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Showing NP-Card for 4-Methylsalicylic acid (NP0002821)

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Record Information
Version1.0
Created at2020-11-23 19:41:16 UTC
Updated at2021-08-19 23:59:26 UTC
NP-MRD IDNP0002821
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Methylsalicylic acid
Provided ByBMRBBMRB logo
Description4-Methylsalicylic acid, also known as m-cresotic acid or 2-hydroxy-p-toluic acid, belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. It was first documented in 2008 (PMID: 17984079). Based on a literature review a small amount of articles have been published on 4-methylsalicylic acid (PMID: 32563965) (PMID: 22520630) (PMID: 20589724) (PMID: 20302107).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002821 (4-Methylsalicylic acid)


     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -3.1675   -0.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0949    1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937    1.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981    0.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7867    0.6218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3708    2.0035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6912   -0.5748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140   -0.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6185   -2.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7745   -1.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525    1.3706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -1.6066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6561   -0.3030    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9993    2.6452    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9778    3.0151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1797   -0.3898    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0344   -3.5230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3586   -2.5113    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 11  2  1  0
  1 12  1  1
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D MOL for NP0002821 (4-Methylsalicylic acid)

NP0002821
     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    3.0951    0.2679   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6258    0.1051    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0158   -0.1192    1.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3427   -0.2703    1.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1956   -0.2034    0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6295   -0.3695    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1244   -0.5733    1.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5277   -0.3180   -0.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    0.0192   -0.9052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3075    0.1050   -2.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8027    0.1718   -1.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5534   -0.5605   -0.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3777    1.2220   -0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5442    0.2692    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6641   -0.1739    2.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8323   -0.4484    2.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1367    0.4833   -0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2370    0.0446   -2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512    0.3483   -1.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0002821 (4-Methylsalicylic acid)


     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -3.1675   -0.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0949    1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937    1.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981    0.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7867    0.6218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3708    2.0035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6912   -0.5748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140   -0.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6185   -2.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7745   -1.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525    1.3706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -1.6066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6561   -0.3030    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9993    2.6452    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9778    3.0151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1797   -0.3898    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0344   -3.5230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3586   -2.5113    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 11  2  1  0
  1 12  1  1
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
M  END
> <DATABASE_ID>
NP0002821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=C(C(O)=O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c1-5-2-3-6(8(10)11)7(9)4-5/h2-4,9H,1H3,(H,10,11)

> <INCHI_KEY>
NJESAXZANHETJV-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.149

> <EXACT_MASS>
152.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.007632009185793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-4-methylbenzoic acid

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.490684791666667

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.30101542116298

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.989419695347209

> <JCHEM_PKA_STRONGEST_BASIC>
-6.287419968343031

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
40.3363

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methylsalicylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002821 (4-Methylsalicylic acid)

NP0002821
     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    3.0951    0.2679   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6258    0.1051    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0158   -0.1192    1.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3427   -0.2703    1.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1956   -0.2034    0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6295   -0.3695    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1244   -0.5733    1.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5277   -0.3180   -0.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    0.0192   -0.9052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3075    0.1050   -2.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8027    0.1718   -1.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5534   -0.5605   -0.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3777    1.2220   -0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5442    0.2692    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6641   -0.1739    2.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8323   -0.4484    2.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1367    0.4833   -0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2370    0.0446   -2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512    0.3483   -1.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

PDB for NP0002821 (4-Methylsalicylic acid)

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      25.666 -17.421   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.666 -18.961   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.004 -19.727   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.004 -16.647   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.326 -17.421   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.320 -18.961   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.651 -19.732   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      29.664 -16.653   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      24.332 -16.646   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      30.989 -18.972   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      29.645 -21.272   0.000  0.00  0.00           O+0
CONECT    1    2    9    4                                                  
CONECT    2    1    3                                                       
CONECT    3    2    6                                                       
CONECT    4    5    1                                                       
CONECT    5    6    8    4                                                  
CONECT    6    3    5    7                                                  
CONECT    7    6   10   11                                                  
CONECT    8    5                                                            
CONECT    9    1                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0002821 (4-Methylsalicylic acid)

COMPND    NP0002821
HETATM    1  C1  UNL     1       3.095   0.268  -0.063  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.626   0.105   0.074  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.016  -0.119   1.290  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.343  -0.270   1.421  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.196  -0.203   0.307  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.629  -0.370   0.494  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.124  -0.573   1.641  1.00  0.00           O  
HETATM    8  O2  UNL     1      -3.528  -0.318  -0.540  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.596   0.019  -0.905  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.308   0.105  -2.057  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.803   0.172  -1.018  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.553  -0.560  -0.655  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.378   1.222  -0.545  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.544   0.269   0.947  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.664  -0.174   2.166  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.832  -0.448   2.383  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.137   0.483  -0.656  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.237   0.045  -2.286  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.251   0.348  -1.998  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   11
CONECT    3    4   15
CONECT    4    5    5   16
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   17
CONECT    9   10   11   11
CONECT   10   18
CONECT   11   19
END
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SMILES for NP0002821 (4-Methylsalicylic acid)

CC1=CC=C(C(O)=O)C(O)=C1
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INCHI for NP0002821 (4-Methylsalicylic acid)

InChI=1S/C8H8O3/c1-5-2-3-6(8(10)11)7(9)4-5/h2-4,9H,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
2,4-Cresotic acidChEBI
2-Hydroxy-4-methylbenzoic acidChEBI
2-Hydroxy-p-toluic acidChEBI
4-Methyl-2-hydroxybenzoic acidChEBI
gamma-Cresotic acidChEBI
m-Cresotic acidChEBI
m-Cresotinic acidChEBI
m-Homosalicylic acidChEBI
2,4-CresotateGenerator
2-Hydroxy-4-methylbenzoateGenerator
2-Hydroxy-p-toluateGenerator
4-Methyl-2-hydroxybenzoateGenerator
g-CresotateGenerator
g-Cresotic acidGenerator
gamma-CresotateGenerator
Γ-cresotateGenerator
Γ-cresotic acidGenerator
m-CresotateGenerator
m-CresotinateGenerator
m-HomosalicylateGenerator
4-MethylsalicylateGenerator
Chemical FormulaC8H8O3
Average Mass152.1490 Da
Monoisotopic Mass152.04734 Da
IUPAC Name2-hydroxy-4-methylbenzoic acid
Traditional Name4-methylsalicylic acid
CAS Registry NumberNot Available
SMILES
CC1=CC=C(C(O)=O)C(O)=C1
InChI Identifier
InChI=1S/C8H8O3/c1-5-2-3-6(8(10)11)7(9)4-5/h2-4,9H,1H3,(H,10,11)
InChI KeyNJESAXZANHETJV-UHFFFAOYSA-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
Description Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylic acids
Alternative Parents
Substituents
  • Salicylic acid
  • Benzoic acid
  • Benzoyl
  • M-cresol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • 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 Solubility19.51 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.39ALOGPS
logP2.49ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.99ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.34 m³·mol⁻¹ChemAxon
Polarizability15.01 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5584
KEGG Compound IDC14103
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylsalicylic acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID20450
Good Scents IDrw1874391
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. Mumtaz A, Saeed K, Mahmood A, Zaib S, Saeed A, Pelletier J, Sevigny J, Iqbal J: Bisthioureas of pimelic acid and 4-methylsalicylic acid derivatives as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP) and intestinal alkaline phosphatase (IAP): Synthesis and molecular docking studies. Bioorg Chem. 2020 Aug;101:103996. doi: 10.1016/j.bioorg.2020.103996. Epub 2020 Jun 3. [PubMed:32563965 ]
  3. Zhang ZM, Zhang XW, Zhao ZZ, Yan R, Xu R, Gong HB, Zhu HL: Synthesis, biological evaluation and molecular docking studies of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents. Bioorg Med Chem. 2012 May 15;20(10):3359-67. doi: 10.1016/j.bmc.2012.03.064. Epub 2012 Apr 4. [PubMed:22520630 ]
  4. Mantel C, Bayle PA, Hediger S, Berthon C, Bardet M: Study of liquid-liquid interfaces by an easily implemented localized NMR sequence. Magn Reson Chem. 2010 Aug;48(8):600-6. doi: 10.1002/mrc.2628. [PubMed:20589724 ]
  5. Guo XX, Hao YY, Lei JF, Fan WH, Wang H, Xu BS: [New highly phosphorescent heteroleptic tris-cyclometalated iridium (III) complexes: synthesis and photophysical characterization]. Guang Pu Xue Yu Guang Pu Fen Xi. 2010 Jan;30(1):170-3. [PubMed:20302107 ]