Showing metabocard for 3-Isopropylmalate (MMDBc0029811)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:42:41 UTC
Update Date2024-04-30 19:42:19 UTC
Metabolite IDMMDBc0029811
Metabolite Identification
Common Name3-Isopropylmalate
Description3-Isopropylmalate is an intermediate in valine, leucine and isoleucine biosynthesis. It is a substrate for 3-isopropylmalate dehydrogenase (TT_C0867)
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005634c2cb4c68>


  Mrv1652309042000342D          

 12 11  0  0  1  0            999 V2000
    0.3562    0.0001    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3562   -0.4092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0687   -0.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562    0.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3562   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    1.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3600    1.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914    0.8983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851   -0.4130    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
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  5 11  2  0  0  0  0
  5 12  1  0  0  0  0
  3  8  2  0  0  0  0
  3  7  1  0  0  0  0
  4 10  1  0  0  0  0
  4  9  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00005634c2cb4c68>

HMDB0012156
     RDKit          3D
3-Isopropylmalic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -1.5392    0.3182   -1.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9392   -0.6098   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0591   -1.0032    0.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802   -0.0398    0.6024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1708    1.1255    1.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    1.0636    2.6504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6526    2.3230    0.8952 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3767    0.3669   -0.2519 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3086    0.8721    0.6687 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9989   -0.7480   -0.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3675   -1.3561   -1.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2837   -1.1385   -0.6694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2886    0.9981   -0.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1405   -0.2863   -1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8043    0.8759   -1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6468   -1.5467   -0.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367   -2.0852    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0515   -0.7777    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9580   -0.3893    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -0.8416    1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369    2.7694    0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1231    1.2221   -0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5126    0.1398    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9557   -1.2523   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  7 21  1  0
  8 22  1  6
  9 23  1  0
 12 24  1  0
M  END
Download

3D SDF for #<Metabolite:0x00005634c2cb4c68>


  Mrv1652309042000342D          

 12 11  0  0  1  0            999 V2000
    0.3562    0.0001    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3562   -0.4092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0687   -0.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562    0.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3562   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    1.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3600    1.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914    0.8983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851   -0.4130    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
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  5 11  2  0  0  0  0
  5 12  1  0  0  0  0
  3  8  2  0  0  0  0
  3  7  1  0  0  0  0
  4 10  1  0  0  0  0
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029811

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-5,8H,1-2H3,(H,9,10)(H,11,12)/t4-,5+/m0/s1

> <INCHI_KEY>
RNQHMTFBUSSBJQ-CRCLSJGQSA-N

> <FORMULA>
C7H12O5

> <MOLECULAR_WEIGHT>
176.1672

> <EXACT_MASS>
176.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.470268701415307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioic acid

> <ALOGPS_LOGP>
0.28

> <JCHEM_LOGP>
0.1609326116666665

> <ALOGPS_LOGS>
-0.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.519667331107795

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6770578154838125

> <JCHEM_PKA_STRONGEST_BASIC>
-4.015599488752675

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
38.5993

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.33e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-3-isopropylmalic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00005634c2cb4c68>

HMDB0012156
     RDKit          3D
3-Isopropylmalic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -1.5392    0.3182   -1.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9392   -0.6098   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0591   -1.0032    0.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802   -0.0398    0.6024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1708    1.1255    1.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    1.0636    2.6504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6526    2.3230    0.8952 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3767    0.3669   -0.2519 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3086    0.8721    0.6687 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9989   -0.7480   -0.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3675   -1.3561   -1.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2837   -1.1385   -0.6694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2886    0.9981   -0.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1405   -0.2863   -1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8043    0.8759   -1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6468   -1.5467   -0.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367   -2.0852    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0515   -0.7777    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9580   -0.3893    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -0.8416    1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369    2.7694    0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1231    1.2221   -0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5126    0.1398    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9557   -1.2523   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  7 21  1  0
  8 22  1  6
  9 23  1  0
 12 24  1  0
M  END
Download

PDB for #<Metabolite:0x00005634c2cb4c68>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       0.665   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.665  -0.764   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.995  -0.764   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.665   1.542   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.665  -2.306   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.332   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.995  -2.306   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.002   2.306   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.672   2.306   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.037   1.677   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.332  -0.771   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    8    7                                                  
CONECT    4    1   10    9                                                  
CONECT    5    2   11   12                                                  
CONECT    6    2                                                            
CONECT    7    3                                                            
CONECT    8    3                                                            
CONECT    9    4                                                            
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    5                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
Download

3D PDB for #<Metabolite:0x00005634c2cb4c68>

COMPND    HMDB0012156
HETATM    1  C1  UNL     1      -1.539   0.318  -1.201  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.939  -0.610  -0.206  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.059  -1.003   0.768  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.180  -0.040   0.602  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.171   1.126   1.403  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.035   1.064   2.650  1.00  0.00           O  
HETATM    7  O2  UNL     1      -0.653   2.323   0.895  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.377   0.367  -0.252  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.309   0.872   0.669  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.999  -0.748  -0.967  1.00  0.00           C  
HETATM   11  O4  UNL     1       1.368  -1.356  -1.856  1.00  0.00           O  
HETATM   12  O5  UNL     1       3.284  -1.138  -0.669  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.289   0.998  -0.705  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.141  -0.286  -1.918  1.00  0.00           H  
HETATM   15  H3  UNL     1      -0.804   0.876  -1.805  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.647  -1.547  -0.714  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.037  -2.085   0.978  1.00  0.00           H  
HETATM   18  H6  UNL     1      -3.051  -0.778   0.339  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.958  -0.389   1.680  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.552  -0.842   1.268  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.337   2.769   0.067  1.00  0.00           H  
HETATM   22  H10 UNL     1       1.123   1.222  -0.912  1.00  0.00           H  
HETATM   23  H11 UNL     1       2.513   0.140   1.306  1.00  0.00           H  
HETATM   24  H12 UNL     1       3.956  -1.252  -1.419  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5    8   20
CONECT    5    6    6    7
CONECT    7   21
CONECT    8    9   10   22
CONECT    9   23
CONECT   10   11   11   12
CONECT   12   24
END
Download

SMILES for #<Metabolite:0x00005634c2cb4c68>

CC(C)[C@@H]([C@@H](O)C(O)=O)C(O)=O
Download

INCHI for #<Metabolite:0x00005634c2cb4c68>

InChI=1S/C7H12O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-5,8H,1-2H3,(H,9,10)(H,11,12)/t4-,5+/m0/s1
Download
Synonyms
ValueSource
(2R,3S)-2-Hydroxy-3-isopropylsuccinic acidChEBI
(2R,3S)-3-Carboxy-2-hydroxy-4-methylpentanoic acidChEBI
2-D-Threo-hydroxy-3-carboxy-isocaproateChEBI
2-D-Threo-hydroxy-3-carboxyisocaproic acidChEBI
3-Carboxy-2-hydroxy-4-methylpentanoateChEBI
3-IsopropylmalateChEBI
(2R,3S)-2-Hydroxy-3-isopropylsuccinateGenerator
(2R,3S)-3-Carboxy-2-hydroxy-4-methylpentanoateGenerator
2-D-Threo-hydroxy-3-carboxy-isocaproic acidGenerator
2-D-Threo-hydroxy-3-carboxyisocaproateGenerator
3-Carboxy-2-hydroxy-4-methylpentanoic acidGenerator
3-Isopropylmalic acidGenerator
(2R,3S)-2-Hydroxy-3-(propan-2-yl)butanedioateHMDB
(2R,3S)-2-Hydroxy-3-(propan-2-yl)butanedioic acidHMDB
(2R,3S)-3-IsopropylmalateHMDB
(2R,3S)-3-Isopropylmalic acidHMDB
3-3-Isopropylmalic acidHMDB
IPMHMDB
beta-Isopropylmalate, erythro-(L)-isomerMeSH, HMDB
beta-IsopropylmalateMeSH, HMDB
(2R,3S)-2-Hydroxy-3-(1-methylethyl)butanedioic acidHMDB
2-Hydroxy-3-(1-methylethyl)butanedioic acidHMDB
IsopropylmalateHMDB
Isopropylmalic acidHMDB
beta-Isopropylmalic acidHMDB
β-Isopropylmalic acidHMDB
Molecular FormulaC7H12O5
Average Mass176.1672
Monoisotopic Mass176.068473494
IUPAC Name(2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioic acid
Traditional Name(2R,3S)-3-isopropylmalic acid
CAS Registry Number921-28-8
SMILES
CC(C)[C@@H]([C@@H](O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H12O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-5,8H,1-2H3,(H,9,10)(H,11,12)/t4-,5+/m0/s1
InChI KeyRNQHMTFBUSSBJQ-CRCLSJGQSA-N