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Showing NP-Card for 1,2,3-Propanetricarboxylic acid (NP0001186)

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Record Information
Version2.0
Created at2012-09-11 17:41:33 UTC
Updated at2024-09-03 04:22:05 UTC
NP-MRD IDNP0001186
Natural Product DOIhttps://doi.org/10.57994/2735
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,2,3-Propanetricarboxylic acid
Description1,2,3-Propanetricarboxylic acid is found in corn. 1,2,3-Propanetricarboxylic acid is isolated from plants e.G. Sugarbeet sap, sap of Acer saccharinum (maple syrup). Propane-1,2,3-tricarboxylic acid, also known as tricarballylic acid, carballylic acid, and beta-carboxyglutaric acid, is a tricarboxylic acid that has three carboxylic acid functional groups. The compound is an inhibitor of the enzyme aconitase and interferes with the Krebs cycle. 1,2,3-Propanetricarboxylic acid can be produced by Bacteroides, Butyrivibrio, Megasphaera, Wolinella and fungi Nectriaceae (PMID:22815244 ; PMID:16346691 ). It is also associated with Fumonisins. Fumonisins are fungal toxins produced by Fusarium verticilloides. Detection of this compound indicates presence of fumonisins in gastrointestinal tract. Corn intake or corn contaminated with fumonisins can lead to increased levels of tricarballylic acid (PMID:22815244 ).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0001186 (1,2,3-Propanetricarboxylic acid)


  Mrv1652305261923522D          

 12 11  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 O   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
    2.4750    0.6039    0.0000 O   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
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   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
    3.9039    0.6039    0.0000 C   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
    3.1895    0.1914    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
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3D MOL for NP0001186 (1,2,3-Propanetricarboxylic acid)

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3D SDF for NP0001186 (1,2,3-Propanetricarboxylic acid)

  Mrv1652305261923522D          

 12 11  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 O   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
    2.4750    0.6039    0.0000 O   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
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   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
    3.9039    0.6039    0.0000 C   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
    3.1895    0.1914    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001186

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O6/c7-4(8)1-3(6(11)12)2-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

> <INCHI_KEY>
KQTIIICEAUMSDG-UHFFFAOYSA-N

> <FORMULA>
C6H8O6

> <MOLECULAR_WEIGHT>
176.1241

> <EXACT_MASS>
176.032087988

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.79262659473791

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.56

> <JCHEM_LOGP>
-0.7311697890000002

> <ALOGPS_LOGS>
-0.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.856543738559703

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.594567578813867

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
34.377900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tricarballylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0001186 (1,2,3-Propanetricarboxylic acid)
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PDB for NP0001186 (1,2,3-Propanetricarboxylic acid)
HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0       3.286   3.437   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.287   1.127   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.621   0.357   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.954   0.357   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0001186 (1,2,3-Propanetricarboxylic acid)
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SMILES for NP0001186 (1,2,3-Propanetricarboxylic acid)
OC(=O)CC(CC(O)=O)C(O)=O
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INCHI for NP0001186 (1,2,3-Propanetricarboxylic acid)
InChI=1S/C6H8O6/c7-4(8)1-3(6(11)12)2-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
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Synonyms
ValueSource
3-Carboxyglutaric acidChEBI
3-Carboxypentanedioic acidChEBI
beta-Carboxyglutaric acidChEBI
Carballylic acidChEBI
Carboxymethylsuccinic acidChEBI
TricarballylateKegg
3-CarboxyglutarateGenerator
3-CarboxypentanedioateGenerator
b-CarboxyglutarateGenerator
b-Carboxyglutaric acidGenerator
beta-CarboxyglutarateGenerator
Β-carboxyglutarateGenerator
Β-carboxyglutaric acidGenerator
CarballylateGenerator
CarboxymethylsuccinateGenerator
Tricarballylic acidGenerator
1,2,3-PropanetricarboxylateGenerator
1,2,3-Tripropanetricarboxylic acidHMDB
Propane 1,2,3-tricarboxylic acidHMDB
Tricarballylic acid, trisodium saltHMDB
Propane-1,2,3-tricarboxylateHMDB
Tricarballylic acid, sodium saltHMDB
1,2,3-Propanetricarboxylic acidChEBI
Chemical FormulaC6H8O6
Average Mass176.1241 Da
Monoisotopic Mass176.03209 Da
IUPAC Namepropane-1,2,3-tricarboxylic acid
Traditional Nametricarballylic acid
CAS Registry Number99-14-9
SMILES
OC(=O)CC(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H8O6/c7-4(8)1-3(6(11)12)2-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChI KeyKQTIIICEAUMSDG-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, D2O, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
Species
Species of Origin
Species NameSourceReference
Acer saccharinumPlant
Zea mays L.FooDB
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
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point166 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility37.8 g/LALOGPS
logP-0.56ALOGPS
logP-0.73ChemAxon
logS-0.67ALOGPS
pKa (Strongest Acidic)3.59ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.38 m³·mol⁻¹ChemAxon
Polarizability14.79 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031193  
DrugBank IDDB04562  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003213  
KNApSAcK IDNot Available
Chemspider ID14220  
KEGG Compound IDC19806  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropane-1,2,3-tricarboxylic acid  
METLIN IDNot Available
PubChem Compound14925  
PDB IDTRC  
ChEBI ID45969  
Good Scents IDNot Available
References
General References
  1. Russell JB: Enrichment and Isolation of Rumen Bacteria That Reduce trans- Aconitic Acid to Tricarballylic Acid. Appl Environ Microbiol. 1985 Jan;49(1):120-6. doi: 10.1128/aem.49.1.120-126.1985. [PubMed:16346691  ] 
  2.  (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .