Showing NP-Card for Ethylmethylacetic acid (NP0000690)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Show more...Show more...
Record Information
Version2.0
Created at2006-05-22 14:17:39 UTC
Updated at2021-10-07 20:40:43 UTC
NP-MRD IDNP0000690
Secondary Accession NumbersNone
Natural Product Identification
Common NameEthylmethylacetic acid
DescriptionEthylmethylacetic acid, also known as alpha-methyl butyric acid or a-methyl butyrate, 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. Ethylmethylacetic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000690 (Ethylmethylacetic acid)

  Mrv1652304272018562D          

  7  6  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
Download

3D MOL for NP0000690 (Ethylmethylacetic acid)

HMDB0002176
     RDKit          3D
Ethylmethylacetic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.7818   -0.6211    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8987    0.5489    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646    0.1752   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1588    1.4535   -0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1892   -0.7934    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666   -0.5540    0.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -2.0300    0.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8698   -0.3950    0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7034   -0.8270    1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5397   -1.5308   -0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4456    1.2751   -0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978    1.1009    1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1408   -0.2781   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    1.6441   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445    1.3819   -0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6506    2.3330   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381   -2.8832    0.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
Download

3D SDF for NP0000690 (Ethylmethylacetic acid)

  Mrv1652304272018562D          

  7  6  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000690

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)

> <INCHI_KEY>
WLAMNBDJUVNPJU-UHFFFAOYSA-N

> <FORMULA>
C5H10O2

> <MOLECULAR_WEIGHT>
102.1317

> <EXACT_MASS>
102.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
10.98492198543893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylbutanoic acid

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.464745076

> <ALOGPS_LOGS>
-0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.969194504225091

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
26.446099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.72e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-2-methylbutyrate

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000690 (Ethylmethylacetic acid)

HMDB0002176
     RDKit          3D
Ethylmethylacetic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.7818   -0.6211    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8987    0.5489    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646    0.1752   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1588    1.4535   -0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1892   -0.7934    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666   -0.5540    0.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -2.0300    0.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8698   -0.3950    0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7034   -0.8270    1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5397   -1.5308   -0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4456    1.2751   -0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978    1.1009    1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1408   -0.2781   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    1.6441   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445    1.3819   -0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6506    2.3330   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381   -2.8832    0.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
Download

PDB for NP0000690 (Ethylmethylacetic acid)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.334  -2.310   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
Download

3D PDB for NP0000690 (Ethylmethylacetic acid)

COMPND    HMDB0002176
HETATM    1  C1  UNL     1       1.782  -0.621   0.515  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.899   0.549   0.232  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.365   0.175  -0.506  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.159   1.453  -0.724  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.189  -0.793   0.261  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.367  -0.554   0.631  1.00  0.00           O  
HETATM    7  O2  UNL     1      -0.654  -2.030   0.597  1.00  0.00           O  
HETATM    8  H1  UNL     1       2.870  -0.395   0.338  1.00  0.00           H  
HETATM    9  H2  UNL     1       1.703  -0.827   1.623  1.00  0.00           H  
HETATM   10  H3  UNL     1       1.540  -1.531  -0.037  1.00  0.00           H  
HETATM   11  H4  UNL     1       1.446   1.275  -0.395  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.598   1.101   1.157  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.141  -0.278  -1.482  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.330   1.644  -1.800  1.00  0.00           H  
HETATM   15  H8  UNL     1      -2.144   1.382  -0.213  1.00  0.00           H  
HETATM   16  H9  UNL     1      -0.651   2.333  -0.301  1.00  0.00           H  
HETATM   17  H10 UNL     1      -0.838  -2.883   0.104  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4    5   13
CONECT    4   14   15   16
CONECT    5    6    6    7
CONECT    7   17
END
Download

SMILES for NP0000690 (Ethylmethylacetic acid)

CCC(C)C(O)=O
Download

INCHI for NP0000690 (Ethylmethylacetic acid)

InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)
Download
View in JSmol
Synonyms
Chemical FormulaC5H10O2
Average Mass102.1317 Da
Monoisotopic Mass102.06808 Da
IUPAC Name2-methylbutanoic acid
Traditional Name(+-)-2-methylbutyrate
CAS Registry Number116-53-0
SMILES
CCC(C)C(O)=O
InChI Identifier
InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)
InChI KeyWLAMNBDJUVNPJU-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Homo sapiens (Skin microbiota)KNApSAcK 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
  • 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point176.00 to 177.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility45 mg/mL at 20 °CNot Available
LogP1.18Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility57.2 g/LALOGPS
logP1.47ALOGPS
logP1.46ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.45 m³·mol⁻¹ChemAxon
Polarizability10.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002176
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008135
KNApSAcK IDC00029461
Chemspider ID8012
KEGG Compound IDC18319
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6528
PubChem Compound8314
PDB IDNot Available
ChEBI ID37070
Good Scents IDrw1056421
References
General References
  1. Korman SH, Andresen BS, Zeharia A, Gutman A, Boneh A, Pitt JJ: 2-ethylhydracrylic aciduria in short/branched-chain acyl-CoA dehydrogenase deficiency: application to diagnosis and implications for the R-pathway of isoleucine oxidation. Clin Chem. 2005 Mar;51(3):610-7. Epub 2004 Dec 22. [PubMed:15615815 ]
  2. Ganesan B, Dobrowolski P, Weimer BC: Identification of the leucine-to-2-methylbutyric acid catabolic pathway of Lactococcus lactis. Appl Environ Microbiol. 2006 Jun;72(6):4264-73. doi: 10.1128/AEM.00448-06. [PubMed:16751541 ]
  3. Hayashida-Soiza G, Uchida A, Mori N, Kuwahara Y, Ishida Y: Purification and characterization of antibacterial substances produced by a marine bacterium Pseudoalteromonas haloplanktis strain. J Appl Microbiol. 2008 Nov;105(5):1672-7. doi: 10.1111/j.1365-2672.2008.03878.x. Epub 2008 Oct 1. [PubMed:18828792 ]
  4. Gutsche KA, Tran TB, Vogel RF: Production of volatile compounds by Lactobacillus sakei from branched chain alpha-keto acids. Food Microbiol. 2012 Apr;29(2):224-8. doi: 10.1016/j.fm.2011.06.010. Epub 2011 Jun 21. [PubMed:22202876 ]