Showing metabocard for N,N-dimethylformamide (MMDBc0054592)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:19:41 UTC
Update Date2024-09-27 18:01:20 UTC
Metabolite IDMMDBc0054592
Metabolite Identification
Common NameN,N-dimethylformamide
DescriptionN,N-Dimethylformamide (DMF) is a clear liquid that has been widely used in industries as a solvent, an additive, or an intermediate because of its extensive miscibility with water and most common organic solvents. Its health effects include hepatotoxicity and male reproductoxicity, possibly linked with mitochondrial DNA (mtDNA) alterations including mtDNA common deletion (delta-mtDNA4977) and mtDNA copy number; during the biotransformation of DMF in the body, free radicals are formed, including hydroxyl radicals. The world-wide consumption of DMF in 2001 was approximately 285,000 metric tonnes and most of that was used as an industrial solvent. Overexposure to DMF could result in hepatotoxicity, alcohol intolerance, possible embryotoxicity and teratogenicity in humans and animals, and decline of human sperm motility. Based on its wide application and a wide range of toxic effects, DMF has been selected as one of the four priority compounds for human field studies by the National Toxicology Program (NTP) of the US National Institute of Environmental Health Sciences (NIEHS). The current permissible exposure limit for DMF in the working environment is 10 ppm in both USA and Taiwan. The concentrations of two major DMF metabolites in urine, N-methylformamide (U-NMF) of 15 mg/L and N-acetyl-S-(N-methylcarbamoyl) cysteine (U-AMCC) of 40 mg/L, were recommended as the biological exposure indices (BEIs) by the American Conference of Governmental Industrial Hygienists for DMF exposure in workplace. (PMID: 17254560 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f46e0010c38>


  Mrv1652305271900232D          

  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
    1.2375   -0.7145    0.0000 N   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 C   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f46e0010c38>

HMDB0001888
     RDKit          3D
N,N-Dimethylformamide
 12 11  0  0  0  0  0  0  0  0999 V2000
    0.6821   -1.1498   -0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544    0.1500   -0.0036 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3895    0.1729    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8727    1.2828   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1126    1.1891   -0.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6009   -1.6276    0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162   -1.7100   -0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662   -1.0838   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313   -0.7355   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157    0.2240    1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    1.0301   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4496    2.2578    0.0559 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
  4 12  1  0
M  END
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3D SDF for #<Metabolite:0x00007f46e0010c38>


  Mrv1652305271900232D          

  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
    1.2375   -0.7145    0.0000 N   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 C   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054592

> <DATABASE_NAME>
MIME

> <SMILES>
CN(C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3

> <INCHI_KEY>
ZMXDDKWLCZADIW-UHFFFAOYSA-N

> <FORMULA>
C3H7NO

> <MOLECULAR_WEIGHT>
73.0938

> <EXACT_MASS>
73.052763851

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
7.685931294003059

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N,N-dimethylformamide

> <ALOGPS_LOGP>
-0.77

> <JCHEM_LOGP>
-0.6316349046666669

> <ALOGPS_LOGS>
1.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2635984671629683

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
19.768800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.25e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethylformamide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007f46e0010c38>

HMDB0001888
     RDKit          3D
N,N-Dimethylformamide
 12 11  0  0  0  0  0  0  0  0999 V2000
    0.6821   -1.1498   -0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544    0.1500   -0.0036 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3895    0.1729    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8727    1.2828   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1126    1.1891   -0.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6009   -1.6276    0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162   -1.7100   -0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662   -1.0838   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313   -0.7355   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157    0.2240    1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    1.0301   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4496    2.2578    0.0559 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
  4 12  1  0
M  END
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PDB for #<Metabolite:0x00007f46e0010c38>

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       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.310  -1.334   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for #<Metabolite:0x00007f46e0010c38>

COMPND    HMDB0001888
HETATM    1  C1  UNL     1       0.682  -1.150  -0.111  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.054   0.150  -0.004  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.389   0.173   0.115  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.873   1.283  -0.021  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.113   1.189  -0.126  1.00  0.00           O  
HETATM    6  H1  UNL     1       0.601  -1.628   0.890  1.00  0.00           H  
HETATM    7  H2  UNL     1       0.116  -1.710  -0.894  1.00  0.00           H  
HETATM    8  H3  UNL     1       1.766  -1.084  -0.358  1.00  0.00           H  
HETATM    9  H4  UNL     1      -1.831  -0.735  -0.296  1.00  0.00           H  
HETATM   10  H5  UNL     1      -1.616   0.224   1.199  1.00  0.00           H  
HETATM   11  H6  UNL     1      -1.818   1.030  -0.449  1.00  0.00           H  
HETATM   12  H7  UNL     1       0.450   2.258   0.056  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    4
CONECT    3    9   10   11
CONECT    4    5    5   12
END
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SMILES for #<Metabolite:0x00007f46e0010c38>

CN(C)C=O
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INCHI for #<Metabolite:0x00007f46e0010c38>

InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
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Synonyms
ValueSource
DimethylformamideChEBI
DMFChEBI
N,N-DimethylmethanamideChEBI
N-FormyldimethylamineChEBI
Dimethyl formamideHMDB
Dimethyl-formamideHMDB
Dimethylamid kyseliny mravenciHMDB
DimethylforamideHMDB
DimethylformamidHMDB
DimetilformamideHMDB
DimetylformamiduHMDB
DwumetyloformamidHMDB
FormyldimethylamineHMDB
N,N- Dimethyl formamideHMDB
N,N- DimethylformamideHMDB
N,N-Dimethyl-formamideHMDB
N,N DimethylformamideHMDB
Molecular FormulaC3H7NO
Average Mass73.0938
Monoisotopic Mass73.052763851
IUPAC NameN,N-dimethylformamide
Traditional Namedimethylformamide
CAS Registry NumberNot Available
SMILES
CN(C)C=O
InChI Identifier
InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
InChI KeyZMXDDKWLCZADIW-UHFFFAOYSA-N