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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:44:37 UTC
Update Date2020-03-25 17:07:32 UTC
HMDB IDHMDB0031645
Secondary Accession Numbers
  • HMDB31645
Metabolite Identification
Common NameAcetamide
DescriptionAcetamide, also known as ethanamid or acetic acid amide, 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). Acetamide is an extremely weak basic (essentially neutral) compound (based on its pKa). On 30 July 2015, scientists reported that upon the first touchdown of the Philae lander on comet 67/P's surface, measurements by the COSAC and Ptolemy instruments revealed sixteen organic compounds, four of which – acetamide, acetone, methyl isocyanate, and propionaldehyde – were seen for the first time on a comet. Acetamide is a mousy tasting compound. Outside of the human body, Acetamide has been detected, but not quantified in, red beetroots. This could make acetamide a potential biomarker for the consumption of these foods. Acetamide is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. It is the simplest amide derived from acetic acid. The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. In a similar fashion to some laboratory methods, acetamide is produced by dehydrating ammonium acetate or via the hydration of acetonitrile, a byproduct of the production of acrylonitrile:CH3CN + H2O → CH3C(O)NH2A precursor to thioacetamideAcetamide has been detected near the center of the Milky Way galaxy. Acetamide can be considered an intermediate between acetone, which has two methyl (CH3) groups either side of the carbonyl (CO), and urea which has two amide (NH2) groups in those locations. Yield is typically low (up to 35%), and the acetamide made this way is generated as a salt with HCl. It finds some use as a plasticizer and as an industrial solvent. Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. Acetamide can be produced in the laboratory from ammonium acetate by dehydration:[NH4][CH3CO2] → CH3C(O)NH2 + H2OAlternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination. It can also be made from anhydrous acetic acid, acetonitrile and very well dried hydrogen chloride gas, using an ice bath, alongside more valuable reagent acetyl chloride. This finding lends support to the theory that organic molecules that can lead to life (as we know it on Earth) can form in space. This finding is potentially significant because acetamide has an amide bond, similar to the essential bond between amino acids in proteins.
Structure
Data?1585156052
Synonyms
ValueSource
AcetamidChEBI
Acetic acid amideChEBI
AzetamidChEBI
CH3CONH2ChEBI
EssigsaeureamidChEBI
EthanamidChEBI
EthanamideChEBI
MethanecarboxamideChEBI
Acetate amideGenerator
Acetimidic acidHMDB
ACMHMDB
Amid kyseliny octoveHMDB
Acetamide, monosodium saltHMDB
Chemical FormulaC2H5NO
Average Molecular Weight59.0672
Monoisotopic Molecular Weight59.037113787
IUPAC Nameacetamide
Traditional Nameacetamide
CAS Registry Number60-35-5
SMILES
CC(N)=O
InChI Identifier
InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
InChI KeyDLFVBJFMPXGRIB-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point82 - 83 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2250 mg/mL at 25 °CNot Available
LogP-1.26Not Available
Predicted Properties
PropertyValueSource
Water Solubility369 g/LALOGPS
logP-1.1ALOGPS
logP-1ChemAxon
logS0.8ALOGPS
pKa (Strongest Acidic)16.75ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.47 m³·mol⁻¹ChemAxon
Polarizability5.76 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-94d49b439405d0f3ad41Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-94d49b439405d0f3ad41Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-44ec47d45cbb6740fd6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-a6a33bf7f6d8f960c8bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-3fadaee55485aba6adcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c8d15248967cca08c9c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-505a068d8b00d3030e68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-0164236da39cd57f6f08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c6fa97895f0c45a9186bSpectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-245f2dcb7e62391b1c0aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.2 (5.5) uMAdult (>18 years old)FemaleDown syndrome pregnancy details
BloodDetected and Quantified6.4 (4.9) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified6.56 (3.47) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified7.78 (5.04) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified9.6 (5.4) uMAdult (>18 years old)FemaleEarly preeclampsia details
BloodDetected and Quantified10.0 (6.3) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified11.9 (7.8) uMAdult (>18 years old)FemaleLate-onset preeclampsia details
BloodDetected and Quantified16.1 (6.4) uMAdult (>18 years old)FemalePregnancy details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
Associated Disorders and Diseases
Disease References
Early preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
Pregnancy
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
  2. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
  3. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ]
  4. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Late-onset preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
Associated OMIM IDsNone
DrugBank IDDB02736
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008298
KNApSAcK IDNot Available
Chemspider ID173
KEGG Compound IDC06244
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetamide
METLIN IDNot Available
PubChem Compound178
PDB IDNot Available
ChEBI ID27856
Food Biomarker OntologyNot Available
VMH IDAD
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yalcin I, Kaymakcioglu BK, Oren I, Sener E, Temiz O, Akin A, Altanlar N: Synthesis and microbiological activity of some novel N-(2-hydroxyl-5-substitutedphenyl)benzacetamides, phenoxyacetamides and thiophenoxyacetamides as the possible metabolites of antimicrobial active benzoxazoles. Farmaco. 1997 Nov;52(11):685-9. [PubMed:9550095 ]
  2. Jawed H, Shah SU, Jamall S, Simjee SU: N-(2-hydroxy phenyl) acetamide inhibits inflammation-related cytokines and ROS in adjuvant-induced arthritic (AIA) rats. Int Immunopharmacol. 2010 Aug;10(8):900-5. doi: 10.1016/j.intimp.2010.04.028. Epub 2010 May 7. [PubMed:20452462 ]
  3. Muri EM, Williamson JS: Anti-Helicobacter pylori agents. An update. Mini Rev Med Chem. 2004 Feb;4(2):201-6. [PubMed:14965292 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .