Showing metabocard for (S)-2-ethyl-2-hydroxy-3-oxobutanoic acid (MMDBc0055058)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-17 19:40:56 UTC
Update Date2022-08-12 20:09:12 UTC
Metabolite IDMMDBc0055058
Metabolite Identification
Common Name(S)-2-ethyl-2-hydroxy-3-oxobutanoic acid
Description(S)-2-acetyl-2-hydroxybutanoate, also known as (S)-2-hydroxy-2-ethyl-3-oxobutanoate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms (S)-2-acetyl-2-hydroxybutanoate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on (S)-2-acetyl-2-hydroxybutanoate.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fdb709bfe80>


  Mrv1652306172221402D          

 10  9  0  0  1  0            999 V2000
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    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
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  6  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
  6 10  1  1  0  0  0
M  CHG  1   9  -1
M  END
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3D MOL for #<Metabolite:0x00007fdb709bfe80>

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3D SDF for #<Metabolite:0x00007fdb709bfe80>

  Mrv1652306172221402D          

 10  9  0  0  1  0            999 V2000
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    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
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  6  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
  6 10  1  1  0  0  0
M  CHG  1   9  -1
M  END
> <DATABASE_ID>
MMDBc0055058

> <DATABASE_NAME>
MIME

> <SMILES>
CC[C@](O)(C(C)=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/p-1/t6-/m0/s1

> <INCHI_KEY>
VUQLHQFKACOHNZ-LURJTMIESA-M

> <FORMULA>
C6H9O4

> <MOLECULAR_WEIGHT>
145.135

> <EXACT_MASS>
145.05063235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.299613973966837

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-ethyl-2-hydroxy-3-oxobutanoate

> <JCHEM_LOGP>
0.23863807466666656

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.22864662869457

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.602709116384785

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6693092913361545

> <JCHEM_POLAR_SURFACE_AREA>
77.43

> <JCHEM_REFRACTIVITY>
43.9515

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(S)-2-aceto-2-hydroxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fdb709bfe80>
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PDB for #<Metabolite:0x00007fdb709bfe80>
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       4.207   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.207   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.644  -0.564   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       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.874  -1.897   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.206   0.770   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    6                                                       
CONECT    4    2    6    7                                                  
CONECT    5    6    8    9                                                  
CONECT    6    3    4    5   10                                             
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for #<Metabolite:0x00007fdb709bfe80>
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SMILES for #<Metabolite:0x00007fdb709bfe80>
CC[C@](O)(C(C)=O)C([O-])=O
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INCHI for #<Metabolite:0x00007fdb709bfe80>
InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/p-1/t6-/m0/s1
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Synonyms
ValueSource
(S)-2-Aceto-2-hydroxybutanoateChEBI
(S)-2-Acetyl-2-hydroxybutyrateChEBI
(S)-2-Ethyl-2-hydroxy-3-oxobutanoateChEBI
(S)-2-Hydroxy-2-ethyl-3-oxobutanoateChEBI
(S)-2-Aceto-2-hydroxybutanoic acidGenerator
(S)-2-Acetyl-2-hydroxybutyric acidGenerator
(S)-2-Ethyl-2-hydroxy-3-oxobutanoic acidGenerator
(S)-2-Hydroxy-2-ethyl-3-oxobutanoic acidGenerator
(S)-2-Acetyl-2-hydroxybutanoic acidGenerator
Molecular FormulaC6H9O4
Average Mass145.135
Monoisotopic Mass145.05063235
IUPAC Name(2S)-2-ethyl-2-hydroxy-3-oxobutanoate
Traditional Name(S)-2-aceto-2-hydroxybutanoate
CAS Registry NumberNot Available
SMILES
CC[C@](O)(C(C)=O)C([O-])=O
InChI Identifier
InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/p-1/t6-/m0/s1
InChI KeyVUQLHQFKACOHNZ-LURJTMIESA-M