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Showing metabocard for Methacrolein (HMDB0061874)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:56:22 UTC
Update Date2023-02-21 17:30:30 UTC
HMDB IDHMDB0061874
Secondary Accession Numbers
  • HMDB61874
Metabolite Identification
Common NameMethacrolein
DescriptionMethacrolein, also known as methacrylaldehyde, belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position. Methacrolein is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1677000630
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061874 (Methacrolein)


  Mrv1652303202019012D          

  5  4  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
    0.8250    0.0000    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
    0.0000    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
  4  3  1  0  0  0  0
  5  3  2  0  0  0  0
M  END
Download

3D MOL for HMDB0061874 (Methacrolein)

HMDB0061874
     RDKit          3D
Methacrolein
 11 10  0  0  0  0  0  0  0  0999 V2000
    0.0511    1.3678   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1225    0.0761   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1463   -0.7039   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090   -0.5481    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4419    0.1656    0.2481 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9515    1.9529   -0.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738    1.8819   -0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0118   -1.7572    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8712   -0.1974    0.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657   -0.6229   -1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929   -1.6148    0.4021 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
  1  6  1  0
  1  7  1  0
  3  8  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
M  END
Download

3D SDF for HMDB0061874 (Methacrolein)


  Mrv1652303202019012D          

  5  4  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
    0.8250    0.0000    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
    0.0000    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
  4  3  1  0  0  0  0
  5  3  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061874

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3

> <INCHI_KEY>
STNJBCKSHOAVAJ-UHFFFAOYSA-N

> <FORMULA>
C4H6O

> <MOLECULAR_WEIGHT>
70.0898

> <EXACT_MASS>
70.041864814

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
7.484029461521466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylprop-2-enal

> <ALOGPS_LOGP>
0.59

> <JCHEM_LOGP>
0.7698815296666668

> <ALOGPS_LOGS>
-0.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.243159103392516

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
20.723100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methacrolein

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0061874 (Methacrolein)

HMDB0061874
     RDKit          3D
Methacrolein
 11 10  0  0  0  0  0  0  0  0999 V2000
    0.0511    1.3678   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1225    0.0761   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1463   -0.7039   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090   -0.5481    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4419    0.1656    0.2481 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9515    1.9529   -0.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738    1.8819   -0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0118   -1.7572    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8712   -0.1974    0.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657   -0.6229   -1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929   -1.6148    0.4021 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
  1  6  1  0
  1  7  1  0
  3  8  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
M  END
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PDB for HMDB0061874 (Methacrolein)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         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       1.540   0.000   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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    4    5                                                       
CONECT    4    1    2    3                                                  
CONECT    5    3                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0061874 (Methacrolein)

COMPND    HMDB0061874
HETATM    1  C1  UNL     1       0.051   1.368  -0.233  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.122   0.076  -0.027  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.146  -0.704  -0.065  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.409  -0.548   0.229  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.442   0.166   0.248  1.00  0.00           O  
HETATM    6  H1  UNL     1       0.952   1.953  -0.210  1.00  0.00           H  
HETATM    7  H2  UNL     1      -0.874   1.882  -0.427  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.012  -1.757   0.225  1.00  0.00           H  
HETATM    9  H4  UNL     1      -1.871  -0.197   0.612  1.00  0.00           H  
HETATM   10  H5  UNL     1      -1.566  -0.623  -1.108  1.00  0.00           H  
HETATM   11  H6  UNL     1       1.493  -1.615   0.402  1.00  0.00           H  
CONECT    1    2    2    6    7
CONECT    2    3    4
CONECT    3    8    9   10
CONECT    4    5    5   11
END
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SMILES for HMDB0061874 (Methacrolein)

CC(=C)C=O
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INCHI for HMDB0061874 (Methacrolein)

InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-MethylacroleinHMDB
MethacrylaldehydeHMDB
Chemical FormulaC4H6O
Average Molecular Weight70.0898
Monoisotopic Molecular Weight70.041864814
IUPAC Name2-methylprop-2-enal
Traditional Namemethacrolein
CAS Registry NumberNot Available
SMILES
CC(=C)C=O
InChI Identifier
InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3
InChI KeySTNJBCKSHOAVAJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnals
Alternative Parents
Substituents
  • Enal
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological location
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
Water Solubility61.4 g/LALOGPS
logP0.59ALOGPS
logP0.77ChemAxon
logS-0.06ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.72 m³·mol⁻¹ChemAxon
Polarizability7.48 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
DarkChem[M+H]+112.89331661259
DarkChem[M-H]-106.20231661259
DeepCCS[M+H]+119.31330932474
DeepCCS[M-H]-117.41830932474
DeepCCS[M-2H]-152.82330932474
DeepCCS[M+Na]+127.23130932474
AllCCS[M+H]+119.932859911
AllCCS[M+H-H2O]+115.432859911
AllCCS[M+NH4]+124.232859911
AllCCS[M+Na]+125.432859911
AllCCS[M-H]-128.432859911
AllCCS[M+Na-2H]-134.032859911
AllCCS[M+HCOO]-140.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethacroleinCC(=C)C=O852.9Standard polar33892256
MethacroleinCC(=C)C=O532.3Standard non polar33892256
MethacroleinCC(=C)C=O549.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methacrolein GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-e9fce90afc0d563bb7542017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methacrolein GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methacrolein GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 10V, Positive-QTOFsplash10-00di-9000000000-b09f171e7339d27f8a142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 20V, Positive-QTOFsplash10-00di-9000000000-5fec8f83e1aea1a554092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 40V, Positive-QTOFsplash10-0596-9000000000-1aaf49c3682bc4feff102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 10V, Negative-QTOFsplash10-014i-9000000000-66bbd6afc3250c768fa92016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 20V, Negative-QTOFsplash10-014i-9000000000-9de313b3b845cb249c262016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 40V, Negative-QTOFsplash10-0uxr-9000000000-6d875ba145f8c281d4222016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 10V, Negative-QTOFsplash10-014i-9000000000-1fe3e74f4451b5653b932021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 20V, Negative-QTOFsplash10-014i-9000000000-11b89cb85a2481163c362021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 40V, Negative-QTOFsplash10-0gbc-9000000000-bc4b995c8394ef6a29172021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 10V, Positive-QTOFsplash10-00di-9000000000-2c321e49c0a9728673ee2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 20V, Positive-QTOFsplash10-0006-9000000000-7aa8a05bade372ff883d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methacrolein 40V, Positive-QTOFsplash10-0006-9000000000-1104d40a7596119610cf2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethacrolein
METLIN IDNot Available
PubChem Compound6562
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wikipedia [Link]
  2. Masato Kawakami, Naoki Andoh, Akira Iio, 'Process for producing methacrolein.' U.S. Patent US4039583, issued July, 1975. [Link]
  3. James Leacock, 'Recovery of methacrolein.' U.S. Patent US4092132, issued August, 1976. [Link]
  4. Teruhisa Sakamoto, Kazuhiko Sekizawa, Keiichi Kihara, 'Process for producing methacrolein.' U.S. Patent US4250339, issued January, 1980. [Link]
  5. Atsushi Aoshima, Ryoichi Mitsui, Tatsuo Yamaguchi, 'Process for producing methacrolein.' U.S. Patent US4258217, issued May, 1974. [Link]
  6. Wilfrid G. Shaw, Philip L. Kuch, Christos Paparizos, 'Methacrolein oxidation catalysts.' U.S. Patent US4301031, issued August, 1977. [Link]
  7. Shuzo Nakamura, Hiroshi Ichihashi, Yoshihiko Nagaoka, Koichi Nagai, 'Production of methacrolein.' U.S. Patent US4306088, issued May, 1975. [Link]
  8. Atsushi Aoshima, Ryoichi Mitsui, Hitoshi Nihei, 'Method for preparing methacrolein.' U.S. Patent US4354044, issued October, 1961. [Link]
  9. Ikuya Matsuura, 'Method for preparing methacrolein.' U.S. Patent US5138100, issued October, 1968. [Link]