Acetamide (T3D4209) - T3DB

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Record Information
Version	2.0
Creation Date	2014-08-29 05:53:06 UTC
Update Date	2014-12-24 20:26:42 UTC
Accession Number	T3D4209
Identification
Common Name	Acetamide
Class	Small Molecule
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. 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	MOLSDFPDBSMILESInChI × Structure for T3D4209: Acetamide Close
Synonyms	Synonym Acetic acid amide Acetimidic acid ACM Amid kyseliny octove CH3CONH2 Ethanamide Methanecarboxamide
Chemical Formula	C2H5NO
Average Molecular Mass	59.067 g/mol
Monoisotopic Mass	59.037 g/mol
CAS Registry Number	60-35-5
IUPAC Name	acetamide
Traditional Name	acetamide
SMILES	CC(O)=N
InChI Identifier	InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
InChI Key	InChIKey=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).
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboximidic acids and derivatives
Sub Class	Carboximidic acids
Direct Parent	Carboximidic acids
Alternative Parents	Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Hydrocarbon derivatives
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	carboximidic acid (CHEBI:49028 ) a small molecule (ACETAMIDE )
Biological Properties
Status	Detected and Not Quantified
Origin	Endogenous
Cellular Locations	Cytoplasm Extracellular Membrane
Biofluid Locations	Not Available
Tissue Locations	Not Available
Pathways	Not Available
Applications	Not Available
Biological Roles	Not Available
Chemical Roles	Not Available
Physical Properties
State	Solid
Appearance	White powder.
Experimental Properties	Property Value Melting Point 82 - 83°C Boiling Point 223°C (433.4°F) Solubility 2250 mg/mL at 25°C LogP -1.26
Predicted Properties	Property Value Source Water Solubility 369 g/L ALOGPS logP -1.1 ALOGPS logP -1 ChemAxon logS 0.8 ALOGPS pKa (Strongest Acidic) 16.75 ChemAxon pKa (Strongest Basic) -1.4 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 43.09 Ų ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 14.47 m³·mol⁻¹ ChemAxon Polarizability 5.76 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Spectra
Spectra	Spectrum Type Description Splash Key Deposition Date View GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-0006-9000000000-94d49b439405d0f3ad41 2017-09-12 View Spectrum GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-0006-9000000000-94d49b439405d0f3ad41 2018-05-18 View Spectrum Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-052f-9000000000-44ec47d45cbb6740fd6e 2016-09-22 View Spectrum Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available 2021-10-12 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 7V, positive splash10-0a4i-9000000000-62a9b7d69257dd565e22 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 8V, positive splash10-0a4i-9000000000-eca97902d04e534ac2d3 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 9V, positive splash10-0a4i-9000000000-51b4caaf1d8caa1dcd66 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 10V, positive splash10-0a4i-9000000000-41fb86e31e458684dcc1 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 11V, positive splash10-0a4i-9000000000-377e3699217c3ddf653e 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 12V, positive splash10-0a4l-9000000000-9ff14ca7216ed562a12b 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 13V, positive splash10-0a4l-9000000000-c5d1fbf0f4ac79ba8500 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 14V, positive splash10-052f-9000000000-6404591bd64c77b77610 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 15V, positive splash10-052f-9000000000-cb5bcad9d2d9b6b736f2 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 16V, positive splash10-052f-9000000000-11dd3535e54d6ff8ef85 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 17V, positive splash10-052f-9000000000-c49a0918dbfba17724c6 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 18V, positive splash10-052f-9000000000-14175a412c1916e3d851 2020-07-22 View Spectrum LC-MS/MS LC-MS/MS Spectrum - QqQ 19V, positive splash10-052f-9000000000-215f69c60943a78528a0 2020-07-22 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4i-9000000000-505a068d8b00d3030e68 2016-08-03 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a4i-9000000000-0164236da39cd57f6f08 2016-08-03 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9000000000-c6fa97895f0c45a9186b 2016-08-03 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4i-9000000000-0d3d5066ba65a1714c21 2021-09-25 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a4i-9000000000-0d3d5066ba65a1714c21 2021-09-25 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9000000000-90726b17dc36e29c5299 2021-09-25 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-9000000000-a6a33bf7f6d8f960c8bf 2016-08-02 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-9000000000-3fadaee55485aba6adcd 2016-08-02 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-c8d15248967cca08c9c5 2016-08-02 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03dl-9000000000-5361b148690025f74837 2021-09-23 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01ox-9000000000-a69a370c97bfa9746f6d 2021-09-23 View Spectrum Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-87bbaed151efac084591 2021-09-23 View Spectrum MS Mass Spectrum (Electron Ionization) splash10-052f-9000000000-245f2dcb7e62391b1c0a 2014-09-20 View Spectrum 1D NMR 1H NMR Spectrum (1D, 90 MHz, D2O, experimental) Not Available 2014-09-20 View Spectrum 1D NMR 13C NMR Spectrum (1D, 50.18 MHz, D2O, experimental) Not Available 2014-09-23 View Spectrum 1D NMR 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum 1D NMR 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) Not Available 2021-09-30 View Spectrum
Toxicity Profile
Route of Exposure	Not Available
Mechanism of Toxicity	Not Available
Metabolism	Not Available
Toxicity Values	Not Available
Lethal Dose	Not Available
Carcinogenicity (IARC Classification)	2B, possibly carcinogenic to humans. (5)
Uses/Sources	This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk Level	Not Available
Health Effects	Not Available
Symptoms	Not Available
Treatment	Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
External Links
DrugBank ID	DB02736
HMDB ID	HMDB31645
PubChem Compound ID	178
ChEMBL ID	CHEMBL16081
ChemSpider ID	173
KEGG ID	C06244
UniProt ID	Not Available
OMIM ID
ChEBI ID	27856
BioCyc ID	Not Available
CTD ID	Not Available
Stitch ID	Not Available
PDB ID	ACM
ACToR ID	Not Available
Wikipedia Link	Acetamide
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.
MSDS	Link
General 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. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated Genes	Not Available
Down-Regulated Genes	Not Available

Targets

Target Details1. Histone deacetylase 6General Function:Zinc ion bindingSpecific 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:HDAC6Uniprot ID:Q9UBN7 Molecular Weight:131418.19 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	0.07 uM	NVS_ENZ_hHDAC6	Novascreen

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 ]