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Showing metabocard for Lauroyl-CoA (BMDB0003571)
Record Information | |||||||||||||||||
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Version | 1.0 | ||||||||||||||||
Creation Date | 2016-09-30 23:05:22 UTC | ||||||||||||||||
Update Date | 2020-05-21 16:29:09 UTC | ||||||||||||||||
BMDB ID | BMDB0003571 | ||||||||||||||||
Secondary Accession Numbers |
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Metabolite Identification | |||||||||||||||||
Common Name | Lauroyl-CoA | ||||||||||||||||
Description | Lauroyl-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 | |||||||||||||||||
Synonyms |
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Chemical Formula | C33H58N7O17P3S | ||||||||||||||||
Average Molecular Weight | 949.837 | ||||||||||||||||
Monoisotopic Molecular Weight | 949.282273691 | ||||||||||||||||
IUPAC Name | Not Available | ||||||||||||||||
Traditional Name | Not Available | ||||||||||||||||
CAS Registry Number | 6244-92-4 | ||||||||||||||||
SMILES | Not Available | ||||||||||||||||
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 Key | YMCXGHLSVALICC-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. | ||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||
Super Class | Organic acids and derivatives | ||||||||||||||||
Class | Hydroxy acids and derivatives | ||||||||||||||||
Sub Class | Beta hydroxy acids and derivatives | ||||||||||||||||
Direct Parent | Beta hydroxy acids and derivatives | ||||||||||||||||
Alternative Parents |
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Substituents |
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Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||
External Descriptors |
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Ontology | |||||||||||||||||
Status | Expected but not Quantified | ||||||||||||||||
Origin |
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Biofunction | Not Available | ||||||||||||||||
Application | Not Available | ||||||||||||||||
Cellular locations |
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Physical Properties | |||||||||||||||||
State | Solid | ||||||||||||||||
Experimental Properties |
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Predicted Properties | Not Available | ||||||||||||||||
Spectra | |||||||||||||||||
Spectra |
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Biological Properties | |||||||||||||||||
Cellular Locations |
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Biospecimen Locations |
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Pathways | |||||||||||||||||
Normal Concentrations | |||||||||||||||||
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Abnormal Concentrations | |||||||||||||||||
Not Available | |||||||||||||||||
External Links | |||||||||||||||||
HMDB ID | HMDB0003571 | ||||||||||||||||
DrugBank ID | DB03264 | ||||||||||||||||
Phenol Explorer Compound ID | Not Available | ||||||||||||||||
FooDB ID | FDB023198 | ||||||||||||||||
KNApSAcK ID | Not Available | ||||||||||||||||
Chemspider ID | 145018 | ||||||||||||||||
KEGG Compound ID | C01832 | ||||||||||||||||
BioCyc ID | LAUROYLCOA-CPD | ||||||||||||||||
BiGG ID | 38504 | ||||||||||||||||
Wikipedia Link | Not Available | ||||||||||||||||
METLIN ID | 6959 | ||||||||||||||||
PubChem Compound | 165436 | ||||||||||||||||
PDB ID | Not Available | ||||||||||||||||
ChEBI ID | 15521 | ||||||||||||||||
References | |||||||||||||||||
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 | ||||||||||||||||
General References | Not Available |
Enzymes
- 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 + Pyrophosphate | details |
- 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 A | details |
DG(20:0/14:0/0:0) + Lauroyl-CoA → TG(20:0/14:0/12:0) + Coenzyme A | details |
DG(19:0/22:0/0:0) + Lauroyl-CoA → TG(19:0/22:0/12:0) + Coenzyme A | details |
DG(20:0/15:0/0:0) + Lauroyl-CoA → TG(20:0/15:0/12:0) + Coenzyme A | details |
DG(20:0/12:0/0:0) + Lauroyl-CoA → TG(20:0/12:0/12:0) + Coenzyme A | details |
DG(20:0/20:0/0:0) + Lauroyl-CoA → TG(20:0/20:0/12:0) + Coenzyme A | details |
DG(21:0/8:0/0:0) + Lauroyl-CoA → TG(21:0/8:0/12:0) + Coenzyme A | details |
DG(21:0/12:0/0:0) + Lauroyl-CoA → TG(21:0/12:0/12:0) + Coenzyme A | details |
DG(21:0/10:0/0:0) + Lauroyl-CoA → TG(21:0/10:0/12:0) + Coenzyme A | details |
DG(21:0/17:0/0:0) + Lauroyl-CoA → TG(21:0/17:0/12:0) + Coenzyme A | details |
DG(22:0/17:0/0:0) + Lauroyl-CoA → TG(22:0/17:0/12:0) + Coenzyme A | details |
DG(22:0/12:0/0:0) + Lauroyl-CoA → TG(22:0/12:0/12:0) + Coenzyme A | details |
DG(22:0/16:0/0:0) + Lauroyl-CoA → TG(22:0/16:0/12:0) + Coenzyme A | details |
DG(22:0/10:0/0:0) + Lauroyl-CoA → TG(22:0/10:0/12:0) + Coenzyme A | details |
DG(22:0/22:0/0:0) + Lauroyl-CoA → TG(22:0/22:0/12:0) + Coenzyme A | details |
DG(8:0/19:0/0:0) + Lauroyl-CoA → TG(8:0/19:0/12:0) + Coenzyme A | details |
DG(8:0/13:0/0:0) + Lauroyl-CoA → TG(8:0/13:0/12:0) + Coenzyme A | details |
DG(10:0/17:0/0:0) + Lauroyl-CoA → TG(10:0/17:0/12:0) + Coenzyme A | details |
DG(10:0/12:0/0:0) + Lauroyl-CoA → TG(10:0/12:0/12:0) + Coenzyme A | details |
DG(8:0/14:0/0:0) + Lauroyl-CoA → TG(8:0/14:0/12:0) + Coenzyme A | details |
DG(10:0/16:0/0:0) + Lauroyl-CoA → TG(10:0/16:0/12:0) + Coenzyme A | details |
DG(8:0/15:0/0:0) + Lauroyl-CoA → TG(8:0/15:0/12:0) + Coenzyme A | details |
DG(10:0/18:0/0:0) + Lauroyl-CoA → TG(10:0/18:0/12:0) + Coenzyme A | details |
DG(8:0/12:0/0:0) + Lauroyl-CoA → TG(8:0/12:0/12:0) + Coenzyme A | details |
DG(10:0/19:0/0:0) + Lauroyl-CoA → TG(10:0/19:0/12:0) + Coenzyme A | details |
DG(8:0/17:0/0:0) + Lauroyl-CoA → TG(8:0/17:0/12:0) + Coenzyme A | details |
DG(19:0/a-21:0/0:0) + Lauroyl-CoA → TG(19:0/a-21:0/12:0) + Coenzyme A | details |
DG(19:0/a-25:0/0:0) + Lauroyl-CoA → TG(19:0/a-25:0/12:0) + Coenzyme A | details |
DG(19:0/i-21:0/0:0) + Lauroyl-CoA → TG(19:0/i-21:0/12:0) + Coenzyme A | details |
DG(19:0/i-22:0/0:0) + Lauroyl-CoA → TG(19:0/i-22:0/12:0) + Coenzyme A | details |
DG(19:0/i-24:0/0:0) + Lauroyl-CoA → TG(19:0/i-24:0/12:0) + Coenzyme A | details |
DG(20:0/a-21:0/0:0) + Lauroyl-CoA → TG(20:0/a-21:0/12:0)[rac] + Coenzyme A | details |
DG(a-21:0/12:0/0:0) + Lauroyl-CoA → TG(a-21:0/12:0/12:0)[rac] + Coenzyme A | details |
DG(a-21:0/a-21:0/0:0) + Lauroyl-CoA → TG(a-21:0/a-21:0/12:0)[rac] + Coenzyme A | details |
DG(a-25:0/12:0/0:0) + Lauroyl-CoA → TG(a-25:0/12:0/12:0)[rac] + Coenzyme A | details |
DG(a-25:0/a-25:0/0:0) + Lauroyl-CoA → TG(a-25:0/a-25:0/12:0)[rac] + Coenzyme A | details |
DG(i-19:0/i-21:0/0:0) + Lauroyl-CoA → TG(i-19:0/i-21:0/12:0) + Coenzyme A | details |
DG(i-19:0/i-22:0/0:0) + Lauroyl-CoA → TG(i-19:0/i-22:0/12:0) + Coenzyme A | details |
DG(i-19:0/i-24:0/0:0) + Lauroyl-CoA → TG(i-19:0/i-24:0/12:0) + Coenzyme A | details |
DG(i-20:0/12:0/0:0) + Lauroyl-CoA → TG(i-20:0/12:0/12:0) + Coenzyme A | details |
DG(i-20:0/i-20:0/0:0) + Lauroyl-CoA → TG(i-20:0/i-20:0/12:0) + Coenzyme A | details |
DG(i-21:0/12:0/0:0) + Lauroyl-CoA → TG(i-21:0/12:0/12:0) + Coenzyme A | details |
DG(i-21:0/i-21:0/0:0) + Lauroyl-CoA → TG(i-21:0/i-21:0/12:0) + Coenzyme A | details |
DG(i-22:0/12:0/0:0) + Lauroyl-CoA → TG(i-22:0/12:0/12:0) + Coenzyme A | details |
DG(i-22:0/i-22:0/0:0) + Lauroyl-CoA → TG(i-22:0/i-22:0/12:0) + Coenzyme A | details |
DG(i-24:0/12:0/0:0) + Lauroyl-CoA → TG(i-24:0/12:0/12:0) + Coenzyme A | details |
DG(i-24:0/i-24:0/0:0) + Lauroyl-CoA → TG(i-24:0/i-24:0/12:0) + Coenzyme A | details |