Showing metabocard for 2-Aceto-2-hydroxy-butyrate (MMDBc0029752)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:40:11 UTC
Update Date2022-08-31 17:16:40 UTC
Metabolite IDMMDBc0029752
Metabolite Identification
Common Name2-Aceto-2-hydroxy-butyrate
Description(S)-2-Aceto-2-hydroxybutanoic acid is an intermediate in branched chain amino acid metabolism. It is converted from 2-oxobutanoate or 2-hydoxyethyl ThPP via acetolactate synthase.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fecf0acc3f0>


  Mrv1652306222023452D          

 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  0  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  END
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3D MOL for #<Metabolite:0x00007fecf0acc3f0>

HMDB0006900
     RDKit          3D
(S)-2-Aceto-2-hydroxybutanoic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
    2.1067   -1.0442    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0629   -0.0341    0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1274   -0.0570   -0.1039 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2702    0.2109   -1.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734    1.0072    0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4615    2.1309   -0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172    0.9003    1.4807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369   -1.3463   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655   -1.7334    1.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0343   -2.1198   -1.1441 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2816   -1.1522   -0.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9080   -2.0311    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -0.6781    0.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6707   -0.3062    1.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139    0.9633    0.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7397    1.0661   -1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108    3.0834   -0.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1247    1.8954   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5628    2.1888   -0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6194   -2.9437   -1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  6 19  1  0
 10 20  1  0
M  END
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3D SDF for #<Metabolite:0x00007fecf0acc3f0>


  Mrv1652306222023452D          

 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  0  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  END
> <DATABASE_ID>
MMDBc0029752

> <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)/t6-/m0/s1

> <INCHI_KEY>
VUQLHQFKACOHNZ-LURJTMIESA-N

> <FORMULA>
C6H10O4

> <MOLECULAR_WEIGHT>
146.1412

> <EXACT_MASS>
146.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.72478643988865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid

> <ALOGPS_LOGP>
-0.58

> <JCHEM_LOGP>
0.23863807466666656

> <ALOGPS_LOGS>
0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.228646628694571

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.602709116384785

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6693092913361545

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
33.114399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fecf0acc3f0>

HMDB0006900
     RDKit          3D
(S)-2-Aceto-2-hydroxybutanoic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
    2.1067   -1.0442    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0629   -0.0341    0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1274   -0.0570   -0.1039 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2702    0.2109   -1.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734    1.0072    0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4615    2.1309   -0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172    0.9003    1.4807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369   -1.3463   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655   -1.7334    1.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0343   -2.1198   -1.1441 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2816   -1.1522   -0.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9080   -2.0311    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -0.6781    0.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6707   -0.3062    1.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139    0.9633    0.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7397    1.0661   -1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108    3.0834   -0.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1247    1.8954   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5628    2.1888   -0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6194   -2.9437   -1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  6 19  1  0
 10 20  1  0
M  END
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PDB for #<Metabolite:0x00007fecf0acc3f0>

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         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+0
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:0x00007fecf0acc3f0>

COMPND    HMDB0006900
HETATM    1  C1  UNL     1       2.107  -1.044   0.470  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.063  -0.034   0.829  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.127  -0.057  -0.104  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.270   0.211  -1.398  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.073   1.007   0.334  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.462   2.131  -0.552  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.517   0.900   1.481  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.837  -1.346  -0.025  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.266  -1.733   1.100  1.00  0.00           O  
HETATM   10  O4  UNL     1      -1.034  -2.120  -1.144  1.00  0.00           O  
HETATM   11  H1  UNL     1       2.282  -1.152  -0.610  1.00  0.00           H  
HETATM   12  H2  UNL     1       1.908  -2.031   0.967  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.080  -0.678   0.906  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.671  -0.306   1.840  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.514   0.963   0.829  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.740   1.066  -1.453  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.011   3.083  -0.208  1.00  0.00           H  
HETATM   18  H8  UNL     1      -1.125   1.895  -1.581  1.00  0.00           H  
HETATM   19  H9  UNL     1      -2.563   2.189  -0.585  1.00  0.00           H  
HETATM   20  H10 UNL     1      -1.619  -2.944  -1.095  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4    5    8
CONECT    4   16
CONECT    5    6    7    7
CONECT    6   17   18   19
CONECT    8    9    9   10
CONECT   10   20
END
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SMILES for #<Metabolite:0x00007fecf0acc3f0>

CC[C@](O)(C(C)=O)C(O)=O
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INCHI for #<Metabolite:0x00007fecf0acc3f0>

InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/t6-/m0/s1
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Synonyms
ValueSource
(S)-2-Acetyl-2-hydroxybutyric acidChEBI
(S)-2-Hydroxy-2-ethyl-3-oxobutanoateKegg
(S)-2-Acetyl-2-hydroxybutyrateGenerator
(S)-2-Hydroxy-2-ethyl-3-oxobutanoic acidGenerator
(S)-2-Aceto-2-hydroxybutanoateGenerator
(2S)-2-Ethyl-2-hydroxy-3-oxobutanoateHMDB
(2S)-2-Ethyl-2-hydroxy-3-oxobutanoic acidHMDB
2S-Acetyl-2-hydroxy-butanoateGenerator, HMDB
(S)-2-Aceto-2-hydroxy-butyrateHMDB
2-Aceto-2-hydroxybutyric acidHMDB
2-Ethyl-2-hydroxy-3-oxobutanoic acidHMDB
Acetohydroxybutyric acidHMDB
alpha-Aceto-alpha-hydroxybutyric acidHMDB
alpha-Acetohydroxybutyric acidHMDB
α-Aceto-α-hydroxybutyric acidHMDB
α-Acetohydroxybutyric acidHMDB
Molecular FormulaC6H10O4
Average Mass146.1412
Monoisotopic Mass146.057908808
IUPAC Name(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid
Traditional Name(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid
CAS Registry Number3142-65-2
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)/t6-/m0/s1
InChI KeyVUQLHQFKACOHNZ-LURJTMIESA-N