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Record Information
Version1.0
Creation Date2016-09-30 23:05:22 UTC
Update Date2020-05-21 16:29:09 UTC
BMDB IDBMDB0003571
Secondary Accession Numbers
  • BMDB03571
Metabolite Identification
Common NameLauroyl-CoA
DescriptionLauroyl-CoA, also known as dodecanoyl-CoA or C12:0-CoA, 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. Thus, lauroyl-CoA is considered to be a fatty ester lipid molecule. Lauroyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lauroyl-CoA exists in all living species, ranging from bacteria to humans. Lauroyl-CoA and L-carnitine can be biosynthesized from dodecanoic acid and coenzyme A; which is mediated by the enzyme carnitine O-palmitoyltransferase 2, mitochondrial. In cattle, lauroyl-CoA is involved in the metabolic pathway called the Beta oxidation OF very long chain fatty acids pathway.
Structure
Thumb
Synonyms
ValueSource
C12:0-CoAChEBI
coenzyme A, S-DodecanoateChEBI
Dodecanoyl-CoAChEBI
Dodecanoyl-coenzyme AChEBI
Lauroyl coenzyme AChEBI
Lauroyl-coenzyme AChEBI
coenzyme A, S-Dodecanoic acidGenerator
Chemical FormulaC33H58N7O17P3S
Average Molecular Weight949.837
Monoisotopic Molecular Weight949.282273691
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 Namelauroyl-coa
CAS Registry Number6244-92-4
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=C1N=CN=C2N
InChI Identifier
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
InChI KeyYMCXGHLSVALICC-GMHMEAMDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Morpholine
  • Oxazinane
  • Piperidine
  • N-alkylpyrrolidine
  • Benzenoid
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.35ALOGPS
logP-1.2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity218.24 m³·mol⁻¹ChemAxon
Polarizability91.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Peroxisome
Biospecimen Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003571
DrugBank IDDB03264
Phenol Explorer Compound IDNot Available
FooDB IDFDB023198
KNApSAcK IDNot Available
Chemspider ID145018
KEGG Compound IDC01832
BioCyc IDLAUROYLCOA-CPD
BiGG ID38504
Wikipedia LinkNot Available
METLIN ID6959
PubChem Compound165436
PDB IDNot Available
ChEBI ID15521
References
Synthesis ReferenceEaton, 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
General ReferencesNot Available

Enzymes

General function:
Involved in carnitine O-octanoyltransferase activity
Specific function:
Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate.
Gene Name:
CROT
Uniprot ID:
O19094
Molecular weight:
70263.0
Reactions
Lauroyl-CoA → Coenzyme A + Dodecanoic aciddetails
General function:
Involved in carnitine O-palmitoyltransferase activity
Specific function:
Not Available
Gene Name:
CPT2
Uniprot ID:
Q2KJB7
Molecular weight:
74483.0
Reactions
Dodecanoic acid + Coenzyme A → Lauroyl-CoA + L-Carnitinedetails
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the activation of fatty acids by CoA to produce an acyl-CoA, the first step in fatty acid metabolism (PubMed:11382754, PubMed:10561077). Capable of activating medium-chain fatty acids (e.g. butyric (C4) to decanoic (C10) acids), and certain carboxylate-containing xenobiotics, e.g. benzoate (PubMed:10561077, PubMed:11382754). Also catalyzes the activation of lipoate to lipoyl-nucleoside monophosphate (PubMed:11382754). Activates lipoate with GTP at a 1000-fold higher rate than with ATP and activates both (R)- and (S)-lipoate to the respective lipoyl-GMP, with a preference for (R)-lipoate (PubMed:11382754).
Gene Name:
ACSM1
Uniprot ID:
Q9BEA2
Molecular weight:
64923.0
Reactions
Dodecanoic acid + Adenosine triphosphate + Coenzyme A → Lauroyl-CoA + Adenosine monophosphate + Pyrophosphatedetails
General function:
Not Available
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
Gene Name:
DGAT1
Uniprot ID:
Q8MK44
Molecular weight:
55602.0
Reactions
DG(19:0/21:0/0:0) + Lauroyl-CoA → TG(19:0/21:0/12:0) + Coenzyme Adetails
DG(20:0/14:0/0:0) + Lauroyl-CoA → TG(20:0/14:0/12:0) + Coenzyme Adetails
DG(19:0/22:0/0:0) + Lauroyl-CoA → TG(19:0/22:0/12:0) + Coenzyme Adetails
DG(20:0/15:0/0:0) + Lauroyl-CoA → TG(20:0/15:0/12:0) + Coenzyme Adetails
DG(20:0/12:0/0:0) + Lauroyl-CoA → TG(20:0/12:0/12:0) + Coenzyme Adetails
DG(20:0/20:0/0:0) + Lauroyl-CoA → TG(20:0/20:0/12:0) + Coenzyme Adetails
DG(21:0/8:0/0:0) + Lauroyl-CoA → TG(21:0/8:0/12:0) + Coenzyme Adetails
DG(21:0/12:0/0:0) + Lauroyl-CoA → TG(21:0/12:0/12:0) + Coenzyme Adetails
DG(21:0/10:0/0:0) + Lauroyl-CoA → TG(21:0/10:0/12:0) + Coenzyme Adetails
DG(21:0/17:0/0:0) + Lauroyl-CoA → TG(21:0/17:0/12:0) + Coenzyme Adetails
DG(22:0/17:0/0:0) + Lauroyl-CoA → TG(22:0/17:0/12:0) + Coenzyme Adetails
DG(22:0/12:0/0:0) + Lauroyl-CoA → TG(22:0/12:0/12:0) + Coenzyme Adetails
DG(22:0/16:0/0:0) + Lauroyl-CoA → TG(22:0/16:0/12:0) + Coenzyme Adetails
DG(22:0/10:0/0:0) + Lauroyl-CoA → TG(22:0/10:0/12:0) + Coenzyme Adetails
DG(22:0/22:0/0:0) + Lauroyl-CoA → TG(22:0/22:0/12:0) + Coenzyme Adetails
DG(8:0/19:0/0:0) + Lauroyl-CoA → TG(8:0/19:0/12:0) + Coenzyme Adetails
DG(8:0/13:0/0:0) + Lauroyl-CoA → TG(8:0/13:0/12:0) + Coenzyme Adetails
DG(10:0/17:0/0:0) + Lauroyl-CoA → TG(10:0/17:0/12:0) + Coenzyme Adetails
DG(10:0/12:0/0:0) + Lauroyl-CoA → TG(10:0/12:0/12:0) + Coenzyme Adetails
DG(8:0/14:0/0:0) + Lauroyl-CoA → TG(8:0/14:0/12:0) + Coenzyme Adetails
DG(10:0/16:0/0:0) + Lauroyl-CoA → TG(10:0/16:0/12:0) + Coenzyme Adetails
DG(8:0/15:0/0:0) + Lauroyl-CoA → TG(8:0/15:0/12:0) + Coenzyme Adetails
DG(10:0/18:0/0:0) + Lauroyl-CoA → TG(10:0/18:0/12:0) + Coenzyme Adetails
DG(8:0/12:0/0:0) + Lauroyl-CoA → TG(8:0/12:0/12:0) + Coenzyme Adetails
DG(10:0/19:0/0:0) + Lauroyl-CoA → TG(10:0/19:0/12:0) + Coenzyme Adetails
DG(8:0/17:0/0:0) + Lauroyl-CoA → TG(8:0/17:0/12:0) + Coenzyme Adetails
DG(19:0/a-21:0/0:0) + Lauroyl-CoA → TG(19:0/a-21:0/12:0) + Coenzyme Adetails
DG(19:0/a-25:0/0:0) + Lauroyl-CoA → TG(19:0/a-25:0/12:0) + Coenzyme Adetails
DG(19:0/i-21:0/0:0) + Lauroyl-CoA → TG(19:0/i-21:0/12:0) + Coenzyme Adetails
DG(19:0/i-22:0/0:0) + Lauroyl-CoA → TG(19:0/i-22:0/12:0) + Coenzyme Adetails
DG(19:0/i-24:0/0:0) + Lauroyl-CoA → TG(19:0/i-24:0/12:0) + Coenzyme Adetails
DG(20:0/a-21:0/0:0) + Lauroyl-CoA → TG(20:0/a-21:0/12:0)[rac] + Coenzyme Adetails
DG(a-21:0/12:0/0:0) + Lauroyl-CoA → TG(a-21:0/12:0/12:0)[rac] + Coenzyme Adetails
DG(a-21:0/a-21:0/0:0) + Lauroyl-CoA → TG(a-21:0/a-21:0/12:0)[rac] + Coenzyme Adetails
DG(a-25:0/12:0/0:0) + Lauroyl-CoA → TG(a-25:0/12:0/12:0)[rac] + Coenzyme Adetails
DG(a-25:0/a-25:0/0:0) + Lauroyl-CoA → TG(a-25:0/a-25:0/12:0)[rac] + Coenzyme Adetails
DG(i-19:0/i-21:0/0:0) + Lauroyl-CoA → TG(i-19:0/i-21:0/12:0) + Coenzyme Adetails
DG(i-19:0/i-22:0/0:0) + Lauroyl-CoA → TG(i-19:0/i-22:0/12:0) + Coenzyme Adetails
DG(i-19:0/i-24:0/0:0) + Lauroyl-CoA → TG(i-19:0/i-24:0/12:0) + Coenzyme Adetails
DG(i-20:0/12:0/0:0) + Lauroyl-CoA → TG(i-20:0/12:0/12:0) + Coenzyme Adetails
DG(i-20:0/i-20:0/0:0) + Lauroyl-CoA → TG(i-20:0/i-20:0/12:0) + Coenzyme Adetails
DG(i-21:0/12:0/0:0) + Lauroyl-CoA → TG(i-21:0/12:0/12:0) + Coenzyme Adetails
DG(i-21:0/i-21:0/0:0) + Lauroyl-CoA → TG(i-21:0/i-21:0/12:0) + Coenzyme Adetails
DG(i-22:0/12:0/0:0) + Lauroyl-CoA → TG(i-22:0/12:0/12:0) + Coenzyme Adetails
DG(i-22:0/i-22:0/0:0) + Lauroyl-CoA → TG(i-22:0/i-22:0/12:0) + Coenzyme Adetails
DG(i-24:0/12:0/0:0) + Lauroyl-CoA → TG(i-24:0/12:0/12:0) + Coenzyme Adetails
DG(i-24:0/i-24:0/0:0) + Lauroyl-CoA → TG(i-24:0/i-24:0/12:0) + Coenzyme Adetails