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Identification
YMDB IDYMDB00624
NameN-(26-Hydroxyhexacosanyl)phytosphingosine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionN-(26-Hydroxyhexacosanyl)phytosphingosine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-(26-Hydroxyhexacosanyl)phytosphingosine may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • Cer(t18:0/26:0(2-OH))
  • cer3_26
  • ceramide-3 (phytosphingosine:N-C26:2OH)
  • N-(2-hydroxyhexacosanoyl)-4S-hydroxysphinganine
  • N-(2-hydroxyhexacosanoyl)-phytoceramide
CAS numberNot Available
WeightAverage: 712.1812
Monoisotopic: 711.674074963
InChI KeyCOPMYEMNKJZCGO-KZRDWULCSA-N
InChIInChI=1S/C44H89NO5/c1-2-3-4-5-6-7-8-22-25-28-31-34-37-42(48)44(50)41(40-47)45-43(49)38-35-32-29-26-23-20-18-16-14-12-10-9-11-13-15-17-19-21-24-27-30-33-36-39-46/h41-42,44,46-48,50H,2-40H2,1H3,(H,45,49)/t41-,42+,44-/m0/s1
IUPAC Name26-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]hexacosanamide
Traditional IUPAC Name26-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]hexacosanamide
Chemical FormulaC44H89NO5
SMILESCCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO
Chemical Taxonomy
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.4e-05 g/LALOGPS
logP9.44ALOGPS
logP13.01ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)13.26ChemAxon
pKa (Strongest Basic)0.034ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.02 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity214.11 m³·mol⁻¹ChemAxon
Polarizability97.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Golgi
  • endoplasmic reticulum
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
N-Hexacosanoylphytosphingosine + NADPH + hydron + oxygenNADP + N-(26-Hydroxyhexacosanyl)phytosphingosine + water
N-(26-Hydroxyhexacosanyl)phytosphingosine + 1D-myo-inositol 1-phosphateinositol-P-ceramide C (C26)
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
  • Funato, K., Vallee, B., Riezman, H. (2002). "Biosynthesis and trafficking of sphingolipids in the yeast Saccharomyces cerevisiae." Biochemistry 41:15105-15114.12484746
  • Reggiori, F., Conzelmann, A. (1998). "Biosynthesis of inositol phosphoceramides and remodeling of glycosylphosphatidylinositol anchors in Saccharomyces cerevisiae are mediated by different enzymes." J Biol Chem 273:30550-30559.9804825
  • 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 ID52374
HMDB IDNot Available
Pubchem Compound ID25271598
Kegg IDNot Available
ChemSpider ID23106997
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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
General function:
Involved in catalytic activity
Specific function:
Catalyzes the addition of a phosphorylinositol group onto ceramide to form inositol phosphorylceramide, an essential step in sphingolipid biosynthesis
Gene Name:
AUR1
Uniprot ID:
P36107
Molecular weight:
45192.80078
Reactions