MiMeDB: Showing metabocard for N,N-dimethylformamide (MMDBc0054592)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:19:41 UTC

Update Date

2022-08-12 20:09:01 UTC

Metabolite ID

MMDBc0054592

Metabolite Identification

Common Name

N,N-dimethylformamide

Description

N,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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dimethylformamide	ChEBI
DMF	ChEBI
N,N-Dimethylmethanamide	ChEBI
N-Formyldimethylamine	ChEBI
Dimethyl formamide	HMDB
Dimethyl-formamide	HMDB
Dimethylamid kyseliny mravenci	HMDB
Dimethylforamide	HMDB
Dimethylformamid	HMDB
Dimetilformamide	HMDB
Dimetylformamidu	HMDB
Dwumetyloformamid	HMDB
Formyldimethylamine	HMDB
N,N- Dimethyl formamide	HMDB
N,N- Dimethylformamide	HMDB
N,N-Dimethyl-formamide	HMDB
N,N Dimethylformamide	HMDB

Molecular Formula

C₃H₇NO

Average Mass

73.0938

Monoisotopic Mass

73.052763851

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

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

InChI Key

ZMXDDKWLCZADIW-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Tertiary 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 Framework

Aliphatic acyclic compounds

External Descriptors

formamides (CHEBI:17741 )
a small molecule (CPD-581 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193612	Renin	Unknown	P00797	Homo_sapiens
MMDBp0194439	Chymotrypsin-like elastase family member 1	Unknown	Q9UNI1	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	2
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	1.27	0.18	2.24	Adult (>18 years old)	Both	Smoking	HMDB	18666198
Human	Detected and Quantified	0.17	0.06	0.77	Adult (>18 years old)	Both	Normal	HMDB	18666198
Human	Detected and Quantified		0.18	2.2	Adult (>18 years old)	Both	Smoking	HMDB	18666198
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Not Specified	Normal	HMDB	24421258

External Links

HMDB ID

HMDB0001888

DrugBank ID

DB01844

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004724

KNApSAcK ID

Not Available

Chemspider ID

5993

KEGG Compound ID

C03134

BioCyc ID

CPD-581

BiGG ID

Not Available

Wikipedia Link

Dimethylformamide

METLIN ID

Not Available

PubChem Compound

6228

PDB ID

Not Available

ChEBI ID

17741

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

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. doi: 10.7326/0003-4819-108-5-680. [PubMed:3358569 ]
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. doi: 10.1016/j.cbi.2006.12.008. Epub 2006 Dec 20. [PubMed:17254560 ]

Showing metabocard for N,N-dimethylformamide (MMDBc0054592)

MOL for #<Metabolite:0x0000560be24951f8>

3D MOL for #<Metabolite:0x0000560be24951f8>

3D SDF for #<Metabolite:0x0000560be24951f8>

3D-SDF for #<Metabolite:0x0000560be24951f8>

PDB for #<Metabolite:0x0000560be24951f8>

3D PDB for #<Metabolite:0x0000560be24951f8>

SMILES for #<Metabolite:0x0000560be24951f8>

INCHI for #<Metabolite:0x0000560be24951f8>

Structure for #<Metabolite:0x0000560be24951f8>

3D Structure for #<Metabolite:0x0000560be24951f8>