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Showing NP-Card for Mesoxalic acid (NP0047276)

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Record Information
Version2.0
Created at2022-03-17 20:37:30 UTC
Updated at2022-03-17 20:37:30 UTC
NP-MRD IDNP0047276
Secondary Accession NumbersNone
Natural Product Identification
Common NameMesoxalic acid
DescriptionMesoxalic acid, also known as a-ketomalonate or ketomalonic acid, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Mesoxalic acid is a moderately acidic compound (based on its pKa). Outside of the human body, Mesoxalic acid has been detected, but not quantified in, a few different foods, such as cereals and cereal products, common pea, and herbs and spices. This could make mesoxalic acid a potential biomarker for the consumption of these foods. It is also prepared by the oxidation of glycerol with the help of bismuth(III) nitrate. These terms are also used for salts containing this anion, such as sodium mesoxalate, Na2C3O5; and for esters containing the −C3O5− or −O−(CO)3−O− moiety, such as diethyl mesoxalate, (C2H5)2C3O5. In product catalogs and other contexts, the terms "mesoxalic acid", "oxomalonic acid" and so on often refer to this "hydrated" compound. Mesoxalate is one of the oxocarbon anions, which (like carbonate CO2−3 and oxalate C2O2−4) consist solely of carbon and oxygen. It readily loses two protons to yield the divalent anion C3O2−5, called mesoxalate, oxomalonate, or ketomalonate. Mesoxalic acid, also called oxomalonic acid or ketomalonic acid, is an organic compound with formula C3H2O5 or HO−(CO)3−OH.Mesoxalic acid is both a dicarboxylic acid and a ketonic acid. The product can be obtained also by oxidation of tartronic acid or glycerol. In particular, the product traded as "sodium mesoxalate monohydrate" is almost always sodium dihydroxymalonate. Mesoxalic acid readily absorbs and reacts with water to form a product commonly called "mesoxalic acid monohydrate", more properly dihydroxymalonic acid, HO−(CO)−C(OH)2−(CO)−OH. Mesoxalic acid can be obtained synthetically by hydrolysis of alloxan with baryta water, by warming caffuric acid with lead acetate solution, or from glycerin diacetate and concentrated nitric acid in the cold. Since they are carried out in water, these procedures generally give the dihydroxy derivative.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047276 (Mesoxalic acid)


  Mrv0541 02231217022D          

  8  7  0  0  0  0            999 V2000
    1.2375    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for NP0047276 (Mesoxalic acid)

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3D SDF for NP0047276 (Mesoxalic acid)

  Mrv0541 02231217022D          

  8  7  0  0  0  0            999 V2000
    1.2375    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047276

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H2O5/c4-1(2(5)6)3(7)8/h(H,5,6)(H,7,8)

> <INCHI_KEY>
XEEVLJKYYUVTRC-UHFFFAOYSA-N

> <FORMULA>
C3H2O5

> <MOLECULAR_WEIGHT>
118.045

> <EXACT_MASS>
117.990223174

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
8.0490078164927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxopropanedioic acid

> <ALOGPS_LOGP>
-0.43

> <JCHEM_LOGP>
0.025468098333333355

> <ALOGPS_LOGS>
-0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.72307514560714

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5608712626362866

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
19.7846

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mesoxalic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047276 (Mesoxalic acid)
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PDB for NP0047276 (Mesoxalic acid)
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       2.310   4.001   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   2.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    8  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    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0047276 (Mesoxalic acid)
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SMILES for NP0047276 (Mesoxalic acid)
OC(=O)C(=O)C(O)=O
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INCHI for NP0047276 (Mesoxalic acid)
InChI=1S/C3H2O5/c4-1(2(5)6)3(7)8/h(H,5,6)(H,7,8)
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Synonyms
ValueSource
ALPHA-KETOMALONIC ACIDChEBI
Ketomalonic acidChEBI
Oxomalonic acidKegg
a-KETOMALONateGenerator
a-KETOMALONic acidGenerator
alpha-KETOMALONateGenerator
Α-ketomalonateGenerator
Α-ketomalonic acidGenerator
KetomalonateGenerator
OxomalonateGenerator
MesoxalateGenerator
2-Oxomalonic acidHMDB
2-Oxopropanedioic acidHMDB
Mesoxalic acid, 8ciHMDB
Propanedioic acid, oxo- (9ci)HMDB
Mesoxalic acidChEBI
Chemical FormulaC3H2O5
Average Mass118.0450 Da
Monoisotopic Mass117.99022 Da
IUPAC Name2-oxopropanedioic acid
Traditional Namemesoxalic acid
CAS Registry Number473-90-5
SMILES
OC(=O)C(=O)C(O)=O
InChI Identifier
InChI=1S/C3H2O5/c4-1(2(5)6)3(7)8/h(H,5,6)(H,7,8)
InChI KeyXEEVLJKYYUVTRC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pisum sativumFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassDicarboxylic acids and derivatives  
Direct ParentDicarboxylic acids and derivatives  
Alternative Parents
Substituents
  • Keto acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Alpha-keto acid
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.43ALOGPS
logP0.025ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.78 m³·mol⁻¹ChemAxon
Polarizability8.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031522  
DrugBank IDDB03589  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008123  
KNApSAcK IDNot Available
Chemspider ID9727  
KEGG Compound IDC00830  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMesoxalic acid  
METLIN IDNot Available
PubChem Compound10132  
PDB IDMAK  
ChEBI ID30842  
Good Scents IDNot Available
References
General ReferencesNot Available