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Identification
YMDB IDYMDB00537
Namehexacosanoyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionHexacosanoyl-CoA is a coenzyme A derivative of hexacosanoic acid acid. Fatty acids must be activated with CoA before any chemical modification can be applied. Also fatty acid metabolic intermediates will also exists as CoA derivatives until the CoA is enzymatically cleaved. The fatty acid group is linked to the terminal thoil moiety of CoA.
Structure
Thumb
Synonyms
  • C26:0-CoA
  • C26:0-coenzyme A
  • cerotoyl-CoA
  • cerotoyl-coenzyme A
  • hexacosanoyl-CoA (N-C26:0CoA)
  • hexacosanoyl-coenzyme A
CAS numberNot Available
WeightAverage: 1146.209
Monoisotopic: 1145.501374587
InChI KeyFHLYYFPJDVYWQH-CPIGOPAHSA-N
InChIInChI=1S/C47H86N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-38(56)75-31-30-49-37(55)28-29-50-45(59)42(58)47(2,3)33-68-74(65,66)71-73(63,64)67-32-36-41(70-72(60,61)62)40(57)46(69-36)54-35-53-39-43(48)51-34-52-44(39)54/h34-36,40-42,46,57-58H,4-33H2,1-3H3,(H,49,55)(H,50,59)(H,63,64)(H,65,66)(H2,48,51,52)(H2,60,61,62)/t36-,40-,41-,42+,46-/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(hexacosanoylsulfanyl)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 Namecerotoyl-coa
Chemical FormulaC47H86N7O17P3S
SMILESCCCCCCCCCCCCCCCCCCCCCCCCCC(=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
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentVery long-chain 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.025 g/LALOGPS
logP4.87ALOGPS
logP3.95ChemAxon
logS-4.7ALOGPS
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 Count44ChemAxon
Refractivity282.66 m³·mol⁻¹ChemAxon
Polarizability123.21 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • lipid particle
  • endoplasmic reticulum
  • peroxisome
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Biosynthesis of unsaturated fatty acidsPW002403 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Biosynthesis of unsaturated fatty acidsec01040 Map01040
SMPDB Reactions
(2E)-cerotenoyl-CoA + hydron + NADPHhexacosanoyl-CoA + NADP
Phytosphingosine + hexacosanoyl-CoAhydron + Coenzyme A + N-hexacosanoyl-C20-4-hydroxysphinganine
KEGG Reactions
oxygen + hexacosanoyl-CoAHydrogen peroxide + trans-hexacos-2-enoyl-CoA
Sphinganine + hexacosanoyl-CoAN-hexacosanylsphinganine + hydron + Coenzyme A
Phytosphingosine + hexacosanoyl-CoAN-Hexacosanoylphytosphingosine + hydron + Coenzyme A
Adenosine triphosphate + cerotic acid + Coenzyme AAdenosine monophosphate + Pyrophosphate + hexacosanoyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Mao, C., Xu, R., Bielawska, A., Szulc, Z. M., Obeid, L. M. (2000). "Cloning and characterization of a Saccharomyces cerevisiae alkaline ceramidase with specificity for dihydroceramide." J Biol Chem 275:31369-31378.10900202
  • Jiang, J. C., Kirchman, P. A., Zagulski, M., Hunt, J., Jazwinski, S. M. (1998). "Homologs of the yeast longevity gene LAG1 in Caenorhabditis elegans and human." Genome Res 8:1259-1272.9872981
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID52966
HMDB IDNot Available
Pubchem Compound ID25246198
Kegg IDNot Available
ChemSpider ID23107092
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:
Catalyzes the conversion of dihydroceramide and also phytoceramide to dihydrosphingosine or phytosphingosine. Prefers dihydroceramide. Very low reverse hydrolysis activity, catalyzing synthesis of dihydroceramide from fatty acid and dihydrosphingosine. Is not responsible for the breakdown of unsaturated ceramide. May play a role in heat stress response
Gene Name:
YDC1
Uniprot ID:
Q02896
Molecular weight:
37230.5
Reactions
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Acyl-CoA + O(2) = trans-2,3-dehydroacyl-CoA + H(2)O(2)
Gene Name:
POX1
Uniprot ID:
P13711
Molecular weight:
84041.39844
Reactions
Acyl-CoA + O(2) → trans-2,3-dehydroacyl-CoA + H(2)O(2).
General function:
Involved in protein binding
Specific function:
Component of the ceramide synthase complex required for C26-CoA-dependent ceramide synthesis. Redundant with LAC1. Facilitates ER-to-Golgi transport of GPI-anchored proteins. Involved in the aging process. Deletion of LAG1 results in a pronounced increase (approximately 50%) in mean and in maximum life span
Gene Name:
LAG1
Uniprot ID:
P38703
Molecular weight:
48454.10156
Reactions
Acyl-CoA + sphingosine → CoA + N-acylsphingosine.
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:
Hydrolyzes phytoceramide and also dihydroceramide into phytosphingosine or dihydrosphingosine. Prefers phytoceramide. Has also reverse hydrolysis activity, catalyzing synthesis of phytoceramide and dihydroceramide from palmitic acid and phytosphingosine or dihydrosphingosine. Is not responsible for the breakdown of unsaturated ceramide
Gene Name:
YPC1
Uniprot ID:
P38298
Molecular weight:
36419.39844
Reactions
General function:
Involved in identical protein binding
Specific function:
Component of the ceramide synthase complex required for C26-CoA-dependent ceramide synthesis. Redundant with LAG1. Facilitates ER-to-Golgi transport of GPI-anchored proteins
Gene Name:
LAC1
Uniprot ID:
P28496
Molecular weight:
48991.60156
Reactions
Acyl-CoA + sphingosine → CoA + N-acylsphingosine.
General function:
Involved in zinc ion binding
Specific function:
Required for respiration and the maintenance of the mitochondrial compartment. May have a role in the mitochondrial synthesis of fatty acids
Gene Name:
ETR1
Uniprot ID:
P38071
Molecular weight:
42066.5
Reactions
Acyl-[acyl-carrier-protein] + NADP(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADPH.
Acyl-CoA + NADP(+) → trans-2,3-dehydroacyl-CoA + NADPH.

Transporters

General function:
Involved in catalytic activity
Specific function:
May be involved in long-chain fatty acids uptake, and thus may play a pivotal role in regulating their accessibility prior to metabolic utilization. May play an important role in uptake of these hydrophobic compounds under conditions where fatty acid synthesis is compromised
Gene Name:
FAT1
Uniprot ID:
P38225
Molecular weight:
77140.29688
Reactions