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Showing NP-Card for 2-Amino-3-methoxybenzoic acid (NP0002853)

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Record Information
Version2.0
Created at2020-11-23 19:42:03 UTC
Updated at2021-08-12 19:52:20 UTC
NP-MRD IDNP0002853
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Amino-3-methoxybenzoic acid
Provided ByBMRBBMRB logo
Description3-Methoxyanthranilate belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. 3-Methoxyanthranilate exists in all living organisms, ranging from bacteria to humans. 3-Methoxyanthranilate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 2-Amino-3-methoxybenzoic acid was first documented in 1998 (PMID: 9660093). Based on a literature review a small amount of articles have been published on 3-Methoxyanthranilate (PMID: 31731976) (PMID: 16442626).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002853 (2-Amino-3-methoxybenzoic acid)


     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.4852   -0.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368   -1.2451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9748   -0.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    1.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990    2.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1494    1.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357    0.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841    0.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0461    1.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3704   -1.3564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -0.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8599   -2.0254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8754   -2.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    0.5934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9336   -0.4648    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8094    1.6537    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6853    3.7722    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2115    2.9919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8187   -1.7465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022   -3.0847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3083   -2.4156    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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  6
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  6 18  1  0
 10 19  1  0
 12 20  1  0
 12 21  1  0
M  END
Download

3D MOL for NP0002853 (2-Amino-3-methoxybenzoic acid)

NP0002853
     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
    3.3513   -0.7290   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9994   -1.1458   -0.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525   -0.2041   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2230    1.1534   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1985    2.0880    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0943    1.6100    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186    0.2698    0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8052   -0.1843    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0764   -1.4091   -0.0101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613    0.7096    0.0674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3601   -0.6264   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6893   -2.0085   -0.0708 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -0.3618    0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758    0.0826   -0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9394   -1.6336   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564    1.4732   -0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4260    3.1592    0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9218    2.3133    0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605    0.4671    0.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0370   -2.4609    0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5887   -2.5628   -0.9422 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  6 18  1  0
 10 19  1  0
 12 20  1  0
 12 21  1  0
M  END
Download

3D SDF for NP0002853 (2-Amino-3-methoxybenzoic acid)


     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.4852   -0.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368   -1.2451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9748   -0.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    1.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990    2.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1494    1.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357    0.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841    0.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0461    1.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3704   -1.3564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -0.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8599   -2.0254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8754   -2.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    0.5934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9336   -0.4648    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8094    1.6537    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6853    3.7722    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2115    2.9919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8187   -1.7465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022   -3.0847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3083   -2.4156    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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  6
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  6 18  1  0
 10 19  1  0
 12 20  1  0
 12 21  1  0
M  END
> <DATABASE_ID>
NP0002853

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC(C(O)=O)=C1N

> <INCHI_IDENTIFIER>
InChI=1S/C8H9NO3/c1-12-6-4-2-3-5(7(6)9)8(10)11/h2-4H,9H2,1H3,(H,10,11)

> <INCHI_KEY>
SXOPCLUOUFQBJV-UHFFFAOYSA-N

> <FORMULA>
C8H9NO3

> <MOLECULAR_WEIGHT>
167.162

> <EXACT_MASS>
167.058243159

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
16.17590536874073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-3-methoxybenzoic acid

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
1.2942315043333332

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.405594463904542

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9022540114621216

> <JCHEM_PKA_STRONGEST_BASIC>
4.776417364657032

> <JCHEM_POLAR_SURFACE_AREA>
72.55000000000001

> <JCHEM_REFRACTIVITY>
44.4778

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-methoxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002853 (2-Amino-3-methoxybenzoic acid)

NP0002853
     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
    3.3513   -0.7290   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9994   -1.1458   -0.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525   -0.2041   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2230    1.1534   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1985    2.0880    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0943    1.6100    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186    0.2698    0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8052   -0.1843    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0764   -1.4091   -0.0101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613    0.7096    0.0674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3601   -0.6264   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6893   -2.0085   -0.0708 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -0.3618    0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758    0.0826   -0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9394   -1.6336   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564    1.4732   -0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4260    3.1592    0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9218    2.3133    0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605    0.4671    0.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0370   -2.4609    0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5887   -2.5628   -0.9422 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  6 18  1  0
 10 19  1  0
 12 20  1  0
 12 21  1  0
M  END
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PDB for NP0002853 (2-Amino-3-methoxybenzoic acid)

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7    8                                                  
CONECT    6    4    7   12                                                  
CONECT    7    5    6    9                                                  
CONECT    8    5   10   11                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    1    6                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0002853 (2-Amino-3-methoxybenzoic acid)

COMPND    NP0002853
HETATM    1  C1  UNL     1       3.351  -0.729  -0.105  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.999  -1.146  -0.093  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.952  -0.204  -0.046  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.223   1.153  -0.010  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.198   2.088   0.036  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.094   1.610   0.045  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.419   0.270   0.010  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.805  -0.184   0.022  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.076  -1.409  -0.010  1.00  0.00           O  
HETATM   10  O3  UNL     1      -3.861   0.710   0.067  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.360  -0.626  -0.035  1.00  0.00           C  
HETATM   12  N1  UNL     1      -0.689  -2.008  -0.071  1.00  0.00           N  
HETATM   13  H1  UNL     1       3.691  -0.362   0.885  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.476   0.083  -0.880  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.939  -1.634  -0.437  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.256   1.473  -0.019  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.426   3.159   0.064  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.922   2.313   0.081  1.00  0.00           H  
HETATM   19  H7  UNL     1      -4.661   0.467   0.637  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.037  -2.461   0.801  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.589  -2.563  -0.942  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   16
CONECT    5    6    6   17
CONECT    6    7   18
CONECT    7    8   11   11
CONECT    8    9    9   10
CONECT   10   19
CONECT   11   12
CONECT   12   20   21
END
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SMILES for NP0002853 (2-Amino-3-methoxybenzoic acid)

COC1=CC=CC(C(O)=O)=C1N
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INCHI for NP0002853 (2-Amino-3-methoxybenzoic acid)

InChI=1S/C8H9NO3/c1-12-6-4-2-3-5(7(6)9)8(10)11/h2-4H,9H2,1H3,(H,10,11)
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Synonyms
ValueSource
3-Methoxyanthranilic acidKegg
3-MethoxyanthranilateGenerator
Chemical FormulaC8H9NO3
Average Mass167.1620 Da
Monoisotopic Mass167.05824 Da
IUPAC Name2-amino-3-methoxybenzoic acid
Traditional Name2-amino-3-methoxybenzoic acid
CAS Registry NumberNot Available
SMILES
COC1=CC=CC(C(O)=O)=C1N
InChI Identifier
InChI=1S/C8H9NO3/c1-12-6-4-2-3-5(7(6)9)8(10)11/h2-4H,9H2,1H3,(H,10,11)
InChI KeySXOPCLUOUFQBJV-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, ethanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, ethanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, ethanol, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • M-methoxybenzoic acid or derivatives
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Methoxyaniline
  • Aminophenyl ether
  • Anisole
  • Methoxybenzene
  • Aniline or substituted anilines
  • Phenol ether
  • Benzoyl
  • Phenoxy compound
  • Alkyl aryl ether
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP0.77ALOGPS
logP1.29ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.9ChemAxon
pKa (Strongest Basic)4.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.48 m³·mol⁻¹ChemAxon
Polarizability16.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060374
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID224233
KEGG Compound IDC05831
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound255720
PDB IDNot Available
ChEBI ID27440
Good Scents IDNot Available
References
General References
  1. Wlizlo K, Polak J, Jarosz-Wilkolazka A, Pogni R, Petricci E: Novel textile dye obtained through transformation of 2-amino-3-methoxybenzoic acid by free and immobilised laccase from a Pleurotus ostreatus strain. Enzyme Microb Technol. 2020 Jan;132:109398. doi: 10.1016/j.enzmictec.2019.109398. Epub 2019 Aug 17. [PubMed:31731976 ]
  2. Yokoi I, Nishijima Y, Uchida A, Kabuto H, Yamamoto N, Ogawa N: Effects of kynurenine metabolites on the electrocorticographic activity in the rat. J Neural Transm (Vienna). 1998;105(2-3):147-60. doi: 10.1007/s007020050044. [PubMed:9660093 ]
  3. Halova-Lajoie B, Brumas V, Fiallo MM, Berthon G: Copper(II) interactions with non-steroidal anti-inflammatory agents. III--3-Methoxyanthranilic acid as a potential *OH-inactivating ligand: a quantitative investigation of its copper handling role in vivo. J Inorg Biochem. 2006 Mar;100(3):362-73. doi: 10.1016/j.jinorgbio.2005.12.002. Epub 2006 Jan 26. [PubMed:16442626 ]