Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-09-22 18:34:14 UTC |
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HMDB ID | HMDB0000672 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Hexadecanedioic acid |
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Description | Hexadecanedioic acid, also known as thapsic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Hexadecanedioic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Hexadecanedioic acid is activated by mitochondrial and microsomal fractions in the liver (PMID: 4372285 ). It has antitumor activity (PMID: 14987827 ). |
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Structure | OC(=O)CCCCCCCCCCCCCCC(O)=O InChI=1S/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20) |
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Synonyms | Value | Source |
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1,14-Tetradecanedicarboxylic acid | ChEBI | 1,16-Hexadecanedioic acid | ChEBI | Thapsic acid | ChEBI | 1,14-Tetradecanedicarboxylate | Generator | 1,16-Hexadecanedioate | Generator | Thapsate | Generator | Hexadecanedioate | Generator | Α,ω-tetrαdecαnedicαrboxylαte | HMDB | N-Tetradecane-ω,ω'-dicarboxylate | HMDB | N-Tetradecane-ω,ω'-dicarboxylic acid | HMDB | alpha,Omega-tetradecanedicarboxylic acid | HMDB | N-Tetradecane-omega,omega'-dicarboxylic acid | HMDB | N-Tetradecane-ω,ω’-dicarboxylic acid | HMDB | Α,ω-tetradecanedicarboxylic acid | HMDB | Hexadecanedioic acid | MeSH |
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Chemical Formula | C16H30O4 |
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Average Molecular Weight | 286.407 |
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Monoisotopic Molecular Weight | 286.214409448 |
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IUPAC Name | hexadecanedioic acid |
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Traditional Name | hexadecanedioic acid |
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CAS Registry Number | 505-54-4 |
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SMILES | OC(=O)CCCCCCCCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20) |
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InChI Key | QQHJDPROMQRDLA-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Long-chain fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Not Available | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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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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Predicted GC-MS | Predicted GC-MS Spectrum - Hexadecanedioic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-07do-2940000000-8c28631b1022d3318936 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hexadecanedioic acid GC-MS (2 TMS) - 70eV, Positive | splash10-0109-7691100000-587f0a395c2991f76096 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hexadecanedioic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hexadecanedioic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hexadecanedioic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hexadecanedioic acid GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-01ow-9210000000-ae9c39d4b07c3e8cb742 | 2015-03-01 | Not Available | 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 - Hexadecanedioic acid Quattro_QQQ 10V, Negative-QTOF (Annotated) | splash10-000i-0090000000-2311edb5a21bc7c11854 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Quattro_QQQ 25V, Negative-QTOF (Annotated) | splash10-01b9-0090000000-29b1e4612ce1b89fe132 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Quattro_QQQ 40V, Negative-QTOF (Annotated) | splash10-0a4i-9000000000-cb4b2bb791cf66c26ad1 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid n/a 20V, positive-QTOF | splash10-014r-0490000000-dacc672eeb75f850682b | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 2V, positive-QTOF | splash10-014i-0090000000-9e4148fba4082bf62e1e | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 4V, positive-QTOF | splash10-014i-2590000000-8bc2ce9bfb76d9bb26b7 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 5V, positive-QTOF | splash10-066s-4950000000-47159163bf80115de8b2 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 7V, positive-QTOF | splash10-053b-6920000000-8a0094cbb6f9d1650566 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 9V, positive-QTOF | splash10-0012-8910000000-2a109bc90ccab90ea68b | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 10V, positive-QTOF | splash10-00l2-9700000000-d514011d0869df067d52 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 12V, positive-QTOF | splash10-05o1-9500000000-983b1d8b6bb3f3f63b35 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 13V, positive-QTOF | splash10-015a-9300000000-69f141c415f5b32f3403 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 14V, positive-QTOF | splash10-067j-9200000000-7b8fa454eb425f3e106e | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 18V, positive-QTOF | splash10-067i-9100000000-a8b8484850ff331b59c4 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 22V, positive-QTOF | splash10-067i-9000000000-2d72212014cb905b53ba | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 27V, positive-QTOF | splash10-066r-9000000000-5f4d3971357b080285ef | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 33V, positive-QTOF | splash10-0aor-9000000000-1f5e11f8710cbd1da2c2 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 39V, positive-QTOF | splash10-0ar0-9100000000-203172aa59c73e588123 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 49V, positive-QTOF | splash10-0ar0-9200000000-2f3b6e1eff5a4c95e99b | 2020-07-22 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexadecanedioic acid 10V, Positive-QTOF | splash10-014r-0090000000-21fd3982c0181bc06670 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexadecanedioic acid 20V, Positive-QTOF | splash10-014u-0390000000-67df6952912c86a0cd98 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexadecanedioic acid 40V, Positive-QTOF | splash10-001j-5900000000-ff60e3a81da2e330db67 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexadecanedioic acid 10V, Negative-QTOF | splash10-000i-0090000000-6c700a9c0357a7d235a8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexadecanedioic acid 20V, Negative-QTOF | splash10-00kr-0090000000-fb79a4abfe50390ddb88 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hexadecanedioic acid 40V, Negative-QTOF | splash10-0a4l-9140000000-7aba6aa5bd7692dcc532 | 2017-09-01 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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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 | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- 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 ]
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Associated OMIM IDs | |
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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 | FDB003049 |
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KNApSAcK ID | C00007429 |
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Chemspider ID | 10027 |
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KEGG Compound ID | C19615 |
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BioCyc ID | CPD-10511 |
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BiGG ID | Not Available |
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Wikipedia Link | Thapsic acid |
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METLIN ID | 5642 |
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PubChem Compound | 10459 |
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PDB ID | Not Available |
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ChEBI ID | 73722 |
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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 | rw1249661 |
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References |
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Synthesis Reference | Kreuchunas, Algird. The synthesis of higher aliphatic a,w-dicarboxylic acids. Journal of the American Chemical Society (1953), 75 3339-44. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Pettersen JE, Aas M: Subcellular localization of hexadecanedioic acid activation in human liver. J Lipid Res. 1974 Nov;15(6):551-6. [PubMed:4372285 ]
- You YJ, Kim Y, Nam NH, Bang SC, Ahn BZ: Alkyl and carboxylalkyl esters of 4'-demethyl-4-deoxypodophyllotoxin: synthesis, cytotoxic, and antitumor activity. Eur J Med Chem. 2004 Feb;39(2):189-93. [PubMed:14987827 ]
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