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Showing NP-Card for 2-Hydroxy-3-methylbutanoic acid ethyl ester (NP0047127)

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Record Information
Version2.0
Created at2022-03-17 20:35:05 UTC
Updated at2022-03-17 20:35:05 UTC
NP-MRD IDNP0047127
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Hydroxy-3-methylbutanoic acid ethyl ester
DescriptionEthyl 2-hydroxyisovalerate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. Ethyl 2-hydroxyisovalerate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ethyl 2-hydroxyisovalerate has been detected, but not quantified in, bilberries. This could make ethyl 2-hydroxyisovalerate a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047127 (2-Hydroxy-3-methylbutanoic acid ethyl ester)


  Mrv0541 03071314322D          

 10  9  0  0  0  0            999 V2000
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    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
    2.4454   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 10  7  1  0  0  0  0
M  END
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3D MOL for NP0047127 (2-Hydroxy-3-methylbutanoic acid ethyl ester)

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3D SDF for NP0047127 (2-Hydroxy-3-methylbutanoic acid ethyl ester)

  Mrv0541 03071314322D          

 10  9  0  0  0  0            999 V2000
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    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
    2.4454   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 10  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047127

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O3/c1-4-10-7(9)6(8)5(2)3/h5-6,8H,4H2,1-3H3

> <INCHI_KEY>
IZRVEUZYBVGCFC-UHFFFAOYSA-N

> <FORMULA>
C7H14O3

> <MOLECULAR_WEIGHT>
146.1843

> <EXACT_MASS>
146.094294314

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
15.84725791801173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 2-hydroxy-3-methylbutanoate

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
0.9183677140000002

> <ALOGPS_LOGS>
-0.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.490734199611737

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8963528610898264

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
37.353100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 2-hydroxy-3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047127 (2-Hydroxy-3-methylbutanoic acid ethyl ester)
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PDB for NP0047127 (2-Hydroxy-3-methylbutanoic acid ethyl ester)
HEADER    PROTEIN                                 07-MAR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-MAR-13         0                                  
HETATM    1  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.898  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.565  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.897  -1.334   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.231   0.976   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.897  -2.874   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    5                                                            
CONECT    4    1   10                                                       
CONECT    5    2    3    6                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    9   10                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
CONECT   10    4    7                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0047127 (2-Hydroxy-3-methylbutanoic acid ethyl ester)
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SMILES for NP0047127 (2-Hydroxy-3-methylbutanoic acid ethyl ester)
CCOC(=O)C(O)C(C)C
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INCHI for NP0047127 (2-Hydroxy-3-methylbutanoic acid ethyl ester)
InChI=1S/C7H14O3/c1-4-10-7(9)6(8)5(2)3/h5-6,8H,4H2,1-3H3
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Synonyms
ValueSource
Ethyl 2-hydroxyisovaleric acidGenerator
Ethyl 2-hydroxy-3-methylbutanoic acidGenerator
2-Hydroxy-3-methylbutanoate ethyl esterGenerator
Chemical FormulaC7H14O3
Average Mass146.1843 Da
Monoisotopic Mass146.09429 Da
IUPAC Nameethyl 2-hydroxy-3-methylbutanoate
Traditional Nameethyl 2-hydroxy-3-methylbutanoate
CAS Registry NumberNot Available
SMILES
CCOC(=O)C(O)C(C)C
InChI Identifier
InChI=1S/C7H14O3/c1-4-10-7(9)6(8)5(2)3/h5-6,8H,4H2,1-3H3
InChI KeyIZRVEUZYBVGCFC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Vaccinium myrtillusFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acid esters  
Direct ParentFatty acid esters  
Alternative Parents
Substituents
  • Fatty acid ester
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • 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
logP0.67ALOGPS
logP0.92ChemAxon
logS-0.12ALOGPS
pKa (Strongest Acidic)12.49ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity37.35 m³·mol⁻¹ChemAxon
Polarizability15.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0059842  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007449  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound520125  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References