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Record Information
Version3.6
Creation Date2006-08-13 16:24:27 UTC
Update Date2016-02-11 01:06:43 UTC
HMDB IDHMDB04296
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcrylamide
DescriptionAcrylamide (ACR) is a chemical used in many industries around the world and more recently was found to form naturally in foods cooked at high temperatures. Acrylamide is a neurotoxicant, reproductive toxicant, and carcinogen in animal species. Only the neurotoxic effects have been observed in humans and only at high levels of exposure in occupational settings. The mechanism underlying neurotoxic effects of ACR may be basic to the other toxic effects seen in animals. This mechanism involves interference with the kinesin-related motor proteins in nerve cells or with fusion proteins in the formation of vesicles at the nerve terminus and eventual cell death. Neurotoxicity and resulting behavioral changes can affect reproductive performance of ACR-exposed laboratory animals with resulting decreased reproductive performance. Further, the kinesin motor proteins are important in sperm motility, which could alter reproduction parameters. Effects on kinesin proteins could also explain some of the genotoxic effects on ACR. These proteins form the spindle fibers in the nucleus that function in the separation of chromosomes during cell division. This could explain the clastogenic effects of the chemical noted in a number of tests for genotoxicity and assays for germ cell damage. Other mechanisms underlying ACR-induced carcinogenesis or nerve toxicity are likely related to an affinity for sulfhydryl groups on proteins. Binding of the sulfhydryl groups could inactive proteins/enzymes involved in DNA repair and other critical cell functions. Direct interaction with DNA may or may not be a major mechanism for cancer induction in animals. The DNA adducts that form do not correlate with tumor sites and ACR is mostly negative in gene mutation assays except at high doses that may not be achievable in the diet. All epidemiologic studies fail to show any increased risk of cancer from either high-level occupational exposure or the low levels found in the diet. In fact, two of the epidemiologic studies show a decrease in cancer of the large bowel. A number of risk assessment studies were performed to estimate increased cancer risk. The results of these studies are highly variable depending on the model. There is universal consensus among international food safety groups in all countries that examined the issue of ACR in the diet that not enough information is available at this time to make informed decisions on which to base any regulatory action. Too little is known about levels of this chemical in different foods and the potential risk from dietary exposure. Avoidance of foods containing ACR would result in worse health issues from an unbalanced diet or pathogens from under cooked foods. There is some consensus that low levels of ACR in the diet are not a concern for neurotoxicity or reproductive toxicity in humans, although further research is need to study the long-term, low-level cumulative effects on the nervous system. Any relationship to cancer risk from dietary exposure is hypothetical at this point and awaits more definitive studies. (PMID: 17492525 ).
Structure
Thumb
Synonyms
ValueSource
2-PropenamideChEBI
AkrylamidChEBI
EthylenecarboxamideChEBI
2-PropeneamideHMDB
AcrylagelHMDB
Acrylic acid amideHMDB
Acrylic amideHMDB
Aerofloc 3453HMDB
American cyanamid kpamHMDB
American cyanamid P-250HMDB
Amid kyseliny akryloveHMDB
Amide propenoateHMDB
Amide propenoic acidHMDB
Aminogen paHMDB
amresco Acryl-40HMDB
bio-Gel P 2HMDB
BioGel P-100HMDB
Cyanamer P 250HMDB
Cyanamer P 35HMDB
Cytame 5HMDB
Dow et 597HMDB
Ethylene carboxamideHMDB
Flokonit eHMDB
Flygtol GBHMDB
Gelamide 250HMDB
Himoloc SS 200HMDB
K-PamHMDB
Magnafloc R 292HMDB
Nacolyte 673HMDB
OptimumHMDB
PolyacrylamideHMDB
Polyacrylamide resinHMDB
Polyacrylamide solutionHMDB
Polyhall 27HMDB
Polyhall 402HMDB
PolystolonHMDB
PolystoronHMDB
PorisutoronHMDB
Praestol 2800HMDB
PropenamideHMDB
PropeneamideHMDB
PropenoateHMDB
Propenoic acidHMDB
Propenoic acid amideHMDB
Reten 420HMDB
Sanpoly a 520HMDB
Solvitose 433HMDB
Stipix adHMDB
Stokopol D 2624HMDB
Sumirez a 17HMDB
Sumirez a 27HMDB
Sumitex a 1HMDB
Superfloc 84HMDB
Superfloc 900HMDB
Sursolan P 5HMDB
Versicol W 11HMDB
Vinyl amideHMDB
Chemical FormulaC3H5NO
Average Molecular Weight71.0779
Monoisotopic Molecular Weight71.037113787
IUPAC Nameprop-2-enamide
Traditional Nameacrylamide
CAS Registry Number79-06-1
SMILES
NC(=O)C=C
InChI Identifier
InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
InChI KeyInChIKey=HRPVXLWXLXDGHG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as primary carboxylic acid amides. These are compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentPrimary carboxylic acid amides
Alternative Parents
Substituents
  • Primary carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point84.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility390 mg/mL at 25 °CNot Available
LogP-0.67HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility120.0 mg/mLALOGPS
logP-0.65ALOGPS
logP-0.27ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)16.7ChemAxon
pKa (Strongest Basic)0.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity19.11 m3·mol-1ChemAxon
Polarizability6.88 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-9000000000-7b30073e15256ba58af1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-9000000000-26ca703d558096e73e80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kfx-9000000000-da086ba0e1b4f10d534fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-05dl-9000000000-2c812f3ba789fd949662View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0fbc-9000000000-133d475aa82b7785e9d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-05dl-9000000000-1a51b235c01925474be9View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008308
KNApSAcK IDNot Available
Chemspider ID6331
KEGG Compound IDC01659
BioCyc IDCPD-2204
BiGG IDNot Available
Wikipedia LinkAcrylamide
NuGOwiki LinkHMDB04296
Metagene LinkHMDB04296
METLIN IDNot Available
PubChem Compound6579
PDB IDNot Available
ChEBI ID28619
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Exon JH: A review of the toxicology of acrylamide. J Toxicol Environ Health B Crit Rev. 2006 Sep-Oct;9(5):397-412. [17492525 ]