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Record Information
Version3.6
Creation Date2012-09-11 17:41:33 UTC
Update Date2016-02-11 01:56:40 UTC
HMDB IDHMDB31193
Secondary Accession NumbersNone
Metabolite 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. (Wikipedia) 1,2,3-Propanetricarboxylic acid belongs to the family of Tricarboxylic Acids and Derivatives. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof).
Structure
Thumb
Synonyms
ValueSource
1,2,3-Propanetricarboxylic acidChEBI
3-Carboxyglutaric acidChEBI
3-Carboxypentanedioic acidChEBI
beta-Carboxyglutaric acidChEBI
Carballylic acidChEBI
Carboxymethylsuccinic acidChEBI
1,2,3-PropanetricarboxylateGenerator
Propane-1,2,3-tricarboxylateGenerator
3-CarboxyglutarateGenerator
3-CarboxypentanedioateGenerator
b-CarboxyglutarateGenerator
b-Carboxyglutaric acidGenerator
beta-CarboxyglutarateGenerator
β-carboxyglutarateGenerator
β-carboxyglutaric acidGenerator
CarballylateGenerator
CarboxymethylsuccinateGenerator
1,2,3-Tripropanetricarboxylic acidHMDB
Propane 1,2,3-tricarboxylic acidHMDB
TricarballylateHMDB
Tricarballylic acidHMDB
Chemical FormulaC6H8O6
Average Molecular Weight176.1241
Monoisotopic Molecular Weight176.032087988
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 KeyInChIKey=KQTIIICEAUMSDG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
  • Microbial
BiofunctionNot Available
Application
  • Drug
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point166 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility37.8 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.38 m3·mol-1ChemAxon
Polarizability14.79 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
MSMass Spectrum (Electron Ionization)splash10-01p6-9200000000-49fb526d0b36a4723f55View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04562
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003213
KNApSAcK IDNot Available
Chemspider ID14220
KEGG Compound IDC19806
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1,2,3-Propanetricarboxylic_acid
NuGOwiki LinkHMDB31193
Metagene LinkHMDB31193
METLIN IDNot Available
PubChem Compound14925
PDB IDTRC
ChEBI ID45969
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:
ACO2
Uniprot ID:
Q99798
Molecular weight:
85424.745
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]