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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-11-09 23:13:54 UTC |
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HMDB ID | HMDB0000623 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Dodecanedioic acid |
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Description | Dodecanedioic acid is a dicarboxylic acid which is water soluble and involves in a metabolic pathway intermediate to those of lipids and carbohydrates. (PMID 9591306 ). Dodecanedioid acid is an indicator of hepatic carnitine palmitoyltransferase I (CPT IA) deficiency. CPT IA deficiency is characterized by hypoketotic dicarboxylic aciduria with high urinary levels of dodecanedioic acid. This C12 dicarboxylic aciduria suggests that carnitine palmitoyltransferase I may play a role in the uptake of long-chain dicarboxylic acids by mitochondria after their initial shortening by beta-oxidation in peroxisomes. (PMID: 16146704 ). |
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Structure | |
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Synonyms | Value | Source |
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1,10-Decanedicarboxylic acid | ChEBI | 1,10-Dicarboxydecane | ChEBI | 1,12-Dodecanedioic acid | ChEBI | Decamethylenedicarboxylic acid | ChEBI | 1,10-Decanedicarboxylate | Generator | 1,12-Dodecanedioate | Generator | Decamethylenedicarboxylate | Generator | Dodecanedioate | Generator | Corfree m 2 | HMDB | N-Dodecane-a,W-dioate | HMDB | N-Dodecane-a,W-dioic acid | HMDB | N-Dodecanedioate | HMDB | N-Dodecanedioic acid | HMDB | SL-AH | HMDB | Dodecandioic acid | HMDB | Dodecanedioic acid, sodium salt | HMDB |
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Chemical Formula | C12H22O4 |
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Average Molecular Weight | 230.3007 |
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Monoisotopic Molecular Weight | 230.151809192 |
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IUPAC Name | dodecanedioic acid |
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Traditional Name | dodecanedioic acid |
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CAS Registry Number | 693-23-2 |
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SMILES | OC(=O)CCCCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16) |
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InChI Key | TVIDDXQYHWJXFK-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 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 | Medium-chain fatty acids |
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Alternative Parents | |
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Substituents | - Medium-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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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 127 - 129 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.04 mg/mL | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-7900000000-5d432fd0276ce4197d37 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00dr-9761000000-56eb65520fb862c7708d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-004i-0090000000-f724dd88b6f8e6a9df94 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-03di-1490000000-a72724c97d823b0074a4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0imi-9070000000-fa07f2a12f8348b346f6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0090000000-c199a4bd96cfdc048490 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-01t9-0090000000-6505db3e7e746817a6df | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-03xr-0690000000-56354fe558248a04d44a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-02t9-2950000000-dd8e5e957076afb6f92e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004i-9000000000-47f5de4e079211673925 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0090000000-c199a4bd96cfdc048490 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-01t9-0090000000-ef2f6d7d8f208f75e585 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03xr-0690000000-56354fe558248a04d44a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-02t9-2950000000-dd8e5e957076afb6f92e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-47f5de4e079211673925 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03e9-0390000000-3459b535817428e62815 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03yr-1930000000-90b7ee2c8ff59e744fe2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-056r-9800000000-2eb31cabfac17468bb18 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0190000000-318a28847b6f7ea593d3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01t9-0390000000-6eebd7cb7ac16fb6b4b3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9310000000-cb68f38e9dc18d2470d4 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | 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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Blood | Detected and Quantified | 219.7 +/- 14.0 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.12(0.07-0.18) uM | Infant (0-1 year old) | 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 but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.41-8.8 uM | Infant (0-1 year old) | Female | 3-Hydroxydicarboxylic aciduria | | details | Blood | Detected and Quantified | 279.9 +/- 42.7 uM | Adult (>18 years old) | Both | Diabetes | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Iron deficiency | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Ulcerative colitis | | 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 and Quantified | 37-63 umol/mmol creatinine | Newborn (0-30 days old) | Both | Carnitine-acylcarnitine translocase deficiency | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Metabolic syndrome | | details | Urine | Detected and Quantified | 0 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Medium Chain Acyl-CoA Dehydrogenase Deficiency | | details | Urine | Detected and Quantified | 0 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Medium Chain Acyl-CoA Dehydrogenase Deficiency | | details | Urine | Detected and Quantified | 12.273 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Medium Chain Acyl-CoA Dehydrogenase Deficiency | | details | Urine | Detected and Quantified | 45.165 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Medium Chain Acyl-CoA Dehydrogenase Deficiency | | details | Urine | Detected and Quantified | 73.639 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Medium Chain Acyl-CoA Dehydrogenase Deficiency | | details |
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Associated Disorders and Diseases |
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Disease References | Diabetes mellitus type 2 |
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- Greco AV, Mingrone G, Capristo E, Benedetti G, De Gaetano A, Gasbarrini G: The metabolic effect of dodecanedioic acid infusion in non-insulin-dependent diabetic patients. Nutrition. 1998 Apr;14(4):351-7. [PubMed:9591306 ]
| 3-Hydroxydicarboxylic aciduria |
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- Hagenfeldt L, von Dobeln U, Holme E, Alm J, Brandberg G, Enocksson E, Lindeberg L: 3-Hydroxydicarboxylic aciduria--a fatty acid oxidation defect with severe prognosis. J Pediatr. 1990 Mar;116(3):387-92. [PubMed:2308028 ]
| Iron deficiency |
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- Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
| Ulcerative colitis |
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- Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
| 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 ]
| Metabolic syndrome |
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- Tulipani S, Llorach R, Jauregui O, Lopez-Uriarte P, Garcia-Aloy M, Bullo M, Salas-Salvado J, Andres-Lacueva C: Metabolomics unveils urinary changes in subjects with metabolic syndrome following 12-week nut consumption. J Proteome Res. 2011 Nov 4;10(11):5047-58. doi: 10.1021/pr200514h. Epub 2011 Sep 29. [PubMed:21905751 ]
| Medium Chain Acyl-CoA Dehydrogenase Deficiency |
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- Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]
| Carnitine-acylcarnitine translocase deficiency |
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- Ogier de Baulny H, Slama A, Touati G, Turnbull DM, Pourfarzam M, Brivet M: Neonatal hyperammonemia caused by a defect of carnitine-acylcarnitine translocase. J Pediatr. 1995 Nov;127(5):723-8. [PubMed:7472823 ]
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Associated OMIM IDs | - 125853 (Diabetes mellitus type 2)
- 114500 (Colorectal cancer)
- 605552 (Metabolic syndrome)
- 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
- 212138 (Carnitine-acylcarnitine translocase deficiency)
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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 | FDB022148 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 12213 |
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KEGG Compound ID | C02678 |
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BioCyc ID | CPD-10670 |
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BiGG ID | Not Available |
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Wikipedia Link | Dodecanedioic acid |
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METLIN ID | 5596 |
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PubChem Compound | 12736 |
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PDB ID | Not Available |
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ChEBI ID | 4676 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Zhang, Xuwen; Li, Yuwei; He, Jianhua; Wang, Chen. Method for separating and purifying dodecanedioic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 9 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Bertuzzi A, Mingrone G, Gandolfi A, Greco AV, Salinari S: Pharmacokinetic analysis of dodecanedioic acid in humans from bolus data. JPEN J Parenter Enteral Nutr. 1995 Nov-Dec;19(6):498-501. [PubMed:8748365 ]
- Greco AV, Mingrone G, Capristo E, Benedetti G, De Gaetano A, Gasbarrini G: The metabolic effect of dodecanedioic acid infusion in non-insulin-dependent diabetic patients. Nutrition. 1998 Apr;14(4):351-7. [PubMed:9591306 ]
- Korman SH, Waterham HR, Gutman A, Jakobs C, Wanders RJ: Novel metabolic and molecular findings in hepatic carnitine palmitoyltransferase I deficiency. Mol Genet Metab. 2005 Nov;86(3):337-43. Epub 2005 Sep 16. [PubMed:16146704 ]
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