Showing metabocard for 2-Isopropylmalic acid (MMDBc0000343)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:35:46 UTC
Update Date2024-04-30 19:31:52 UTC
Metabolite IDMMDBc0000343
Metabolite Identification
Common Name2-Isopropylmalic acid
Description2-Isopropylmalic acid (CAS: 3237-44-3), also known as 3-carboxy-3-hydroxyisocaproic acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Isopropylmalic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Isopropylmalic acid is an alpha-hydroxy organic acid regularly occurring in the urine of healthy individuals (PMID: 2338430 , 544608 ), and in hemofiltrates (PMID: 7251751 ). 2-Isopropylmalic acid is elevated during fasting and diabetic ketoacidosis (PMID: 1591279 ). It is also a metabolite found in Acetobacter (PMID: 6035258 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb58cb7df8>

 
  Mrv1652309042000012D          
 
 12 11  0  0  1  0            999 V2000
   10.5611   -8.7683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2737   -8.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -8.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5611   -9.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9900   -8.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1323   -8.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -7.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8864  -10.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2775  -10.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0089   -9.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7026   -8.3551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1931   -9.1702    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  1  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  1 12  1  6  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fdb58cb7df8>

HMDB0000402
     RDKit          3D
2-Isopropylmalic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -2.1116   -0.6181    0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6157   -0.6108   -0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0111   -1.7475    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0246    0.7427    0.0893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1741    1.0130    1.4487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908    0.9135   -0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3712   -0.0008    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8352    0.1678    1.3424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -1.0860   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381    1.7304   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8524    1.6725   -1.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    2.6939   -0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1762   -0.4263    1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4490   -1.6771   -0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849    0.0525   -0.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5909   -0.7560   -1.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643   -2.4239   -0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659   -1.4876    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7918   -2.4267    1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639    0.1722    1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7081    1.9577   -0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070    0.9540   -1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416   -2.0456   -0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2637    3.2361    0.7796 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  1
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  4 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
  5 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
 12 24  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fdb58cb7df8>

 
  Mrv1652309042000012D          
 
 12 11  0  0  1  0            999 V2000
   10.5611   -8.7683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2737   -8.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -8.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5611   -9.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9900   -8.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1323   -8.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -7.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8864  -10.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2775  -10.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0089   -9.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7026   -8.3551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1931   -9.1702    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  1  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  1 12  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000343

> <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)/t7-/m0/s1

> <INCHI_KEY>
BITYXLXUCSKTJS-ZETCQYMHSA-N

> <FORMULA>
C7H12O5

> <MOLECULAR_WEIGHT>
176.1672

> <EXACT_MASS>
176.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.372264381734986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
0.20661967933333347

> <ALOGPS_LOGS>
0.01

> <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>
94.83

> <JCHEM_REFRACTIVITY>
38.5841

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-isopropyl-malic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fdb58cb7df8>

HMDB0000402
     RDKit          3D
2-Isopropylmalic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -2.1116   -0.6181    0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6157   -0.6108   -0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0111   -1.7475    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0246    0.7427    0.0893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1741    1.0130    1.4487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908    0.9135   -0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3712   -0.0008    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8352    0.1678    1.3424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -1.0860   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381    1.7304   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8524    1.6725   -1.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    2.6939   -0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1762   -0.4263    1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4490   -1.6771   -0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849    0.0525   -0.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5909   -0.7560   -1.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643   -2.4239   -0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659   -1.4876    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7918   -2.4267    1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639    0.1722    1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7081    1.9577   -0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070    0.9540   -1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416   -2.0456   -0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2637    3.2361    0.7796 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  1
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  4 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
  5 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
 12 24  1  0
M  END
Download

PDB for #<Metabolite:0x00007fdb58cb7df8>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      19.714 -16.367   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.044 -15.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.384 -15.603   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.714 -17.910   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.381 -16.367   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.047 -16.367   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.384 -14.061   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      18.455 -18.674   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      21.051 -18.674   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      22.417 -18.044   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      23.712 -15.596   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      20.894 -17.118   0.000  0.00  0.00           O+0
CONECT    1    2    3    4   12                                             
CONECT    2    1    5                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    5                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for #<Metabolite:0x00007fdb58cb7df8>

COMPND    HMDB0000402
HETATM    1  C1  UNL     1      -2.112  -0.618   0.142  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.616  -0.611  -0.213  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.011  -1.748   0.539  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.025   0.743   0.089  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.174   1.013   1.449  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.391   0.913  -0.378  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.371  -0.001   0.184  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.835   0.168   1.342  1.00  0.00           O  
HETATM    9  O3  UNL     1       2.829  -1.086  -0.528  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.838   1.730  -0.654  1.00  0.00           C  
HETATM   11  O4  UNL     1      -0.852   1.672  -1.897  1.00  0.00           O  
HETATM   12  O5  UNL     1      -1.565   2.694  -0.006  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.176  -0.426   1.216  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.449  -1.677  -0.042  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.685   0.052  -0.499  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.591  -0.756  -1.321  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.464  -2.424  -0.231  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.666  -1.488   1.347  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.792  -2.427   1.001  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.364   0.172   1.932  1.00  0.00           H  
HETATM   21  H9  UNL     1       1.708   1.958  -0.079  1.00  0.00           H  
HETATM   22  H10 UNL     1       1.407   0.954  -1.494  1.00  0.00           H  
HETATM   23  H11 UNL     1       2.842  -2.046  -0.182  1.00  0.00           H  
HETATM   24  H12 UNL     1      -1.264   3.236   0.780  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5    6   10
CONECT    5   20
CONECT    6    7   21   22
CONECT    7    8    8    9
CONECT    9   23
CONECT   10   11   11   12
CONECT   12   24
END
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SMILES for #<Metabolite:0x00007fdb58cb7df8>

CC(C)[C@@](O)(CC(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007fdb58cb7df8>

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)/t7-/m0/s1
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Synonyms
ValueSource
(2S)-2-Hydroxy-2-isopropylsuccinic acidChEBI
(2S)-2-IsopropylmalateChEBI
(3S)-3-Carboxy-3-hydroxy-4-methylpentanoic acidChEBI
(3S)-3-Carboxy-3-hydroxyisocaproic acidChEBI
(S)-2-Hydroxy-2-(isopropyl)succinic acidChEBI
3-Carboxy-3-hydroxy-4-methylpentanoateChEBI
3-Carboxy-3-hydroxyisocaproateChEBI
(2S)-2-Hydroxy-2-isopropylsuccinateGenerator
(2S)-2-Isopropylmalic acidGenerator
(3S)-3-Carboxy-3-hydroxy-4-methylpentanoateGenerator
(3S)-3-Carboxy-3-hydroxyisocaproateGenerator
(S)-2-Hydroxy-2-(isopropyl)succinateGenerator
3-Carboxy-3-hydroxy-4-methylpentanoic acidGenerator
3-Carboxy-3-hydroxyisocaproic acidGenerator
2-IsopropylmalateGenerator
2-Hydroxy-2-isopropylsuccinateHMDB
2-Hydroxy-2-isopropylsuccinic acidHMDB
2-Isopropyl-2-hydroxybutanedioateHMDB
2-Isopropyl-2-hydroxybutanedioic acidHMDB
2-Isopropyl-malic acidHMDB
a-IsopropylmalateHMDB
a-Isopropylmalic acidHMDB
alpha-IsopropylmalateHMDB
alpha-Isopropylmalic acidHMDB
(2S)-2-Hydroxy-2-(1-methylethyl)butanedioic acidHMDB
(2S)-2-Hydroxy-2-(propan-2-yl)butanedioic acidHMDB
(S)-(+)-2-Isopropylmalic acidHMDB
2-Hydroxy-2-(1-methylethyl)butanedioic acidHMDB
Α-isopropylmalateHMDB
Α-isopropylmalic acidHMDB
2-Isopropylmalic acidHMDB
Molecular FormulaC7H12O5
Average Mass176.1672
Monoisotopic Mass176.068473494
IUPAC Name(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid
Traditional Name2-isopropyl-malic acid
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)/t7-/m0/s1
InChI KeyBITYXLXUCSKTJS-ZETCQYMHSA-N