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Showing NP-Card for Phenylmethanesulfonyl fluoride (NP0002896)

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Record Information
Version2.0
Created at2020-11-23 19:43:04 UTC
Updated at2021-08-12 19:52:27 UTC
NP-MRD IDNP0002896
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhenylmethanesulfonyl fluoride
Provided ByBMRBBMRB logo
DescriptionPhenylmethylsulfonyl fluoride, also known as alpha-toluenesulfonyl fluoride or PMSF, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Phenylmethanesulfonyl fluoride is found in Ixora coccinea. Phenylmethanesulfonyl fluoride was first documented in 2013 (PMID: 23290539). Based on a literature review a small amount of articles have been published on Phenylmethylsulfonyl fluoride (PMID: 24211707).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002896 (Phenylmethanesulfonyl fluoride)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    4.5833    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0833    0.0000    0.0000 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.0833    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0833   -1.5000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1667   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9167   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1667    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833   -2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9167   -2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4167   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9167    2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833    2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  6
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  5 12  1  1
  5 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
 11 18  1  0
M  END
Download

3D MOL for NP0002896 (Phenylmethanesulfonyl fluoride)

NP0002896
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.3627   -1.0698    1.2710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5872    0.1510    0.4036 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.0102    0.2240   -0.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392    1.4834    1.3564 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4670    0.1027   -0.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0781    0.0080   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717    1.1439   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9534    1.0473    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5361   -0.1849    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135   -1.3340    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5282   -1.2182   -0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7247   -0.7727   -1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5479    1.0515   -1.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    2.1186   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5514    1.9385    0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5607   -0.2564    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2398   -2.3340    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -2.0987   -0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  5 12  1  0
  5 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
 11 18  1  0
M  END
Download

3D SDF for NP0002896 (Phenylmethanesulfonyl fluoride)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    4.5833    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0833    0.0000    0.0000 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.0833    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0833   -1.5000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1667   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9167   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1667    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833   -2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9167   -2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4167   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9167    2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833    2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  6
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  5 12  1  1
  5 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
 11 18  1  0
M  END
> <DATABASE_ID>
NP0002896

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H7FO2S/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2

> <INCHI_KEY>
YBYRMVIVWMBXKQ-UHFFFAOYSA-N

> <FORMULA>
C7H7FO2S

> <MOLECULAR_WEIGHT>
174.19

> <EXACT_MASS>
174.015078802

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
15.483951658518368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
phenylmethanesulfonyl fluoride

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
1.39409583

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.608813441741436

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
40.2046

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylmethylsulfonyl fluoride

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002896 (Phenylmethanesulfonyl fluoride)

NP0002896
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.3627   -1.0698    1.2710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5872    0.1510    0.4036 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.0102    0.2240   -0.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392    1.4834    1.3564 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4670    0.1027   -0.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0781    0.0080   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717    1.1439   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9534    1.0473    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5361   -0.1849    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135   -1.3340    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5282   -1.2182   -0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7247   -0.7727   -1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5479    1.0515   -1.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    2.1186   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5514    1.9385    0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5607   -0.2564    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2398   -2.3340    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -2.0987   -0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  5 12  1  0
  5 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
 11 18  1  0
M  END
Download

PDB for NP0002896 (Phenylmethanesulfonyl fluoride)

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  F   UNK     0      -1.334   5.390   0.000  0.00  0.00           F+0
HETATM    2  S   UNK     0       0.000   4.620   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      -0.770   3.286   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.770   5.954   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   3.850   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0002896 (Phenylmethanesulfonyl fluoride)

COMPND    NP0002896
HETATM    1  O1  UNL     1      -2.363  -1.070   1.271  1.00  0.00           O  
HETATM    2  S1  UNL     1      -2.587   0.151   0.404  1.00  0.00           S  
HETATM    3  O2  UNL     1      -4.010   0.224  -0.053  1.00  0.00           O  
HETATM    4  F1  UNL     1      -2.239   1.483   1.356  1.00  0.00           F  
HETATM    5  C1  UNL     1      -1.467   0.103  -0.998  1.00  0.00           C  
HETATM    6  C2  UNL     1      -0.078   0.008  -0.472  1.00  0.00           C  
HETATM    7  C3  UNL     1       0.672   1.144  -0.197  1.00  0.00           C  
HETATM    8  C4  UNL     1       1.953   1.047   0.288  1.00  0.00           C  
HETATM    9  C5  UNL     1       2.536  -0.185   0.518  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.814  -1.334   0.254  1.00  0.00           C  
HETATM   11  C7  UNL     1       0.528  -1.218  -0.232  1.00  0.00           C  
HETATM   12  H1  UNL     1      -1.725  -0.773  -1.614  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.548   1.051  -1.540  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.244   2.119  -0.367  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.551   1.939   0.507  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.561  -0.256   0.906  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.240  -2.334   0.424  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.081  -2.099  -0.456  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4    5
CONECT    5    6   12   13
CONECT    6    7    7   11
CONECT    7    8   14
CONECT    8    9    9   15
CONECT    9   10   16
CONECT   10   11   11   17
CONECT   11   18
END
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SMILES for NP0002896 (Phenylmethanesulfonyl fluoride)

FS(=O)(=O)CC1=CC=CC=C1
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INCHI for NP0002896 (Phenylmethanesulfonyl fluoride)

InChI=1S/C7H7FO2S/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2
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View in JSmol
Synonyms
ValueSource
alpha-Toluenesulfonyl fluorideChEBI
alpha-Toluenesulphonyl fluorideChEBI
Benzenemethanesulfonyl fluorideChEBI
PMSFChEBI
a-Toluenesulfonyl fluorideGenerator
a-Toluenesulphonyl fluorideGenerator
Α-toluenesulfonyl fluorideGenerator
Α-toluenesulphonyl fluorideGenerator
Benzenemethanesulphonyl fluorideGenerator
Phenylmethylsulphonyl fluorideGenerator
PhenylmethylsulphonylfluorideHMDB
Fluoride, benzenemethanesulfonylHMDB
Fluoride, phenylmethanesulfonylHMDB
Fluoride, phenylmethylsulfonylHMDB
Phenylmethanesulfonyl fluorideHMDB
Phenylmethylsulfonyl fluorideChEBI
Chemical FormulaC7H7FO2S
Average Mass174.1900 Da
Monoisotopic Mass174.01508 Da
IUPAC Namephenylmethanesulfonyl fluoride
Traditional Namephenylmethylsulfonyl fluoride
CAS Registry NumberNot Available
SMILES
FS(=O)(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H7FO2S/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2
InChI KeyYBYRMVIVWMBXKQ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Baptisia arachniferaKNApSAcK Database
Baptisia bracteataKNApSAcK Database
Baptisia calycosaKNApSAcK Database
Baptisia cinereaKNApSAcK Database
Baptisia lanceolataKNApSAcK Database
Baptisia leconteiKNApSAcK Database
Baptisia megacarpaKNApSAcK Database
Baptisia nuttallianaKNApSAcK Database
Baptisia perfoliataKNApSAcK Database
Baptisia simplicifoliaKNApSAcK Database
Begonia nantoensisKNApSAcK Database
Bituminaria acaulisKNApSAcK Database
Froelichia floridanaKNApSAcK Database
Genista lydiaKNApSAcK Database
Glycine maxKNApSAcK Database
Ixora coccineaLOTUS Database
Medicago sativaKNApSAcK Database
Medicago truncatulaKNApSAcK Database
Pueraria candollei var. mirificaKNApSAcK Database
Pueraria lobataKNApSAcK Database
Pueraria mirificaKNApSAcK Database
Pueraria spp.KNApSAcK Database
Pueraria tuberosaKNApSAcK Database
Retama sphaerocarpaKNApSAcK Database
Thermopsis macrophyllaKNApSAcK Database
Thermopsis mollisKNApSAcK Database
Thermopsis rhombifoliaKNApSAcK Database
Thermopsis villosaKNApSAcK Database
Trifolium pratenseKNApSAcK Database
Vigna radiataKNApSAcK Database
Species Where Detected
Species NameSourceReference
Streptoverticillium album K-251KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Sulfonyl
  • Sulfonyl halide
  • Sulfonyl fluoride
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.16ALOGPS
logP1.39ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)18.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.2 m³·mol⁻¹ChemAxon
Polarizability15.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0256652
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016982
KNApSAcK IDNot Available
Chemspider ID4620
KEGG Compound IDC06747
BioCyc IDCPD-5541
BiGG IDNot Available
Wikipedia LinkPhenylmethanesulfonylfluoride
METLIN IDNot Available
PubChem Compound4784
PDB IDNot Available
ChEBI ID8102
Good Scents IDNot Available
References
General References
  1. Nemoto W, Sato T, Nakagawasai O, Yaoita F, Silberring J, Tadano T, Tan-No K: Phenylmethanesulfonyl fluoride, a serine protease inhibitor, suppresses naloxone-precipitated withdrawal jumping in morphine-dependent mice. Neuropeptides. 2013 Jun;47(3):187-91. doi: 10.1016/j.npep.2012.11.002. Epub 2013 Jan 3. [PubMed:23290539 ]
  2. Yuan L, Jian W, Zhang D, Aubry AF, Arnold ME: Application of a stabilizer cocktail of N-ethylmaleimide and phenylmethanesulfonyl fluoride to concurrently stabilize the disulfide and ester containing compounds in a plasma LC-MS/MS assay. J Pharm Biomed Anal. 2014 Jan;88:552-61. doi: 10.1016/j.jpba.2013.10.014. Epub 2013 Oct 23. [PubMed:24211707 ]