Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:29:54 UTC
HMDB IDHMDB0000623
Secondary Accession Numbers
  • HMDB00623
Metabolite Identification
Common NameDodecanedioic acid
DescriptionDodecanedioic acid is an aliphatic dicarboxylic acid containing 12 carbon atoms. More formally it is an alpha,omega-dicarboxylic acid with both the first and last carbons of the aliphatic chain having carboxylic acids. Dodecanedioic acid is water soluble. It can be produced in yeast and fungi through the oxidation of dodecane via fungal peroxygenases (PMID: 27573441 ). High levels of dodecanedioic acid is an indicator of hepatic carnitine palmitoyltransferase I (CPT IA) deficiency (PMID: 16146704 ). CPT IA deficiency is characterized by hypoketotic dicarboxylic aciduria with high urinary levels of dodecanedioic acid. It is thought 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 ). CPT IA deficiency is characterized by acute encephalopathy with hypoglycemia and hepatomegaly.
Structure
Data?1582752144
Synonyms
ValueSource
1,10-Decanedicarboxylic acidChEBI
1,10-DicarboxydecaneChEBI
1,12-Dodecanedioic acidChEBI
Decamethylenedicarboxylic acidChEBI
1,10-DecanedicarboxylateGenerator
1,12-DodecanedioateGenerator
DecamethylenedicarboxylateGenerator
DodecanedioateGenerator
Corfree m 2HMDB
N-Dodecane-a,W-dioateHMDB
N-Dodecane-a,W-dioic acidHMDB
N-DodecanedioateHMDB
N-Dodecanedioic acidHMDB
SL-AHHMDB
Dodecandioic acidHMDB
Dodecanedioic acid, sodium saltHMDB
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
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.
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

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point127 - 129 °CNot Available
Boiling Point393.98 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.04 mg/mLNot Available
LogP2.920 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP10(2.86) g/LALOGPS
logP10(3.16) g/LChemAxon
logS10(-2.9) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.07131661259
DarkChem[M-H]-154.5731661259
AllCCS[M+H]+154.76832859911
AllCCS[M-H]-157.67232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dodecanedioic acidOC(=O)CCCCCCCCCCC(O)=O2943.1Standard polar33892256
Dodecanedioic acidOC(=O)CCCCCCCCCCC(O)=O1780.6Standard non polar33892256
Dodecanedioic acidOC(=O)CCCCCCCCCCC(O)=O1962.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dodecanedioic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCCCC(=O)O2012.7Semi standard non polar33892256
Dodecanedioic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCCCC(=O)O[Si](C)(C)C2108.1Semi standard non polar33892256
Dodecanedioic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(=O)O2266.7Semi standard non polar33892256
Dodecanedioic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2609.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dodecanedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7900000000-5d432fd0276ce4197d372017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dodecanedioic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9761000000-56eb65520fb862c7708d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dodecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dodecanedioic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dodecanedioic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dodecanedioic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-004i-0090000000-f724dd88b6f8e6a9df942012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-03di-1490000000-a72724c97d823b0074a42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0imi-9070000000-fa07f2a12f8348b346f62012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-004i-0090000000-c199a4bd96cfdc0484902012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-01t9-0090000000-6505db3e7e746817a6df2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-03xr-0690000000-56354fe558248a04d44a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-02t9-2950000000-dd8e5e957076afb6f92e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-004i-9000000000-47f5de4e0792116739252012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid LC-ESI-QQ , negative-QTOFsplash10-004i-0090000000-c199a4bd96cfdc0484902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid LC-ESI-QQ , negative-QTOFsplash10-01t9-0090000000-ef2f6d7d8f208f75e5852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid LC-ESI-QQ , negative-QTOFsplash10-03xr-0690000000-56354fe558248a04d44a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid LC-ESI-QQ , negative-QTOFsplash10-02t9-2950000000-dd8e5e957076afb6f92e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-47f5de4e0792116739252017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid 45V, Positive-QTOFsplash10-03xr-0690000000-bf3cc3d05f2fb73c10bc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid 90V, Negative-QTOFsplash10-001i-9000000000-7f04696d8f7d6df248512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid 75V, Negative-QTOFsplash10-014i-5940000000-d01b340287eb7349c5dd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid 15V, Negative-QTOFsplash10-004i-0090000000-8d1a41276750ca937f0a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid 30V, Negative-QTOFsplash10-03fr-0290000000-08bb11dac2b0f4e054c82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dodecanedioic acid 60V, Negative-QTOFsplash10-02t9-0960000000-245c0d86a1c4461734d32021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dodecanedioic acid 10V, Positive-QTOFsplash10-03e9-0390000000-3459b535817428e628152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dodecanedioic acid 20V, Positive-QTOFsplash10-03yr-1930000000-90b7ee2c8ff59e744fe22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dodecanedioic acid 40V, Positive-QTOFsplash10-056r-9800000000-2eb31cabfac17468bb182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dodecanedioic acid 10V, Negative-QTOFsplash10-004i-0190000000-318a28847b6f7ea593d32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dodecanedioic acid 20V, Negative-QTOFsplash10-01t9-0390000000-6eebd7cb7ac16fb6b4b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dodecanedioic acid 40V, Negative-QTOFsplash10-0a4l-9310000000-cb68f38e9dc18d2470d42017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
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 but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.12(0.07-0.18) uMInfant (0-1 year old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 QuantifiedNot QuantifiedAdult (>18 years old)BothIron deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>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
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1231691
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 ]