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Showing metabocard for N,N-Dimethylformamide (HMDB0001888)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-28 12:00:41 UTC
Update Date2023-02-21 17:15:55 UTC
HMDB IDHMDB0001888
Secondary Accession Numbers
  • HMDB01888
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
Data?1676999755
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001888 (N,N-Dimethylformamide)

  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 HMDB0001888 (N,N-Dimethylformamide)

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 HMDB0001888 (N,N-Dimethylformamide)

  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>
HMDB0001888

> <DATABASE_NAME>
hmdb

> <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 HMDB0001888 (N,N-Dimethylformamide)

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 HMDB0001888 (N,N-Dimethylformamide)

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 HMDB0001888 (N,N-Dimethylformamide)

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 HMDB0001888 (N,N-Dimethylformamide)

CN(C)C=O
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INCHI for HMDB0001888 (N,N-Dimethylformamide)

InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC3H7NO
Average Molecular Weight73.0938
Monoisotopic Molecular Weight73.052763851
IUPAC NameN,N-dimethylformamide
Traditional Namedimethylformamide
CAS Registry Number68-12-2
SMILES
CN(C)C=O
InChI Identifier
InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
InChI KeyZMXDDKWLCZADIW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tertiary carboxylic acid amides. Tertiary carboxylic acid amides are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentTertiary carboxylic acid amides
Alternative Parents
Substituents
  • Tertiary carboxylic acid amide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationEnvironmental roleIndirect biological roleBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-60.4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L at 25 °CNot Available
LogP-1.01HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.17 (0.06-0.77) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified1.27 (0.18-2.24) umol/mmol creatinineAdult (>18 years old)BothSmoking details
Associated Disorders and Diseases
Disease References
Smoking
  1. Schettgen T, Musiol A, Kraus T: Simultaneous determination of mercapturic acids derived from ethylene oxide (HEMA), propylene oxide (2-HPMA), acrolein (3-HPMA), acrylamide (AAMA) and N,N-dimethylformamide (AMCC) in human urine using liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2008 Sep;22(17):2629-38. doi: 10.1002/rcm.3659. [PubMed:18666198 ]
Associated OMIM IDsNone
DrugBank IDDB01844
Phenol Explorer Compound IDNot Available
FooDB IDFDB004724
KNApSAcK IDNot Available
Chemspider ID5993
KEGG Compound IDC03134
BioCyc IDCPD-581
BiGG IDNot Available
Wikipedia LinkDimethylformamide
METLIN IDNot Available
PubChem Compound6228
PDB IDNot Available
ChEBI ID17741
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000352
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Shieh DB, Chen CC, Shih TS, Tai HM, Wei YH, Chang HY: Mitochondrial DNA alterations in blood of the humans exposed to N,N-dimethylformamide. Chem Biol Interact. 2007 Feb 20;165(3):211-9. Epub 2006 Dec 20. [PubMed:17254560 ]
  2. Redlich CA, Beckett WS, Sparer J, Barwick KW, Riely CA, Miller H, Sigal SL, Shalat SL, Cullen MR: Liver disease associated with occupational exposure to the solvent dimethylformamide. Ann Intern Med. 1988 May;108(5):680-6. [PubMed:3358569 ]

Enzymes

Enzyme Details
1. Renin
General function:
Involved in aspartic-type endopeptidase activity
Specific function:
Renin is a highly specific endopeptidase, whose only known function is to generate angiotensin I from angiotensinogen in the plasma, initiating a cascade of reactions that produce an elevation of blood pressure and increased sodium retention by the kidney
Gene Name:
REN
Uniprot ID:
P00797
Molecular weight:
45057.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Enzyme Details
2. Chymotrypsin-like elastase family member 1
General function:
Involved in serine-type endopeptidase activity
Specific function:
Acts upon elastin
Gene Name:
CELA1
Uniprot ID:
Q9UNI1
Molecular weight:
27798.0
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]