Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001617
Identification
Name: Dodecanoate (N-C12:0)
Description:Dodecanoate (n-c12:0) belongs to the class of Carboxylic Acid Salts. These are ionic derivatives of carboxylic acid. (inferred from compound structure) Dodecanoic acid, also known as lauric acid is a saturated fatty acid with a 12-carbon atom chain, thus falling into the medium chain fatty acids. It is a white, powdery solid with a faint odor of bay oil or soap. (Wikipedia) In plants and bacteria like Pseudomonas aeruginosa, dodecanoate is a by-product in one palmitate biosynthesis pathway. (EcoCyc)
Structure
Thumb
Synonyms:
  • n-dodecanoic acid
  • Dodecanoate
  • Dodecanoic acid
  • Dodecanoic acid (N-C12:0)
  • Laate
  • Laic acid
  • Laurate
  • Lauric acid
  • N-Dodecanoate
  • N-Dodecanoic acid
  • Tin II 2-ethylhexanoate
  • Tin II 2-ethylhexanoic acid
Chemical Formula: C12H23O2
Average Molecular Weight: 199.3098
Monoisotopic Molecular Weight: 199.16980498
InChI Key: POULHZVOKOAJMA-UHFFFAOYSA-M
InChI:InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)/p-1
CAS number: Not Available
IUPAC Name:dodecanoate
Traditional IUPAC Name: laurate
SMILES:CCCCCCCCCCCC([O-])=O
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Medium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Carboxylic acid salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00414 mg/mLALOGPS
logP5.24ALOGPS
logP4.48ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity69.52 m3·mol-1ChemAxon
Polarizability25.37 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Adenosine triphosphate + Coenzyme A + Dodecanoate (N-C12:0) + Hydrogen ion > Adenosine monophosphate + Lauroyl-CoA + Hydrogen ion + Pyrophosphate
acyl carrier protein + Adenosine triphosphate + Dodecanoate (N-C12:0) > Adenosine monophosphate + Dodecanoyl-ACP (n-C12:0ACP) + Pyrophosphate
Dodecanoyl-ACP (n-C12:0ACP) + Water > acyl carrier protein + Dodecanoate (N-C12:0) + Hydrogen ion
Lauroyl-CoA + Water > Coenzyme A + Dodecanoate (N-C12:0) + Hydrogen ion
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerylphosphorylethanolamine + Hydrogen ion
1-Acyl-sn-glycero-3-phosphoglycerol (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerophosphoglycerol + Hydrogen ion
1-Dodecanoyl-sn-glycerol 3-phosphate + Water > Dodecanoate (N-C12:0) + Glycerol 3-phosphate + Hydrogen ion
Dodecanoly-phosphate (n-C12:0) + Water > Dodecanoate (N-C12:0) +2 Hydrogen ion + Phosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Adenosine triphosphate + Dodecanoate (N-C12:0) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Adenosine triphosphate + Dodecanoate (N-C12:0) > Adenosine monophosphate + PG(12:0/12:0) + Pyrophosphate
Water + PA(16:0/16:0) > 1-Dodecanoyl-sn-glycerol 3-phosphate + Dodecanoate (N-C12:0) + Hydrogen ion
Water + PA(16:0/16:0) > 2-dodecanoyl-sn-glycerol 3-phosphate + Dodecanoate (N-C12:0)
Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion
Water + PG(12:0/12:0) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion
Water + PG(12:0/12:0) > 2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerylphosphorylethanolamine + Hydrogen ion
2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerophosphoglycerol + Hydrogen ion
2-dodecanoyl-sn-glycerol 3-phosphate + Water > Dodecanoate (N-C12:0) + Glycerol 3-phosphate +2 Hydrogen ion
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0960000000-3e1846923458f5bb9529View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zg3-4930000000-414993f3db6de0f0b3bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9200000000-35b840908e5424a76b65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-bf0996263147bd90d4fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-0900000000-d85dd53fb13261fa3515View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-5900000000-3c1ae0ab327e98ffd30aView in MoNA
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID18262
HMDB IDNot Available
Pubchem Compound ID4149208
Kegg IDC02679
ChemSpider ID3361474
Wikipedia IDLauric acid
BioCyc IDDODECANOATE
EcoCyc IDDODECANOATE

Enzymes

General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Locus Tag:
PA5089
Molecular weight:
83.4 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:
tesA
Locus Tag:
PA2856
Molecular weight:
21 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids
Gene Name:
fadD
Locus Tag:
PA3299
Molecular weight:
61.7 kDa
Reactions
ATP + a long-chain fatty acid + CoA = AMP + diphosphate + an acyl-CoA.
General function:
Involved in acyl-CoA hydrolase activity
Specific function:
Can hydrolyze a broad range of acyl-CoA thioesters. Its physiological function is not known
Gene Name:
tesB
Locus Tag:
PA3942
Molecular weight:
32.9 kDa
General function:
Involved in fatty acid biosynthetic process
Specific function:
Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:
acpP
Locus Tag:
PA2966
Molecular weight:
8.7 kDa

Transporters