Showing metabocard for 3-Carboxy-3-hydroxy-isocaproate (MMDBc0029761)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:40:32 UTC
Update Date2022-08-31 17:16:45 UTC
Metabolite IDMMDBc0029761
Metabolite Identification
Common Name3-Carboxy-3-hydroxy-isocaproate
Description3-carboxy-3-hydroxy-isocaproate is a member of the chemical class known as Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups. Alpha isopropylmalate is involved in the biosynthesis of leucine. The protein product of MJ0720 was found to be alpha-isopropylmalate dehydrogenase (LeuB) and was found to catalyze the NAD-dependent decarboxylation of one isomer of DL-threo-isopropylmalate to 2-ketoisocaproate; thus, it is involved in the biosynthesis of leucine. (PMID 10940051 )
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00005645c6c0c440>

Structure #1
  Mrv0541 02241206292D          

 12 11  0  0  0  0            999 V2000
    1.5395   -1.0164    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
    2.2539    1.6500    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  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    2.0625    0.0000 O   0  5  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
    0.8250   -0.8250    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
  1  4  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
M  CHG  2   9  -1  11  -1
M  END
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3D MOL for #<Metabolite:0x00005645c6c0c440>

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3D SDF for #<Metabolite:0x00005645c6c0c440>
Structure #1
  Mrv0541 02241206292D          

 12 11  0  0  0  0            999 V2000
    1.5395   -1.0164    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
    2.2539    1.6500    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  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    2.0625    0.0000 O   0  5  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
    0.8250   -0.8250    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
  1  4  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
M  CHG  2   9  -1  11  -1
M  END
> <DATABASE_ID>
MMDBc0029761

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/p-2

> <INCHI_KEY>
BITYXLXUCSKTJS-UHFFFAOYSA-L

> <FORMULA>
C7H10O5

> <MOLECULAR_WEIGHT>
174.1513

> <EXACT_MASS>
174.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
15.486856051775783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2-(propan-2-yl)butanedioate

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
0.20661967933333347

> <ALOGPS_LOGS>
-0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.566000838313116

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.629835264652623

> <JCHEM_PKA_STRONGEST_BASIC>
-4.140578200901909

> <JCHEM_POLAR_SURFACE_AREA>
100.49

> <JCHEM_REFRACTIVITY>
60.2583

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-isopropylmalate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00005645c6c0c440>
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PDB for #<Metabolite:0x00005645c6c0c440>
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.874  -1.897   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       4.207   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.541   3.850   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0       0.206   0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    5    7                                                       
CONECT    4    1    2    7                                                  
CONECT    5    3    8    9                                                  
CONECT    6    7   10   11                                                  
CONECT    7    3    4    6   12                                             
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for #<Metabolite:0x00005645c6c0c440>
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SMILES for #<Metabolite:0x00005645c6c0c440>
CC(C)C(O)(CC([O-])=O)C([O-])=O
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INCHI for #<Metabolite:0x00005645c6c0c440>
InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/p-2
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Synonyms
ValueSource
2-Hydroxy-2-isopropylsuccinateChEBI
3-Carboxy-3-hydroxy-4-methylpentanoateChEBI
3-Carboxy-3-hydroxyisocaproateChEBI
3-Hydroxy-4-methyl-3-carboxypentanoateChEBI
alpha-IsopropylmalateChEBI
2-Hydroxy-2-isopropylsuccinic acidGenerator
3-Carboxy-3-hydroxy-4-methylpentanoic acidGenerator
3-Carboxy-3-hydroxyisocaproic acidGenerator
3-Hydroxy-4-methyl-3-carboxypentanoic acidGenerator
a-IsopropylmalateGenerator
a-Isopropylmalic acidGenerator
alpha-Isopropylmalic acidGenerator
Α-isopropylmalateGenerator
Α-isopropylmalic acidGenerator
3-Carboxy-3-hydroxy-isocaproic acidGenerator
Molecular FormulaC7H10O5
Average Mass174.1513
Monoisotopic Mass174.05282343
IUPAC Name2-hydroxy-2-(propan-2-yl)butanedioate
Traditional Name2-isopropylmalate
CAS Registry NumberNot Available
SMILES
CC(C)C(O)(CC([O-])=O)C([O-])=O
InChI Identifier
InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/p-2
InChI KeyBITYXLXUCSKTJS-UHFFFAOYSA-L