Acetamide (T3D4209)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-08-29 05:53:06 UTC
Update Date2014-12-24 20:26:42 UTC
Accession NumberT3D4209
Identification
Common NameAcetamide
ClassSmall Molecule
DescriptionAcetamide 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. 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. (1, 2, 2, 3).
Compound Type
  • Cigarette Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Pollutant
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Acetic acid amide
Acetimidic acid
ACM
Amid kyseliny octove
CH3CONH2
Ethanamide
Methanecarboxamide
Chemical FormulaC2H5NO
Average Molecular Mass59.067 g/mol
Monoisotopic Mass59.037 g/mol
CAS Registry Number60-35-5
IUPAC Nameacetamide
Traditional Nameacetamide
SMILESCC(O)=N
InChI IdentifierInChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
InChI KeyInChIKey=DLFVBJFMPXGRIB-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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point82 - 83°C
Boiling Point223°C (433.4°F)
Solubility2250 mg/mL at 25°C
LogP-1.26
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-94d49b439405d0f3ad412017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-94d49b439405d0f3ad412018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-44ec47d45cbb6740fd6e2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-0a4i-9000000000-62a9b7d69257dd565e222020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0a4i-9000000000-eca97902d04e534ac2d32020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-0a4i-9000000000-51b4caaf1d8caa1dcd662020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-0a4i-9000000000-41fb86e31e458684dcc12020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 11V, positivesplash10-0a4i-9000000000-377e3699217c3ddf653e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0a4l-9000000000-9ff14ca7216ed562a12b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 13V, positivesplash10-0a4l-9000000000-c5d1fbf0f4ac79ba85002020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 14V, positivesplash10-052f-9000000000-6404591bd64c77b776102020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 15V, positivesplash10-052f-9000000000-cb5bcad9d2d9b6b736f22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-052f-9000000000-11dd3535e54d6ff8ef852020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 17V, positivesplash10-052f-9000000000-c49a0918dbfba17724c62020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 18V, positivesplash10-052f-9000000000-14175a412c1916e3d8512020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 19V, positivesplash10-052f-9000000000-215f69c60943a78528a02020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-505a068d8b00d3030e682016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-0164236da39cd57f6f082016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c6fa97895f0c45a9186b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-0d3d5066ba65a1714c212021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-0d3d5066ba65a1714c212021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90726b17dc36e29c52992021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-a6a33bf7f6d8f960c8bf2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-3fadaee55485aba6adcd2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c8d15248967cca08c9c52016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-9000000000-5361b148690025f748372021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9000000000-a69a370c97bfa9746f6d2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-87bbaed151efac0845912021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-245f2dcb7e62391b1c0a2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, D2O, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, D2O, experimental)Not Available2014-09-23View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (5)
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB02736
HMDB IDHMDB31645
PubChem Compound ID178
ChEMBL IDCHEMBL16081
ChemSpider ID173
KEGG IDC06244
UniProt IDNot Available
OMIM ID
ChEBI ID27856
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDACM
ACToR IDNot Available
Wikipedia LinkAcetamide
References
Synthesis Reference

Youichi Shiokawa, Kazuo Okumura, Kazuhiko Take, Kazunori Tsubaki, “Novel substituted-acetamide compound and a process for the preparation thereof.” U.S. Patent US5066680, issued February, 1963.

MSDSLink
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. [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. [20452462 ]
  3. Muri EM, Williamson JS: Anti-Helicobacter pylori agents. An update. Mini Rev Med Chem. 2004 Feb;4(2):201-6. [14965292 ]
  4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Histone deacetylase 6
General Function:
Zinc ion binding
Specific Function:
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an important role in transcriptional regulation, cell cycle progression and developmental events. Histone deacetylases act via the formation of large multiprotein complexes (By similarity). Plays a central role in microtubule-dependent cell motility via deacetylation of tubulin. Involved in the MTA1-mediated epigenetic regulation of ESR1 expression in breast cancer.In addition to its protein deacetylase activity, plays a key role in the degradation of misfolded proteins: when misfolded proteins are too abundant to be degraded by the chaperone refolding system and the ubiquitin-proteasome, mediates the transport of misfolded proteins to a cytoplasmic juxtanuclear structure called aggresome. Probably acts as an adapter that recognizes polyubiquitinated misfolded proteins and target them to the aggresome, facilitating their clearance by autophagy.
Gene Name:
HDAC6
Uniprot ID:
Q9UBN7
Molecular Weight:
131418.19 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.07 uMNVS_ENZ_hHDAC6Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]