Record Information |
---|
Version | 5.0 |
---|
Status | Detected but not Quantified |
---|
Creation Date | 2012-09-11 17:41:33 UTC |
---|
Update Date | 2023-02-21 17:20:00 UTC |
---|
HMDB ID | HMDB0031193 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | 1,2,3-Propanetricarboxylic acid |
---|
Description | 1,2,3-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 | 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) |
---|
Synonyms | Value | Source |
---|
3-Carboxyglutaric acid | ChEBI | 3-Carboxypentanedioic acid | ChEBI | beta-Carboxyglutaric acid | ChEBI | Carballylic acid | ChEBI | Carboxymethylsuccinic acid | ChEBI | Tricarballylate | Kegg | 3-Carboxyglutarate | Generator | 3-Carboxypentanedioate | Generator | b-Carboxyglutarate | Generator | b-Carboxyglutaric acid | Generator | beta-Carboxyglutarate | Generator | Β-carboxyglutarate | Generator | Β-carboxyglutaric acid | Generator | Carballylate | Generator | Carboxymethylsuccinate | Generator | Tricarballylic acid | Generator | 1,2,3-Propanetricarboxylate | Generator | 1,2,3-Tripropanetricarboxylic acid | HMDB | Propane 1,2,3-tricarboxylic acid | HMDB | Tricarballylic acid, trisodium salt | MeSH, HMDB | Propane-1,2,3-tricarboxylate | MeSH, HMDB | Tricarballylic acid, sodium salt | MeSH, HMDB | 1,2,3-Propanetricarboxylic acid | ChEBI |
|
---|
Chemical Formula | C6H8O6 |
---|
Average Molecular Weight | 176.1241 |
---|
Monoisotopic Molecular Weight | 176.032087988 |
---|
IUPAC Name | propane-1,2,3-tricarboxylic acid |
---|
Traditional Name | tricarballylic acid |
---|
CAS Registry Number | 99-14-9 |
---|
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 Key | KQTIIICEAUMSDG-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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Tricarboxylic acids and derivatives |
---|
Direct Parent | Tricarboxylic 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 Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | |
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
1,2,3-Propanetricarboxylic acid,1TMS,isomer #1 | C[Si](C)(C)OC(=O)CC(CC(=O)O)C(=O)O | 1606.0 | Semi standard non polar | 33892256 | 1,2,3-Propanetricarboxylic acid,1TMS,isomer #2 | C[Si](C)(C)OC(=O)C(CC(=O)O)CC(=O)O | 1617.6 | Semi standard non polar | 33892256 | 1,2,3-Propanetricarboxylic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)CC(CC(=O)O[Si](C)(C)C)C(=O)O | 1674.4 | Semi standard non polar | 33892256 | 1,2,3-Propanetricarboxylic acid,2TMS,isomer #2 | C[Si](C)(C)OC(=O)CC(CC(=O)O)C(=O)O[Si](C)(C)C | 1656.8 | Semi standard non polar | 33892256 | 1,2,3-Propanetricarboxylic acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)CC(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1720.9 | Semi standard non polar | 33892256 | 1,2,3-Propanetricarboxylic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CC(CC(=O)O)C(=O)O | 1864.4 | Semi standard non polar | 33892256 | 1,2,3-Propanetricarboxylic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)CC(=O)O | 1882.8 | Semi standard non polar | 33892256 | 1,2,3-Propanetricarboxylic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CC(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O | 2153.7 | Semi standard non polar | 33892256 | 1,2,3-Propanetricarboxylic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)CC(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C | 2140.8 | Semi standard non polar | 33892256 | 1,2,3-Propanetricarboxylic acid,3TBDMS,isomer #1 | CC(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)C | 2329.7 | Semi standard non polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - 1,2,3-Propanetricarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-5900000000-71d0f07709d92d993b77 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 1,2,3-Propanetricarboxylic acid GC-MS (3 TMS) - 70eV, Positive | splash10-00b9-9154000000-a5760521d0e943c5a188 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 1,2,3-Propanetricarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 1,2,3-Propanetricarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-01p6-9200000000-49fb526d0b36a4723f55 | 2015-03-01 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Negative-QTOF | splash10-0a4i-2900000000-09ae1148bf0e5924cd86 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Negative-QTOF | splash10-014r-9100000000-222cb35a32f888421db7 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Negative-QTOF | splash10-014l-9000000000-89281ca5096f1def31a5 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Negative-QTOF | splash10-004r-9500000000-2be0c267efe352a03236 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 30V, Negative-QTOF | splash10-002r-6900000000-07615c72f45a8c1af8f1 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Negative-QTOF | splash10-0a4r-3900000000-30c6cb52a165f67adc79 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Negative-QTOF | splash10-000i-6900000000-b5059f3f2bed0f835b21 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Positive-QTOF | splash10-057i-0900000000-ca7860b303dcd2f2c2e7 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Positive-QTOF | splash10-00m0-4900000000-096c308c50609212658c | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Positive-QTOF | splash10-000i-9200000000-504813f916f35f099fd4 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Negative-QTOF | splash10-0059-1900000000-75e14da97e618b8087db | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Negative-QTOF | splash10-0040-3900000000-74e5a6e0a0b40c87e001 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Negative-QTOF | splash10-0a4i-9200000000-62af859e2a81f90f8b55 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Negative-QTOF | splash10-000i-9100000000-2d50b55dedd12855fe01 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Negative-QTOF | splash10-000i-9300000000-9771ed0fd1268ec64531 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Negative-QTOF | splash10-0a4l-9000000000-bd85aa22caa1da35ab86 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 10V, Positive-QTOF | splash10-06r6-0900000000-5a19b6ded794c8ac5a9c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 20V, Positive-QTOF | splash10-029i-5900000000-f9d16e54ccf2b042be60 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,2,3-Propanetricarboxylic acid 40V, Positive-QTOF | splash10-0079-9000000000-15c9b1294cfa6364b10b | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
|
---|
Disease References | Colorectal cancer |
---|
- 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 ]
- 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 ]
- 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 ]
|
|
---|