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Showing NP-Card for Methyl methacrylate (NP0338553)

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Record Information
Version2.0
Created at2024-09-11 16:00:58 UTC
Updated at2024-09-11 16:00:59 UTC
NP-MRD IDNP0338553
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl methacrylate
DescriptionMethyl methacrylate, also known as MMA or methylmethacrylic acid, belongs to the class of organic compounds known as enoate esters. These are an alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position. An enoate ester compound having methacrylic acid as the carboxylic acid component and methanol as the alcohol component. Methyl methacrylate is an extremely weak basic (essentially neutral) compound (based on its pKa). Methyl methacrylate is an acrylic, aromatic, and fruity tasting compound. Outside of the human body, Methyl methacrylate has been detected, but not quantified in, evergreen blackberries. Methyl methacrylate was first documented in 1999 (PMID: 10444249). This could make methyl methacrylate a potential biomarker for the consumption of these foods (PMID: 16020090) (PMID: 22566411) (PMID: 23242048) (PMID: 23306624) (PMID: 23342990) (PMID: 23432523).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0338553 (Methyl methacrylate)


  Mrv0541 05061306292D          

  7  6  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    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
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
M  END
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3D MOL for NP0338553 (Methyl methacrylate)

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3D SDF for NP0338553 (Methyl methacrylate)

  Mrv0541 05061306292D          

  7  6  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    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
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338553

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3

> <INCHI_KEY>
VVQNEPGJFQJSBK-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
10.474545823728604

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-methylprop-2-enoate

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
1.3077251713333333

> <ALOGPS_LOGS>
-0.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.824750057242007

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
26.417600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl methacrylate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0338553 (Methyl methacrylate)
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PDB for NP0338553 (Methyl methacrylate)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   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       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    7                                                            
CONECT    4    1    2    5                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    3    5                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0338553 (Methyl methacrylate)
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SMILES for NP0338553 (Methyl methacrylate)
COC(=O)C(C)=C
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INCHI for NP0338553 (Methyl methacrylate)
InChI=1S/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3
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View in JSmol
Synonyms
ValueSource
2-(Methoxycarbonyl)-1-propeneChEBI
2-Methyl-2-propenoic acid methyl esterChEBI
2-Methylacrylic acid methyl esterChEBI
Methacrylate de methyleChEBI
Methacrylic acid methyl esterChEBI
Methacrylsaeuremethyl esterChEBI
Methyl 2-methyl-2-propenoateChEBI
Methyl 2-methylacrylateChEBI
Methyl 2-methylpropenoateChEBI
Methyl alpha-methylacrylateChEBI
Methyl methylacrylateChEBI
Methyl-methacrylatChEBI
MethylmethacrylateChEBI
MMAChEBI
2-Methyl-2-propenoate methyl esterGenerator
2-Methylacrylate methyl esterGenerator
Methacrylic acid de methyleGenerator
Methacrylate methyl esterGenerator
Methyl 2-methyl-2-propenoic acidGenerator
Methyl 2-methylacrylic acidGenerator
Methyl 2-methylpropenoic acidGenerator
Methyl a-methylacrylateGenerator
Methyl a-methylacrylic acidGenerator
Methyl alpha-methylacrylic acidGenerator
Methyl α-methylacrylateGenerator
Methyl α-methylacrylic acidGenerator
Methyl methylacrylic acidGenerator
Methylmethacrylic acidGenerator
Methyl methacrylic acidGenerator
Polymethyl methacrylic acidHMDB
2-Methyl-acrylic acid methyl esterHMDB
2-Propenoic acid, 2-methyl-, methyl esterHMDB
Acrylic acid, 2-methyl-, methyl esterHMDB
Methyl ester OF 2-methyl-2-propenoic acidHMDB
MetaplicesMeSH
Methyl monomer, methacrylateMeSH
SintexMeSH
Zimmer bone cementsMeSH
Bone cements, zimmerMeSH
Cement, zimmer boneMeSH
Cements, zimmer boneMeSH
CranioplastsMeSH
Kallocryl aMeSH
Methacrylate methyl monomersMeSH
Methylmethacrylate methyl monomerMeSH
Monomer, methacrylate methylMeSH
Monomers, methylmethacrylate methylMeSH
CranioplastMeSH
MetaplexMeSH
Monomer, methylmethacrylate methylMeSH
Monomers, methacrylate methylMeSH
Simplex pMeSH
Bone cement, zimmerMeSH
KallocrylMeSH
KallocrylsMeSH
Methacrylate methyl monomerMeSH
Methyl monomer, methylmethacrylateMeSH
Methyl monomers, methacrylateMeSH
Methyl monomers, methylmethacrylateMeSH
Methylmethacrylate methyl monomersMeSH
SinticesMeSH
Zimmer bone cementMeSH
Chemical FormulaC5H8O2
Average Mass100.1158 Da
Monoisotopic Mass100.05243 Da
IUPAC Namemethyl 2-methylprop-2-enoate
Traditional Namemethyl methacrylate
CAS Registry NumberNot Available
SMILES
COC(=O)C(C)=C
InChI Identifier
InChI=1S/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3
InChI KeyVVQNEPGJFQJSBK-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as enoate esters. These are an alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassCarboxylic acid derivatives  
Direct ParentEnoate esters  
Alternative Parents
Substituents
  • Enoate ester
    • 

  • Methyl 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
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
logP1.1ALOGPS
logP1.31ChemAxon
logS-0.3ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.42 m³·mol⁻¹ChemAxon
Polarizability10.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032385  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB009805  
KNApSAcK IDNot Available
Chemspider ID6406  
KEGG Compound IDC19504  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl_methacrylate  
METLIN IDNot Available
PubChem Compound6658  
PDB IDNot Available
ChEBI ID34840  
Good Scents IDNot Available
References
General References
  1. Rustemeyer T, De Ligter S, Von Blomberg BM, Frosch PJ, Scheper RJ: Human T lymphocyte priming in vitro by haptenated autologous dendritic cells. Clin Exp Immunol. 1999 Aug;117(2):209-16. doi: 10.1046/j.1365-2249.1999.00958.x. [PubMed:10444249  ] 
  2. Hagberg S, Ljungkvist G, Andreasson H, Karlsson S, Barregard L: Exposure to volatile methacrylates in dental personnel. J Occup Environ Hyg. 2005 Jun;2(6):302-6. doi: 10.1080/15459620590958732. [PubMed:16020090  ] 
  3. Grifka RG, Tapio J, Lee KJ: Transcatheter retrieval of an embolized methylmethacrylate glue fragment adherent to the right atrium using bidirectional snares. Catheter Cardiovasc Interv. 2013 Mar;81(4):648-50. doi: 10.1002/ccd.24333. Epub  2012 May 4. [PubMed:22566411  ] 
  4. Agrawal G, Wright CL, Rhodes NG, Sharma A: Mismatched perfusion defects secondary to recent methyl methacrylate embolization. Clin Nucl Med. 2013 Jan;38(1):50-2. doi: 10.1097/RLU.0b013e3182708548. [PubMed:23242048  ] 
  5. Araujo AM, Alves GR, Avanco GT, Parizi JL, Nai GA: Assessment of methyl methacrylate genotoxicity by the micronucleus test. Braz Oral Res. 2013 Jan-Feb;27(1):31-6. doi: 10.1590/s1806-83242013000100006. [PubMed:23306624  ] 
  6. Domingo LR, Saez JA, Joule JA, Rhyman L, Ramasami P: A DFT study of the [3 + 2] versus [4 + 2] cycloaddition reactions of 1,5,6-trimethylpyrazinium-3-olate with methyl methacrylate. J Org Chem. 2013 Feb 15;78(4):1621-9. doi: 10.1021/jo302730q. Epub 2013 Feb 6. [PubMed:23342990  ] 
  7. Shi Y, Shan G, Shang Y: Role of poly(ethylene glycol) in surfactant-free emulsion polymerization of styrene and methyl methacrylate. Langmuir. 2013 Mar 5;29(9):3024-33. doi: 10.1021/la304847a. Epub 2013 Feb 22. [PubMed:23432523  ] 
  8. Fang J, Tschan MJ, Brule E, Robert C, Thomas CM, Maron L: A joint experimental/theoretical investigation of the MMA polymerization initiated by yttrium phenoxyamine complexes. Dalton Trans. 2013 Jul 7;42(25):9226-32. doi: 10.1039/c3dt00039g. Epub 2013 Mar  1. [PubMed:23450227  ] 
  9. Brisbane C, McCluskey A, Bowyer M, Holdsworth CI: Molecularly imprinted films of acrylonitrile/methyl methacrylate/acrylic acid terpolymers: influence of methyl methacrylate in the binding performance of L-ephedrine imprinted films. Org Biomol Chem. 2013 May 7;11(17):2872-84. doi: 10.1039/c3ob40332g. Epub 2013  Mar 18. [PubMed:23508285  ]