Np mrd loader

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:48 UTC
NP-MRD IDNP0001111
Secondary Accession NumbersNone
Natural Product 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
Thumb
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 Mass230.3007 Da
Monoisotopic Mass230.15181 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Phaseolus vulgarisLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
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
Physical Properties
StateSolid
Experimental 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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000623
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
Good Scents IDrw1231691
References
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 ]
  4. Malaisse WJ, Doherty M, Ladriere L, Greco AV, Mingrone G: Oxidation of D-[U-(14)C] glucose and [1,12-(14)C] dodecanedioic acid by pancreatic islets from Goto-Kakizaki rats. Horm Metab Res. 2001 Aug;33(8):463-6. doi: 10.1055/s-2001-16938. [PubMed:11544559 ]
  5. Moore VC, Manney S, Vellore AD, Burge PS: Occupational asthma to gel flux containing dodecanedioic acid. Allergy. 2009 Jul;64(7):1099-100. doi: 10.1111/j.1398-9995.2009.01992.x. Epub 2009 Feb 16. [PubMed:19222421 ]
  6. Olmedo A, Aranda C, Del Rio JC, Kiebist J, Scheibner K, Martinez AT, Gutierrez A: From Alkanes to Carboxylic Acids: Terminal Oxygenation by a Fungal Peroxygenase. Angew Chem Int Ed Engl. 2016 Sep 26;55(40):12248-51. doi: 10.1002/anie.201605430. Epub 2016 Aug 30. [PubMed:27573441 ]