Lauroyl-CoA (PAMDB000516)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000516
Identification
Name: Lauroyl-CoA
Description:Lauroyl-CoA is a substrate for Long chain fatty acyl-CoA synthetase. This enzyme is a member of the ligase family that activates the breakdown of complex fatty acids. Long chain fatty acyl-CoA synthetase plays a crucial role in intermediary metabolism by catalyzing the formation of fatty acyl-CoA by a two-step process proceeding through an adenylated intermediate. It is an enzyme present in all organisms from bacteria to humans.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Dodecanoyl-CoA
  • Dodecanoyl-CoA (N-C12:0CoA)
  • Dodecanoyl-Coenzyme A
  • Lauroyl coenzyme A
Chemical Formula: C33H58N7O17P3S
Average Molecular Weight: 949.837
Monoisotopic Molecular Weight: 949.282273691
InChI Key: YMCXGHLSVALICC-GMHMEAMDSA-N
InChI:InChI=1S/C33H58N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h20-22,26-28,32,43-44H,4-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/t22-,26-,27-,28+,32-/m1/s1
CAS number: 6244-92-4
IUPAC Name:{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(dodecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name: lauroyl-coa
SMILES:CCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent 2,3,4-saturated fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Beta amino acid or derivatives
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.59 mg/mLALOGPS
logP1.35ALOGPS
logP-2.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 Å2ChemAxon
Rotatable Bond Count30ChemAxon
Refractivity218.24 m3·mol-1ChemAxon
Polarizability91.8 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + Coenzyme A + Dodecanoate (N-C12:0) + Hydrogen ion > Adenosine monophosphate + Lauroyl-CoA + Hydrogen ion + Pyrophosphate
Acetyl-CoA + Lauroyl-CoA <> 3-Oxotetradecanoyl-CoA + Coenzyme A
Lauroyl-CoA + FAD <> (2E)-Dodecenoyl-CoA + FADH2
Lauroyl-CoA + Water > Coenzyme A + Dodecanoate (N-C12:0) + Hydrogen ion
3-Oxodecanoyl-CoA + Coenzyme A > Acetyl-CoA + Lauroyl-CoA
Lauroyl-CoA + electron-transfer flavoprotein > (2E)-Tetradecenoyl-CoA + Reduced electron-transfer flavoprotein
Dodecanoic acid + Coenzyme A + Adenosine triphosphate > Adenosine monophosphate + Lauroyl-CoA
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1911101102-687968f22ae76ca547b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0931300000-f614ebfa62da3b2be8e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1910102000-031217cf76abed1b705fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-3922021304-259fa0e4c2115b5176b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2901100001-efdce198394adecd9a34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-7e1a4d11b2e1da20a826View in MoNA
References
References:
  • Hunt MC, Ruiter J, Mooyer P, van Roermond CW, Ofman R, Ijlst L, Wanders RJ: Identification of fatty acid oxidation disorder patients with lowered acyl-CoA thioesterase activity in human skin fibroblasts. Eur J Clin Invest. 2005 Jan;35(1):38-46. Pubmed: 15638818
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
Synthesis Reference: Eaton, Simon; Turnbull, Douglass M.; Bartlett, Kim. Redox control of b-oxidation in rat liver mitochondria. European Journal of Biochemistry (1994), 220(3), 671-81.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15521
HMDB IDHMDB03571
Pubchem Compound ID165436
Kegg IDC01832
ChemSpider ID145018
Wikipedia IDNot Available
BioCyc IDLAUROYLCOA-CPD
EcoCyc IDLAUROYLCOA-CPD
Ligand ExpoDCC

Enzymes

Protein Details
• 3-ketoacyl-CoA thiolase
General function:
Involved in acetyl-CoA C-acyltransferase activity
Specific function:
Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadA
Locus Tag:
PA3013
Molecular weight:
41.6 kDa
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
Protein Details
• Long-chain-fatty-acid--CoA ligase
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.
Protein Details
• Acyl-coenzyme A dehydrogenase
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the dehydrogenation of acyl-CoA
Gene Name:
fadE
Locus Tag:
PA2815
Molecular weight:
88.8 kDa
Reactions
An acyl-CoA + FAD = a dehydrogenated acyl-CoA + FADH(2).
Protein Details
• Acyl-CoA thioesterase 2
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