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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 00:16:15 UTC
HMDB IDHMDB0001536
Secondary Accession Numbers
  • HMDB01536
Metabolite Identification
Common NameFormamide
DescriptionFormamide is a metabolite used for biological monitoring of workers exposed to N-N-dimethylformamide (DMF).(PMID 7622279 ). There is a case of significant association between ever having been exposed to DMF and subsequent development of prostate cancer (PMID 2715850 ).
Structure
Thumb
Synonyms
ValueSource
AmeisensaeureamidChEBI
CarbamaldehydeChEBI
FormamidChEBI
Formimidic acidChEBI
MethanamidChEBI
MethanamideChEBI
FormimidateGenerator
Chemical FormulaCH3NO
Average Molecular Weight45.0406
Monoisotopic Molecular Weight45.021463723
IUPAC Nameformamide
Traditional Nameformamide
CAS Registry Number75-12-7
SMILES
NC=O
InChI Identifier
InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3)
InChI KeyZHNUHDYFZUAESO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassCarboximidic acids
Direct ParentCarboximidic acids
Alternative Parents
Substituents
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point2.55 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP-1.51HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility503 g/LALOGPS
logP-1.5ALOGPS
logP-1.1ChemAxon
logS1.05ALOGPS
pKa (Strongest Acidic)16.67ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity9.98 m³·mol⁻¹ChemAxon
Polarizability3.83 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-f6326cc6c67041284b52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-4a58cc52ed1f85a41b4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-52b8e3cce362934e1d52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-9000000000-32c53cf62ffc73e10c84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-0a22a0222cfe33823b8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-2473e800b4396749f887View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9000000000-3221c668103b22c85e42View in MoNA
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
Tissue Locations
  • Adrenal Gland
  • Epidermis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022677
KNApSAcK IDNot Available
Chemspider ID693
KEGG Compound IDC00488
BioCyc IDFORMAMIDE
BiGG IDNot Available
Wikipedia LinkFormamide
METLIN ID4182
PubChem Compound713
PDB IDARF
ChEBI ID16397
References
Synthesis ReferenceMagill, P. L. Formamide. Journal of Industrial and Engineering Chemistry (Washington, D. C.) (1934), 26 611-14.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lareo AC, Perbellini L: Biological monitoring of workers exposed to N-N-dimethylformamide. II. Dimethylformamide and its metabolites in urine of exposed workers. Int Arch Occup Environ Health. 1995;67(1):47-52. [PubMed:7622279 ]
  2. Kawashima K, Doi H, Ito Y, Shibata MA, Yoshinaka R, Otsuki Y: Evaluation of cell death and proliferation in psoriatic epidermis. J Dermatol Sci. 2004 Sep;35(3):207-14. [PubMed:15381242 ]
  3. Major J, Hudak A, Kiss G, Jakab MG, Szaniszlo J, Naray M, Nagy I, Tompa A: Follow-up biological and genotoxicological monitoring of acrylonitrile- and dimethylformamide-exposed viscose rayon plant workers. Environ Mol Mutagen. 1998;31(4):301-10. [PubMed:9654238 ]
  4. Al-Soud WA, Ouis IS, Li DQ, Ljungh S, Wadstrom T: Characterization of the PCR inhibitory effect of bile to optimize real-time PCR detection of Helicobacter species. FEMS Immunol Med Microbiol. 2005 May 1;44(2):177-82. [PubMed:15866213 ]
  5. Eizuru Y, Minamishima Y, Matsumoto T, Hamakado T, Mizukoshi M, Nabeshima K, Koono M, Yoshida A, Yoshida H, Kikuchi M: Application of in situ hybridization with a novel phenytoin-labeled probe to conventional formalin-fixed, paraffin-embedded tissue sections. J Virol Methods. 1995 Apr;52(3):309-16. [PubMed:7601905 ]
  6. Walrath J, Fayerweather WE, Gilby PG, Pell S: A case-control study of cancer among du pont employees with potential for exposure to dimethylformamide. J Occup Med. 1989 May;31(5):432-8. [PubMed:2715850 ]