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Showing NP-Card for 5-Methoxysalicylic acid (NP0000067)

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Record Information
Version2.0
Created at2006-02-23 11:14:42 UTC
Updated at2024-09-03 04:16:28 UTC
NP-MRD IDNP0000067
Natural Product DOIhttps://doi.org/10.57994/0679
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Methoxysalicylic acid
Description5-Methoxysalicylic acid is a methoxysalicylic acid that is salicylic acid which is carrying a methoxy group at position 5. It has a role as a bacterial metabolite and a human urinary metabolite. 5-Methoxysalicylic acid is also known as 2-hydroxy-5-methoxybenzoate or 5-methoxy-2-hydroxybenzoate and 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. Outside of the human body, 5-Methoxysalicylic acid has been detected, but not quantified in herbs and spices and tea.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000067 (5-Methoxysalicylic acid)


  Mrv1652305271900002D          

 12 12  0  0  0  0            999 V2000
   18.9347   -6.3195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -3.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0769   -4.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -3.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9347   -7.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -3.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -5.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -5.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -4.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -5.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -5.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -6.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  8  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  6  2  0  0  0  0
  6  9  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8 10  2  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for NP0000067 (5-Methoxysalicylic acid)

HMDB0001868
     RDKit          3D
5-Methoxysalicylic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.2037   -0.8397    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273    0.4508    0.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    0.5850    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635    1.8339    0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079    1.9666    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5004    0.8326    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728    0.9559    0.1647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535   -0.4493    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131   -1.6237    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401   -2.7826    0.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -1.5025    0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161   -0.5169    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3227   -0.7108    0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057   -1.3919    1.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9447   -1.4048   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166    2.7122    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1361    2.9597    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182    1.8602    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606   -1.4142    0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481   -1.5204    0.0979 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
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  2  0
 12  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0000067 (5-Methoxysalicylic acid)


  Mrv1652305271900002D          

 12 12  0  0  0  0            999 V2000
   18.9347   -6.3195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -3.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0769   -4.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -3.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9347   -7.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -3.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -5.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -5.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -4.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2203   -5.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7913   -5.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5058   -6.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  8  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  6  2  0  0  0  0
  6  9  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8 10  2  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000067

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C(O)=O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3,(H,10,11)

> <INCHI_KEY>
IZZIWIAOVZOBLF-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.804565431840857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-5-methoxybenzoic acid

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.8195921366666663

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.23780861467641

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.522487836846782

> <JCHEM_PKA_STRONGEST_BASIC>
-4.819836853933018

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
41.758300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxysalicylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000067 (5-Methoxysalicylic acid)

HMDB0001868
     RDKit          3D
5-Methoxysalicylic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.2037   -0.8397    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273    0.4508    0.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    0.5850    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635    1.8339    0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079    1.9666    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5004    0.8326    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728    0.9559    0.1647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535   -0.4493    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131   -1.6237    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401   -2.7826    0.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -1.5025    0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161   -0.5169    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3227   -0.7108    0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057   -1.3919    1.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9447   -1.4048   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166    2.7122    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1361    2.9597    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182    1.8602    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606   -1.4142    0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481   -1.5204    0.0979 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
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  2  0
 12  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

PDB for NP0000067 (5-Methoxysalicylic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      35.345 -11.796   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      34.011  -6.407   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      30.010  -8.716   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      31.344  -6.407   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      35.345 -13.336   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.677  -7.177   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.344  -9.486   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.011 -11.027   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.677  -8.716   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.011  -9.486   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.344 -11.027   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.677 -11.796   0.000  0.00  0.00           C+0
CONECT    1    5    8                                                       
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    6                                                            
CONECT    5    1                                                            
CONECT    6    2    4    9                                                  
CONECT    7    3    9   11                                                  
CONECT    8    1   10   12                                                  
CONECT    9    6    7   10                                                  
CONECT   10    8    9                                                       
CONECT   11    7   12                                                       
CONECT   12    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0000067 (5-Methoxysalicylic acid)

COMPND    HMDB0001868
HETATM    1  C1  UNL     1       3.204  -0.840   0.107  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.627   0.451   0.139  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.245   0.585   0.145  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.664   1.834   0.176  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.708   1.967   0.182  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.500   0.833   0.158  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.873   0.956   0.165  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.954  -0.449   0.127  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.813  -1.624   0.102  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.340  -2.783   0.075  1.00  0.00           O  
HETATM   11  O4  UNL     1      -3.191  -1.503   0.109  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.416  -0.517   0.122  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.323  -0.711   0.120  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.906  -1.392   1.024  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.945  -1.405  -0.812  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.317   2.712   0.194  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.136   2.960   0.206  1.00  0.00           H  
HETATM   18  H6  UNL     1      -3.318   1.860   0.187  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.661  -1.414   0.995  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.848  -1.520   0.098  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   16
CONECT    5    6    6   17
CONECT    6    7    8
CONECT    7   18
CONECT    8    9   12   12
CONECT    9   10   10   11
CONECT   11   19
CONECT   12   20
END
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SMILES for NP0000067 (5-Methoxysalicylic acid)

COC1=CC(C(O)=O)=C(O)C=C1
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INCHI for NP0000067 (5-Methoxysalicylic acid)

InChI=1S/C8H8O4/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
5-MeOSAChEBI
5-Methoxy-2-hydroxybenzoic acidChEBI
5-O-Methyl gentisic acidChEBI
6-Hydroxy-m-anisic acidChEBI
Acid5-methoxysalicylicChEBI
5-Methoxy-2-hydroxybenzoateGenerator
5-O-Methyl gentisateGenerator
6-Hydroxy-m-anisateGenerator
5-MethoxysalicylateGenerator
2-Hydroxy-5-methoxybenzoateHMDB
2-Hydroxy-5-methoxybenzoic acidHMDB
6-Methoxy-m-anisateHMDB
6-Methoxy-m-anisic acidHMDB
5-Methoxysalicylic acid, sodium saltHMDB
5-Methoxysalicylic acidMeSH
Chemical FormulaC8H8O4
Average Mass168.1467 Da
Monoisotopic Mass168.04226 Da
IUPAC Name2-hydroxy-5-methoxybenzoic acid
Traditional Name5-methoxysalicylic acid
CAS Registry Number2612-02-4
SMILES
COC1=CC(C(O)=O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3,(H,10,11)
InChI KeyIZZIWIAOVZOBLF-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 Goel2023-10-09View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-09View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-09View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-09View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-09View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-08View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-08View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-08View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-08View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, 5%_DMSO, 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
Not Available
Species
Species of Origin
Species NameSourceReference
Conyza bonariensisLOTUS Database
Epehdra sinica-
Primula verisKNApSAcK Database
Thalictrum fargesiiLOTUS Database
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
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • 4-alkoxyphenol
  • Benzoic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142 - 146 °CNot Available
Boiling Point347.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility9 mg/mLNot Available
LogP2.100 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility3.38 g/LALOGPS
logP1.85ALOGPS
logP1.82ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.76 m³·mol⁻¹ChemAxon
Polarizability15.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001868
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011959
KNApSAcK IDC00055625
Chemspider ID68296
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-Methoxysalicylic_acid
METLIN ID4164
PubChem Compound75787
PDB IDNot Available
ChEBI ID89830
Good Scents IDrw1210831
References
General References
  1. Nishihata T, Higuchi T, Kamada A: Salicylate-promoted permeation of cefoxitin, insulin and phenylalanine across red cell membrane. Possible mechanism. Life Sci. 1984 Jan 30;34(5):437-45. [PubMed:6319944 ]
  2. Alanis-Sanchez BM, Perez-Tapia SM, Vazquez-Leyva S, Mejia-Calvo I, Macias-Palacios Z, Vallejo-Castillo L, Flores-Ortiz CM, Guerrero-Barajas C, Cruz-Maya JA, Jan-Roblero J: Utilization of naproxen by Amycolatopsis sp. Poz 14 and detection of the enzymes involved in the degradation metabolic pathway. World J Microbiol Biotechnol. 2019 Nov 14;35(12):186. doi: 10.1007/s11274-019-2764-0. [PubMed:31728655 ]
  3. Lee C, Ni CK: Soft Matrix-Assisted Laser Desorption/Ionization for Labile Glycoconjugates. J Am Soc Mass Spectrom. 2019 Aug;30(8):1455-1463. doi: 10.1007/s13361-019-02208-4. Epub 2019 Apr 16. [PubMed:30993639 ]
  4. Lee D, Cha S: 5-Methoxysalicylic acid matrix for ganglioside analysis with matrix-assisted laser desorption/ionization mass spectrometry. J Am Soc Mass Spectrom. 2015 Mar;26(3):522-5. doi: 10.1007/s13361-014-1037-2. Epub 2014 Dec 11. [PubMed:25503079 ]
  5. Yasuda A, Ishimaru T, Nishihara S, Sakai M, Kawasaki H, Arakawa R, Shigeri Y: A thiophene-containing compound as a matrix for matrix-assisted laser desorption/ ionization mass spectrometry and the electrical conductivity of matrix crystals. Eur J Mass Spectrom (Chichester). 2013;19(1):29-37. doi: 10.1255/ejms.1215. [PubMed:23841223 ]
  6. Ostertag LM, O'Kennedy N, Horgan GW, Kroon PA, Duthie GG, de Roos B: In vitro anti-platelet effects of simple plant-derived phenolic compounds are only found at high, non-physiological concentrations. Mol Nutr Food Res. 2011 Nov;55(11):1624-36. doi: 10.1002/mnfr.201100135. Epub 2011 Sep 5. [PubMed:21898791 ]
  7. Gunes E, Parlak C: DFT, FT-Raman and FT-IR investigations of 5-methoxysalicylic acid. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Nov;82(1):504-12. doi: 10.1016/j.saa.2011.07.089. Epub 2011 Aug 4. [PubMed:21840249 ]
  8. Tsubery H, Mrksich M: Biochemical assays of immobilized oligonucleotides with mass spectrometry. Langmuir. 2008 May 20;24(10):5433-8. doi: 10.1021/la7040482. Epub 2008 Apr 12. [PubMed:18407676 ]
  9. Abou El-Nasr EA, Fujii A, Yahagi T, Ebata T, Mikami N: Laser spectroscopic investigation of salicylic acids hydrogen bonded with water in supersonic jets: Microsolvation effects for excited state proton dislocation. J Phys Chem A. 2005 Mar 24;109(11):2498-504. doi: 10.1021/jp046381a. [PubMed:16833551 ]
  10. Smoluch M, Joshi H, Gerssen A, Gooijer C, van der Zwan G: Fast excited-state intramolecular proton transfer and subnanosecond dynamic stokes shift of time-resolved fluorescence spectra of the 5-methoxysalicylic acid/diethyl ether complex. J Phys Chem A. 2005 Feb 3;109(4):535-41. doi: 10.1021/jp0475281. [PubMed:16833377 ]