Record Information
Version2.0
Creation Date2012-05-31 13:59:55 -0600
Update Date2015-06-03 15:54:30 -0600
Secondary Accession Numbers
  • ECMDB03571
Identification
Name:Lauroyl-CoA
DescriptionLauroyl-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
Synonyms:
  • Dodecanoyl-CoA
  • Dodecanoyl-CoA (N-C12:0CoA)
  • Dodecanoyl-Coenzyme A
  • Lauroyl coenzyme A
Chemical Formula:C33H58N7O17P3S
Weight:Average: 949.837
Monoisotopic: 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
Description belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentThiamine phosphates
Alternative Parents
Substituents
  • Thiamine-phosphate
  • Organic pyrophosphate
  • 2,4,5-trisubstituted 1,3-thiazole
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Imidolactam
  • Phosphoric acid ester
  • Alkyl phosphate
  • Azole
  • Heteroaromatic compound
  • Thiazole
  • Amino acid or derivatives
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic alcohol
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.59 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity218.24 m³·mol⁻¹ChemAxon
Polarizability91.8 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Fatty acid metabolismPW000796 ThumbThumb?image type=greyscaleThumb?image type=simple
fatty acid oxidation (Decanoate)PW001018 ThumbThumb?image type=greyscaleThumb?image type=simple
fatty acid oxidation (laurate)PW001020 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
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

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
Uniprot ID:
P21151
Molecular weight:
40876
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
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
Uniprot ID:
P69451
Molecular weight:
62332
Reactions
ATP + a long-chain fatty acid + CoA = AMP + diphosphate + an acyl-CoA.
General function:
Involved in transferase 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. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long- chain fatty acids
Gene Name:
fadI
Uniprot ID:
P76503
Molecular weight:
46530
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the dehydrogenation of acyl-CoA
Gene Name:
fadE
Uniprot ID:
Q47146
Molecular weight:
89224
Reactions
An acyl-CoA + FAD = a dehydrogenated acyl-CoA + FADH(2).
General function:
Involved in catalytic activity
Specific function:
Catalyzes the esterification, concomitant with transport, of exogenous fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It has a low activity on medium or long chain fatty acids and is maximally active on C6 and C8 substrates
Gene Name:
fadK
Uniprot ID:
P38135
Molecular weight:
60773
Reactions
ATP + a short-chain carboxylic 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
Uniprot ID:
P0AGG2
Molecular weight:
31966