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Showing NP-Card for glycol dimethacrylate (NP0154646)

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Record Information
Version2.0
Created at2022-09-02 11:35:35 UTC
Updated at2022-09-02 11:35:35 UTC
NP-MRD IDNP0154646
Secondary Accession NumbersNone
Natural Product Identification
Common Nameglycol dimethacrylate
DescriptionEthylene glycol dimethacrylate, also known as ethylene dimethacrylic acid or 1,2-ethanediol dimethacrylate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. The enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol. glycol dimethacrylate is found in Bletilla striata. glycol dimethacrylate was first documented in 2001 (PMID: 11714252). Ethylene glycol dimethacrylate is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 19091218) (PMID: 23161346) (PMID: 23180752).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0154646 (glycol dimethacrylate)


  Mrv1572004191604322D          

 14 13  0  0  0  0            999 V2000
    5.8263    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    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
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.0000    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
    4.3974    0.4125    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
    4.3974    1.2375    0.0000 O   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
    3.6829    0.0000    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
  6  5  1  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 13  5  1  0  0  0  0
 13  9  1  0  0  0  0
 14  6  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
Download

3D MOL for NP0154646 (glycol dimethacrylate)

     RDKit          3D

 28 27  0  0  0  0  0  0  0  0999 V2000
   -2.1337   -3.9860    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171   -3.2388   -0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8870   -3.7411   -1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1864   -1.9092   -0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7425   -1.1992   -1.7927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0836   -1.4096   -0.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6408   -0.1002   -0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5382    0.2070    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0767    1.4914    0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1802    1.9389    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    1.1148    1.6348 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632    3.2496    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2649    4.0724   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345    3.6284    1.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2811   -3.5995    0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278   -4.9703    0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757   -4.5806   -0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6241   -2.9298   -1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6219   -4.0477   -2.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4945    0.5762   -0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243   -0.0986   -1.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2056    0.1834    1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981   -0.5920    0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129    3.7952   -0.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973    5.0422   -0.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7911    2.9408    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2732    4.6624    1.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6555    3.4997    2.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 14  1  0
 12 13  2  3
  3 17  1  0
  3 18  1  0
  3 19  1  0
  1 15  1  0
  1 16  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
 14 26  1  0
 14 27  1  0
 14 28  1  0
 13 24  1  0
 13 25  1  0
M  END
Download

3D SDF for NP0154646 (glycol dimethacrylate)


  Mrv1572004191604322D          

 14 13  0  0  0  0            999 V2000
    5.8263    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    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
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.0000    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
    4.3974    0.4125    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
    4.3974    1.2375    0.0000 O   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
    3.6829    0.0000    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
  6  5  1  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 13  5  1  0  0  0  0
 13  9  1  0  0  0  0
 14  6  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C(=O)OCCOC(=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O4/c1-7(2)9(11)13-5-6-14-10(12)8(3)4/h1,3,5-6H2,2,4H3

> <INCHI_KEY>
STVZJERGLQHEKB-UHFFFAOYSA-N

> <FORMULA>
C10H14O4

> <MOLECULAR_WEIGHT>
198.218

> <EXACT_MASS>
198.089208931

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.030024766192174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2-methylprop-2-enoyl)oxy]ethyl 2-methylprop-2-enoate

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
2.443925399333333

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.535811511082419

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
50.86620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycol dimethacrylate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0154646 (glycol dimethacrylate)

Download
PDB for NP0154646 (glycol dimethacrylate)
HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0      10.876   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.542  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.127  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.206   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.542   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.208   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.208   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.875   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.874   0.770   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    8                                                            
CONECT    5    6   13                                                       
CONECT    6    5   14                                                       
CONECT    7    1    2    9                                                  
CONECT    8    3    4   10                                                  
CONECT    9    7   11   13                                                  
CONECT   10    8   12   14                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13    5    9                                                       
CONECT   14    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

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3D PDB for NP0154646 (glycol dimethacrylate)
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SMILES for NP0154646 (glycol dimethacrylate)
CC(=C)C(=O)OCCOC(=O)C(C)=C
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INCHI for NP0154646 (glycol dimethacrylate)
InChI=1S/C10H14O4/c1-7(2)9(11)13-5-6-14-10(12)8(3)4/h1,3,5-6H2,2,4H3
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View in JSmol
Synonyms
ValueSource
1,2-Bis(methacryloyloxy)ethaneChEBI
1,2-Ethanediol dimethacrylateChEBI
1,2-Ethanediyl 2-methyl-2-propenoateChEBI
2-(Methacryloyloxy)ethyl 2-methylacrylateChEBI
2-Methyl-2-propenoic acid 1,2-ethanediyl esterChEBI
Diglycol dimethacrylateChEBI
EGDMAChEBI
Ethanediol dimethacrylateChEBI
Ethyldiol metacrylateChEBI
Ethyldiol methacrylateChEBI
Ethylene dimethacrylateChEBI
Ethylene glycol bis(methacrylate)ChEBI
Ethylene methacrylateChEBI
EthylenedimethyacrylateChEBI
Glycol dimethacrylateChEBI
Methacrylic acid ethylene esterChEBI
1,2-Ethanediol dimethacrylic acidGenerator
1,2-Ethanediyl 2-methyl-2-propenoic acidGenerator
2-(Methacryloyloxy)ethyl 2-methylacrylic acidGenerator
2-Methyl-2-propenoate 1,2-ethanediyl esterGenerator
Diglycol dimethacrylic acidGenerator
Ethanediol dimethacrylic acidGenerator
Ethyldiol metacrylic acidGenerator
Ethyldiol methacrylic acidGenerator
Ethylene dimethacrylic acidGenerator
Ethylene glycol bis(methacrylic acid)Generator
Ethylene methacrylic acidGenerator
Ethylenedimethyacrylic acidGenerator
Glycol dimethacrylic acidGenerator
Methacrylate ethylene esterGenerator
Ethylene glycol dimethacrylic acidGenerator
2-(2-Methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoic acidGenerator
EGDMA CPDMeSH
Ethylene glycol dimethacrylateMeSH
Ethyleneglycol dimethacrylateMeSH
Chemical FormulaC10H14O4
Average Mass198.2180 Da
Monoisotopic Mass198.08921 Da
IUPAC Name2-[(2-methylprop-2-enoyl)oxy]ethyl 2-methylprop-2-enoate
Traditional Nameglycol dimethacrylate
CAS Registry NumberNot Available
SMILES
CC(=C)C(=O)OCCOC(=O)C(C)=C
InChI Identifier
InChI=1S/C10H14O4/c1-7(2)9(11)13-5-6-14-10(12)8(3)4/h1,3,5-6H2,2,4H3
InChI KeySTVZJERGLQHEKB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Bletilla striataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassDicarboxylic acids and derivatives  
Direct ParentDicarboxylic acids and derivatives  
Alternative Parents
Substituents
  • Dicarboxylic acid or derivatives
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.74ALOGPS
logP2.44ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity50.87 m³·mol⁻¹ChemAxon
Polarizability21.03 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthylene_glycol_dimethacrylate  
METLIN IDNot Available
PubChem Compound7355  
PDB IDNot Available
ChEBI ID53436  
Good Scents IDNot Available
References
General References
  1. Rustemeyer T, de Groot J, von Blomberg BM, Frosch PJ, Scheper RJ: Induction of tolerance and cross-tolerance to methacrylate contact sensitizers. Toxicol Appl Pharmacol. 2001 Nov 1;176(3):195-202. doi: 10.1006/taap.2001.9266. [PubMed:11714252  ] 
  2. Roche E, de la Cuadra J, Alegre V: [Sensitization to acrylates caused by artificial acrylic nails: review of 15 cases]. Actas Dermosifiliogr. 2008 Dec;99(10):788-94. [PubMed:19091218  ] 
  3. Golgelioglu C, Tuncel A: Butyl methacrylate based monoliths with different cross-linking agents using DMF-aqueous buffer as porogen. Electrophoresis. 2013 Jan;34(2):331-42. doi: 10.1002/elps.201200029. Epub 2012  Dec 13. [PubMed:23161346  ] 
  4. Liu Z, Peng Y, Wang T, Yuan G, Zhang Q, Guo J, Jiang Z: Preparation and application of novel zwitterionic monolithic column for hydrophilic interaction chromatography. J Sep Sci. 2013 Jan;36(2):262-9. doi: 10.1002/jssc.201200682. Epub 2012 Nov 26. [PubMed:23180752  ] 
  5. LOTUS database [Link]