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Showing NP-Card for 2-Ethylacrylic acid (NP0001347)

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Record Information
Version2.0
Created at2006-02-23 10:17:33 UTC
Updated at2021-06-29 00:47:14 UTC
NP-MRD IDNP0001347
Secondary Accession NumbersNone
Natural Product 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 NP0001347 (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 NP0001347 (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
Download

3D SDF for NP0001347 (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>
NP0001347

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0001347 (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 NP0001347 (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 NP0001347 (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 NP0001347 (2-Ethylacrylic acid)

CCC(=C)C(O)=O
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INCHI for NP0001347 (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 JSmol
Synonyms
ValueSource
2-Ethyl-2-propenoic acidChEBI
2-Ethylpropenoic acidChEBI
alpha-Methylene-butanoic acidChEBI
2-Ethyl-2-propenoateGenerator
2-EthylpropenoateGenerator
a-Methylene-butanoateGenerator
a-Methylene-butanoic acidGenerator
alpha-Methylene-butanoateGenerator
Α-methylene-butanoateGenerator
Α-methylene-butanoic acidGenerator
2-EthylacrylateGenerator
2-Methylene-6ci,7ci,8ci)-butyrateHMDB
2-Methylene-6ci,7ci,8ci)-butyric acidHMDB
2-MethylenebutyrateHMDB
2-Methylenebutyric acidHMDB
EthacrylateHMDB
Ethacrylic acidHMDB
Poly(2-ethylacrylic acid)HMDB
2-Ethyl acrylateHMDB
Chemical FormulaC5H8O2
Average Mass100.1158 Da
Monoisotopic Mass100.05243 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility62.6 g/LALOGPS
logP1.23ALOGPS
logP1.37ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.25 m³·mol⁻¹ChemAxon
Polarizability10.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001862
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  2. Zhu Z, Shi L, Huang J: Synthesis of poly(maleimide-co-2-ethylacrylic acid) and its properties of suppressing metastasis and growth of carcinoma. Bioorg Med Chem Lett. 2002 Oct 21;12(20):2843-6. doi: 10.1016/s0960-894x(02)00626-1. [PubMed:12270159 ]
  3. Attygalle AB, Wu X, Ruzicka J, Rao S, Garcia S, Herath K, Meinwald J, Maddison DR, Will KW: Defensive chemicals of two species of Trachypachus Motschulski. J Chem Ecol. 2004 Mar;30(3):577-88. doi: 10.1023/b:joec.0000018630.79922.94. [PubMed:15139309 ]
  4. Lu Y, Wu Y, Liang J, Libera MR, Sukhishvili SA: Self-defensive antibacterial layer-by-layer hydrogel coatings with pH-triggered hydrophobicity. Biomaterials. 2015 Mar;45:64-71. doi: 10.1016/j.biomaterials.2014.12.048. Epub 2015 Jan 14. [PubMed:25662496 ]
  5. Lu Y, Sarshar MA, Du K, Chou T, Choi CH, Sukhishvili SA: Large-amplitude, reversible, pH-triggered wetting transitions enabled by layer-by-layer films. ACS Appl Mater Interfaces. 2013 Dec 11;5(23):12617-23. doi: 10.1021/am403944m. Epub 2013 Nov 19. [PubMed:24191775 ]