Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:23 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?1582752203
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
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.6 g/LALOGPS
logP10(-0.59) g/LALOGPS
logP10(-2.4) g/LChemAxon
logS10(-2.4) g/LALOGPS
pKa (Strongest Basic)4.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.88 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.43 m³·mol⁻¹ChemAxon
Polarizability14.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.24331661259
DarkChem[M-H]-125.56531661259
AllCCS[M+H]+127.32332859911
AllCCS[M-H]-137.8132859911

Predicted Kovats Retention Indices

Not Available
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

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
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
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
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
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
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