Showing metabocard for Acrylamide (MMDBc0049927)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 22:46:27 UTC
Update Date2022-09-01 02:17:25 UTC
Metabolite IDMMDBc0049927
Metabolite Identification
Common NameAcrylamide
DescriptionAcrylamide (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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fe2a919d7f8>


  Mrv1652305271900012D          

  5  4  0  0  0  0            999 V2000
    0.2847    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4290    0.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847   -0.8275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0021    0.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1426    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fe2a919d7f8>

HMDB0004296
     RDKit          3D
Acrylamide
 10  9  0  0  0  0  0  0  0  0999 V2000
    1.7952    0.1086   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160    0.3349    0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641   -0.3326   -0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8613   -0.0950    0.2880 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880   -1.1238   -1.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6611    0.6043    0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.5721   -1.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4850    1.0245    1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -0.7668    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0230    0.8181    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  2  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  4  9  1  0
  4 10  1  0
M  END
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3D SDF for #<Metabolite:0x00007fe2a919d7f8>


  Mrv1652305271900012D          

  5  4  0  0  0  0            999 V2000
    0.2847    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4290    0.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847   -0.8275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0021    0.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1426    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049927

> <DATABASE_NAME>
MIME

> <SMILES>
NC(=O)C=C

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

> <INCHI_KEY>
HRPVXLWXLXDGHG-UHFFFAOYSA-N

> <FORMULA>
C3H5NO

> <MOLECULAR_WEIGHT>
71.0779

> <EXACT_MASS>
71.037113787

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
6.8797619223654936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
prop-2-enamide

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.273995321

> <ALOGPS_LOGS>
0.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.699757208503446

> <JCHEM_PKA_STRONGEST_BASIC>
0.0025770974210549413

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
19.113599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acrylamide

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fe2a919d7f8>

HMDB0004296
     RDKit          3D
Acrylamide
 10  9  0  0  0  0  0  0  0  0999 V2000
    1.7952    0.1086   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160    0.3349    0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641   -0.3326   -0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8613   -0.0950    0.2880 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880   -1.1238   -1.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6611    0.6043    0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.5721   -1.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4850    1.0245    1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -0.7668    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0230    0.8181    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  2  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  4  9  1  0
  4 10  1  0
M  END
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PDB for #<Metabolite:0x00007fe2a919d7f8>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       0.531   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.801   0.772   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.531  -1.545   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0       1.871   0.772   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.133   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for #<Metabolite:0x00007fe2a919d7f8>

COMPND    HMDB0004296
HETATM    1  C1  UNL     1       1.795   0.109  -0.249  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.616   0.335   0.264  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.564  -0.333  -0.262  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.861  -0.095   0.288  1.00  0.00           N  
HETATM    5  O1  UNL     1      -0.388  -1.124  -1.219  1.00  0.00           O  
HETATM    6  H1  UNL     1       2.661   0.604   0.144  1.00  0.00           H  
HETATM    7  H2  UNL     1       1.923  -0.572  -1.067  1.00  0.00           H  
HETATM    8  H3  UNL     1       0.485   1.025   1.093  1.00  0.00           H  
HETATM    9  H4  UNL     1      -2.644  -0.767   0.246  1.00  0.00           H  
HETATM   10  H5  UNL     1      -2.023   0.818   0.762  1.00  0.00           H  
CONECT    1    2    2    6    7
CONECT    2    3    8
CONECT    3    4    5    5
CONECT    4    9   10
END
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SMILES for #<Metabolite:0x00007fe2a919d7f8>

NC(=O)C=C
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INCHI for #<Metabolite:0x00007fe2a919d7f8>

InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
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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
Prop-2-enamideHMDB
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
Molecular FormulaC3H5NO
Average Mass71.0779
Monoisotopic Mass71.037113787
IUPAC Nameprop-2-enamide
Traditional Nameacrylamide
CAS Registry NumberNot Available
SMILES
NC(=O)C=C
InChI Identifier
InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
InChI KeyHRPVXLWXLXDGHG-UHFFFAOYSA-N