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Showing NP-Card for Methacrolein (NP0045156)

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Record Information
Version2.0
Created at2022-03-10 18:58:55 UTC
Updated at2022-03-10 22:21:39 UTC
NP-MRD IDNP0045156
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethacrolein
DescriptionMethacrolein, also known as methacrylaldehyde, belongs to the class of organic compounds known as enals. These are alpha, beta unsaturated aldehydes, with the general chemical formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C double bond. It is a clear, colorless, flammable liquid. Methacrolein a major product from the reaction of isoprene with atmospheric OH, methyl vinyl ketone (MVK) being the other mayor product from that reaction (https://Doi.Org/10.1029/92JD02382). Both are important components of the atmospheric oxidation chemistry of biogenic chemicals. Methacrolein is highly irritating to the eyes, nose, throat and lungs. The primary industrial use of methacrolein is for the manufacture of synthetic resins and polymers. Methacrolein can naturally be found in the essential oil of the plant Big Sagebrush (Artemisia tridentata), which contains approximately 5% of methacrolein. Methacrolein has also been reported to be present in cigarette smoke. Furthermore, it has been reported to be a volatile component of cannabis samples (PMID: 26657499 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045156 (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
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3D MOL for NP0045156 (Methacrolein)

     RDKit          3D

 11 10  0  0  0  0  0  0  0  0999 V2000
    0.9724   -0.9394   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1614   -0.0028   -0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332   -0.3749    0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4061    1.3803   -0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3495    2.2880   -0.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7826   -1.9685   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8301   -0.6859   -1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6277   -1.1778    0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7093    0.5048    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6858   -0.6535    1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529    1.6297   -1.0326 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
  3  8  1  0
  3  9  1  0
  3 10  1  0
  1  6  1  0
  1  7  1  0
  4 11  1  0
M  END
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3D SDF for NP0045156 (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>
NP0045156

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
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3D-SDF for NP0045156 (Methacrolein)

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PDB for NP0045156 (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 NP0045156 (Methacrolein)
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SMILES for NP0045156 (Methacrolein)
CC(=C)C=O
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INCHI for NP0045156 (Methacrolein)
InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3
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View in JSmol
Synonyms
ValueSource
2-MethylacroleinHMDB
MethacrylaldehydeHMDB
Chemical FormulaC4H6O
Average Mass70.0898 Da
Monoisotopic Mass70.04186 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cannabis sativaNULL
      Not Available
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
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
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
HMDB IDHMDB0061874  
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 LinkMethacrolein  
METLIN IDNot Available
PubChem Compound6562  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References