Showing metabocard for (S)-2-Acetolactate (MMDBc0029843)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:43:56 UTC
Update Date2022-08-31 17:19:19 UTC
Metabolite IDMMDBc0029843
Metabolite Identification
Common Name(S)-2-Acetolactate
Description(S)-2-Acetolactate is an intermediate in the biosynthesis of valine, leucine and isoleucine (KEGG ID C06010 ). It is the sixth to last step in the synthesis of protein and is converted from 2-hydroxy-3-methyl-2-oxobutanoate via the enzyme acetolactate synthase [EC:2.2.1.6]. It is then converted to 3-hydroxy-3-methyl-2-oxobutanoate via the enzyme ketol-acid reductoisomerase [EC:1.1.1.86].
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fecd400cf08>


  Mrv1652309092000142D          

  9  8  0  0  0  0            999 V2000
10004.526510004.2360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.811110004.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.242010004.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.113910003.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.938910003.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.096610004.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.811110005.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.957410004.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.242010005.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  1  5  1  1  0  0  0
  2  6  1  0  0  0  0
  2  7  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fecd400cf08>

HMDB0006855
     RDKit          3D
(S)-2-Acetolactate
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.6902   -0.7638    0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0989    0.5616    0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7719    1.5761    0.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543    0.6191   -0.2310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6882   -0.2058   -1.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7182    1.9314   -0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1232    0.1691    0.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289    0.9308    1.4891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -1.1101    1.4412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2510   -1.5729   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009   -0.7564    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976   -0.9902    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7561   -0.0467   -1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876   -1.2836   -1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757    0.2060   -2.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3969    2.4878    0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342   -1.7525    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  4  6  1  6
  4  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  9 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007fecd400cf08>


  Mrv1652309092000142D          

  9  8  0  0  0  0            999 V2000
10004.526510004.2360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.811110004.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.242010004.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.113910003.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.938910003.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.096610004.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.811110005.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.957410004.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.242010005.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  1  5  1  1  0  0  0
  2  6  1  0  0  0  0
  2  7  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029843

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)/t5-/m0/s1

> <INCHI_KEY>
NMDWGEGFJUBKLB-YFKPBYRVSA-N

> <FORMULA>
C5H8O4

> <MOLECULAR_WEIGHT>
132.1146

> <EXACT_MASS>
132.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.807991180939668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.2838843203333333

> <ALOGPS_LOGS>
0.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.416069462259802

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4493929439633346

> <JCHEM_PKA_STRONGEST_BASIC>
-4.591623143588905

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
28.590400000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.86e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetolactic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fecd400cf08>

HMDB0006855
     RDKit          3D
(S)-2-Acetolactate
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.6902   -0.7638    0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0989    0.5616    0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7719    1.5761    0.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543    0.6191   -0.2310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6882   -0.2058   -1.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7182    1.9314   -0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1232    0.1691    0.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289    0.9308    1.4891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -1.1101    1.4412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2510   -1.5729   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009   -0.7564    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976   -0.9902    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7561   -0.0467   -1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876   -1.2836   -1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757    0.2060   -2.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3969    2.4878    0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342   -1.7525    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  4  6  1  6
  4  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  9 17  1  0
M  END
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PDB for #<Metabolite:0x00007fecd400cf08>

HEADER    PROTEIN                                 09-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-20         0                                  
HETATM    1  C   UNK     0    8675.1168674.574   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8673.7818675.342   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8676.4528675.342   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8674.3468673.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8675.8868673.240   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8672.4478674.574   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8673.7818676.882   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8677.7878674.574   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8676.4528676.882   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7                                                  
CONECT    3    1    8    9                                                  
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    3                                                            
CONECT    9    3                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for #<Metabolite:0x00007fecd400cf08>

COMPND    HMDB0006855
HETATM    1  C1  UNL     1       1.690  -0.764   0.410  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.099   0.562   0.071  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.772   1.576   0.038  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.354   0.619  -0.231  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.688  -0.206  -1.463  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.718   1.931  -0.522  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.123   0.169   0.943  1.00  0.00           C  
HETATM    8  O3  UNL     1      -1.929   0.931   1.489  1.00  0.00           O  
HETATM    9  O4  UNL     1      -0.947  -1.110   1.441  1.00  0.00           O  
HETATM   10  H1  UNL     1       1.251  -1.573  -0.208  1.00  0.00           H  
HETATM   11  H2  UNL     1       2.801  -0.756   0.207  1.00  0.00           H  
HETATM   12  H3  UNL     1       1.598  -0.990   1.508  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.756  -0.047  -1.698  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.488  -1.284  -1.314  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.076   0.206  -2.287  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.397   2.488   0.221  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.734  -1.752   1.392  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    4
CONECT    4    5    6    7
CONECT    5   13   14   15
CONECT    6   16
CONECT    7    8    8    9
CONECT    9   17
END
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SMILES for #<Metabolite:0x00007fecd400cf08>

CC(=O)[C@](C)(O)C(O)=O
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INCHI for #<Metabolite:0x00007fecd400cf08>

InChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)/t5-/m0/s1
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Synonyms
ValueSource
(S)-2-Hydroxy-2-methyl-3-oxobutanoateChEBI
(2S)-2-Hydroxy-2-methyl-3-oxobutanoateKegg
(S)-2-Hydroxy-2-methyl-3-oxobutanoic acidGenerator
(2S)-2-Hydroxy-2-methyl-3-oxobutanoic acidGenerator
(S)-2-Acetolactic acidGenerator
13-Biotinyl-lys-dynorphin a amide (1-13)HMDB
b-DYN aHMDB
(S)-alpha-Acetolactic acidHMDB
(S)-α-Acetolactic acidHMDB
2-Acetolactic acidHMDB
2-Hydroxy-2-methyl-3-oxobutanoic acidHMDB
Acetolactic acidHMDB
Molecular FormulaC5H8O4
Average Mass132.1146
Monoisotopic Mass132.042258744
IUPAC Name(2S)-2-hydroxy-2-methyl-3-oxobutanoic acid
Traditional Nameacetolactic acid
CAS Registry NumberNot Available
SMILES
CC(=O)[C@](C)(O)C(O)=O
InChI Identifier
InChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)/t5-/m0/s1
InChI KeyNMDWGEGFJUBKLB-YFKPBYRVSA-N