Showing metabocard for 2-hydroxybutanoic acid (MMDBc0055244)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 19:47:11 UTC
Update Date2025-10-07 16:04:19 UTC
Metabolite IDMMDBc0055244
Metabolite Identification
Common Name2-hydroxybutanoic acid
Description2-hydroxybutanoic acid is a carboxylic acid and a key metabolite in various biochemical pathways. Its chemical structure features a hydroxyl group (-OH) attached to the second carbon of a four-carbon butanoic acid chain, making it an important intermediate in metabolic processes. This compound plays a role in the metabolism of amino acids and carbohydrates, participating in pathways such as the conversion of pyruvate and the production of lactic acid. Notably, shifts in the levels of metabolites, including 2-hydroxybutanoic acid, have been observed in studies examining metabolic regulation, indicating its involvement in broader metabolic changes. For instance, one study reported that these shifts were accompanied by regulation of fecal and serum metabolites, including pyruvate, 2-hydroxybutanoic acid, and lactic acid (PMID:40944169 ). This suggests that 2-hydroxybutanoic acid could be a marker for metabolic alterations and may have implications for understanding energy metabolism and homeostasis in biological systems.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fade4870ed0>


  Mrv1652306172221472D          

  7  6  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
    0.8250    1.4289    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
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   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  5  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
M  CHG  1   7  -1
M  END
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3D MOL for #<Metabolite:0x00007fade4870ed0>

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3D SDF for #<Metabolite:0x00007fade4870ed0>

  Mrv1652306172221472D          

  7  6  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
    0.8250    1.4289    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
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   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  5  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
M  CHG  1   7  -1
M  END
> <DATABASE_ID>
MMDBc0055244

> <DATABASE_NAME>
MIME

> <SMILES>
CCC(O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/p-1

> <INCHI_KEY>
AFENDNXGAFYKQO-UHFFFAOYSA-M

> <FORMULA>
C4H7O3

> <MOLECULAR_WEIGHT>
103.098

> <EXACT_MASS>
103.040067665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.554896731565593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxybutanoate

> <JCHEM_LOGP>
0.050692876999999914

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.293154365104638

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.989998858113875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7935876935907205

> <JCHEM_POLAR_SURFACE_AREA>
60.36

> <JCHEM_REFRACTIVITY>
34.200900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxybutyrate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fade4870ed0>
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PDB for #<Metabolite:0x00007fade4870ed0>
HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3    6    7                                                  
CONECT    5    3                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for #<Metabolite:0x00007fade4870ed0>
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SMILES for #<Metabolite:0x00007fade4870ed0>
CCC(O)C([O-])=O
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INCHI for #<Metabolite:0x00007fade4870ed0>
InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/p-1
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Synonyms
ValueSource
alpha-HydroxybutanoateChEBI
alpha-HydroxybutyrateChEBI
a-HydroxybutanoateGenerator
a-Hydroxybutanoic acidGenerator
alpha-Hydroxybutanoic acidGenerator
Α-hydroxybutanoateGenerator
Α-hydroxybutanoic acidGenerator
a-HydroxybutyrateGenerator
a-Hydroxybutyric acidGenerator
alpha-Hydroxybutyric acidGenerator
Α-hydroxybutyrateGenerator
Α-hydroxybutyric acidGenerator
2-Hydroxybutanoic acidGenerator
2-Hydroxybutyric acid, (+-)-isomerMeSH
2-Hydroxybutyric acid, (R)-isomerMeSH
2-Hydroxybutyric acid, monosodium salt, (+-)-isomerMeSH
2-Hydroxybutyric acidMeSH
2-Hydroxybutyric acid, monosodium saltMeSH
Molecular FormulaC4H7O3
Average Mass103.098
Monoisotopic Mass103.040067665
IUPAC Name2-hydroxybutanoate
Traditional Name2-hydroxybutyrate
CAS Registry NumberNot Available
SMILES
CCC(O)C([O-])=O
InChI Identifier
InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/p-1
InChI KeyAFENDNXGAFYKQO-UHFFFAOYSA-M