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Showing NP-Card for 2,2-dimethyl butyric acid (NP0271994)

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Record Information
Version2.0
Created at2022-09-08 18:27:58 UTC
Updated at2022-09-08 18:27:58 UTC
NP-MRD IDNP0271994
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,2-dimethyl butyric acid
Description2,2-Dimethylbutyric acid, also known as DMB or a,a-dimethylbutanoate, 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. 2,2-dimethyl butyric acid is found in Vitis vinifera. 2,2-dimethyl butyric acid was first documented in 1991 (PMID: 1814736). 2,2-Dimethylbutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 18155649) (PMID: 20712788).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0271994 (2,2-dimethyl butyric acid)


  Mrv1572004221603532D          

  8  7  0  0  0  0            999 V2000
    1.2375    2.1434    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
    1.9520    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    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
    1.2375   -0.7145    0.0000 O   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  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
M  END
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3D MOL for NP0271994 (2,2-dimethyl butyric acid)

     RDKit          3D

 20 19  0  0  0  0  0  0  0  0999 V2000
    1.9705   -0.5169    0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479    0.3747   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3973   -0.0036   -0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7196   -1.3518   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    0.0139    1.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1573    1.0138   -0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8299    0.6798   -1.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1229    2.3266   -0.5081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979   -1.5872    0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0386   -0.2232    1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0022   -0.4475    0.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1382    1.4039    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3799    0.4298   -1.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2192   -2.1835   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097   -1.5191   -0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520   -1.4317   -1.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368   -0.8500    1.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0104   -0.0657    1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6861    0.9936    1.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369    2.9442   -0.7599 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
  3  6  1  0
  6  8  1  0
  6  7  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  4 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
M  END
Download

3D SDF for NP0271994 (2,2-dimethyl butyric acid)


  Mrv1572004221603532D          

  8  7  0  0  0  0            999 V2000
    1.2375    2.1434    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
    1.9520    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    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
    1.2375   -0.7145    0.0000 O   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  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0271994

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O2/c1-4-6(2,3)5(7)8/h4H2,1-3H3,(H,7,8)

> <INCHI_KEY>
VUAXHMVRKOTJKP-UHFFFAOYSA-N

> <FORMULA>
C6H12O2

> <MOLECULAR_WEIGHT>
116.16

> <EXACT_MASS>
116.083729626

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
12.835410477468546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2-dimethylbutanoic acid

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
2.020759378

> <ALOGPS_LOGS>
-0.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.0009040584471665

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
30.947100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2-dimethyl butyric acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0271994 (2,2-dimethyl butyric acid)

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PDB for NP0271994 (2,2-dimethyl butyric acid)
HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.644   0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    1    6                                                       
CONECT    5    6    7    8                                                  
CONECT    6    2    3    4    5                                             
CONECT    7    5                                                            
CONECT    8    5                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0271994 (2,2-dimethyl butyric acid)
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SMILES for NP0271994 (2,2-dimethyl butyric acid)
CCC(C)(C)C(O)=O
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INCHI for NP0271994 (2,2-dimethyl butyric acid)
InChI=1S/C6H12O2/c1-4-6(2,3)5(7)8/h4H2,1-3H3,(H,7,8)
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View in JSmol
Synonyms
ValueSource
alpha,alpha-Dimethylbutanoic acidChEBI
alpha,alpha-Dimethylbutyric acidChEBI
DMBChEBI
a,a-DimethylbutanoateGenerator
a,a-Dimethylbutanoic acidGenerator
alpha,alpha-DimethylbutanoateGenerator
Α,α-dimethylbutanoateGenerator
Α,α-dimethylbutanoic acidGenerator
a,a-DimethylbutyrateGenerator
a,a-Dimethylbutyric acidGenerator
alpha,alpha-DimethylbutyrateGenerator
Α,α-dimethylbutyrateGenerator
Α,α-dimethylbutyric acidGenerator
2,2-DimethylbutyrateGenerator
2,2-DMBMeSH
Sodium 2,2-dimethylbutyrateMeSH
SDMBMeSH
2,2-Dimethylbutanoic acidMeSH
ST-20 CompoundMeSH
2,2-DimethylbutanoateGenerator
2,2-Dimethylbutyric acidMeSH
Chemical FormulaC6H12O2
Average Mass116.1600 Da
Monoisotopic Mass116.08373 Da
IUPAC Name2,2-dimethylbutanoic acid
Traditional Name2,2-dimethyl butyric acid
CAS Registry NumberNot Available
SMILES
CCC(C)(C)C(O)=O
InChI Identifier
InChI=1S/C6H12O2/c1-4-6(2,3)5(7)8/h4H2,1-3H3,(H,7,8)
InChI KeyVUAXHMVRKOTJKP-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
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
    • 

  • 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
logP1.84ALOGPS
logP2.02ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity30.95 m³·mol⁻¹ChemAxon
Polarizability12.84 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
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 Compound11684  
PDB IDNot Available
ChEBI ID38649  
Good Scents IDNot Available
References
General References
  1. Uchiyama N, Kagami Y, Saito Y, Abe S, Ohtawa M, Hata S: Metabolic fate of 2,2-dimethylbutyryl moiety of simvastatin in rats: identification of metabolites by gas chromatography/mass spectrometry. Eur J Drug Metab Pharmacokinet. 1991 Jul-Sep;16(3):189-96. doi:  10.1007/BF03189958. [PubMed:1814736  ] 
  2. Parise RA, Beumer JH, Kangani CO, Holleran JL, Eiseman JL, Smith NF, Covey JM, Perrine SP, Egorin MJ: Liquid chromatography-mass spectrometric assay for quantitation of the short-chain fatty acid, 2,2-dimethylbutyrate (NSC 741804), in rat plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Feb 1;862(1-2):168-74. doi:  10.1016/j.jchromb.2007.12.002. Epub 2007 Dec 8. [PubMed:18155649  ] 
  3. Perrine SP, Castaneda SA, Chui DH, Faller DV, Berenson RJ, Siritanaratku N, Fucharoen S: Fetal globin gene inducers: novel agents and new potential. Ann N Y Acad Sci. 2010 Aug;1202:158-64. doi: 10.1111/j.1749-6632.2010.05593.x. [PubMed:20712788  ] 
  4. LOTUS database [Link]