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
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:03 UTC
HMDB IDHMDB00623
Secondary Accession NumbersNone
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
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 KeyInChIKey=TVIDDXQYHWJXFK-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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Energy source
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity60.34 m3·mol-1ChemAxon
Polarizability26.85 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified219.7 +/- 14.0 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified279.9 +/- 42.7 uMAdult (>18 years old)Both
Diabetes
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. [9591306 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022148
KNApSAcK IDNot Available
Chemspider ID12213
KEGG Compound IDC02678
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00623
Metagene LinkHMDB00623
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. [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. [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. [16146704 ]