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Showing NP-Card for 2-Ethyl-2-Hydroxybutyric acid (NP0000241)

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Record Information
Version1.0
Created at2006-05-22 14:17:30 UTC
Updated at2021-06-29 00:47:18 UTC
NP-MRD IDNP0000241
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000241 (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
Download

3D MOL for NP0000241 (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
Download

3D SDF for NP0000241 (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>
NP0000241

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000241 (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
Download

PDB for NP0000241 (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 NP0000241 (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 NP0000241 (2-Ethyl-2-Hydroxybutyric acid)

CCC(O)(CC)C(O)=O
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INCHI for NP0000241 (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 JSmol
Synonyms
ValueSource
2-Ethyl-2-hydroxybutyrateGenerator
2-Et-2-hbaHMDB
2-Ethyl-2-hydroxybutanoateHMDB
2-Ethyl-2-hydroxybutanoic acidHMDB
2-Ethyl-2-hydroxy-butyrateHMDB
2-Ethyl-2-hydroxybutyric acidMeSH
Chemical FormulaC6H12O3
Average Mass132.1577 Da
Monoisotopic Mass132.07864 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility26 mg/mL at 18 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility187 g/LALOGPS
logP0.52ALOGPS
logP1.01ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.6 m³·mol⁻¹ChemAxon
Polarizability13.67 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001975
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  2. Levina A, Codd R, Foran GJ, Hambley TW, Maschmeyer T, Masters AF, Lay PA: X-ray absorption spectroscopic studies of chromium(V/IV/III)- 2-ethyl-2-hydroxybutanoato(2-/1-) complexes. Inorg Chem. 2004 Feb 9;43(3):1046-55. doi: 10.1021/ic030239r. [PubMed:14753827 ]
  3. Hati S, Batchelor RJ, Einstein FW, Tracey AS: Vanadium(V) complexes of alpha-hydroxycarboxylic acids in aqueous solution. Inorg Chem. 2001 Nov 19;40(24):6258-65. doi: 10.1021/ic010427m. [PubMed:11703128 ]
  4. Bu Y, Wang H, Ma X, Han C, Jia X, Zhang J, Liu Y, Peng Y, Yang M, Yu K, Wang C: Untargeted Metabolomic Profiling of the Correlation Between Prognosis Differences and PD-1 Expression in Sepsis: A Preliminary Study. Front Immunol. 2021 Apr 1;12:594270. doi: 10.3389/fimmu.2021.594270. eCollection 2021. [PubMed:33868224 ]
  5. Sugden KD, Rigby KM, Martin BD: Oxidative activation of the human carcinogen chromate by arsenite: a model for synergistic metal activation leading to oxidative DNA damage. Toxicol In Vitro. 2004 Dec;18(6):741-8. doi: 10.1016/j.tiv.2004.03.001. [PubMed:15465638 ]