Showing metabocard for Oxalic acid (MMDBc0000217)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:40:08 UTC
Update Date2022-08-31 00:14:57 UTC
Metabolite IDMMDBc0000217
Metabolite Identification
Common NameOxalic acid
DescriptionOxalic acid is a strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent (Pubchem). Oxalic acid (IUPAC name: ethanedioic acid, formula H2C2O4) is a dicarboxylic acid with structure (HOOC)-(COOH). Because of the joining of two carboxyl groups, this is one of the strongest organic acids. It is also a reducing agent. The anions of oxalic acid as well as its salts and esters are known as oxalates (Wikipedia ). Bodily oxalic acid may also be synthesized via the metabolism of either glyoxylic acid or unused ascorbic acid (vitamin C), which is a serious health consideration for long term megadosers of vitamin C supplements. 80% of kidney stones are formed from calcium oxalate. Some Aspergillus species produce oxalic acid, which reacts with blood or tissue calcium to precipitate calcium oxalate. There is some preliminary evidence that the administration of probiotics can affect oxalic acid excretion rates (and presumably oxalic acid levels as well) (Wikipedia ). Oxalic acid is found to be associated with fumarase deficiency and primary hyperoxaluria I, which are inborn errors of metabolism. Oxalic acid is a marker for yeast overgrowth from Aspergillus, Penicillum and/or Candida. Can also be elevated due to exposures from vitamin C or ethylene glycol poisoning. Oxalate is elevated in the urine of children with autism. (PMID: 21911305 ). Oxalic acid has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f5a9c140160>


  Mrv0541 02231217162D          

  6  5  0  0  0  0            999 V2000
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f5a9c140160>

HMDB0002329
     RDKit          3D
Oxalic acid
  8  7  0  0  0  0  0  0  0  0999 V2000
   -0.9001   -0.9019   -1.4683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7712   -0.2195   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8812    0.3943    0.1098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -0.0699    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6127    0.6164    1.2443 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510   -0.6760   -0.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853    1.2076    0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5587   -0.3510   -0.0568 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  2  0
  4  6  1  0
  3  7  1  0
  6  8  1  0
M  END
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3D SDF for #<Metabolite:0x00007f5a9c140160>


  Mrv0541 02231217162D          

  6  5  0  0  0  0            999 V2000
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000217

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)

> <INCHI_KEY>
MUBZPKHOEPUJKR-UHFFFAOYSA-N

> <FORMULA>
C2H2O4

> <MOLECULAR_WEIGHT>
90.0349

> <EXACT_MASS>
89.995308552

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
6.229225106776085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
oxalic acid

> <ALOGPS_LOGP>
-0.51

> <JCHEM_LOGP>
-0.2637515693333333

> <ALOGPS_LOGS>
-0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.110222978861222

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3639908147001307

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
14.4386

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.57e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxalic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f5a9c140160>

HMDB0002329
     RDKit          3D
Oxalic acid
  8  7  0  0  0  0  0  0  0  0999 V2000
   -0.9001   -0.9019   -1.4683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7712   -0.2195   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8812    0.3943    0.1098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -0.0699    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6127    0.6164    1.2443 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510   -0.6760   -0.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853    1.2076    0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5587   -0.3510   -0.0568 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  2  0
  4  6  1  0
  3  7  1  0
  6  8  1  0
M  END
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PDB for #<Metabolite:0x00007f5a9c140160>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for #<Metabolite:0x00007f5a9c140160>

COMPND    HMDB0002329
HETATM    1  O1  UNL     1      -0.900  -0.902  -1.468  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.771  -0.220  -0.428  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.881   0.394   0.110  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.515  -0.070   0.209  1.00  0.00           C  
HETATM    5  O3  UNL     1       0.613   0.616   1.244  1.00  0.00           O  
HETATM    6  O4  UNL     1       1.651  -0.676  -0.310  1.00  0.00           O  
HETATM    7  H1  UNL     1      -1.785   1.208   0.700  1.00  0.00           H  
HETATM    8  H2  UNL     1       2.559  -0.351  -0.057  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    7
CONECT    4    5    5    6
CONECT    6    8
END
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SMILES for #<Metabolite:0x00007f5a9c140160>

OC(=O)C(O)=O
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INCHI for #<Metabolite:0x00007f5a9c140160>

InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)
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Synonyms
ValueSource
EthandisaeureChEBI
Ethane-1,2-dioic acidChEBI
Ethanedioic acidChEBI
H2OxChEBI
HOOCCOOHChEBI
OxalsaeureChEBI
Ethane-1,2-dioateGenerator
EthanedioateGenerator
OxalateGenerator
Ammonium oxalateHMDB
Ethanedioic acid dihydrateHMDB
EthanedionateHMDB
Ethanedionic acidHMDB
Kyselina stavelovaHMDB
OxaalzuurHMDB
Oxalic acid 2-hydrateHMDB
Oxalic acid anhydrousHMDB
Oxalic acid diammonium saltHMDB
Oxalic acid dihydrateHMDB
Acid, oxalicHMDB
Aluminum oxalateHMDB
Chromium (3+) oxalate (3:2)HMDB
Dipotassium oxalateHMDB
Iron oxalateHMDB
Magnesium oxalateHMDB
Magnesium oxalate (1:1)HMDB
Oxalate, dilithiumHMDB
Oxalate, disodiumHMDB
Oxalate, monohydrogen monopotassiumHMDB
Oxalate, monopotassiumHMDB
Oxalate, potassiumHMDB
Chromium oxalateHMDB
Dilithium oxalateHMDB
Manganese (2+) oxalate (1:1)HMDB
Monosodium oxalateHMDB
Oxalate, chromiumHMDB
Oxalate, dipotassiumHMDB
Oxalate, magnesiumHMDB
Oxalate, monosodiumHMDB
Oxalate, potassium chromiumHMDB
Oxalate, sodiumHMDB
Potassium oxalateHMDB
Potassium oxalate (2:1)HMDB
Diammonium oxalateHMDB
Disodium oxalateHMDB
Oxalate, aluminumHMDB
Oxalate, diammoniumHMDB
Oxalate, ferricHMDB
Oxalate, monoammoniumHMDB
Potassium chromium oxalateHMDB
Chromium (2+) oxalateHMDB
Ferric oxalateHMDB
Iron (2+) oxalate (1:1)HMDB
Iron (3+) oxalateHMDB
Monoammonium oxalateHMDB
Monohydrogen monopotassium oxalateHMDB
Monopotassium oxalateHMDB
Oxalate, ironHMDB
Sodium oxalateHMDB
Oxalic acidKEGG
Molecular FormulaC2H2O4
Average Mass90.0349
Monoisotopic Mass89.995308552
IUPAC Nameoxalic acid
Traditional Nameoxalic acid
CAS Registry Number144-62-7
SMILES
OC(=O)C(O)=O
InChI Identifier
InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)
InChI KeyMUBZPKHOEPUJKR-UHFFFAOYSA-N