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Showing metabocard for Isocitric acid (HMDB0000193)

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enzymes (7) Show 7 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:56:00 UTC
HMDB IDHMDB0000193
Secondary Accession Numbers
  • HMDB00193
Metabolite Identification
Common NameIsocitric acid
DescriptionIsocitric acid, also known as isocitrate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Isocitric acid is a TCA (tricarboxylic acid) cycle intermediate. It is a structural isomer of citric acid and is formed from citrate with the help of the enzyme aconitase. More specifically, Isocitric acid is synthesized from citric acid via the intermediate cis-aconitic acid by the enzyme aconitase (aconitate hydratase). Isocitrate is acted upon by isocitrate dehydrogenase (IDH) to form alpha-ketoglutarate. This is a two-step process, which involves oxidation of isocitrate to oxalosuccinate (a ketone), followed by the decarboxylation of the carboxyl group beta to the ketone, forming alpha-ketoglutarate. In humans, IDH exists in three isoforms: IDH3 catalyzes the third step of the citric acid cycle while converting NAD+ to NADH in the mitochondria. The isoforms IDH1 and IDH2 catalyze the same reaction outside the context of the citric acid cycle and use NADP+ as a cofactor instead of NAD+. They localize to the cytosol as well as the mitochondrion and peroxisome. Isocitric acid exists in all living species, ranging from bacteria to plants to humans. Isocitric acid is a minor organic acid found in most fruit juices, especially in blackberries, youngberries, and boyberries, and in vegetables, especially in carrots. The determination of D-isocitric acid has become of importance in the analysis of fruit juices for the detection of illegal additives (adulteration). Since the quantities of citric and isocitric acids are correlated in fruit juices, a high ratio of citric to isocitric acid can indicate the addition of citric acid as an alduterant. In authentic orange juice, for example, the ratio of citric acid to D-isocitric acid is usually less than 130. Isocitric acid is mostly used in the food industry (food additive) as a food acidulant.
Structure
Data?1582752115
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000193 (Isocitric acid)


  Mrv1652305271900172D          

 13 12  0  0  0  0            999 V2000
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
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3D MOL for HMDB0000193 (Isocitric acid)

HMDB0000193
     RDKit          3D
Isocitric acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.4382    0.1096    1.2675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0067    0.8823    0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014    1.9199    0.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    0.7439   -0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549   -0.4730    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645   -1.6952   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383   -2.4499   -1.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562   -2.1206    0.2680 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4414   -0.5255   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -1.7409   -0.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3216    0.5620   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3025    0.2693    0.6803 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349    1.8906   -0.3598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676    2.7432    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780    0.7684   -1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1390    1.6896   -0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -0.4718    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5374   -2.5482   -0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726   -0.5652   -1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -1.6526    0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3952    2.6642    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 13 21  1  0
M  END
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3D SDF for HMDB0000193 (Isocitric acid)


  Mrv1652305271900172D          

 13 12  0  0  0  0            999 V2000
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000193

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(C(CC(O)=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)

> <INCHI_KEY>
ODBLHEXUDAPZAU-UHFFFAOYSA-N

> <FORMULA>
C6H8O7

> <MOLECULAR_WEIGHT>
192.1235

> <EXACT_MASS>
192.02700261

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.55020163539311

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-hydroxypropane-1,2,3-tricarboxylic acid

> <ALOGPS_LOGP>
-0.35

> <JCHEM_LOGP>
-1.4463282496666667

> <ALOGPS_LOGS>
-0.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.676758742531203

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.068323851495594

> <JCHEM_PKA_STRONGEST_BASIC>
-4.021353286822632

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
35.7161

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isocitric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000193 (Isocitric acid)

HMDB0000193
     RDKit          3D
Isocitric acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.4382    0.1096    1.2675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0067    0.8823    0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014    1.9199    0.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    0.7439   -0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549   -0.4730    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645   -1.6952   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383   -2.4499   -1.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562   -2.1206    0.2680 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4414   -0.5255   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -1.7409   -0.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3216    0.5620   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3025    0.2693    0.6803 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349    1.8906   -0.3598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676    2.7432    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780    0.7684   -1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1390    1.6896   -0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -0.4718    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5374   -2.5482   -0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726   -0.5652   -1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -1.6526    0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3952    2.6642    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 13 21  1  0
M  END
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PDB for HMDB0000193 (Isocitric acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.286   3.437   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.287   1.127   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.954   0.357   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.621   0.357   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0000193 (Isocitric acid)

COMPND    HMDB0000193
HETATM    1  O1  UNL     1      -2.438   0.110   1.267  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.007   0.882   0.384  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.901   1.920   0.041  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.700   0.744  -0.248  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.055  -0.473   0.142  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.665  -1.695  -0.236  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.138  -2.450  -1.126  1.00  0.00           O  
HETATM    8  O4  UNL     1      -1.856  -2.121   0.268  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.441  -0.526  -0.503  1.00  0.00           C  
HETATM   10  O5  UNL     1       1.980  -1.741  -0.016  1.00  0.00           O  
HETATM   11  C6  UNL     1       2.322   0.562  -0.043  1.00  0.00           C  
HETATM   12  O6  UNL     1       3.302   0.269   0.680  1.00  0.00           O  
HETATM   13  O7  UNL     1       2.135   1.891  -0.360  1.00  0.00           O  
HETATM   14  H1  UNL     1      -2.968   2.743   0.638  1.00  0.00           H  
HETATM   15  H2  UNL     1      -0.878   0.768  -1.362  1.00  0.00           H  
HETATM   16  H3  UNL     1      -0.139   1.690  -0.047  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.290  -0.472   1.257  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.537  -2.548  -0.344  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.373  -0.565  -1.616  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.934  -1.653   0.989  1.00  0.00           H  
HETATM   21  H8  UNL     1       2.395   2.664   0.234  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6    9   17
CONECT    6    7    7    8
CONECT    8   18
CONECT    9   10   11   19
CONECT   10   20
CONECT   11   12   12   13
CONECT   13   21
END
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SMILES for HMDB0000193 (Isocitric acid)

OC(C(CC(O)=O)C(O)=O)C(O)=O
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INCHI for HMDB0000193 (Isocitric acid)

InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-Hydroxypropane-1,2,3-tricarboxylic acidChEBI
1-Hydroxytricarballylic acidChEBI
1-Hydroxypropane-1,2,3-tricarboxylateGenerator
1-HydroxytricarballylateGenerator
IsocitrateGenerator
1-Hydroxy-1,2,3-propanetricarboxylateHMDB
1-Hydroxy-1,2,3-propanetricarboxylic acidHMDB
3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylateHMDB
3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acidHMDB
3-Carboxy-2,3-dideoxy-pentarateHMDB
3-Carboxy-2,3-dideoxy-pentaric acidHMDB
D-IsocitrateHMDB
I-citHMDB
Threo-D(S)-iso-citrateHMDB
Threo-DS-isocitrateHMDB
Isocitric acid, sodium saltHMDB
Isocitric acid, trisodium saltHMDB
Isocitric acid, disodium saltHMDB
Isocitric acid, (11)C-labeledHMDB
Isocitric acid, calcium saltHMDB
Isocitric acid, potassium saltHMDB
Chemical FormulaC6H8O7
Average Molecular Weight192.1235
Monoisotopic Molecular Weight192.02700261
IUPAC Name1-hydroxypropane-1,2,3-tricarboxylic acid
Traditional Nameisocitric acid
CAS Registry Number320-77-4
SMILES
OC(C(CC(O)=O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)
InChI KeyODBLHEXUDAPZAU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Monosaccharide
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point162 - 165 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility466 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available127.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00000008
Predicted Molecular Properties
PropertyValueSource
Water Solubility52.5 g/LALOGPS
logP-0.35ALOGPS
logP-1.4ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.72 m³·mol⁻¹ChemAxon
Polarizability15.55 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]+142.23631661259
DarkChem[M-H]-136.97731661259
AllCCS[M+H]+141.80432859911
AllCCS[M-H]-132.73832859911
DeepCCS[M+H]+131.1330932474
DeepCCS[M-H]-127.30530932474
DeepCCS[M-2H]-164.92930932474
DeepCCS[M+Na]+140.46830932474
AllCCS[M+H]+141.832859911
AllCCS[M+H-H2O]+138.132859911
AllCCS[M+NH4]+145.332859911
AllCCS[M+Na]+146.332859911
AllCCS[M-H]-132.732859911
AllCCS[M+Na-2H]-133.932859911
AllCCS[M+HCOO]-135.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isocitric acidOC(C(CC(O)=O)C(O)=O)C(O)=O2892.0Standard polar33892256
Isocitric acidOC(C(CC(O)=O)C(O)=O)C(O)=O1240.9Standard non polar33892256
Isocitric acidOC(C(CC(O)=O)C(O)=O)C(O)=O1765.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isocitric acid,1TMS,isomer #1C[Si](C)(C)OC(C(=O)O)C(CC(=O)O)C(=O)O1727.0Semi standard non polar33892256
Isocitric acid,1TMS,isomer #2C[Si](C)(C)OC(=O)CC(C(=O)O)C(O)C(=O)O1715.6Semi standard non polar33892256
Isocitric acid,1TMS,isomer #3C[Si](C)(C)OC(=O)C(CC(=O)O)C(O)C(=O)O1720.3Semi standard non polar33892256
Isocitric acid,1TMS,isomer #4C[Si](C)(C)OC(=O)C(O)C(CC(=O)O)C(=O)O1702.5Semi standard non polar33892256
Isocitric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(CC(=O)O)C(=O)O1763.5Semi standard non polar33892256
Isocitric acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CC(C(=O)O)C(O[Si](C)(C)C)C(=O)O1759.1Semi standard non polar33892256
Isocitric acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C(CC(=O)O)C(O[Si](C)(C)C)C(=O)O1779.8Semi standard non polar33892256
Isocitric acid,2TMS,isomer #4C[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C)C(O)C(=O)O1755.5Semi standard non polar33892256
Isocitric acid,2TMS,isomer #5C[Si](C)(C)OC(=O)CC(C(=O)O)C(O)C(=O)O[Si](C)(C)C1737.8Semi standard non polar33892256
Isocitric acid,2TMS,isomer #6C[Si](C)(C)OC(=O)C(O)C(CC(=O)O)C(=O)O[Si](C)(C)C1754.5Semi standard non polar33892256
Isocitric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CC(C(=O)O)C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1791.9Semi standard non polar33892256
Isocitric acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C(CC(=O)O)C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1794.3Semi standard non polar33892256
Isocitric acid,3TMS,isomer #3C[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)O1795.8Semi standard non polar33892256
Isocitric acid,3TMS,isomer #4C[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C)C(O)C(=O)O[Si](C)(C)C1776.9Semi standard non polar33892256
Isocitric acid,4TMS,isomer #1C[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1864.1Semi standard non polar33892256
Isocitric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C(=O)O)C(CC(=O)O)C(=O)O1978.9Semi standard non polar33892256
Isocitric acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC(C(=O)O)C(O)C(=O)O1971.6Semi standard non polar33892256
Isocitric acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)C(O)C(=O)O1972.5Semi standard non polar33892256
Isocitric acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(O)C(CC(=O)O)C(=O)O1960.3Semi standard non polar33892256
Isocitric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(CC(=O)O)C(=O)O2198.1Semi standard non polar33892256
Isocitric acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)O2193.1Semi standard non polar33892256
Isocitric acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)O2210.3Semi standard non polar33892256
Isocitric acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)C(=O)O2216.3Semi standard non polar33892256
Isocitric acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)CC(C(=O)O)C(O)C(=O)O[Si](C)(C)C(C)(C)C2202.8Semi standard non polar33892256
Isocitric acid,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)C(O)C(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2207.8Semi standard non polar33892256
Isocitric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2433.8Semi standard non polar33892256
Isocitric acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2449.2Semi standard non polar33892256
Isocitric acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)O2451.0Semi standard non polar33892256
Isocitric acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)C(=O)O[Si](C)(C)C(C)(C)C2434.5Semi standard non polar33892256
Isocitric acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2625.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Isocitric acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0002-1952000000-7c34751686a6bdb54cab2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isocitric acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0002-0963000000-459b45ff9246b5f559142014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isocitric acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0942000000-61204d02a28e43d216072014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isocitric acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9420000000-4e1a59fe735855d52ce22014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isocitric acid GC-MS (4 TMS)splash10-00ea-3793000000-84858fa896697420275f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isocitric acid GC-EI-TOF (Non-derivatized)splash10-0002-1952000000-7c34751686a6bdb54cab2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isocitric acid GC-EI-TOF (Non-derivatized)splash10-0002-0963000000-459b45ff9246b5f559142017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isocitric acid GC-EI-TOF (Non-derivatized)splash10-00di-9420000000-4e1a59fe735855d52ce22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isocitric acid GC-MS (Non-derivatized)splash10-00ea-3793000000-84858fa896697420275f2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ba-7900000000-96194d87d52b155cf1b92016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (4 TMS) - 70eV, Positivesplash10-02vi-7029500000-2bb65fc897e48cc217502017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocitric acid GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0006-0901310000-883764bf7b686ca7fd172012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-03di-0900000000-66d03405eeb126c6ad9d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-00di-0900000000-cdad17a11f419421c7872012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0udi-0009000000-d3440c84a488b3e222122012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0006-0900000000-3aa263561a7a49df7d3d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0006-1900000000-3636f87026e4206a16382012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-01w3-9600000000-ab1a2b9a29528a623d0b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0079-9000000000-3c33cefeb87f85efd5de2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-059m-9000000000-34775db8bbc0080186332012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-QQ , negative-QTOFsplash10-0006-0900000000-3aa263561a7a49df7d3d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-QQ , negative-QTOFsplash10-0006-1900000000-3636f87026e4206a16382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-QQ , negative-QTOFsplash10-01w3-9600000000-ab1a2b9a29528a623d0b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-QQ , negative-QTOFsplash10-0079-9000000000-3c33cefeb87f85efd5de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-QQ , negative-QTOFsplash10-059m-9000000000-34775db8bbc0080186332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-ITFT , negative-QTOFsplash10-03di-0900000000-66d03405eeb126c6ad9d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid LC-ESI-ITFT , negative-QTOFsplash10-00di-0900000000-cdad17a11f419421c7872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid , negative-QTOFsplash10-03k9-2900000000-e5336d859bf90bcd904c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid 10V, Negative-QTOFsplash10-03k9-2900000000-8ef1bf8afd67194ddf652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid 40V, Negative-QTOFsplash10-059f-9000000000-37227e36af9ba4db4a7e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid 20V, Negative-QTOFsplash10-022i-9500000000-cb0234d7a355d54f17552021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid 10V, Negative-QTOFsplash10-03k9-3900000000-1b8cb16b24c65e87915b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid 20V, Negative-QTOFsplash10-03ki-9500000000-d264dd60719df8b72ef32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid 40V, Negative-QTOFsplash10-00di-9000000000-bf62fc70edcee073c5172021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid 30V, Negative-QTOFsplash10-02mi-9200000000-42ca838ca7f08cc3882e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocitric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0udi-1900000000-8e1185b0504ea15477152012-07-24HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H 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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Semen
  • Urine
Tissue Locations
  • Adrenal Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.0 (0.0-10.0) uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified38 (23-53) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified10.0 +/- 9.0 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified4.17 +/- 1.75 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified0.988 +/- 0.531 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.294 +/- 0.267 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
 details
SalivaDetected and Quantified0.616 +/- 0.351 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.616 +/- 0.351 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SemenDetected and Quantified400 - 1500 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified52.403 +/- 28.756 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified56.8(19.4-119.1) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified30-57 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified94.3 (29.8-154.4) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified120.1 (101.1-265.3) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified53.7 (31.9-83.1) umol/mmol creatinineChildren (1-13 years old)Both
Normal		 details
UrineDetected and Quantified45.0 (18.0-69.9) umol/mmol creatinineChildren (1-13 years old)Both
Normal		 details
UrineDetected and Quantified38.9 (16.0-118.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified19.0 (5.0-34.0) umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified7.7 (5.0-12.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified24.52 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
 details
UrineDetected and Quantified58 (36-84) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified46.9 (20.4-89.2) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified19.08 (5.26 - 42.76) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified22.0 +/- 13.8 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified27-43 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified14.7 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified45.72 +/- 2.77 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cellular CytoplasmDetected and Quantified15 (14.8-15.2) uMAdult (>18 years old)BothAnoxia details
SalivaDetected and Quantified3.75 +/- 2.89 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified3.28 +/- 1.43 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified3.98 +/- 0.15 uMAdult (>18 years old)BothLewy body disease details
UrineDetected and Quantified90.008 +/- 97.639 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
Anoxia
  1. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [PubMed:8579834 ]
Alzheimer's disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
  • 104300 (Alzheimer's disease)
  • 600274 (Frontotemporal dementia)
  • 601313 (Autosomal dominant polycystic kidney disease)
  • 610247 (Eosinophilic esophagitis)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003281
KNApSAcK IDC00001188
Chemspider ID1161
KEGG Compound IDC00311
BioCyc IDIsocitrate
BiGG ID34579
Wikipedia LinkIsocitric_acid
METLIN ID3328
PubChem Compound1198
PDB IDNot Available
ChEBI ID30887
Food Biomarker OntologyNot Available
VMH IDICIT
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceFinogenova, T. V.; Kamzolova, S. V.; Dedyukhina, E. G.; Shishkanova, N. V.; Il'chenko, A. P.; Morgunov, I. G.; Chernyavskaya, O. G.; Sokolov, A. P. Biosynthesis of citric and isocitric acids from ethanol by mutant Yarrowia lipolytica N 1 under continuous cultivation. Applied Microbiology and Biotechnology (2002), 59(4-5), 493-500.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  3. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [PubMed:8579834 ]
  4. Stromme JH, Borud O, Moe PJ: Fatal lactic acidosis in a newborn attributable to a congenital defect of pyruvate dehydrogenase. Pediatr Res. 1976 Jan;10(1):62-6. [PubMed:813176 ]
  5. Sutor DJ, Percival JM, Doonan S: Isolation and identification of some urinary inhibitors of calcium phosphate formation. Clin Chim Acta. 1978 Oct 16;89(2):273-8. [PubMed:213213 ]
  6. Ebeling K, Ruckhaberle KE, Bilek K: [Studies on the recording of cytostatic effects on organ cultures of squamous cell carcinoma of the uterine cervix]. Zentralbl Gynakol. 1977;99(20):1249-59. [PubMed:595962 ]
  7. Sutor DJ, Percival JM, Doonan S: Urinary inhibitor of the formation of calcium oxalate. Br J Urol. 1979 Aug;51(4):253-5. [PubMed:223711 ]
  8. Hennequin C, Lalanne V, Daudon M, Lacour B, Drueke T: A new approach to studying inhibitors of calcium oxalate crystal growth. Urol Res. 1993 Mar;21(2):101-8. [PubMed:8389069 ]
  9. Kavanagh JP: Isocitric and citric acid in human prostatic and seminal fluid: implications for prostatic metabolism and secretion. Prostate. 1994;24(3):139-42. [PubMed:8115279 ]
  10. Mikosha AS, Monissarenko VP, Bychkovskaia LA: [Properties of adrenocortical isocitrate dehydrogenase]. Vopr Med Khim. 1981 Nov-Dec;27(6):736-9. [PubMed:7336646 ]
  11. Sutor DJ, Percival JM: The estimation of D-isocitric acid in urine using isocitrate dehydrogenase. Clin Chim Acta. 1978 Jun;86(2):223-5. [PubMed:657545 ]

Enzymes

Enzyme Details
1. Aconitate hydratase, mitochondrial
General function:
Involved in metabolic process
Specific function:
Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:
ACO2
Uniprot ID:
Q99798
Molecular weight:
85424.745
Reactions
Citric acid → Isocitric aciddetails
Isocitric acid → cis-Aconitic acid + Waterdetails
Enzyme Details
2. Cytoplasmic aconitate hydratase
General function:
Involved in metabolic process
Specific function:
Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding. Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:
ACO1
Uniprot ID:
P21399
Molecular weight:
98398.14
Reactions
Citric acid → Isocitric aciddetails
Isocitric acid → cis-Aconitic acid + Waterdetails
Enzyme Details
3. Isocitrate dehydrogenase [NADP], mitochondrial
General function:
Involved in magnesium ion binding
Specific function:
Plays a role in intermediary metabolism and energy production. It may tightly associate or interact with the pyruvate dehydrogenase complex.
Gene Name:
IDH2
Uniprot ID:
P48735
Molecular weight:
50908.915
Reactions
Isocitric acid + NADP → Oxoglutaric acid + CO(2) + NADPHdetails
Isocitric acid + NADP → Oxoglutaric acid + Carbon dioxide + NADPH + Hydrogen Iondetails
Isocitric acid + NADP → Oxalosuccinic acid + NADPH + Hydrogen Iondetails
Enzyme Details
4. Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial
General function:
Involved in magnesium ion binding
Specific function:
Not Available
Gene Name:
IDH3B
Uniprot ID:
O43837
Molecular weight:
42183.39
Reactions
Isocitric acid + NAD → Oxoglutaric acid + CO(2) + NADHdetails
Isocitric acid + NAD → Oxoglutaric acid + Carbon dioxide + NADH + Hydrogen Iondetails
Enzyme Details
5. Isocitrate dehydrogenase [NADP] cytoplasmic
General function:
Involved in magnesium ion binding
Specific function:
Not Available
Gene Name:
IDH1
Uniprot ID:
O75874
Molecular weight:
46659.005
Reactions
Isocitric acid + NADP → Oxoglutaric acid + CO(2) + NADPHdetails
Isocitric acid + NADP → Oxoglutaric acid + Carbon dioxide + NADPH + Hydrogen Iondetails
Isocitric acid + NADP → Oxalosuccinic acid + NADPH + Hydrogen Iondetails
Enzyme Details
6. Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrial
General function:
Involved in magnesium ion binding
Specific function:
Not Available
Gene Name:
IDH3A
Uniprot ID:
P50213
Molecular weight:
39591.365
Reactions
Isocitric acid + NAD → Oxoglutaric acid + CO(2) + NADHdetails
Isocitric acid + NAD → Oxoglutaric acid + Carbon dioxide + NADH + Hydrogen Iondetails
Enzyme Details
7. Isocitrate dehydrogenase [NAD] subunit gamma, mitochondrial
General function:
Involved in magnesium ion binding
Specific function:
Not Available
Gene Name:
IDH3G
Uniprot ID:
P51553
Molecular weight:
42793.97
Reactions
Isocitric acid + NAD → Oxoglutaric acid + CO(2) + NADHdetails
Isocitric acid + NAD → Oxoglutaric acid + Carbon dioxide + NADH + Hydrogen Iondetails