874    2.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2606    1.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3237    3.0521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9282   -0.9124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0286   -1.6822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8633   -2.7470    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673   -1.9639    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -2.2390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -3.6919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4949    0.5605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634    1.7392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5723    3.8352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7717    2.6605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13  3  1  0
  1 15  1  1
  1 16  1  0
  1 17  1  0
  4 18  1  0
  6 19  1  6
  7 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
M  END
> <DATABASE_ID>
NP0002861

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)[C@@H](O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m1/s1

> <INCHI_KEY>
CGQCWMIAEPEHNQ-MRVPVSSYSA-N

> <FORMULA>
C9H10O5

> <MOLECULAR_WEIGHT>
198.174

> <EXACT_MASS>
198.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.468175431607094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid

> <JCHEM_LOGP>
0.43459905733333315

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.913823964089037

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.113631257291667

> <JCHEM_PKA_STRONGEST_BASIC>
-4.128024057113833

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
47.1479

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(R)-hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002861 (4-Hydroxy-3-methoxymandelic acid)

NP0002861
     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
    2.1986    2.2554   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374    0.8934   -0.2537 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4877   -0.0617   -0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279    0.2101   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8156   -0.7683    0.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618   -0.5481    0.1377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8505   -1.2062    1.2308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037    0.8388    0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5103    1.2639    0.9507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.7502   -0.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3528   -2.0487    0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9764   -2.3819    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8935   -1.3597    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -1.7097    0.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1243    2.8044   -0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3842    2.6807    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0164    2.3868   -1.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1773    1.2113   -0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6826   -1.0799   -0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2843   -0.5570    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1006    2.6923   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0658   -2.8593    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2927   -3.4047    0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -1.0022    0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  6 19  1  6
  7 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
M  END
Download

PDB for NP0002861 (4-Hydroxy-3-methoxymandelic acid)

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   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  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2    3    5                                                       
CONECT    3    2    6                                                       
CONECT    4    5    7                                                       
CONECT    5    2    4    8                                                  
CONECT    6    3    7   10                                                  
CONECT    7    4    6   14                                                  
CONECT    8    5    9   11                                                  
CONECT    9    8   12   13                                                  
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14    1    7                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for NP0002861 (4-Hydroxy-3-methoxymandelic acid)

COMPND    NP0002861
HETATM    1  C1  UNL     1       2.199   2.255  -0.494  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.437   0.893  -0.254  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.488  -0.062  -0.054  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.128   0.210  -0.066  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.816  -0.768   0.138  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.262  -0.548   0.138  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.851  -1.206   1.231  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.704   0.839   0.056  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.510   1.264   0.951  1.00  0.00           O  
HETATM   10  O4  UNL     1      -2.338   1.750  -0.897  1.00  0.00           O  
HETATM   11  C7  UNL     1      -0.353  -2.049   0.358  1.00  0.00           C  
HETATM   12  C8  UNL     1       0.976  -2.382   0.382  1.00  0.00           C  
HETATM   13  C9  UNL     1       1.894  -1.360   0.171  1.00  0.00           C  
HETATM   14  O5  UNL     1       3.237  -1.710   0.197  1.00  0.00           O  
HETATM   15  H1  UNL     1       3.124   2.804  -0.209  1.00  0.00           H  
HETATM   16  H2  UNL     1       1.384   2.681   0.125  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.016   2.387  -1.580  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.177   1.211  -0.238  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.683  -1.080  -0.766  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.284  -0.557   1.831  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.101   2.692  -0.598  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.066  -2.859   0.525  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.293  -3.405   0.559  1.00  0.00           H  
HETATM   24  H10 UNL     1       3.968  -1.002   0.048  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   18
CONECT    5    6   11   11
CONECT    6    7    8   19
CONECT    7   20
CONECT    8    9    9   10
CONECT   10   21
CONECT   11   12   22
CONECT   12   13   13   23
CONECT   13   14
CONECT   14   24
END
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SMILES for NP0002861 (4-Hydroxy-3-methoxymandelic acid)

COC1=C(O)C=CC(=C1)[C@@H](O)C(O)=O
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INCHI for NP0002861 (4-Hydroxy-3-methoxymandelic acid)

InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m1/s1
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Synonyms
ValueSource
(2R)-2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetateGenerator
(-)-VanilmandelateGenerator
Chemical FormulaC9H10O5
Average Mass198.1740 Da
Monoisotopic Mass198.05282 Da
IUPAC Name(2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
Traditional Name(R)-hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(=C1)[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m1/s1
InChI KeyCGQCWMIAEPEHNQ-MRVPVSSYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.43ChemAxon
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.15 m³·mol⁻¹ChemAxon
Polarizability18.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID643308
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound736173
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Valko-Rokytovska M, Hubkova B, Birkova A, Maslankova J, Stupak M, Zabavnikova M, Cizmarova B, Marekova M: Specific Urinary Metabolites in Malignant Melanoma. Medicina (Kaunas). 2019 May 16;55(5). pii: medicina55050145. doi: 10.3390/medicina55050145. [PubMed:31100919 ]
  3. Martinez-Morillo E, Valdes Gallego N, Eguia Angeles E, Fernandez Fernandez JC, Prieto Garcia B, Alvarez FV: Performance of plasma free metanephrines in diagnosis of pheochromocytomas and paragangliomas in the population of Asturias. Endocrinol Diabetes Nutr (Engl Ed). 2019 May;66(5):312-319. doi: 10.1016/j.endinu.2018.08.009. Epub 2018 Nov 1. [PubMed:30391255 ]
  4. Magagi A, Adamou H, Magagi IA, Halidou M, Habou O, Diongole HM, Rabiou MS, Baoua MB: [Peculiarities of anesthesia for the surgical treatment of pheochromocytoma: about a case]. Pan Afr Med J. 2018 Jan 15;29:31. doi: 10.11604/pamj.2018.29.31.11156. eCollection 2018. [PubMed:29875913 ]
  5. Flieger J, Feder-Kubis J, Tatarczak-Michalewska M, Plazinska A, Madejska A, Swatko-Ossor M: Natural terpene derivatives as new structural task-specific ionic liquids to enhance the enantiorecognition of acidic enantiomers on teicoplanin-based stationary phase by high-performance liquid chromatography. J Sep Sci. 2017 Jun;40(11):2374-2381. doi: 10.1002/jssc.201700197. Epub 2017 May 8. [PubMed:28426156 ]