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Showing NP-Card for (s)-2-methylbutanoic acid (NP0267310)

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Record Information
Version2.0
Created at2022-09-08 12:03:17 UTC
Updated at2022-09-08 12:03:17 UTC
NP-MRD IDNP0267310
Secondary Accession NumbersNone
Natural Product Identification
Common Name(s)-2-methylbutanoic acid
Description(S)-2-Methylbutanoic acid, also known as (S)-a-methylbutanoate, 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 (S)-2-Methylbutanoic acid is a weakly acidic compound (based on its pKa). Outside of the human body, (S)-2-Methylbutanoic acid has been detected, but not quantified in, fats and oils. This could make (S)-2-methylbutanoic acid a potential biomarker for the consumption of these foods. (s)-2-methylbutanoic acid is found in Homo sapiens, Ipomoea capillacea and Lithospermum erythrorhizon. The (S)-enantiomer of 2-methylbutanoic acid (S)-2-Methylbutanoic acid, with regard to humans, has been found to be associated with the diseases such as perillyl alcohol administration for cancer treatment; (S)-2-methylbutanoic acid has also been linked to the inborn metabolic disorder celiac disease.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0267310 ((s)-2-methylbutanoic acid)


  Mrv0541 02241217422D          

  7  6  0  0  1  0            999 V2000
   -0.4703    0.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2442    0.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9586    0.4356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9586   -0.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    0.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876    0.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    1.6731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
Download

3D MOL for NP0267310 ((s)-2-methylbutanoic acid)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
    1.9327    0.0870   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966   -0.7608   -0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4977   -0.0932    0.4936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6628   -1.0486    0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8388    1.1850   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    1.3579   -0.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792    2.2183   -0.2597 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0485    0.4693    0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7993   -0.5925   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9257    0.9096   -0.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981   -1.6818    0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707   -1.1176   -1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2376    0.1455    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6285   -0.4987    0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5706   -1.7796    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5763   -1.5515   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1239    2.7515   -1.1189 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  7  1  0
  5  6  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  1
  4 14  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
Download

3D SDF for NP0267310 ((s)-2-methylbutanoic acid)


  Mrv0541 02241217422D          

  7  6  0  0  1  0            999 V2000
   -0.4703    0.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2442    0.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9586    0.4356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9586   -0.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    0.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876    0.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    1.6731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0267310

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)/t4-/m0/s1

> <INCHI_KEY>
WLAMNBDJUVNPJU-BYPYZUCNSA-N

> <FORMULA>
C5H10O2

> <MOLECULAR_WEIGHT>
102.1317

> <EXACT_MASS>
102.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
10.978767155383991

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-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>
26.446100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.72e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-2-methylbutanoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0267310 ((s)-2-methylbutanoic acid)

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PDB for NP0267310 ((s)-2-methylbutanoic acid)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.878   0.813   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.456   1.583   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.789   0.813   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.789  -0.727   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.123   1.583   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.457   0.813   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.123   3.123   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    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 NP0267310 ((s)-2-methylbutanoic acid)
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SMILES for NP0267310 ((s)-2-methylbutanoic acid)
CC[C@H](C)C(O)=O
Download
INCHI for NP0267310 ((s)-2-methylbutanoic acid)
InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)/t4-/m0/s1
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View in JSmol
Synonyms
ValueSource
(S)-alpha-Methylbutanoic acidChEBI
(S)-a-MethylbutanoateGenerator
(S)-a-Methylbutanoic acidGenerator
(S)-alpha-MethylbutanoateGenerator
(S)-Α-methylbutanoateGenerator
(S)-Α-methylbutanoic acidGenerator
(S)-2-MethylbutanoateGenerator
(+)-(S)-2-Methylbutanoic acidHMDB
(+)-2-Methylbutanoic acidHMDB
(+)-2-Methylbutyric acidHMDB
(+)-alpha-Methylbutyric acidHMDB
(2S)-2-Methylbutanoic acidHMDB
(S)-(+)-2-Methylbutyric acidHMDB
(S)-2-Methylbutyric acidHMDB
2-Methyl-(2S)-butanoic acidHMDB
2-Methyl-(S)-butanoic acidHMDB
Butyric acid, 2-methyl-, (S)- (8ci)HMDB
Butyric acid, 2-methyl-, L- (6ci)HMDB
S-(+)-2-Methylbutanoic acidHMDB
(S)-2-Methylbutanoic acidChEBI
(S)-2-MethylbutyrateGenerator
Chemical FormulaC5H10O2
Average Mass102.1317 Da
Monoisotopic Mass102.06808 Da
IUPAC Name(2S)-2-methylbutanoic acid
Traditional Name(S)-2-methylbutanoic acid
CAS Registry NumberNot Available
SMILES
CC[C@H](C)C(O)=O
InChI Identifier
InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)/t4-/m0/s1
InChI KeyWLAMNBDJUVNPJU-BYPYZUCNSA-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
Homo sapiensLOTUS Database
Ipomoea capillaceaLOTUS Database
Lithospermum erythrorhizonLOTUS 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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 IDHMDB0033742  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011870  
KNApSAcK IDNot Available
Chemspider ID395556  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound448893  
PDB IDSMB  
ChEBI ID38655  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]