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Showing metabocard for N-Nitrosodimethylamine (HMDB0031419)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:01 UTC
Update Date2023-02-21 17:20:31 UTC
HMDB IDHMDB0031419
Secondary Accession Numbers
  • HMDB31419
Metabolite Identification
Common NameN-Nitrosodimethylamine
DescriptionN-Nitrosodimethylamine is found in pepper (Capsicum annuum). N-Nitrosodimethylamine is a food contaminant especially in cured meat products. N-Nitrosodimethylamine (NDMA), also known as dimethylnitrosamine (DMN), is a semi-volatile organic chemical that is highly toxic and is a suspected human carcinogen. The US Environmental Protection Agency has determined that the maximum admissible concentration of NDMA in drinking water is 7 ng L 1. The EPA has not yet set a regulatory maximum contaminant level (MCL) for drinking water. At high doses, it is a "potent hepatotoxin that can cause fibrosis of the liver" in rats. The induction of liver tumors in rats after chronic exposure to low doses is well-documented. Its toxic effects on humans are inferred from animal experiments but not well-established experimentally. NDMA is an industrial by-product or waste product of several industrial processes. It first came to attention as a groundwater contaminant in California in 1998 and 1999 at several sites that produced rocket fuel. Manufacturing of unsymmetrical dimethylhydrazine (UDMH), which is a component of rocket fuel that requires NDMA for its synthesis, proved to be the culprit in these cases. Of more general concern, water treatment via chlorination or chloramination of organic nitrogen-containing wastewater can lead to the production of NDMA at potentially harmful levels. Further, NDMA can form or be leached during treatment of water by anion exchange resins. Finally, NDMA is found at low levels in numerous items of human consumption including cured meat, fish, beer, and tobacco smoke, it is, however, unlikely to bioaccumulate
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031419 (N-Nitrosodimethylamine)

  Mrv1652302102020342D          

  5  4  0  0  0  0            999 V2000
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  2  0  0  0  0
M  END
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3D MOL for HMDB0031419 (N-Nitrosodimethylamine)

HMDB0031419
     RDKit          3D
N-Nitrosodimethylamine
 11 10  0  0  0  0  0  0  0  0999 V2000
   -0.9989    0.7543    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297   -0.2609   -0.1594 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3974   -0.0626    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300   -1.4946   -0.6781 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -1.8859   -0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    0.5760    1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265    0.7149   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4869    1.7329    0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6529   -0.5319    1.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6395    1.0020    0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9795   -0.5441   -0.7916 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
  4  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
M  END
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3D SDF for HMDB0031419 (N-Nitrosodimethylamine)

  Mrv1652302102020342D          

  5  4  0  0  0  0            999 V2000
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031419

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)N=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H6N2O/c1-4(2)3-5/h1-2H3

> <INCHI_KEY>
UMFJAHHVKNCGLG-UHFFFAOYSA-N

> <FORMULA>
C2H6N2O

> <MOLECULAR_WEIGHT>
74.0818

> <EXACT_MASS>
74.048012824

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
7.118126838694144

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
dimethyl(nitroso)amine

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
0.03861382233333321

> <ALOGPS_LOGS>
0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.520320416642765

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
20.0505

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nitrosodimethylamine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031419 (N-Nitrosodimethylamine)

HMDB0031419
     RDKit          3D
N-Nitrosodimethylamine
 11 10  0  0  0  0  0  0  0  0999 V2000
   -0.9989    0.7543    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297   -0.2609   -0.1594 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3974   -0.0626    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300   -1.4946   -0.6781 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -1.8859   -0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    0.5760    1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265    0.7149   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4869    1.7329    0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6529   -0.5319    1.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6395    1.0020    0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9795   -0.5441   -0.7916 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
  4  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
M  END
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PDB for HMDB0031419 (N-Nitrosodimethylamine)

HEADER    PROTEIN                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.540   0.000   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       2.310  -1.334   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    4    5                                                       
CONECT    4    1    2    3                                                  
CONECT    5    3                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0031419 (N-Nitrosodimethylamine)

COMPND    HMDB0031419
HETATM    1  C1  UNL     1      -0.999   0.754   0.162  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.030  -0.261  -0.159  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.397  -0.063   0.034  1.00  0.00           C  
HETATM    4  N2  UNL     1      -0.430  -1.495  -0.678  1.00  0.00           N  
HETATM    5  O1  UNL     1      -1.572  -1.886  -0.363  1.00  0.00           O  
HETATM    6  H1  UNL     1      -1.326   0.576   1.217  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.826   0.715  -0.560  1.00  0.00           H  
HETATM    8  H3  UNL     1      -0.487   1.733   0.060  1.00  0.00           H  
HETATM    9  H4  UNL     1       1.653  -0.532   1.005  1.00  0.00           H  
HETATM   10  H5  UNL     1       1.640   1.002   0.074  1.00  0.00           H  
HETATM   11  H6  UNL     1       1.980  -0.544  -0.792  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    4
CONECT    3    9   10   11
CONECT    4    5    5
END
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SMILES for HMDB0031419 (N-Nitrosodimethylamine)

CN(C)N=O
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INCHI for HMDB0031419 (N-Nitrosodimethylamine)

InChI=1S/C2H6N2O/c1-4(2)3-5/h1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC2H6N2O
Average Molecular Weight74.0818
Monoisotopic Molecular Weight74.048012824
IUPAC Namedimethyl(nitroso)amine
Traditional Namenitrosodimethylamine
CAS Registry Number62-75-9
SMILES
CN(C)N=O
InChI Identifier
InChI=1S/C2H6N2O/c1-4(2)3-5/h1-2H3
InChI KeyUMFJAHHVKNCGLG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic n-nitroso compounds. These are organic compounds containing a n-nitroso group -NN=O.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassOrganic nitroso compounds
Direct ParentOrganic N-nitroso compounds
Alternative Parents
Substituents
  • Organic n-nitroso compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Industrial process
Role
Environmental roleBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 24 °CNot Available
LogP-0.57Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB003496
KNApSAcK IDNot Available
Chemspider ID5894
KEGG Compound IDC14704
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Nitrosodimethylamine
METLIN IDNot Available
PubChem Compound6124
PDB IDNot Available
ChEBI ID35807
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1664021
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Godoy W, Albano RM, Moraes EG, Pinho PR, Nunes RA, Saito EH, Higa C, Filho IM, Kruel CD, Schirmer CC, Gurski R, Lang MA, Pinto LF: CYP2A6/2A7 and CYP2E1 expression in human oesophageal mucosa: regional and inter-individual variation in expression and relevance to nitrosamine metabolism. Carcinogenesis. 2002 Apr;23(4):611-6. [PubMed:11960914 ]
  2. Lee MF, Liu ML, Cheng AC, Tsai ML, Ho CT, Liou WS, Pan MH: Pterostilbene inhibits dimethylnitrosamine-induced liver fibrosis in rats. Food Chem. 2013 Jun 1;138(2-3):802-7. doi: 10.1016/j.foodchem.2012.11.094. Epub 2012 Dec 1. [PubMed:23411180 ]
  3. Lee MF, Tsai ML, Sun PP, Chien LL, Cheng AC, Ma NJ, Ho CT, Pan MH: Phyto-power dietary supplement potently inhibits dimethylnitrosamine-induced liver fibrosis in rats. Food Funct. 2013 Feb 26;4(3):470-5. doi: 10.1039/c2fo30306j. [PubMed:23291610 ]
  4. Kao HW, Chen CL, Chang WY, Chen JT, Lin WJ, Liu RS, Wang HE: (18)F-FBHGal for asialoglycoprotein receptor imaging in a hepatic fibrosis mouse model. Bioorg Med Chem. 2013 Feb 15;21(4):912-21. doi: 10.1016/j.bmc.2012.12.022. Epub 2012 Dec 22. [PubMed:23321012 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .