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Showing NP-Card for Methacrylic anhydride (NP0045157)

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Record Information
Version2.0
Created at2022-03-10 18:58:56 UTC
Updated at2022-03-10 22:21:40 UTC
NP-MRD IDNP0045157
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethacrylic anhydride
DescriptionMethacrylic anhydride, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing two carboxylic acid groups. Methacrylic anhydride is a liquid which reacts exothermically with water. It can also react with hydroxyl- and amino-groups present in some organic compounds leading to covalent attachment of methacryloyl moieties. These functional groups could be successfully used either in subsequent polymerisation or reactions with thiols. For example, chitosan modified by methacryloylation exhibits better ability to adhere to mucosal surfaces (mucoadhesion) due to its reactivity with thiol groups present in cysteine domains of mucins (PMID: 30130604 ). Methacrylic anhydride it has been reported to be a volatile component of cannabis samples (PMID: 26657499 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045157 (Methacrylic anhydride)


  Mrv1652303202018592D          

 11 10  0  0  0  0            999 V2000
   -1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -0.1105    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
    1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
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3D MOL for NP0045157 (Methacrylic anhydride)

     RDKit          3D

 21 20  0  0  0  0  0  0  0  0999 V2000
    2.4183    0.6624   -1.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4767   -0.0307   -0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -0.4876    0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -0.3509    0.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3101   -1.0105    1.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    0.0326   -0.0473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1889   -0.2592    0.5926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0842   -0.9330    1.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4832    0.1584    0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5585    0.8479   -1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -0.1776    0.8132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4904    1.0011   -1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377    0.8968   -1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9873    0.0880    1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069   -0.2833   -0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7690   -1.5743    0.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633    1.1068   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944    1.1883   -1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5190   -0.3889    1.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4962    0.6265    0.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1861   -1.1130    0.3942 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  2  0
  7  9  1  0
  9 11  1  0
  9 10  2  3
  3 14  1  0
  3 15  1  0
  3 16  1  0
  1 12  1  0
  1 13  1  0
 11 19  1  0
 11 20  1  0
 11 21  1  0
 10 17  1  0
 10 18  1  0
M  END
Download

3D SDF for NP0045157 (Methacrylic anhydride)


  Mrv1652303202018592D          

 11 10  0  0  0  0            999 V2000
   -1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -0.1105    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
    1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045157

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3

> <INCHI_KEY>
DCUFMVPCXCSVNP-UHFFFAOYSA-N

> <FORMULA>
C8H10O3

> <MOLECULAR_WEIGHT>
154.165

> <EXACT_MASS>
154.062994182

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.741915033249095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylprop-2-enoyl 2-methylprop-2-enoate

> <ALOGPS_LOGP>
1.57

> <JCHEM_LOGP>
2.457834241

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.763205542589045

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
40.09160000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methacrylic anhydride

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0045157 (Methacrylic anhydride)

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PDB for NP0045157 (Methacrylic anhydride)
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      -3.644   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.310  -0.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.358   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.025  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.025   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.976   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.691   2.104   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.976   3.644   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.691   3.644   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.357   1.334   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    6                                                            
CONECT    5    1    2    7                                                  
CONECT    6    3    4    8                                                  
CONECT    7    5    9   11                                                  
CONECT    8    6   10   11                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
CONECT   11    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0045157 (Methacrylic anhydride)
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SMILES for NP0045157 (Methacrylic anhydride)
CC(=C)C(=O)OC(=O)C(C)=C
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INCHI for NP0045157 (Methacrylic anhydride)
InChI=1S/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H10O3
Average Mass154.1650 Da
Monoisotopic Mass154.06299 Da
IUPAC Name2-methylprop-2-enoyl 2-methylprop-2-enoate
Traditional Namemethacrylic anhydride
CAS Registry Number760-93-0
SMILES
CC(=C)C(=O)OC(=O)C(C)=C
InChI Identifier
InChI=1S/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3
InChI KeyDCUFMVPCXCSVNP-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 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
    • 

  • Carboxylic acid anhydride
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP1.57ALOGPS
logP2.46ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity40.09 m³·mol⁻¹ChemAxon
Polarizability15.74 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
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 LinkNot Available
METLIN IDNot Available
PubChem Compound12974  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kolawole OM, Lau WM, Khutoryanskiy VV: Methacrylated chitosan as a polymer with enhanced mucoadhesive properties for transmucosal drug delivery. Int J Pharm. 2018 Oct 25;550(1-2):123-129. doi: 10.1016/j.ijpharm.2018.08.034. Epub 2018 Aug 18. [PubMed:30130604  ]