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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:41:33 UTC
Update Date2021-10-13 06:14:06 UTC
HMDB IDHMDB0031193
Secondary Accession Numbers
  • HMDB31193
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. 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
Data?1563862093
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 saltMeSH, HMDB
Propane-1,2,3-tricarboxylateMeSH, HMDB
Tricarballylic acid, sodium saltMeSH, HMDB
1,2,3-Propanetricarboxylic acidChEBI
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 KeyKQTIIICEAUMSDG-UHFFFAOYSA-N
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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point166 °CNot Available
Boiling Point266.43 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility332000 mg/L @ 18C (exp)The Good Scents Company Information System
LogP-1.420 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility37.8 g/LALOGPS
logP10(-0.56) g/LALOGPS
logP10(-0.73) g/LChemAxon
logS10(-0.67) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.65731661259
DarkChem[M-H]-131.95831661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,2,3-Propanetricarboxylic acid,1TMS,#1C[Si](C)(C)OC(=O)CC(CC(=O)O)C(=O)O1606.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,3-Propanetricarboxylic acid,1TMS,#2C[Si](C)(C)OC(=O)C(CC(=O)O)CC(=O)O1617.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,3-Propanetricarboxylic acid,2TMS,#1C[Si](C)(C)OC(=O)CC(CC(=O)O[Si](C)(C)C)C(=O)O1674.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,3-Propanetricarboxylic acid,2TMS,#2C[Si](C)(C)OC(=O)CC(CC(=O)O)C(=O)O[Si](C)(C)C1656.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,3-Propanetricarboxylic acid,3TMS,#1C[Si](C)(C)OC(=O)CC(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1720.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,3-Propanetricarboxylic acid,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CC(CC(=O)O)C(=O)O1864.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,3-Propanetricarboxylic acid,1TBDMS,#2CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)CC(=O)O1882.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,3-Propanetricarboxylic acid,2TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CC(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2153.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,3-Propanetricarboxylic acid,2TBDMS,#2CC(C)(C)[Si](C)(C)OC(=O)CC(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2140.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,3-Propanetricarboxylic acid,3TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CC(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2329.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,3-Propanetricarboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-5900000000-71d0f07709d92d993b772017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,3-Propanetricarboxylic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00b9-9154000000-a5760521d0e943c5a1882017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,3-Propanetricarboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,3-Propanetricarboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-01p6-9200000000-49fb526d0b36a4723f552015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Negative-QTOFsplash10-0a4i-2900000000-09ae1148bf0e5924cd862021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Negative-QTOFsplash10-014r-9100000000-222cb35a32f888421db72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Negative-QTOFsplash10-014l-9000000000-89281ca5096f1def31a52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Negative-QTOFsplash10-004r-9500000000-2be0c267efe352a032362021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 30V, Negative-QTOFsplash10-002r-6900000000-07615c72f45a8c1af8f12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Negative-QTOFsplash10-0a4r-3900000000-30c6cb52a165f67adc792021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Negative-QTOFsplash10-000i-6900000000-b5059f3f2bed0f835b212021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Positive-QTOFsplash10-057i-0900000000-ca7860b303dcd2f2c2e72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Positive-QTOFsplash10-00m0-4900000000-096c308c50609212658c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Positive-QTOFsplash10-000i-9200000000-504813f916f35f099fd42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Negative-QTOFsplash10-0059-1900000000-75e14da97e618b8087db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Negative-QTOFsplash10-0040-3900000000-74e5a6e0a0b40c87e0012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Negative-QTOFsplash10-0a4i-9200000000-62af859e2a81f90f8b552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Negative-QTOFsplash10-000i-9100000000-2d50b55dedd12855fe012021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Negative-QTOFsplash10-000i-9300000000-9771ed0fd1268ec645312021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Negative-QTOFsplash10-0a4l-9000000000-bd85aa22caa1da35ab862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Positive-QTOFsplash10-06r6-0900000000-5a19b6ded794c8ac5a9c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Positive-QTOFsplash10-029i-5900000000-f9d16e54ccf2b042be602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Positive-QTOFsplash10-0079-9000000000-15c9b1294cfa6364b10b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB04562
Phenol Explorer Compound IDNot Available
FooDB IDFDB003213
KNApSAcK IDC00054029
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
Food Biomarker OntologyNot Available
VMH IDTCB
MarkerDB IDNot Available
Good Scents IDrw1292061
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Riley RT, Torres O, Showker JL, Zitomer NC, Matute J, Voss KA, Gelineau-van Waes J, Maddox JR, Gregory SG, Ashley-Koch AE: The kinetics of urinary fumonisin B1 excretion in humans consuming maize-based diets. Mol Nutr Food Res. 2012 Sep;56(9):1445-55. doi: 10.1002/mnfr.201200166. Epub 2012 Jul 20. [PubMed:22815244 ]
  2. 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. [PubMed:16346691 ]
  3. (). 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. [PubMed: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. [PubMed: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. [PubMed:10592235 ]