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Showing metabocard for Ethyl acrylate (HMDB0033978)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:45:10 UTC
Update Date2023-02-21 17:23:51 UTC
HMDB IDHMDB0033978
Secondary Accession Numbers
  • HMDB33978
Metabolite Identification
Common NameEthyl acrylate
DescriptionEthyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. Ethyl acrylate is found in pineapple. Ethyl acrylate is a flavouring ingredient Although there are some reports claiming that ethyl acrylate is a carcinogen, major respected bodies regard the evidence of human carcinogenicity as weak and/or inconsistent. The International Agency for Research on Cancer stated, "Overall evaluation, Ethyl acrylate is possibly carcinogenic to humans (Group 2B)." The United States Environmental Protection Agency (EPA) states, "Human studies on occupational exposure to ethyl acrylate have suggested a relationship between exposure to the chemical(s) and colorectal cancer, but the evidence is conflicting and inconclusive. In a study by the National Toxicology Program (NTP), increased incidences of squamous cell papillomas and carcinomas of the forestomach were observed in rats and mice exposed via gavage (experimentally placing the chemical in the stomach). However, the NTP recently determined that these data were not relevant to human carcinogenicity and removed ethyl acrylate from its list of carcinogens." (Occupational exposure generally involves exposure that occurs regularly, over an extended period of time). Ethyl acrylate is an organic compound primarily used in the preparation of various polymers. It is a clear liquid with an acrid penetrating odor. The human nose is capable of detecting this odor at a thousand times lower concentration then is considered harmful if continuously exposed for some period of time.
Structure
Data?1677000231
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033978 (Ethyl acrylate)

  Mrv1652305271900112D          

  7  6  0  0  0  0            999 V2000
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
M  END
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3D MOL for HMDB0033978 (Ethyl acrylate)

HMDB0033978
     RDKit          3D
Ethyl acrylate
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.5796    0.6990   -0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2596   -0.5672    0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8908   -1.0479    0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772   -2.2440    0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1228   -0.1173    0.0997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979   -0.4313    0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2724    0.8642   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769    1.0751   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768    1.4427   -0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0620   -1.2784    0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7135   -1.1361   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.9621    1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0331    0.7970   -0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7093    1.2065    0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    1.6999   -0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  6 11  1  0
  6 12  1  0
  7 13  1  0
  7 14  1  0
  7 15  1  0
M  END
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3D SDF for HMDB0033978 (Ethyl acrylate)

  Mrv1652305271900112D          

  7  6  0  0  0  0            999 V2000
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033978

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3

> <INCHI_KEY>
JIGUQPWFLRLWPJ-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.496640224298261

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl prop-2-enoate

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
1.2689826366666663

> <ALOGPS_LOGS>
-0.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.779735120466316

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
26.8091

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.88e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl acrylate

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0033978 (Ethyl acrylate)

HMDB0033978
     RDKit          3D
Ethyl acrylate
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.5796    0.6990   -0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2596   -0.5672    0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8908   -1.0479    0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772   -2.2440    0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1228   -0.1173    0.0997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979   -0.4313    0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2724    0.8642   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769    1.0751   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768    1.4427   -0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0620   -1.2784    0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7135   -1.1361   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.9621    1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0331    0.7970   -0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7093    1.2065    0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    1.6999   -0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  6 11  1  0
  6 12  1  0
  7 13  1  0
  7 14  1  0
  7 15  1  0
M  END
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PDB for HMDB0033978 (Ethyl acrylate)

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      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.874   0.770   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    4    5                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0033978 (Ethyl acrylate)

COMPND    HMDB0033978
HETATM    1  C1  UNL     1       2.580   0.699  -0.006  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.260  -0.567   0.154  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.891  -1.048   0.216  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.577  -2.244   0.367  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.123  -0.117   0.100  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.498  -0.431   0.141  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.272   0.864  -0.022  1.00  0.00           C  
HETATM    8  H1  UNL     1       3.577   1.075  -0.055  1.00  0.00           H  
HETATM    9  H2  UNL     1       1.777   1.443  -0.099  1.00  0.00           H  
HETATM   10  H3  UNL     1       3.062  -1.278   0.243  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.714  -1.136  -0.699  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.786  -0.962   1.083  1.00  0.00           H  
HETATM   13  H6  UNL     1      -3.033   0.797  -0.830  1.00  0.00           H  
HETATM   14  H7  UNL     1      -2.709   1.206   0.947  1.00  0.00           H  
HETATM   15  H8  UNL     1      -1.588   1.700  -0.338  1.00  0.00           H  
CONECT    1    2    2    8    9
CONECT    2    3   10
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   11   12
CONECT    7   13   14   15
END
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SMILES for HMDB0033978 (Ethyl acrylate)

CCOC(=O)C=C
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INCHI for HMDB0033978 (Ethyl acrylate)

InChI=1S/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Nameethyl prop-2-enoate
Traditional Nameethyl acrylate
CAS Registry Number140-88-5
SMILES
CCOC(=O)C=C
InChI Identifier
InChI=1S/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3
InChI KeyJIGUQPWFLRLWPJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acrylic acid esters. These are organic compounds containing and ester acrylic acid (CH2=CHC(=O)OH).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAcrylic acids and derivatives
Direct ParentAcrylic acid esters
Alternative Parents
Substituents
  • Acrylic acid ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Environmental roleIndustrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-71.2 °CNot Available
Boiling Point99.00 to 100.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility15 mg/mL at 25 °CNot Available
LogP1.32Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012210
KNApSAcK IDNot Available
Chemspider ID8490
KEGG Compound IDC19238
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl acrylate
METLIN IDNot Available
PubChem Compound8821
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008231
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .