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Showing metabocard for 2-Isopropylmalic acid (HMDB0000402)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:47 UTC
HMDB IDHMDB0000402
Secondary Accession Numbers
  • HMDB00402
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
Data?1676999687
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000402 (2-Isopropylmalic acid)

 
  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 HMDB0000402 (2-Isopropylmalic acid)

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 HMDB0000402 (2-Isopropylmalic acid)

 
  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>
HMDB0000402

> <DATABASE_NAME>
hmdb

> <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 HMDB0000402 (2-Isopropylmalic acid)

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 HMDB0000402 (2-Isopropylmalic acid)

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 HMDB0000402 (2-Isopropylmalic acid)

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 HMDB0000402 (2-Isopropylmalic acid)

CC(C)[C@@](O)(CC(O)=O)C(O)=O
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INCHI for HMDB0000402 (2-Isopropylmalic acid)

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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View in JSmolView NMR AssignmentsView Stereo Labels
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
Chemical FormulaC7H12O5
Average Molecular Weight176.1672
Monoisotopic Molecular Weight176.068473494
IUPAC Name(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid
Traditional Name2-isopropyl-malic acid
CAS Registry Number49601-06-1
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point144 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg128.12230932474
[M-H]-Not Available128.122http://allccs.zhulab.cn/database/detail?ID=AllCCS00000191
Predicted Molecular Properties
PropertyValueSource
Water Solubility181 g/LALOGPS
logP-0.29ALOGPS
logP0.21ChemAxon
logS0.01ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.58 m³·mol⁻¹ChemAxon
Polarizability16.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.70631661259
DarkChem[M-H]-132.65831661259
AllCCS[M+H]+139.39532859911
AllCCS[M-H]-134.54132859911
DeepCCS[M+H]+131.93330932474
DeepCCS[M-H]-128.9830932474
DeepCCS[M-2H]-165.44930932474
DeepCCS[M+Na]+140.9530932474
AllCCS[M+H]+139.432859911
AllCCS[M+H-H2O]+135.632859911
AllCCS[M+NH4]+142.932859911
AllCCS[M+Na]+144.032859911
AllCCS[M-H]-134.532859911
AllCCS[M+Na-2H]-136.232859911
AllCCS[M+HCOO]-138.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.75 minutes32390414
Predicted by Siyang on May 30, 202210.2644 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.89 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid173.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid957.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid315.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid73.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid169.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid53.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid317.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid342.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)122.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid647.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid224.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid964.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid203.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid243.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate491.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA246.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water303.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Isopropylmalic acidCC(C)[C@@](O)(CC(O)=O)C(O)=O2540.7Standard polar33892256
2-Isopropylmalic acidCC(C)[C@@](O)(CC(O)=O)C(O)=O1125.9Standard non polar33892256
2-Isopropylmalic acidCC(C)[C@@](O)(CC(O)=O)C(O)=O1484.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Isopropylmalic acid,1TMS,isomer #1CC(C)[C@](CC(=O)O)(O[Si](C)(C)C)C(=O)O1510.8Semi standard non polar33892256
2-Isopropylmalic acid,1TMS,isomer #2CC(C)[C@@](O)(CC(=O)O[Si](C)(C)C)C(=O)O1483.2Semi standard non polar33892256
2-Isopropylmalic acid,1TMS,isomer #3CC(C)[C@@](O)(CC(=O)O)C(=O)O[Si](C)(C)C1448.4Semi standard non polar33892256
2-Isopropylmalic acid,2TMS,isomer #1CC(C)[C@](CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O1548.8Semi standard non polar33892256
2-Isopropylmalic acid,2TMS,isomer #2CC(C)[C@](CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1544.2Semi standard non polar33892256
2-Isopropylmalic acid,2TMS,isomer #3CC(C)[C@@](O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1497.6Semi standard non polar33892256
2-Isopropylmalic acid,3TMS,isomer #1CC(C)[C@](CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1595.8Semi standard non polar33892256
2-Isopropylmalic acid,1TBDMS,isomer #1CC(C)[C@](CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O1743.0Semi standard non polar33892256
2-Isopropylmalic acid,1TBDMS,isomer #2CC(C)[C@@](O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1726.4Semi standard non polar33892256
2-Isopropylmalic acid,1TBDMS,isomer #3CC(C)[C@@](O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1722.3Semi standard non polar33892256
2-Isopropylmalic acid,2TBDMS,isomer #1CC(C)[C@](CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O1994.3Semi standard non polar33892256
2-Isopropylmalic acid,2TBDMS,isomer #2CC(C)[C@](CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1987.9Semi standard non polar33892256
2-Isopropylmalic acid,2TBDMS,isomer #3CC(C)[C@@](O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1955.7Semi standard non polar33892256
2-Isopropylmalic acid,3TBDMS,isomer #1CC(C)[C@](CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2225.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-1c869c73651e7e4e5dda2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00bl-9134000000-30fabfd0c26c38444fff2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-004i-0900000000-1bb48f5ddadbf88b8f6c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-00kr-9400000000-5df8f3f29d2e8a962cac2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-05n0-9200000000-c62b1543d0e6a41388f12012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Negative-QTOFsplash10-014r-6900000000-983e4a8edd0725d269792021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Negative-QTOFsplash10-016r-1900000000-5aa4d41c6ff31081d9d72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Positive-QTOFsplash10-00di-9200000000-d4b84f7b5f2a53ac58002021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Positive-QTOFsplash10-0006-9000000000-c680094e514a83eea9782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Negative-QTOFsplash10-052o-9000000000-365c84abb7ec259fb43e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Positive-QTOFsplash10-0006-9000000000-e28ea8cd657f96ff83572021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Positive-QTOFsplash10-0690-1900000000-3b83300261e0daab2ef12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Positive-QTOFsplash10-0006-9700000000-2652db028b01706ac0422016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Positive-QTOFsplash10-00di-9300000000-808bda4307e96bcfcc832016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Negative-QTOFsplash10-003r-2900000000-9fa33cd594a81b5d67cd2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Negative-QTOFsplash10-055r-9700000000-8ab90438d0e6c9b7d0be2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Negative-QTOFsplash10-0a4r-9100000000-41e1c40b755f8bfaf0002016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Positive-QTOFsplash10-01x9-9800000000-53afadde706df1ef69ab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Positive-QTOFsplash10-0006-9000000000-4bfe3581b4b94540fea02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Positive-QTOFsplash10-0006-9000000000-1470f6a6a1859e4527122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Negative-QTOFsplash10-014i-2900000000-9a718ee22b675ce189802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Negative-QTOFsplash10-00kr-8900000000-188b5287c7dbbce2559f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Negative-QTOFsplash10-000l-9000000000-2a93d25f081bcaa86a532021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified0.114 +/- 0.0493 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.159 +/- 0.0746 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.218 +/- 0.138 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.247 +/- 0.161 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma 		details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011983
KNApSAcK IDC00019690
Chemspider ID4444155
KEGG Compound IDC02504
BioCyc ID3-CARBOXY-3-HYDROXY-ISOCAPROATE
BiGG IDNot Available
Wikipedia LinkIsopropylmalic acid
METLIN ID339
PubChem Compound5280523
PDB IDNot Available
ChEBI ID35128
Food Biomarker OntologyNot Available
VMH ID3C3HMP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSchloss J V; Magolda R; Emptage M Synthesis of alpha-isopropylmalate, beta-isopropylmalate, and dimethylcitraconate. Methods in enzymology (1988), 166 92-6.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Spiteller M, Spiteller G: [Occurrence of alpha-alkyl-substituted malic acids, and beta-hydroxy-beta-alkyl-substituted dicarboxylic and tricarboxylic acid derivatives in normal urine (author's transl)]. J Chromatogr. 1979 Nov 11;164(3):319-29. [PubMed:544608 ]
  2. Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. [PubMed:2338430 ]
  3. Verhaeghe BJ, Van Bocxlaer JF, De Leenheer AP: Gas chromatographic/mass spectrometric identification of 3-hydroxydicarboxylic acids in urine. Biol Mass Spectrom. 1992 Jan;21(1):27-32. [PubMed:1591279 ]
  4. Pinkston D, Spiteller G, Von Henning H, Matthaei D: High resolution gas chromatography mass spectrometry of the methyl esters of organic acids from uremic hemofiltrates. J Chromatogr. 1981 Apr 10;223(1):1-19. [PubMed:7251751 ]
  5. Maragoudakis ME, Strassman M: Biosynthesis of alpha-isopropylmalic and citric acids in Acetobacter suboxydans. J Bacteriol. 1967 Sep;94(3):512-6. [PubMed:6035258 ]