Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110466
Identification
Name: acetamide
Description:Acetamide is found in red beetroot. Acetamide (or acetic acid amide or ethanamide), CH3CONH2, the amide of acetic acid, is a white crystalline solid in pure form. It is produced by dehydrating ammonium acetate:Acetamide has been shown to exhibit anti-microbial, anti-inflammatory, anti-arthritic and antibiotic functions (PMID 9550095 , 20452462 , 20452462 , 14965292 ).Acetamide belongs to the family of Primary Carboxylic Acid Amides. These are compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2.
Structure
Thumb
Synonyms:
  • Acetamid
  • Acetic acid amide
  • Azetamid
  • CH3CONH2
  • Essigsaeureamid
  • Ethanamid
  • Ethanamide
  • Methanecarboxamide
  • Acetate amide
  • Acetimidic acid
  • ACM
  • Amid kyseliny octove
  • Acetamide, monosodium salt
Chemical Formula: C2H5NO
Average Molecular Weight: 59.068
Monoisotopic Molecular Weight: 59.0371137878
InChI Key: DLFVBJFMPXGRIB-UHFFFAOYSA-N
InChI: InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
CAS number: 60-35-5
IUPAC Name:acetamide
Traditional IUPAC Name: acetamide
SMILES:CC(=O)N
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboximidic acids and derivatives
Direct Parent Carboximidic acids
Alternative Parents
Substituents
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: 82 - 83 °C
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 Solubility369.0 mg/mLALOGPS
logP-1.1ALOGPS
logP-1ChemAxon
logS0.8ALOGPS
pKa (Strongest Acidic)16.75ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.47 m3·mol-1ChemAxon
Polarizability5.76 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-245f2dcb7e62391b1c0aView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
References:
  • 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. [9550095 ]
  • 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. [20452462 ]
  • Muri EM, Williamson JS: Anti-Helicobacter pylori agents. An update. Mini Rev Med Chem. 2004 Feb;4(2):201-6. [14965292 ]
  • Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS60-35-5
ChEBI27856
ChemSpider173
DrugBankDB02736
HMDBHMDB31645
KEGGC06244
MetaboLightsMTBLC27856
PubChem178