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Showing metabocard for 2-Ethyl-2-Hydroxybutyric acid (HMDB0001975)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:30 UTC
Update Date2023-02-21 17:16:00 UTC
HMDB IDHMDB0001975
Secondary Accession Numbers
  • HMDB01975
Metabolite Identification
Common Name2-Ethyl-2-Hydroxybutyric acid
Description2-Ethyl-2-Hydroxybutyric acid, also known as 2-ethyl-2-hydroxybutanoate or 2-et-2-hba, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Ethyl-2-Hydroxybutyric acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001975 (2-Ethyl-2-Hydroxybutyric acid)

  Mrv1652305261923532D          

  9  8  0  0  0  0            999 V2000
   13.4655  -11.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1800  -12.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8945  -11.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6090  -12.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8945  -11.0058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1800  -13.0684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1800  -11.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3832  -11.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7511  -12.2434    0.0000 C   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  0  0  0  0
  3  5  2  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  9  1  0  0  0  0
M  END
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3D MOL for HMDB0001975 (2-Ethyl-2-Hydroxybutyric acid)

HMDB0001975
     RDKit          3D
2-Ethyl-2-Hydroxybutyric acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -1.7770    0.3939   -1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0987    0.5659    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1368   -0.2823    0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841   -0.0521    1.6921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776   -0.0185   -0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6633    1.3949   -0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762   -1.6971    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8128   -2.1925   -0.6426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0886   -2.5555    1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278    1.3859   -1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7794   -0.1177   -0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2010   -0.1787   -1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8876    1.6196    0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    0.2160    1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128    0.2183    2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8306   -0.2930   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0480   -0.6659   -0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311    1.9534    0.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7669    1.4395   -0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2296    1.9212   -1.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7866   -3.0554    1.4920 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  1  0
  3  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  6 20  1  0
  9 21  1  0
M  END
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3D SDF for HMDB0001975 (2-Ethyl-2-Hydroxybutyric acid)

  Mrv1652305261923532D          

  9  8  0  0  0  0            999 V2000
   13.4655  -11.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1800  -12.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8945  -11.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6090  -12.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8945  -11.0058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1800  -13.0684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1800  -11.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3832  -11.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7511  -12.2434    0.0000 C   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  0  0  0  0
  3  5  2  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001975

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O3/c1-3-6(9,4-2)5(7)8/h9H,3-4H2,1-2H3,(H,7,8)

> <INCHI_KEY>
LXVSANCQXSSLPA-UHFFFAOYSA-N

> <FORMULA>
C6H12O3

> <MOLECULAR_WEIGHT>
132.1577

> <EXACT_MASS>
132.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
13.672227167482507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethyl-2-hydroxybutanoic acid

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
1.005981158

> <ALOGPS_LOGS>
0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.916560738917497

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.208748201721341

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9382417854830125

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
32.601099999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ethyl-2-hydroxybutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001975 (2-Ethyl-2-Hydroxybutyric acid)

HMDB0001975
     RDKit          3D
2-Ethyl-2-Hydroxybutyric acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -1.7770    0.3939   -1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0987    0.5659    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1368   -0.2823    0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841   -0.0521    1.6921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776   -0.0185   -0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6633    1.3949   -0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762   -1.6971    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8128   -2.1925   -0.6426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0886   -2.5555    1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278    1.3859   -1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7794   -0.1177   -0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2010   -0.1787   -1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8876    1.6196    0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    0.2160    1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128    0.2183    2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8306   -0.2930   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0480   -0.6659   -0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311    1.9534    0.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7669    1.4395   -0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2296    1.9212   -1.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7866   -3.0554    1.4920 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  1  0
  3  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  6 20  1  0
  9 21  1  0
M  END
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PDB for HMDB0001975 (2-Ethyl-2-Hydroxybutyric acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      25.136 -22.084   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.469 -22.854   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.803 -22.084   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      29.137 -22.854   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      27.803 -20.544   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      26.469 -24.394   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      26.469 -21.314   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.982 -20.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.802 -22.854   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3    6    7                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    2    8                                                       
CONECT    8    7                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0001975 (2-Ethyl-2-Hydroxybutyric acid)

COMPND    HMDB0001975
HETATM    1  C1  UNL     1      -1.777   0.394  -1.025  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.099   0.566   0.290  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.137  -0.282   0.457  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.684  -0.052   1.692  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.178  -0.018  -0.593  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.663   1.395  -0.606  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.276  -1.697   0.382  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.813  -2.193  -0.643  1.00  0.00           O  
HETATM    9  O3  UNL     1      -0.089  -2.556   1.454  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.028   1.386  -1.493  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.779  -0.118  -0.932  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.201  -0.179  -1.764  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.888   1.620   0.532  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.818   0.216   1.083  1.00  0.00           H  
HETATM   15  H6  UNL     1       0.013   0.218   2.375  1.00  0.00           H  
HETATM   16  H7  UNL     1       0.831  -0.293  -1.620  1.00  0.00           H  
HETATM   17  H8  UNL     1       2.048  -0.666  -0.360  1.00  0.00           H  
HETATM   18  H9  UNL     1       1.431   1.953   0.323  1.00  0.00           H  
HETATM   19  H10 UNL     1       2.767   1.439  -0.733  1.00  0.00           H  
HETATM   20  H11 UNL     1       1.230   1.921  -1.480  1.00  0.00           H  
HETATM   21  H12 UNL     1       0.787  -3.055   1.492  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4    5    7
CONECT    4   15
CONECT    5    6   16   17
CONECT    6   18   19   20
CONECT    7    8    8    9
CONECT    9   21
END
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SMILES for HMDB0001975 (2-Ethyl-2-Hydroxybutyric acid)

CCC(O)(CC)C(O)=O
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INCHI for HMDB0001975 (2-Ethyl-2-Hydroxybutyric acid)

InChI=1S/C6H12O3/c1-3-6(9,4-2)5(7)8/h9H,3-4H2,1-2H3,(H,7,8)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Ethyl-2-hydroxybutyrateGenerator
2-Et-2-hbaMeSH
2-Ethyl-2-hydroxybutanoateHMDB
2-Ethyl-2-hydroxybutanoic acidHMDB
2-Ethyl-2-hydroxy-butyrateGenerator, HMDB
2-Ethyl-2-hydroxybutyric acidMeSH
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
IUPAC Name2-ethyl-2-hydroxybutanoic acid
Traditional Name2-ethyl-2-hydroxybutyric acid
CAS Registry Number3639-21-2
SMILES
CCC(O)(CC)C(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-3-6(9,4-2)5(7)8/h9H,3-4H2,1-2H3,(H,7,8)
InChI KeyLXVSANCQXSSLPA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Branched fatty acid
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility26 mg/mL at 18 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022773
KNApSAcK IDNot Available
Chemspider ID69629
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6411
PubChem Compound77199
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. SCHMIDT G: [Incidence and excretion alpha-ethyl-alpha-hydroxybutyric acid after carbromal intake]. Naunyn Schmiedebergs Arch Exp Pathol Pharmakol. 1956;229(1):67-74. [PubMed:13348692 ]