Canmetcon
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Identification
YMDB IDYMDB00621
NameN-hexacosanylsphinganine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description

N-Hexacosanylsphinganine is a ceramide (a sphingolipid). Ceramides are found in high concentrations within the cell membrane of cells. Ceramides are composed of a sphingosine and a fatty acid. Ceramides are found in high concentrations within the cell membrane of cells. Caramides are known to promote transport of secretory vesicles from the ER to the Golgi apparatus. Sphingolipids like ceramide play import roles in lipid rafts which in yeast are responsible for delivering and sorting membrane bound proteins. Lipid rafts also play roles in membrane fusion during mating.[PMID: 16730802]

There are three major pathways of ceramide generation. The sphingomyelinase pathway uses an enzyme to breakdown IPC, MIPC and M(IP)2C in the cell membrane and release ceramide. The de novo pathway creates ceramide from less complex molecules. Ceramide generation can also occur through breakdown of complex sphingolipids that are ultimately broken down into sphingosine, which is then reused by reacylation to form ceramide. This latter pathway is termed the Salvage pathway.[Wikipedia, PMID: 16730802]

Structure
Thumb
Synonyms
  • C26DH Cer
  • Cer(d18:0/26:0)
  • ceramide-1 (sphinganine:N-C26:0)
  • N-(hexacosanoyl)-sphinganine
  • N-[(2S,3R)-1,3-Bis(oxidanyl)octadecan-2-yl]hexacosanamide
CAS numberNot Available
WeightAverage: 680.1824
Monoisotopic: 679.684245719
InChI KeyNWERZHCPHDHUMO-WZYYJWNZSA-N
InChIInChI=1S/C44H89NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-44(48)45-42(41-46)43(47)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2/h42-43,46-47H,3-41H2,1-2H3,(H,45,48)/t42-,43+/m0/s1
IUPAC NameN-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]hexacosanamide
Traditional IUPAC NameC26DH cer
Chemical FormulaC44H89NO3
SMILESCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)CCCCCCCCCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassCeramides
Direct ParentCeramides
Alternative Parents
Substituents
  • Ceramide
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.0e-05 g/LALOGPS
logP10.35ALOGPS
logP15.52ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)13.83ChemAxon
pKa (Strongest Basic)0.034ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity210.82 m³·mol⁻¹ChemAxon
Polarizability95.16 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
N-hexacosanylsphinganine + NADPH + hydron + oxygenNADP + N-Hexacosanoylphytosphingosine + water
N-hexacosanylsphinganine + NADPH + hydron + oxygenNADP + water + N-(26-hydroxyhexacosanoyl)sphinganine
Sphinganine + hexacosanoyl-CoAN-hexacosanylsphinganine + hydron + Coenzyme A
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
  • 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
  • Dickson, R. C. (2008). "Thematic review series: sphingolipids. New insights into sphingolipid metabolism and function in budding yeast." J Lipid Res 49:909-921.18296751
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID52962
HMDB IDHMDB0011771
Pubchem Compound ID644245
Kegg IDNot Available
ChemSpider ID559264
FOODB IDFDB028441
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 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 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 iron ion binding
Specific function:
Required for hydroxylation of C-4 in the sphingoid moiety of ceramide. Involved in the response to syringomycin
Gene Name:
SUR2
Uniprot ID:
P38992
Molecular weight:
40734.0
Reactions
General function:
Involved in heme binding
Specific function:
Ceramide hydroxylase involved in the alpha-hydroxylation of sphingolipid-associated very long chain fatty acids. Hydroxylates the very long chain fatty acid of ceramides at C2 and C3
Gene Name:
SCS7
Uniprot ID:
Q03529
Molecular weight:
44881.10156
Reactions