Hmdb loader

Showing metabocard for N-Methyl-n-benzylnitrosamine (HMDB0254625)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 14:00:24 UTC
Update Date2021-09-26 23:08:44 UTC
HMDB IDHMDB0254625
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Methyl-n-benzylnitrosamine
DescriptionN-Methyl-n-benzylnitrosamine, also known as N-methyl-N-nitrosobenzylamine or N-nitrosomethylbenzylamine, 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. Based on a literature review very few articles have been published on N-Methyl-n-benzylnitrosamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-methyl-n-benzylnitrosamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Methyl-n-benzylnitrosamine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0254625 (N-Methyl-n-benzylnitrosamine)


  Mrv1652309112116002D          

 11 11  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for HMDB0254625 (N-Methyl-n-benzylnitrosamine)

HMDB0254625
     RDKit          3D
N-Methyl-n-benzylnitrosamine
 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.2593   -0.2566    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8674    0.0716    0.1762 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9005   -0.7319   -0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4831   -0.3089   -0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668    0.5933   -1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697    0.9616   -0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1305    0.4105    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4935   -0.4848    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1778   -0.8407    0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4498    1.1319    0.9575 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8752    2.2901    0.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9306    0.6066    0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109   -0.9627    0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4846   -0.8304   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166   -1.7778   -0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1498   -0.7912   -1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6602    1.0322   -1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886    1.6846   -1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.6979    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9999   -0.9355    1.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245   -1.5598    1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
  9  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
M  END
Download

3D SDF for HMDB0254625 (N-Methyl-n-benzylnitrosamine)


  Mrv1652309112116002D          

 11 11  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254625

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(CC1=CC=CC=C1)N=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10N2O/c1-10(9-11)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3

> <INCHI_KEY>
NGXUJKBJBFLCAR-UHFFFAOYSA-N

> <FORMULA>
C8H10N2O

> <MOLECULAR_WEIGHT>
150.181

> <EXACT_MASS>
150.07931295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.68907663332486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzyl(methyl)nitrosoamine

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
1.7630869396666666

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.2566975602570216

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
44.6631

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-benzyl-N-methylnitrosoamine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0254625 (N-Methyl-n-benzylnitrosamine)

HMDB0254625
     RDKit          3D
N-Methyl-n-benzylnitrosamine
 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.2593   -0.2566    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8674    0.0716    0.1762 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9005   -0.7319   -0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4831   -0.3089   -0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668    0.5933   -1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697    0.9616   -0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1305    0.4105    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4935   -0.4848    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1778   -0.8407    0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4498    1.1319    0.9575 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8752    2.2901    0.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9306    0.6066    0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109   -0.9627    0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4846   -0.8304   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166   -1.7778   -0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1498   -0.7912   -1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6602    1.0322   -1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886    1.6846   -1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.6979    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9999   -0.9355    1.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245   -1.5598    1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
  9  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
M  END
Download

PDB for HMDB0254625 (N-Methyl-n-benzylnitrosamine)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.000   4.620   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   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       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    2   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
Download

3D PDB for HMDB0254625 (N-Methyl-n-benzylnitrosamine)

COMPND    HMDB0254625
HETATM    1  C1  UNL     1      -3.259  -0.257   0.038  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.867   0.072   0.176  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.901  -0.732  -0.521  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.483  -0.309  -0.309  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.167   0.593  -1.099  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.470   0.962  -0.859  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.131   0.410   0.215  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.494  -0.485   1.021  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.178  -0.841   0.759  1.00  0.00           C  
HETATM   10  N2  UNL     1      -1.450   1.132   0.957  1.00  0.00           N  
HETATM   11  O1  UNL     1      -1.875   2.290   0.892  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.931   0.607   0.173  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.511  -0.963   0.882  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.485  -0.830  -0.885  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.017  -1.778  -0.109  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.150  -0.791  -1.603  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.660   1.032  -1.943  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.989   1.685  -1.507  1.00  0.00           H  
HETATM   19  H8  UNL     1       4.150   0.698   0.404  1.00  0.00           H  
HETATM   20  H9  UNL     1       3.000  -0.935   1.881  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.724  -1.560   1.438  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   10
CONECT    3    4   15   16
CONECT    4    5    5    9
CONECT    5    6   17
CONECT    6    7    7   18
CONECT    7    8   19
CONECT    8    9    9   20
CONECT    9   21
CONECT   10   11   11
END
Download

SMILES for HMDB0254625 (N-Methyl-n-benzylnitrosamine)

CN(CC1=CC=CC=C1)N=O
Download

INCHI for HMDB0254625 (N-Methyl-n-benzylnitrosamine)

InChI=1S/C8H10N2O/c1-10(9-11)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
N-Methyl-N-nitrosobenzylamineMeSH
N-NitrosomethylbenzylamineMeSH
NMBzAMeSH
NitrosobenzylmethylamineMeSH
Chemical FormulaC8H10N2O
Average Molecular Weight150.181
Monoisotopic Molecular Weight150.07931295
IUPAC Namebenzyl(methyl)nitrosoamine
Traditional NameN-benzyl-N-methylnitrosoamine
CAS Registry NumberNot Available
SMILES
CN(CC1=CC=CC=C1)N=O
InChI Identifier
InChI=1S/C8H10N2O/c1-10(9-11)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3
InChI KeyNGXUJKBJBFLCAR-UHFFFAOYSA-N
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
  • Organic n-nitroso compound
  • Organic nitroso compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.44ALOGPS
logP1.76ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)3.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.66 m³·mol⁻¹ChemAxon
Polarizability15.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+129.81830932474
DeepCCS[M-H]-126.5830932474
DeepCCS[M-2H]-163.75730932474
DeepCCS[M+Na]+138.74330932474
AllCCS[M+H]+131.132859911
AllCCS[M+H-H2O]+126.632859911
AllCCS[M+NH4]+135.332859911
AllCCS[M+Na]+136.532859911
AllCCS[M-H]-131.532859911
AllCCS[M+Na-2H]-132.932859911
AllCCS[M+HCOO]-134.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Methyl-n-benzylnitrosamineCN(CC1=CC=CC=C1)N=O2057.9Standard polar33892256
N-Methyl-n-benzylnitrosamineCN(CC1=CC=CC=C1)N=O1288.8Standard non polar33892256
N-Methyl-n-benzylnitrosamineCN(CC1=CC=CC=C1)N=O1417.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Methyl-n-benzylnitrosamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-c7f35d96ab24ceec9e3b2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methyl-n-benzylnitrosamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-n-benzylnitrosamine 10V, Positive-QTOFsplash10-0f6x-8900000000-d982bfa0a4c5c9c745fb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-n-benzylnitrosamine 20V, Positive-QTOFsplash10-0006-9000000000-259f2699bbd49757e7ac2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-n-benzylnitrosamine 40V, Positive-QTOFsplash10-0006-9000000000-248a8b4cec421a22ce812021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-n-benzylnitrosamine 10V, Negative-QTOFsplash10-0002-0900000000-d3c3da1e9434390539452021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-n-benzylnitrosamine 20V, Negative-QTOFsplash10-056v-9200000000-23fe813c09ab17fc7f542021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methyl-n-benzylnitrosamine 40V, Negative-QTOFsplash10-0006-9000000000-8b463191f01d621f3be32021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13054
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13643
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]