Np mrd loader

Showing NP-Card for Phenyl acetate (NP0001214)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2012-09-12 02:18:36 UTC
Updated at2024-09-17 15:44:34 UTC
NP-MRD IDNP0001214
Natural Product DOIhttps://doi.org/10.57994/3047
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhenyl acetate
DescriptionPhenyl acetate, also known as acetylphenol, is an aromatic fatty acid metabolite of phenylalanine with potential antineoplastic activity. Naturally occurring in mammals, phenylacetate induces differentiation, growth inhibition, and apoptosis in tumor cells. Its mechanisms of action include decreased protein prenylation, activation of the peroxisome proliferation-activated receptors, inhibition of DNA methylation, and depletion of glutamine. Phenyl acetate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Phenyl acetate has a phenolic-like taste.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001214 (Phenyl acetate)


  Mrv1652305271900262D          

 10 10  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  0  0  0  0
M  END
Download

3D MOL for NP0001214 (Phenyl acetate)

HMDB0040733
     RDKit          3D
Phenyl acetate
 18 18  0  0  0  0  0  0  0  0999 V2000
    3.4927    0.6220   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0558    0.2988   -0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6726   -0.1015   -1.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0872    0.4290    0.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2684    0.1343    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1661    1.0433   -0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4755    0.6659   -0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306   -0.6258   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9880   -1.5239    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6720   -1.1624    0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775    1.7040   -0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792    0.3719    0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1716    0.0818   -0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412    2.0539   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145    1.3862   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9729   -0.9036   -0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3335   -2.5515    0.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0260   -1.9223    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

3D SDF for NP0001214 (Phenyl acetate)


  Mrv1652305271900262D          

 10 10  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001214

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3

> <INCHI_KEY>
IPBVNPXQWQGGJP-UHFFFAOYSA-N

> <FORMULA>
C8H8O2

> <MOLECULAR_WEIGHT>
136.1479

> <EXACT_MASS>
136.0524295

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.115643849777472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
phenyl acetate

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
1.5805067903333332

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.141168547963835

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
37.190400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001214 (Phenyl acetate)

HMDB0040733
     RDKit          3D
Phenyl acetate
 18 18  0  0  0  0  0  0  0  0999 V2000
    3.4927    0.6220   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0558    0.2988   -0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6726   -0.1015   -1.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0872    0.4290    0.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2684    0.1343    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1661    1.0433   -0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4755    0.6659   -0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306   -0.6258   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9880   -1.5239    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6720   -1.1624    0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775    1.7040   -0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792    0.3719    0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1716    0.0818   -0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412    2.0539   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145    1.3862   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9729   -0.9036   -0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3335   -2.5515    0.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0260   -1.9223    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

PDB for NP0001214 (Phenyl acetate)

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  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   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  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    8                                                       
CONECT    7    1    9   10                                                  
CONECT    8    5    6   10                                                  
CONECT    9    7                                                            
CONECT   10    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
Download

3D PDB for NP0001214 (Phenyl acetate)

COMPND    HMDB0040733
HETATM    1  C1  UNL     1       3.493   0.622  -0.051  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.056   0.299  -0.338  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.673  -0.102  -1.467  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.087   0.429   0.635  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.268   0.134   0.399  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.166   1.043  -0.045  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.475   0.666  -0.250  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.931  -0.626  -0.019  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.988  -1.524   0.433  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.672  -1.162   0.643  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.678   1.704  -0.215  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.679   0.372   0.999  1.00  0.00           H  
HETATM   13  H3  UNL     1       4.172   0.082  -0.732  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.841   2.054  -0.233  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.214   1.386  -0.608  1.00  0.00           H  
HETATM   16  H6  UNL     1      -3.973  -0.904  -0.187  1.00  0.00           H  
HETATM   17  H7  UNL     1      -2.333  -2.552   0.620  1.00  0.00           H  
HETATM   18  H8  UNL     1       0.026  -1.922   1.002  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    6   10
CONECT    6    7   14
CONECT    7    8    8   15
CONECT    8    9   16
CONECT    9   10   10   17
CONECT   10   18
END
Download

SMILES for NP0001214 (Phenyl acetate)

CC(=O)OC1=CC=CC=C1
Download

INCHI for NP0001214 (Phenyl acetate)

InChI=1S/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3
Download
View in JSmolView NMR Assignments
Synonyms
ValueSource
Acetic acid,phenyl esterChEBI
AcetylphenolChEBI
Phenol acetateChEBI
Acetate,phenyl esterGenerator
Phenol acetic acidGenerator
Phenyl acetic acidGenerator
AcetatesHMDB
Acetic acid phenyl esterHMDB
Acetic acid, phenyl esterHMDB
AcetoxybenzeneHMDB
Acetyl phenolHMDB
FEMA 3958HMDB
Fenylester kyseliny octoveHMDB
Phenyl ester OF acetic acidHMDB
Chemical FormulaC8H8O2
Average Mass136.1479 Da
Monoisotopic Mass136.05243 Da
IUPAC Namephenyl acetate
Traditional Namephenyl acetate
CAS Registry Number122-79-2
SMILES
CC(=O)OC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3
InChI KeyIPBVNPXQWQGGJP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-07-05View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-07-05View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-07-05View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-07-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-07-05View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-07-05View Spectrum
Species
Species of Origin
Species NameSourceReference
Paraburkholderia phymatum-
Saccharomyces cerevisiaeNULL
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol esters
Sub ClassNot Available
Direct ParentPhenol esters
Alternative Parents
Substituents
  • Phenol ester
  • Phenoxy compound
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-30 °CNot Available
Boiling Point196.00 to 198.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4639 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.49Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.19 g/LALOGPS
logP1.59ALOGPS
logP1.58ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.19 m³·mol⁻¹ChemAxon
Polarizability14.12 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040733
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020542
KNApSAcK IDC00053673
Chemspider ID28969
KEGG Compound IDC15583
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenyl_acetate
METLIN IDNot Available
PubChem Compound31229
PDB IDNot Available
ChEBI ID8082
Good Scents IDrw1099401
References
General References
  1. Miller AC, Xu J, Stewart M, McClain D: Suppression of depleted uranium-induced neoplastic transformation of human cells by the phenyl fatty acid, phenyl acetate: chemoprevention by targeting the p21RAS protein pathway. Radiat Res. 2001 Jan;155(1 Pt 2):163-170. doi: 10.1667/0033-7587(2001)155[0163:soduin]2.0.co;2. [PubMed:11121229 ]
  2. Perla-Kajan J, Wloczkowska O, Ziola-Frankowska A, Frankowski M, Smith AD, de Jager CA, Refsum H, Jakubowski H: Paraoxonase 1, B Vitamins Supplementation, and Mild Cognitive Impairment. J Alzheimers Dis. 2021;81(3):1211-1229. doi: 10.3233/JAD-210137. [PubMed:33935094 ]
  3. Vijay K, Kiran GS, Divya S, Thangavel K, Thangavelu S, Dhandapani R, Selvin J: Fatty Acid Methyl Esters From the Coral-Associated Bacterium Pseudomonas aeruginosa Inhibit Virulence and Biofilm Phenotypes in Multidrug Resistant Staphylococcus aureus: An in vitro Approach. Front Microbiol. 2021 Mar 23;12:631853. doi: 10.3389/fmicb.2021.631853. eCollection 2021. [PubMed:33833739 ]
  4. Santos SC, La Scala JJ, Palmese GR: Effect of Microcapsule Content on Diels-Alder Room Temperature Self-Healing Thermosets. Polymers (Basel). 2020 Dec 21;12(12). pii: polym12123064. doi: 10.3390/polym12123064. [PubMed:33371328 ]
  5. Parada-Turska J, Wojcicka G, Beltowski J: Paraoxonase 1 Phenotype and Protein N-Homocysteinylation in Patients with Rheumatoid Arthritis: Implications for Cardiovascular Disease. Antioxidants (Basel). 2020 Sep 21;9(9). pii: antiox9090899. doi: 10.3390/antiox9090899. [PubMed:32967340 ]
  6. Mitra M, Nguyen KM, Box TW, Gilpin JS, Hamby SR, Berry TL, Duckett EH: Isolation and characterization of a novel bacterial strain from a Tris-Acetate-Phosphate agar medium plate of the green micro-alga Chlamydomonas reinhardtii that can utilize common environmental pollutants as a carbon source. F1000Res. 2020 Jun 29;9:656. doi: 10.12688/f1000research.24680.1. eCollection 2020. [PubMed:32855811 ]
  7. Ganguly S, Mayans J, Ghosh A: Modulation of Nuclearity in Cu(II) -Mn(II) Complexes of a N2 O2 Donor Ligand Depending upon Carboxylate Anions: Structures, Magnetic Properties and Catalytic Oxidase Activities. Chem Asian J. 2020 Dec 1;15(23):4055-4069. doi: 10.1002/asia.202000706. Epub 2020 Oct 28. [PubMed:32722886 ]
  8. Matsumoto AK, Maes M, Supasitthumrong T, Maes A, Michelin AP, de Oliveira Semeao L, de Lima Pedrao JV, Moreira EG, Kanchanatawan B, Barbosa DS: Deficit schizophrenia and its features are associated with PON1 Q192R genotypes and lowered paraoxonase 1 (PON1) enzymatic activity: effects on bacterial translocation. CNS Spectr. 2021 Aug;26(4):406-415. doi: 10.1017/S1092852920001388. Epub 2020 Jun 23. [PubMed:32638685 ]
  9. Hong Y, Che X, Su H, Mai Z, Huang Z, Huang W, Chen W, Liu S, Gao W, Zhou Z, Tan G, Li X: Exhaled breath analysis using on-line preconcentration mass spectrometry for gastric cancer diagnosis. J Mass Spectrom. 2021 Apr;56(4):e4588. doi: 10.1002/jms.4588. Epub 2020 Jul 7. [PubMed:32633879 ]
  10. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .