Human Metabolome Database: Showing metabocard for Acrylamide (HMDB0004296)

Record InformationVersion5.0StatusExpected but not QuantifiedCreation Date2006-08-13 16:24:27 UTCUpdate Date2023-02-21 17:16:59 UTCHMDB IDHMDB0004296Secondary Accession Numbers

• HMDB04296

Metabolite IdentificationCommon NameAcrylamideDescriptionAcrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2. It is a white odorless solid, soluble in water and several organic solvents. It is produced industrially as a precursor to polyacrylamides, which find many uses as water-soluble thickeners and flocculation agents. It is highly toxic, likely to be carcinogenic,and partly for that reason it is mainly handled as an aqueous solution. It 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

Synonyms

Value	Source
2-Propenamide	ChEBI
Akrylamid	ChEBI
Ethylenecarboxamide	ChEBI
2-Propeneamide	HMDB
Acrylagel	HMDB
Acrylic acid amide	HMDB
Acrylic amide	HMDB
Aerofloc 3453	HMDB
American cyanamid kpam	HMDB
American cyanamid P-250	HMDB
Amid kyseliny akrylove	HMDB
Amide propenoate	HMDB
Amide propenoic acid	HMDB
Aminogen pa	HMDB
amresco Acryl-40	HMDB
bio-Gel P 2	HMDB
BioGel P-100	HMDB
Cyanamer P 250	HMDB
Cyanamer P 35	HMDB
Cytame 5	HMDB
Dow et 597	HMDB
Ethylene carboxamide	HMDB
Flokonit e	HMDB
Flygtol GB	HMDB
Gelamide 250	HMDB
Himoloc SS 200	HMDB
K-Pam	HMDB
Magnafloc R 292	HMDB
Nacolyte 673	HMDB
Optimum	HMDB
Polyacrylamide	HMDB
Polyacrylamide resin	HMDB
Polyacrylamide solution	HMDB
Polyhall 27	HMDB
Polyhall 402	HMDB
Polystolon	HMDB
Polystoron	HMDB
Porisutoron	HMDB
Praestol 2800	HMDB
Prop-2-enamide	HMDB
Propenamide	HMDB
Propeneamide	HMDB
Propenoate	HMDB
Propenoic acid	HMDB
Propenoic acid amide	HMDB
Reten 420	HMDB
Sanpoly a 520	HMDB
Solvitose 433	HMDB
Stipix ad	HMDB
Stokopol D 2624	HMDB
Sumirez a 17	HMDB
Sumirez a 27	HMDB
Sumitex a 1	HMDB
Superfloc 84	HMDB
Superfloc 900	HMDB
Sursolan P 5	HMDB
Versicol W 11	HMDB
Vinyl amide	HMDB

Chemical FormulaC₃H₅NOAverage Molecular Weight71.0779Monoisotopic Molecular Weight71.037113787IUPAC Nameprop-2-enamideTraditional NameacrylamideCAS Registry Number79-06-1SMILES

NC(=O)C=C

InChI Identifier

InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)

InChI KeyHRPVXLWXLXDGHG-UHFFFAOYSA-NChemical TaxonomyDescription 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

• 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 FrameworkAliphatic acyclic compoundsExternal Descriptors

• acrylamides (CHEBI:28619 )
• a small molecule (ACRYLAMIDE )

OntologyPhysiological effectDispositionProcessNot AvailableRolePhysical PropertiesStateSolidExperimental Molecular Properties

Property	Value	Reference
Melting Point	84.5 °C	Not Available
Boiling Point	192.60 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	390 mg/mL at 25 °C	Not Available
LogP	-0.67	HANSCH,C ET AL. (1995)

Experimental Chromatographic PropertiesNot AvailablePredicted Molecular Properties

Property	Value	Source
Water Solubility	120 g/L	ALOGPS
logP	-0.65	ALOGPS
logP	-0.27	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	16.7	ChemAxon
pKa (Strongest Basic)	0.0026	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	1	ChemAxon
Refractivity	19.11 m³·mol⁻¹	ChemAxon
Polarizability	6.88 ų	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å2)	Reference
DarkChem	[M+H]+	112.08	31661259
DarkChem	[M-H]-	104.174	31661259
DeepCCS	[M+H]+	120.679	30932474
DeepCCS	[M-H]-	118.259	30932474
DeepCCS	[M-2H]-	154.249	30932474
DeepCCS	[M+Na]+	128.794	30932474
AllCCS	[M+H]+	121.5	32859911
AllCCS	[M+H-H2O]+	116.9	32859911
AllCCS	[M+NH4]+	125.8	32859911
AllCCS	[M+Na]+	127.0	32859911
AllCCS	[M-H]-	128.6	32859911
AllCCS	[M+Na-2H]-	134.2	32859911
AllCCS	[M+HCOO]-	140.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acrylamide	NC(=O)C=C	1903.9	Standard polar	33892256
Acrylamide	NC(=O)C=C	726.4	Standard non polar	33892256
Acrylamide	NC(=O)C=C	828.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acrylamide,1TMS,isomer #1	C=CC(=O)N[Si](C)(C)C	961.4	Semi standard non polar	33892256
Acrylamide,1TMS,isomer #1	C=CC(=O)N[Si](C)(C)C	1055.8	Standard non polar	33892256
Acrylamide,1TMS,isomer #1	C=CC(=O)N[Si](C)(C)C	1272.8	Standard polar	33892256
Acrylamide,2TMS,isomer #1	C=CC(=O)N([Si](C)(C)C)[Si](C)(C)C	1118.2	Semi standard non polar	33892256
Acrylamide,2TMS,isomer #1	C=CC(=O)N([Si](C)(C)C)[Si](C)(C)C	1071.7	Standard non polar	33892256
Acrylamide,2TMS,isomer #1	C=CC(=O)N([Si](C)(C)C)[Si](C)(C)C	1202.4	Standard polar	33892256
Acrylamide,1TBDMS,isomer #1	C=CC(=O)N[Si](C)(C)C(C)(C)C	1205.9	Semi standard non polar	33892256
Acrylamide,1TBDMS,isomer #1	C=CC(=O)N[Si](C)(C)C(C)(C)C	1246.1	Standard non polar	33892256
Acrylamide,1TBDMS,isomer #1	C=CC(=O)N[Si](C)(C)C(C)(C)C	1432.7	Standard polar	33892256
Acrylamide,2TBDMS,isomer #1	C=CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1561.4	Semi standard non polar	33892256
Acrylamide,2TBDMS,isomer #1	C=CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1526.3	Standard non polar	33892256
Acrylamide,2TBDMS,isomer #1	C=CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1430.3	Standard polar	33892256