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Showing metabocard for Methacrylic Acid (HMDB0254514)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 13:51:02 UTC
Update Date2022-11-23 22:29:16 UTC
HMDB IDHMDB0254514
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethacrylic Acid
DescriptionMethacrylic acid, also known as a-methacrylate or methakrylsaeure, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Methacrylic acid has been detected, but not quantified in, asparagus (Asparagus officinalis) and roman camomiles (Chamaemelum nobile). This could make methacrylic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Methacrylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Methacrylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Methacrylic Acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0254514 (Methacrylic Acid)


  Mrv1652307301920082D          

  6  5  0  0  0  0            999 V2000
    0.8250    1.4289    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
    2.0625    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
M  END
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3D MOL for HMDB0254514 (Methacrylic Acid)

HMDB0254514
     RDKit          3D
METHACRYLIC ACID
 12 11  0  0  0  0  0  0  0  0999 V2000
   -0.3048   -1.5370    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0679   -0.3393    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662    0.3628    0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036    0.2984   -0.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0540   -0.3062   -1.1680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327    1.5644   -1.3233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1860   -2.1243    0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099   -1.9945    1.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9491    1.4565    0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6049    0.0075    1.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8655    0.3016   -0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466    2.3101   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
  6 12  1  0
M  END
Download

3D SDF for HMDB0254514 (Methacrylic Acid)


  Mrv1652307301920082D          

  6  5  0  0  0  0            999 V2000
    0.8250    1.4289    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
    2.0625    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254514

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)

> <INCHI_KEY>
CERQOIWHTDAKMF-UHFFFAOYSA-N

> <FORMULA>
C4H6O2

> <MOLECULAR_WEIGHT>
86.0892

> <EXACT_MASS>
86.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.37848673508563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylprop-2-enoic acid

> <JCHEM_LOGP>
0.9284977819999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.850525670894635

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
21.6485

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methacrylic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0254514 (Methacrylic Acid)

HMDB0254514
     RDKit          3D
METHACRYLIC ACID
 12 11  0  0  0  0  0  0  0  0999 V2000
   -0.3048   -1.5370    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0679   -0.3393    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662    0.3628    0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036    0.2984   -0.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0540   -0.3062   -1.1680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327    1.5644   -1.3233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1860   -2.1243    0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099   -1.9945    1.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9491    1.4565    0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6049    0.0075    1.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8655    0.3016   -0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466    2.3101   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
  6 12  1  0
M  END
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PDB for HMDB0254514 (Methacrylic Acid)

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0254514 (Methacrylic Acid)

COMPND    HMDB0254514
HETATM    1  C1  UNL     1      -0.305  -1.537   0.511  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.068  -0.339   0.044  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.166   0.363   0.430  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.004   0.298  -0.843  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.054  -0.306  -1.168  1.00  0.00           O  
HETATM    6  O2  UNL     1      -0.733   1.564  -1.323  1.00  0.00           O  
HETATM    7  H1  UNL     1      -1.186  -2.124   0.279  1.00  0.00           H  
HETATM    8  H2  UNL     1       0.410  -1.994   1.173  1.00  0.00           H  
HETATM    9  H3  UNL     1       0.949   1.456   0.589  1.00  0.00           H  
HETATM   10  H4  UNL     1       1.605   0.008   1.380  1.00  0.00           H  
HETATM   11  H5  UNL     1       1.866   0.302  -0.429  1.00  0.00           H  
HETATM   12  H6  UNL     1      -0.647   2.310  -0.644  1.00  0.00           H  
CONECT    1    2    2    7    8
CONECT    2    3    4
CONECT    3    9   10   11
CONECT    4    5    5    6
CONECT    6   12
END
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SMILES for HMDB0254514 (Methacrylic Acid)

CC(=C)C(O)=O
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INCHI for HMDB0254514 (Methacrylic Acid)

InChI=1S/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Methyl-2-propenoic acidChEBI
2-Methylacrylic acidChEBI
2-Methylenepropionic acidChEBI
2-Methylpropenoic acidChEBI
2-MethylpropensaeureChEBI
alpha-Methacrylic acidChEBI
alpha-Methylacrylic acidChEBI
MethacrylsaeureChEBI
MethakrylsaeureChEBI
Methylacrylic acidChEBI
2-Methyl-2-propenoateGenerator
2-MethylacrylateGenerator
2-MethylenepropionateGenerator
2-MethylpropenoateGenerator
a-MethacrylateGenerator
a-Methacrylic acidGenerator
alpha-MethacrylateGenerator
Α-methacrylateGenerator
Α-methacrylic acidGenerator
a-MethylacrylateGenerator
a-Methylacrylic acidGenerator
alpha-MethylacrylateGenerator
Α-methylacrylateGenerator
Α-methylacrylic acidGenerator
MethylacrylateGenerator
MethacrylateGenerator
Methacrylic acid, calcium saltMeSH
Methacrylic acid, sodium saltMeSH
Sodium methacrylateMeSH
Chemical FormulaC4H6O2
Average Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
IUPAC Name2-methylprop-2-enoic acid
Traditional Namemethacrylic acid
CAS Registry NumberNot Available
SMILES
CC(=C)C(O)=O
InChI Identifier
InChI=1S/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)
InChI KeyCERQOIWHTDAKMF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
PropertyValueSource
logP0.93ChemAxon
pKa (Strongest Acidic)4.85ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.65 m³·mol⁻¹ChemAxon
Polarizability8.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+122.91330932474
DeepCCS[M-H]-120.11630932474
DeepCCS[M-2H]-156.51530932474
DeepCCS[M+Na]+131.07830932474
AllCCS[M+H]+123.832859911
AllCCS[M+H-H2O]+119.432859911
AllCCS[M+NH4]+127.932859911
AllCCS[M+Na]+129.132859911
AllCCS[M-H]-122.732859911
AllCCS[M+Na-2H]-127.432859911
AllCCS[M+HCOO]-132.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
METHACRYLIC ACIDCC(=C)C(O)=O1626.2Standard polar33892256
METHACRYLIC ACIDCC(=C)C(O)=O807.7Standard non polar33892256
METHACRYLIC ACIDCC(=C)C(O)=O755.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methacrylic Acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9000000000-bb999734fb45747805482021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methacrylic Acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methacrylic Acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methacrylic Acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 10V, Positive-QTOFsplash10-000i-9000000000-8a46621356d93992cdbc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 20V, Positive-QTOFsplash10-0006-9000000000-7b7840a0b379a88fe1dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 40V, Positive-QTOFsplash10-0006-9000000000-2fa3803e852c3f25b9482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 10V, Negative-QTOFsplash10-000i-9000000000-df06ae42b782163427332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 20V, Negative-QTOFsplash10-000i-9000000000-230b98717ec1d62e4c272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 40V, Negative-QTOFsplash10-000i-9000000000-e2e678221355c25dfd2c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 10V, Positive-QTOFsplash10-014l-9000000000-d7a0f8aaffc6486780a02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 20V, Positive-QTOFsplash10-0006-9000000000-607ef0ce2be3ee0741d42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 40V, Positive-QTOFsplash10-0006-9000000000-b2ae96797452a018841f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 10V, Negative-QTOFsplash10-000i-9000000000-ec20127c74818b1f634d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 20V, Negative-QTOFsplash10-000i-9000000000-203e124061735c8fb3782021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrylic Acid 40V, Negative-QTOFsplash10-0006-9000000000-e9422df076c0e9b5154e2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004841
KNApSAcK IDNot Available
Chemspider ID3951
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethacrylic_acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID25219
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1257421
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]