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Showing metabocard for Dimethylaniline-N-oxide (HMDB0001466)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:44 UTC
HMDB IDHMDB0001466
Secondary Accession Numbers
  • HMDB01466
Metabolite Identification
Common NameDimethylaniline-N-oxide
DescriptionDimethylaniline-N-oxide, also known as dimethyl(phenyl)amine oxide, 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. Dimethylaniline-N-oxide has been detected, but not quantified in, several different foods, such as strawberries (Fragaria X ananassa), cucumbers (Cucumis sativus), black crowberries (Empetrum nigrum), sweet oranges (Citrus sinensis), and red rice (Oryza rufipogon). This could make dimethylaniline-N-oxide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Dimethylaniline-N-oxide.
Structure
Data?1676999744
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001466 (Dimethylaniline-N-oxide)

  Mrv0541 02231219092D          

 10 10  0  0  0  0            999 V2000
    0.0037   -0.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7007   -0.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7195   -0.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037    0.7722    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.7007   -1.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7195   -1.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9267    1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0151    1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869    1.2581    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0037   -1.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 10  1  0  0  0  0
M  CHG  2   4   1   9  -1
M  END
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3D MOL for HMDB0001466 (Dimethylaniline-N-oxide)

HMDB0001466
     RDKit          3D
Dimethylaniline-N-oxide
 21 21  0  0  0  0  0  0  0  0999 V2000
   -1.8838   -0.8621    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2820    0.3755    0.4049 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.8419    0.7869   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440    1.3397    1.3324 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.1284    0.1561    0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -0.9248   -0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919   -1.1053   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8308   -0.2348   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4214    0.8544    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654    1.0238    0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1559   -1.5924    1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.3082   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6555   -0.6242    1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9514    0.7380   -0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5095    1.8104   -1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719    0.0611   -1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1821   -1.6157   -0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2408   -1.9584   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9074   -0.3711   -0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1259    1.5611    0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160    1.8899    1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  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
  3 14  1  0
  3 15  1  0
  3 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
M  CHG  2   2   1   4  -1
M  END
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3D SDF for HMDB0001466 (Dimethylaniline-N-oxide)

  Mrv0541 02231219092D          

 10 10  0  0  0  0            999 V2000
    0.0037   -0.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7007   -0.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7195   -0.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037    0.7722    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.7007   -1.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7195   -1.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9267    1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0151    1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869    1.2581    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0037   -1.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 10  1  0  0  0  0
M  CHG  2   4   1   9  -1
M  END
> <DATABASE_ID>
HMDB0001466

> <DATABASE_NAME>
hmdb

> <SMILES>
C[N+](C)([O-])C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H11NO/c1-9(2,10)8-6-4-3-5-7-8/h3-7H,1-2H3

> <INCHI_KEY>
LKQUDAOAMBKKQW-UHFFFAOYSA-N

> <FORMULA>
C8H11NO

> <MOLECULAR_WEIGHT>
137.179

> <EXACT_MASS>
137.084063979

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
14.984752844730373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-methyl-N-phenylmethanamine oxide

> <ALOGPS_LOGP>
-0.59

> <JCHEM_LOGP>
-2.4082000000000003

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.643630698532784

> <JCHEM_POLAR_SURFACE_AREA>
26.880000000000003

> <JCHEM_REFRACTIVITY>
51.4255

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethylaniline N-oxide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0001466 (Dimethylaniline-N-oxide)

HMDB0001466
     RDKit          3D
Dimethylaniline-N-oxide
 21 21  0  0  0  0  0  0  0  0999 V2000
   -1.8838   -0.8621    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2820    0.3755    0.4049 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.8419    0.7869   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440    1.3397    1.3324 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.1284    0.1561    0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -0.9248   -0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919   -1.1053   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8308   -0.2348   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4214    0.8544    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654    1.0238    0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1559   -1.5924    1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.3082   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6555   -0.6242    1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9514    0.7380   -0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5095    1.8104   -1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719    0.0611   -1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1821   -1.6157   -0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2408   -1.9584   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9074   -0.3711   -0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1259    1.5611    0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160    1.8899    1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  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
  3 14  1  0
  3 15  1  0
  3 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
M  CHG  2   2   1   4  -1
M  END
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PDB for HMDB0001466 (Dimethylaniline-N-oxide)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.007  -0.077   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.308  -0.837   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.343  -0.837   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.007   1.441   0.000  0.00  0.00           N+1
HETATM    5  C   UNK     0      -1.308  -2.377   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.343  -2.377   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.730   2.271   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.028   3.593   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.842   2.348   0.000  0.00  0.00           O-1
HETATM   10  C   UNK     0       0.007  -3.157   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8    9                                             
CONECT    5    2   10                                                       
CONECT    6    3   10                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    5    6                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0001466 (Dimethylaniline-N-oxide)

COMPND    HMDB0001466
HETATM    1  C1  UNL     1      -1.884  -0.862   0.784  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.282   0.376   0.405  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -1.842   0.787  -0.879  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.444   1.340   1.332  1.00  0.00           O1-
HETATM    5  C3  UNL     1       0.128   0.156   0.176  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.542  -0.925  -0.561  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.892  -1.105  -0.761  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.831  -0.235  -0.244  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.421   0.854   0.498  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.065   1.024   0.691  1.00  0.00           C  
HETATM   11  H1  UNL     1      -1.156  -1.592   1.174  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.492  -1.308  -0.056  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.655  -0.624   1.572  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.951   0.738  -0.835  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.510   1.810  -1.150  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.472   0.061  -1.633  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.182  -1.616  -0.973  1.00  0.00           H  
HETATM   18  H8  UNL     1       2.241  -1.958  -1.345  1.00  0.00           H  
HETATM   19  H9  UNL     1       3.907  -0.371  -0.398  1.00  0.00           H  
HETATM   20  H10 UNL     1       3.126   1.561   0.922  1.00  0.00           H  
HETATM   21  H11 UNL     1       0.716   1.890   1.283  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    4    5
CONECT    3   14   15   16
CONECT    5    6    6   10
CONECT    6    7   17
CONECT    7    8    8   18
CONECT    8    9   19
CONECT    9   10   10   20
CONECT   10   21
END
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SMILES for HMDB0001466 (Dimethylaniline-N-oxide)

C[N+](C)([O-])C1=CC=CC=C1
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INCHI for HMDB0001466 (Dimethylaniline-N-oxide)

InChI=1S/C8H11NO/c1-9(2,10)8-6-4-3-5-7-8/h3-7H,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Dimethyl(phenyl)amine oxideChEBI
Dimethylaniline N-oxideChEBI
N,N-Dimethylaniline N-oxideHMDB
NN-Dimethylaniline-N-oxideHMDB
Dimethylaniline N-oxide hydrochlorideMeSH, HMDB
Chemical FormulaC8H11NO
Average Molecular Weight137.179
Monoisotopic Molecular Weight137.084063979
IUPAC NameN-methyl-N-phenylmethanamine oxide
Traditional Namedimethylaniline N-oxide
CAS Registry Number874-52-2
SMILES
C[N+](C)([O-])C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H11NO/c1-9(2,10)8-6-4-3-5-7-8/h3-7H,1-2H3
InChI KeyLKQUDAOAMBKKQW-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
  • Trisubstituted n-oxide
  • N-oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Route of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022640
KNApSAcK IDNot Available
Chemspider ID925
KEGG Compound IDC01183
BioCyc IDNN-DIMETHYLANILINE-N-OXIDE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound950
PDB IDNot Available
ChEBI ID17735
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceZiegler, Daniel M.; Pettit, Flora H. Formation of an intermediate N-oxide in the oxidative demethylation of N,N-dimethylaniline catalyzed by liver microsomes. Biochemical and Biophysical Research Communications (1964), 15(2), 188-93.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Dimethylaniline monooxygenase [N-oxide-forming] 5
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
In contrast with other forms of FMO it does not seem to be a drug-metabolizing enzyme.
Gene Name:
FMO5
Uniprot ID:
P49326
Molecular weight:
32480.04
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails
Enzyme Details
2. Dimethylaniline monooxygenase [N-oxide-forming] 2
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Catalyzes the N-oxidation of certain primary alkylamines to their oximes via an N-hydroxylamine intermediate. Inactive toward certain tertiary amines, such as imipramine or chloropromazine. Can catalyze the S-oxidation of methimazole. The truncated form is catalytically inactive.
Gene Name:
FMO2
Uniprot ID:
Q99518
Molecular weight:
53643.29
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails
Enzyme Details
3. Dimethylaniline monooxygenase [N-oxide-forming] 4
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides.
Gene Name:
FMO4
Uniprot ID:
P31512
Molecular weight:
63342.055
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails
Enzyme Details
4. Dimethylaniline monooxygenase [N-oxide-forming] 3
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds.
Gene Name:
FMO3
Uniprot ID:
P31513
Molecular weight:
60032.975
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails
Enzyme Details
5. Dimethylaniline monooxygenase [N-oxide-forming] 1
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
Gene Name:
FMO1
Uniprot ID:
Q01740
Molecular weight:
60310.285
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails
Enzyme Details
6. Putative dimethylaniline monooxygenase [N-oxide-forming] 6
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
It is probable that this protein is only produced in very small quantity or not at all as the gene coding for it seems to be unable to produce full length transcripts.
Gene Name:
FMO6P
Uniprot ID:
O60774
Molecular weight:
Not Available
Reactions
N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Waterdetails