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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 18:56:16 UTC
HMDB IDHMDB0000623
Secondary Accession Numbers
  • HMDB00623
Metabolite Identification
Common NameDodecanedioic acid
DescriptionDodecanedioic 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 ).
Structure
Thumb
Synonyms
ValueSource
1,10-Decanedicarboxylic acidChEBI
1,10-DicarboxydecaneChEBI
1,12-Dodecanedioic acidChEBI
Decamethylenedicarboxylic acidChEBI
1,10-DecanedicarboxylateGenerator
DodecanedioateGenerator
1,12-DodecanedioateGenerator
DecamethylenedicarboxylateGenerator
Corfree m 2HMDB
N-Dodecane-a,W-dioateHMDB
N-Dodecane-a,W-dioic acidHMDB
N-DodecanedioateHMDB
N-Dodecanedioic acidHMDB
SL-AHHMDB
Dodecandioic acidMeSH
Dodecanedioic acid, sodium saltMeSH
Chemical FormulaC12H22O4
Average Molecular Weight230.3007
Monoisotopic Molecular Weight230.151809192
IUPAC Namedodecanedioic acid
Traditional Namedodecanedioic acid
CAS Registry Number693-23-2
SMILES
OC(=O)CCCCCCCCCCC(O)=O
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)
InChI KeyTVIDDXQYHWJXFK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point127 - 129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.04 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP2.86ALOGPS
logP3.16ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity60.34 m³·mol⁻¹ChemAxon
Polarizability26.85 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7900000000-5d432fd0276ce4197d37View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9761000000-56eb65520fb862c7708dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-0090000000-f724dd88b6f8e6a9df94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-03di-1490000000-a72724c97d823b0074a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0imi-9070000000-fa07f2a12f8348b346f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0090000000-c199a4bd96cfdc048490View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-01t9-0090000000-6505db3e7e746817a6dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03xr-0690000000-56354fe558248a04d44aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-02t9-2950000000-dd8e5e957076afb6f92eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-47f5de4e079211673925View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-c199a4bd96cfdc048490View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01t9-0090000000-ef2f6d7d8f208f75e585View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03xr-0690000000-56354fe558248a04d44aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-02t9-2950000000-dd8e5e957076afb6f92eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-47f5de4e079211673925View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0390000000-3459b535817428e62815View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03yr-1930000000-90b7ee2c8ff59e744fe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9800000000-2eb31cabfac17468bb18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-318a28847b6f7ea593d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0390000000-6eebd7cb7ac16fb6b4b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9310000000-cb68f38e9dc18d2470d4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified219.7 +/- 14.0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.12(0.07-0.18) uMInfant (0-1 year old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.41-8.8 uMInfant (0-1 year old)Female3-Hydroxydicarboxylic aciduria details
BloodDetected and Quantified279.9 +/- 42.7 uMAdult (>18 years old)Both
Diabetes
details
FecesDetected but not Quantified Adult (>18 years old)BothIron deficiency details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified37-63 umol/mmol creatinineNewborn (0-30 days old)BothCarnitine-acylcarnitine translocase deficiency details
UrineDetected but not Quantified Adult (>18 years old)Both
Metabolic syndrome
details
UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified12.273 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified45.165 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified73.639 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
Associated Disorders and Diseases
Disease References
Medium Chain Acyl-CoA Dehydrogenase Deficiency
  1. 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 ]
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 ]
Diabetes mellitus type 2
  1. 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 ]
Metabolic syndrome
  1. 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 ]
Carnitine-acylcarnitine translocase deficiency
  1. 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 ]
3-Hydroxydicarboxylic aciduria
  1. 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 ]
Ulcerative colitis
  1. 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 ]
Iron deficiency
  1. 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 ]
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)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022148
KNApSAcK IDNot Available
Chemspider ID12213
KEGG Compound IDC02678
BioCyc IDCPD-10670
BiGG IDNot Available
Wikipedia LinkDodecanedioic acid
METLIN ID5596
PubChem Compound12736
PDB IDNot Available
ChEBI ID4676
References
Synthesis ReferenceZhang, Xuwen; Li, Yuwei; He, Jianhua; Wang, Chen. Method for separating and purifying dodecanedioic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 9 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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. 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 ]