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Showing NP-Card for 2-methyl-2-butenoic acid (NP0248230)

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Record Information
Version2.0
Created at2022-09-07 10:24:00 UTC
Updated at2022-09-07 10:24:00 UTC
NP-MRD IDNP0248230
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-methyl-2-butenoic acid
Description2-Methylbut-2-enoic acid, also known as 2-methylcrotonic acid or a-methylcrotonate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. 2-methyl-2-butenoic acid is found in Angelica archangelica, Azadirachta indica, Lithospermum erythrorhizon, Lomatium nuttallii, Senecio linifolius and Vitis vinifera. 2-methyl-2-butenoic acid was first documented in 1995 (PMID: 7558511). 2-Methylbut-2-enoic acid is a weakly acidic compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0248230 (2-methyl-2-butenoic acid)


  Mrv1652308221904122D          

  7  6  0  0  0  0            999 V2000
    1.2375    0.7145    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
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    0.0000   -1.4289    0.0000 O   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
  3  1  1  4  0  0  0
  4  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
M  END
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3D MOL for NP0248230 (2-methyl-2-butenoic acid)

     RDKit          3D

 15 14  0  0  0  0  0  0  0  0999 V2000
    2.0995   -0.2002    0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770   -0.4925    0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3592   -0.0458    0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067    0.8183   -1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051   -0.3851    0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5594   -1.1098    1.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196    0.0921    0.3539 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0490    0.2358   -0.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572   -1.1030    0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176    0.5343    0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7771   -1.1126    1.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    1.2819   -1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475    0.2340   -1.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3456    1.6004   -0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1157   -0.3477   -0.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  7  1  0
  5  6  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  4 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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3D SDF for NP0248230 (2-methyl-2-butenoic acid)


  Mrv1652308221904122D          

  7  6  0  0  0  0            999 V2000
    1.2375    0.7145    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
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    0.0000   -1.4289    0.0000 O   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
  3  1  1  4  0  0  0
  4  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248230

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)

> <INCHI_KEY>
UIERETOOQGIECD-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.117

> <EXACT_MASS>
100.052429498

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.403243784351615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylbut-2-enoic acid

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.3151327766666667

> <ALOGPS_LOGS>
-0.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.971335232759619

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
27.322

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-2-butenoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0248230 (2-methyl-2-butenoic acid)

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PDB for NP0248230 (2-methyl-2-butenoic acid)
HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770   1.334   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    4                                                       
CONECT    4    2    3    5                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0248230 (2-methyl-2-butenoic acid)
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SMILES for NP0248230 (2-methyl-2-butenoic acid)
CC=C(C)C(O)=O
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INCHI for NP0248230 (2-methyl-2-butenoic acid)
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)
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View in JSmol
Synonyms
ValueSource
2,3-Dimethylacrylic acidChEBI
2-Methyl-2-butenoic acidChEBI
2-Methylcrotonic acidChEBI
alpha-Methylcrotonic acidChEBI
Methylmethacrylic acidChEBI
Tiglic acidChEBI
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Chemical FormulaC5H8O2
Average Mass100.1170 Da
Monoisotopic Mass100.05243 Da
IUPAC Name2-methylbut-2-enoic acid
Traditional Name2-methyl-2-butenoic acid
CAS Registry NumberNot Available
SMILES
CC=C(C)C(O)=O
InChI Identifier
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)
InChI KeyUIERETOOQGIECD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Angelica archangelicaLOTUS Database
Azadirachta indicaLOTUS Database
Lithospermum erythrorhizonLOTUS Database
Lomatium nuttalliiLOTUS Database
Senecio linifoliusLOTUS Database
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentMethyl-branched fatty acids  
Alternative Parents
Substituents
  • Methyl-branched fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • 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
logP1.13ALOGPS
logP1.32ChemAxon
logS-0.08ALOGPS
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.32 m³·mol⁻¹ChemAxon
Polarizability10.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0132474  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB089673  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID36432  
Good Scents IDNot Available
References
General References
  1. Schlottfeldt J, Blazina LR, Wannmacher CM, Wajner M: The effect of organic acids on phytohaemagglutinin-activated proliferation of human lymphocytes in vitro. Int J Immunopharmacol. 1995 Mar;17(3):175-82. doi: 10.1016/0192-0561(95)00003-k. [PubMed:7558511  ] 
  2. LOTUS database [Link]