Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2012-09-11 17:42:25 UTC |
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Update Date | 2023-02-21 17:20:26 UTC |
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HMDB ID | HMDB0031342 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cyclohexanecarboxylic acid |
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Description | Cyclohexanecarboxylic acid, also known as hexahydrobenzoic acid or carboxycyclohexane, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Cyclohexanecarboxylic acid exists in all living organisms, ranging from bacteria to humans. Cyclohexanecarboxylic acid is an acidic, cheese, and fruity tasting compound. Cyclohexanecarboxylic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on Cyclohexanecarboxylic acid. |
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Structure | InChI=1S/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9) |
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Synonyms | Value | Source |
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Carboxycyclohexane | ChEBI | Cyclohexancarbonsaeure | ChEBI | Cyclohexane-1-carboxylate | ChEBI | Cyclohexanoic acid | ChEBI | Cyclohexylcarboxylic acid | ChEBI | Cyclohexylformic acid | ChEBI | Cyclohexylmethanoic acid | ChEBI | Hexahydrobenzoic acid | ChEBI | Cyclohexane-1-carboxylic acid | Generator | Cyclohexanoate | Generator | Cyclohexylcarboxylate | Generator | Cyclohexylformate | Generator | Cyclohexylmethanoate | Generator | Hexahydrobenzoate | Generator | Cyclohexanecarboxylate | Generator | Cyclohexanecarboxylic acid, calcium salt | MeSH | Cyclohexanecarboxylic acid, cobalt salt | MeSH | Cyclohexanecarboxylic acid, lead salt | MeSH | Cyclohexanecarboxylic acid, potassium salt | MeSH | Cyclohexanecarboxylic acid, sodium salt | MeSH | Cyclohexanecarboxylic acid, sodium salt, 11C-labeled | MeSH | 7549-42-0 (Calcium salt) | HMDB | FEMA 3531 | HMDB | hexahydro-Benzoic acid | HMDB | Naphthenic acid | HMDB | Naphthenoic acid | HMDB |
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Chemical Formula | C7H12O2 |
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Average Molecular Weight | 128.169 |
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Monoisotopic Molecular Weight | 128.083729628 |
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IUPAC Name | cyclohexanecarboxylic acid |
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Traditional Name | cyclohexanecarboxylic acid |
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CAS Registry Number | 98-89-5 |
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SMILES | OC(=O)C1CCCCC1 |
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InChI Identifier | InChI=1S/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9) |
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InChI Key | NZNMSOFKMUBTKW-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Carboxylic acids |
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Direct Parent | Carboxylic acids |
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Alternative Parents | |
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Substituents | - Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 31 - 32 °C | Not Available | Boiling Point | 232.00 to 233.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 4.6 mg/mL at 25 °C | Not Available | LogP | 1.96 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Cyclohexanecarboxylic acid EI-B (Non-derivatized) | splash10-03e9-9700000000-afedc669010cea1fff7a | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cyclohexanecarboxylic acid EI-B (Non-derivatized) | splash10-03e9-9700000000-afedc669010cea1fff7a | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cyclohexanecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0036-9100000000-7b2d7325908346fef2d1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cyclohexanecarboxylic acid GC-MS (1 TMS) - 70eV, Positive | splash10-008i-9300000000-6340158dcee214fd3ad4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cyclohexanecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclohexanecarboxylic acid LC-ESI-QQ , negative-QTOF | splash10-004i-0900000000-69422c2f22908125487e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclohexanecarboxylic acid LC-ESI-QQ , negative-QTOF | splash10-004i-1900000000-2b1c359177d442da9138 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclohexanecarboxylic acid LC-ESI-QQ , negative-QTOF | splash10-056s-9500000000-8b79211c98aa33e6b31a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclohexanecarboxylic acid LC-ESI-QQ , negative-QTOF | splash10-0a4i-9000000000-a73dd06af262b4a9ef25 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclohexanecarboxylic acid LC-ESI-QQ , negative-QTOF | splash10-0006-9000000000-0018f47571feaf232ff8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 10V, Positive-QTOF | splash10-004i-3900000000-5f7af485316f5734f31c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 20V, Positive-QTOF | splash10-01q9-9400000000-4891c30e0de9b93142c0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 40V, Positive-QTOF | splash10-0a4l-9000000000-4e84d360f5dcc7c27e10 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 10V, Negative-QTOF | splash10-004i-3900000000-e6c3bee1d7b7769e57d5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 20V, Negative-QTOF | splash10-003r-9500000000-9de2d40e8ed9e23f88fe | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 40V, Negative-QTOF | splash10-001i-9100000000-e176edd2be2d6a23fcc9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 10V, Positive-QTOF | splash10-001i-9600000000-77f543a59e6f66639edf | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 20V, Positive-QTOF | splash10-053r-9000000000-4a0ef320aa7c76cac141 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 40V, Positive-QTOF | splash10-0536-9000000000-c916f1bfef6f2963671f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 10V, Negative-QTOF | splash10-004i-0900000000-108ecb5ab434b95e7d34 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 20V, Negative-QTOF | splash10-004i-1900000000-f378592e25c39276f7c1 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclohexanecarboxylic acid 40V, Negative-QTOF | splash10-0006-9200000000-453e95f5b7e9124e523b | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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 |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 29.102 +/- 57.424 nmol/g wet feces | Not Specified | Not Specified | Normal | | details | Feces | Detected and Quantified | 205.198 +/- 493.879 nmol/g wet feces | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Nonalcoholic fatty liver disease (NAFLD) | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Immunoglobulin A nephropathy (IgAN) non progressor | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Immunoglobulin A nephropathy (IgAN) progressor | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Campylobacter jejuni infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Diarrhea-predominant IBS | | details |
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Associated Disorders and Diseases |
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Disease References | Nonalcoholic fatty liver disease |
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- Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
| Diarrhoea predominant irritable bowel syndrome |
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- Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB003406 |
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KNApSAcK ID | C00000334 |
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Chemspider ID | 7135 |
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KEGG Compound ID | C09822 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Cyclohexanecarboxylic_acid |
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METLIN ID | Not Available |
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PubChem Compound | 7413 |
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PDB ID | Not Available |
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ChEBI ID | 36096 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1036731 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Mo R, Sun Q, Xue J, Li N, Li W, Zhang C, Ping Q: Multistage pH-responsive liposomes for mitochondrial-targeted anticancer drug delivery. Adv Mater. 2012 Jul 17;24(27):3659-65. doi: 10.1002/adma.201201498. Epub 2012 Jun 8. [PubMed:22678851 ]
- BALTES BJ, ELLIOTT WH, DOISY EA Jr, DOISY EA: Biochemical studies of hexahydrobenzoic acid and hexahydrophenylalanine. J Biol Chem. 1952 Feb;194(2):627-34. [PubMed:14927655 ]
- MITOMA C, POSNER HS, LEONARD F: Aromatization of hexahydrobenzoic acid by mamalian liver mitochondria. Biochim Biophys Acta. 1958 Jan;27(1):156-60. [PubMed:13510261 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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