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Showing metabocard for 2-Ethylacrylic acid (HMDB0001862)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-02-23 10:17:33 UTC
Update Date2023-02-21 17:15:51 UTC
HMDB IDHMDB0001862
Secondary Accession Numbers
  • HMDB01862
Metabolite Identification
Common Name2-Ethylacrylic acid
Description2-ethylacrylic acid is an alpha, beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by an ethyl group. It has a role as a mammalian metabolite. It derives from an acrylic acid. It is a conjugate acid of a 2-ethylacrylate. 2-Ethylacrylic acid is an intermediate metabolite in the conversion of R-2-methylbutyrate into 2-ethylhydracrylic acid, which is variably increased in defects of isoleucine oxidation at distal steps in the catabolic pathway (3-oxoacyl-CoA thiolase deficiency and methylmalonyl-CoA mutase deficiency) (PMID 1016232 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001862 (2-Ethylacrylic acid)

  Mrv1652305261923532D          

  7  6  0  0  0  0            999 V2000
   18.9586   -4.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2441   -2.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8152   -3.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1007   -4.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2441   -3.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5297   -4.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5297   -4.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
M  END
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3D MOL for HMDB0001862 (2-Ethylacrylic acid)

HMDB0001862
     RDKit          3D
2-Ethylacrylic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.0065    0.8302   -1.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083    0.1988   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.5034    0.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8201   -0.3350    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529    0.2080   -0.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6773    0.8080   -0.9353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4550   -0.4743    0.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6629    1.3393   -2.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527    0.8409   -1.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281   -1.5707    0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -0.0569    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762    0.7428    0.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598   -0.8486    0.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9855   -0.7984   -0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9340   -0.3806    1.8378 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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3D SDF for HMDB0001862 (2-Ethylacrylic acid)

  Mrv1652305261923532D          

  7  6  0  0  0  0            999 V2000
   18.9586   -4.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2441   -2.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8152   -3.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1007   -4.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2441   -3.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5297   -4.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5297   -4.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001862

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h2-3H2,1H3,(H,6,7)

> <INCHI_KEY>
WROUWQQRXUBECT-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.25903180397131

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylidenebutanoic acid

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
1.3730664469999998

> <ALOGPS_LOGS>
-0.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9732676188186895

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
26.2495

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.26e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethacrylic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0001862 (2-Ethylacrylic acid)

HMDB0001862
     RDKit          3D
2-Ethylacrylic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.0065    0.8302   -1.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083    0.1988   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.5034    0.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8201   -0.3350    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529    0.2080   -0.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6773    0.8080   -0.9353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4550   -0.4743    0.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6629    1.3393   -2.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527    0.8409   -1.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281   -1.5707    0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -0.0569    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762    0.7428    0.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598   -0.8486    0.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9855   -0.7984   -0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9340   -0.3806    1.8378 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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PDB for HMDB0001862 (2-Ethylacrylic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      35.389  -7.777   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      34.056  -5.467   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      31.388  -7.007   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.055  -7.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      34.056  -7.007   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.722  -7.777   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.722  -9.317   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    4    6                                                       
CONECT    4    3                                                            
CONECT    5    1    2    6                                                  
CONECT    6    3    5    7                                                  
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0001862 (2-Ethylacrylic acid)

COMPND    HMDB0001862
HETATM    1  C1  UNL     1      -0.006   0.830  -1.349  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.508   0.199  -0.321  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.395  -0.503   0.613  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.820  -0.335   0.156  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.953   0.208  -0.130  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.677   0.808  -0.935  1.00  0.00           O  
HETATM    7  O2  UNL     1      -2.455  -0.474   0.975  1.00  0.00           O  
HETATM    8  H1  UNL     1      -0.663   1.339  -2.027  1.00  0.00           H  
HETATM    9  H2  UNL     1       1.053   0.841  -1.516  1.00  0.00           H  
HETATM   10  H3  UNL     1       0.128  -1.571   0.744  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.280  -0.057   1.646  1.00  0.00           H  
HETATM   12  H5  UNL     1       2.076   0.743   0.214  1.00  0.00           H  
HETATM   13  H6  UNL     1       2.460  -0.849   0.909  1.00  0.00           H  
HETATM   14  H7  UNL     1       1.986  -0.798  -0.817  1.00  0.00           H  
HETATM   15  H8  UNL     1      -1.934  -0.381   1.838  1.00  0.00           H  
CONECT    1    2    2    8    9
CONECT    2    3    5
CONECT    3    4   10   11
CONECT    4   12   13   14
CONECT    5    6    6    7
CONECT    7   15
END
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SMILES for HMDB0001862 (2-Ethylacrylic acid)

CCC(=C)C(O)=O
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INCHI for HMDB0001862 (2-Ethylacrylic acid)

InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h2-3H2,1H3,(H,6,7)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name2-methylidenebutanoic acid
Traditional Nameethacrylic acid
CAS Registry Number3586-58-1
SMILES
CCC(=C)C(O)=O
InChI Identifier
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h2-3H2,1H3,(H,6,7)
InChI KeyWROUWQQRXUBECT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentBranched fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB022716
KNApSAcK IDNot Available
Chemspider ID18085
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID4141
PubChem Compound19166
PDB IDNot Available
ChEBI ID84978
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceWang, Yan-jun; Wang, Yu-xia; Tang, Xiang-yang; Zhao, Wen-tao; Qi, Xin. Synthesis and characterization of 2-ethylacrylic acid. Shiyou Huagong (2003), 32(3), 251-253.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mamer OA, Tjoa SS, Scriver CR, Klassen GA: Demonstration of a new mammalian isoleucine catabolic pathway yielding an Rseries of metabolites. Biochem J. 1976 Dec 15;160(3):417-26. [PubMed:1016232 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-Ethylacrylic acid → 3,4,5-trihydroxy-6-[(2-methylidenebutanoyl)oxy]oxane-2-carboxylic aciddetails