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Showing NP-Card for Isocitric acid (NP0001276)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-07-01 14:27:20 UTC
NP-MRD IDNP0001276
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001276 (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 NP0001276 (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 NP0001276 (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>
NP0001276

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0001276 (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 NP0001276 (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 NP0001276 (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 NP0001276 (Isocitric acid)

OC(C(CC(O)=O)C(O)=O)C(O)=O
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INCHI for NP0001276 (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 JSmol
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 Mass192.1235 Da
Monoisotopic Mass192.02700 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
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Actinidia chinensisFooDB
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AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bryophyllum calycinumKNApSAcK Database
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chlamydomonas reinhardtiiLOTUS Database
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonKNApSAcK Database
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Couroupita guianensisLOTUS Database
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Digitalis purpureaLOTUS Database
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Eleusine coracanaLOTUS Database
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyacinthoides non-scriptaLOTUS Database
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Kalanchoe fedtschenkoiLOTUS Database
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
Mycoplasma gallisepticumLOTUS Database
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengKNApSAcK Database
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Populus tremulaLOTUS Database
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Pseudo-nitzschia multistriataLOTUS Database
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
Rubus spp.KNApSAcK Database
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumKNApSAcK Database
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point162 - 165 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility466 mg/mLNot Available
LogPNot AvailableNot Available
Predicted 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
HMDB IDHMDB0000193
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003281
KNApSAcK IDC00001188
Chemspider ID1161
KEGG Compound IDC00311
BioCyc IDIsocitrate
BiGG ID34579
Wikipedia LinkIsocitric_acid
METLIN ID3328
PubChem Compound1198
PDB IDNot Available
ChEBI ID30887
Good Scents IDNot Available
References
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 ]