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Identification
YMDB IDYMDB00190
NameSphingosine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSphingosine, also known as (4E)-sphingenine, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Sphingosine is a very strong basic compound (based on its pKa). Sphingosine exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
Synonyms
  • (-)-D-erythro-Sphingosine
  • (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol
  • (2S,3R)-Sphingosine
  • (4E)-Sphingenine
  • [R-[R*,S*-(E)]]-2-amino-4-Octadecene-1,3-diol
  • 4-Sphingenine
  • 4-trans-Sphingenine
CAS number123-78-4
WeightAverage: 299.4919
Monoisotopic: 299.282429433
InChI KeyWWUZIQQURGPMPG-CCEZHUSRSA-N
InChIInChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+
IUPAC Name(4E)-2-aminooctadec-4-ene-1,3-diol
Traditional IUPAC Namesphingosine
Chemical FormulaC18H37NO2
SMILES[H]OC([H])([H])C([H])(N([H])[H])C([H])(O[H])C([H])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,2-aminoalcohols
Alternative Parents
Substituents
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Primary aliphatic amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting point81 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
logP5.15ALOGPS
logP4.57ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)14.12ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity91.89 m³·mol⁻¹ChemAxon
Polarizability39.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Nuclear Envelope, Plasma Membrane
Organoleptic PropertiesNot Available
SMPDB Pathways
Sphingolipid metabolismPW002479 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Sphingolipid metabolismec00600 Map00600
SMPDB Reactions
Sphingosine + Adenosine triphosphateSphingosine 1-phosphate + ADP
Sphingosine 1-phosphate + ADPSphingosine + Adenosine triphosphate
Sphingosine + phosphateSphingosine 1-phosphate + water
Ceramide (d18:1/18:0) + waterSphingosine
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Synthesis Reference:Obayashi, Michio; Schlosser, Manfred. An efficient synthesis of (2S,3R)- and (2S,3S)-sphingosine. Chemistry Letters (1985), (11), 1715-18.
External Links:
ResourceLink
CHEBI ID46964
HMDB IDHMDB00252
Pubchem Compound ID31270
Kegg IDC00319
ChemSpider ID23937169
FOODB IDFDB021919
WikipediaSphingosine
BioCyc IDSPHINGOSINE

Enzymes

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 diacylglycerol kinase activity
Specific function:
Catalyzes the phosphorylation of the sphingoid long chain bases dihydrosphingosine (DHS or sphinganine) and phytosphingosine (PHS) to form dihydrosphingosine 1-phosphate (DHS-1P) and phytosphingosine 1-phosphate (PHS-1P) respectively. Involved in the biosynthesis of sphingolipids and ceramides. Required with LCB3 for an effective incorporation of DHS into ceramides through a phosphorylation-dephosphorylation cycle. Involved in heat-induced transient cell cycle arrest. Accumulation of phosphorylated sphingoid long chain bases (LCBPs) stimulates calcium influx and activates calcineurin signaling. Involved in heat-stress resistance
Gene Name:
LCB4
Uniprot ID:
Q12246
Molecular weight:
69638.60156
Reactions
ATP + sphinganine → ADP + sphinganine 1-phosphate.
ATP + phytosphingosine → ADP + phytosphingosine 1-phosphate.
General function:
Involved in diacylglycerol kinase activity
Specific function:
Catalyzes the phosphorylation of the sphingoid long chain bases dihydrosphingosine (DHS or sphinganine) and phytosphingosine (PHS) to form dihydrosphingosine 1-phosphate (DHS-1P) and phytosphingosine 1-phosphate (PHS-1P) respectively. Redundant to LCB4, is only responsible for few percent of the total activity. Involved in the biosynthesis of sphingolipids and ceramides. Involved in heat-induced transient cell cycle arrest. Accumulation of phosphorylated sphingoid long chain bases (LCBPs) stimulates calcium influx and activates calcineurin signaling. Involved in heat-stress resistance
Gene Name:
LCB5
Uniprot ID:
Q06147
Molecular weight:
77564.60156
Reactions
ATP + sphinganine → ADP + sphinganine 1-phosphate.
ATP + phytosphingosine → ADP + phytosphingosine 1-phosphate.