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Showing NP-Card for Oxalosuccinic acid (NP0087114)

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Record Information
Version2.0
Created at2022-05-11 16:40:30 UTC
Updated at2022-05-11 16:40:30 UTC
NP-MRD IDNP0087114
Secondary Accession NumbersNone
Natural Product Identification
Common NameOxalosuccinic acid
DescriptionOxalosuccinic acid, also known as oxalosuccinate or oxalbernsteinsaeure, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Oxalosuccinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Oxalosuccinic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Oxalosuccinic acid has been detected, but not quantified in, several different foods, such as buffalo currants, cauliflowers, coconuts, black-eyed pea, and tree ferns. Oxalosuccinic acid was first documented in 1948 (PMID: 18914069). This could make oxalosuccinic acid a potential biomarker for the consumption of these foods (PMID: 14089428).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087114 (Oxalosuccinic acid)


  Mrv0541 02231219512D          

 13 12  0  0  0  0            999 V2000
   22.7418  -10.3701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4563  -12.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3143   -9.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4563   -9.1326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7418  -11.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5997  -11.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8853   -9.1326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1708  -10.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1708  -11.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4563   -9.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4563  -11.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5997  -10.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8853   -9.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4 10  2  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  9 11  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for NP0087114 (Oxalosuccinic acid)

     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
    1.8095    2.0136    0.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8670    0.7507    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    0.1119    1.1255 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1370    0.0381   -0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726   -0.5623   -0.5301 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0724   -1.5871    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0215   -1.8887    1.0167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2299   -2.1758    0.9809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2959    0.3402   -0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2273    0.3409   -1.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807    1.2219    0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6543    1.2551    1.7902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772    2.0563    0.9505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000   -0.1835    0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8023   -0.8359   -1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0412    0.6051   -1.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441   -1.1784   -1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7450   -2.8510    0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0323    2.5289    0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
  5  9  1  0
  9 10  2  0
  9 11  1  0
 11 13  1  0
 11 12  2  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  6
  8 18  1  0
 13 19  1  0
M  END
Download

3D SDF for NP0087114 (Oxalosuccinic acid)


  Mrv0541 02231219512D          

 13 12  0  0  0  0            999 V2000
   22.7418  -10.3701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4563  -12.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3143   -9.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4563   -9.1326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7418  -11.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5997  -11.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8853   -9.1326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1708  -10.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1708  -11.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4563   -9.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4563  -11.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5997  -10.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8853   -9.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4 10  2  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  9 11  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087114

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13)

> <INCHI_KEY>
UFSCUAXLTRFIDC-UHFFFAOYSA-N

> <FORMULA>
C6H6O7

> <MOLECULAR_WEIGHT>
190.1076

> <EXACT_MASS>
190.011352546

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
14.948859457050037

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.55

> <JCHEM_LOGP>
-0.37458442233333333

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.4363481700589906

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.377884943609863

> <JCHEM_PKA_STRONGEST_BASIC>
-9.959494974326967

> <JCHEM_POLAR_SURFACE_AREA>
128.96999999999997

> <JCHEM_REFRACTIVITY>
35.1747

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxalosuccinate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0087114 (Oxalosuccinic acid)

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PDB for NP0087114 (Oxalosuccinic 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      42.451 -19.358   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      43.785 -23.208   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      49.120 -18.588   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      43.785 -17.048   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      42.451 -20.898   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      47.786 -20.898   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      46.453 -17.048   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      45.119 -19.358   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      45.119 -20.898   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      43.785 -18.588   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      43.785 -21.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      47.786 -19.358   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      46.453 -18.588   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   10                                                            
CONECT    5   11                                                            
CONECT    6   12                                                            
CONECT    7   13                                                            
CONECT    8    9   10   13                                                  
CONECT    9    8   11                                                       
CONECT   10    1    4    8                                                  
CONECT   11    2    5    9                                                  
CONECT   12    3    6   13                                                  
CONECT   13    7    8   12                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

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3D PDB for NP0087114 (Oxalosuccinic acid)
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SMILES for NP0087114 (Oxalosuccinic acid)
OC(=O)CC(C(O)=O)C(=O)C(O)=O
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INCHI for NP0087114 (Oxalosuccinic acid)
InChI=1S/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13)
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View in JSmol
Synonyms
ValueSource
1-Oxopropane-1,2,3-tricarboxylateChEBI
OxalbernsteinsaeureChEBI
OxalosuccinateChEBI
1-Oxopropane-1,2,3-tricarboxylic acidGenerator
Oxalosuccinic acidKEGG
Chemical FormulaC6H6O7
Average Mass190.1076 Da
Monoisotopic Mass190.01135 Da
IUPAC Name1-oxopropane-1,2,3-tricarboxylic acid
Traditional Nameoxalosuccinate
CAS Registry NumberNot Available
SMILES
OC(=O)CC(C(O)=O)C(=O)C(O)=O
InChI Identifier
InChI=1S/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13)
InChI KeyUFSCUAXLTRFIDC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
    • 

  • Gamma-keto acid
    • 

  • Beta-keto acid
    • 

  • Alpha-keto acid
    • 

  • Beta-hydroxy ketone
    • 

  • Keto acid
    • 

  • 1,3-dicarbonyl compound
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Carboxylic acid
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • 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-0.55ALOGPS
logP-0.37ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)-10ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.97 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.17 m³·mol⁻¹ChemAxon
Polarizability14.95 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003974  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031076  
KNApSAcK IDNot Available
Chemspider ID947  
KEGG Compound IDC05379  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxalosuccinic_acid  
METLIN ID6996  
PubChem Compound972  
PDB IDNot Available
ChEBI ID7815  
Good Scents IDNot Available
References
General References
  1. HUELSMANN WC: SYNTHESIS OF MALONYL-COENZYME A FROM ACETYL-COENZYME A AND OXALOSUCCINATE IN MITOCHONDRIA. Biochim Biophys Acta. 1963 Nov 8;77:502-3. doi: 10.1016/0006-3002(63)90528-6. [PubMed:14089428  ] 
  2. OCHOA S: Biosynthesis of tricarboxylic acids by carbon dioxide fixation; the preparation and properties of oxalosuccinic acid. J Biol Chem. 1948 May;174(1):115-22. [PubMed:18914069  ]