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Record Information
Version1.0
Creation Date2016-07-13 19:42:42 UTC
Update Date2016-07-20 20:56:38 UTC
LmdbLMDB00116
Secondary Accession NumbersNone
Metabolite Identification
Common NameSphingosine
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. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid. Sphingosine is a 18-carbon amino alcohol with a long unsaturated hydrocarbon chain. Sphingosine is a very strong basic compound (based on its pKa). Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. Sphingosine exists in all eukaryotes, ranging from yeast to humans. Within humans, sphingosine participates in a number of enzymatic reactions. In particular, sphingosine can be converted into sphingosine 1-phosphate through the action of the enzyme sphingosine kinase 2. In addition, sphingosine can be biosynthesized from sphingosine 1-phosphate; which is mediated by the enzyme sphingosine-1-phosphate phosphatase 2. In humans, sphingosine is involved in the metabolic disorder called the fabry disease pathway. Outside of the human body, Sphingosine has been detected, but not quantified in, several different foods, such as towel gourds, common walnuts, sunburst squash (pattypan squash), common persimmons, and oil-seed camellia. This could make sphingosine a potential biomarker for the consumption of these foods. Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2.
Structure
Thumb
Synonyms
ValueSource
(-)-D-Erythro-sphingosineHMDB
(2S,3R)-SphingosineHMDB
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diolHMDB
(4E)-SphingenineHMDB
4-SphingenineHMDB
4-trans-SphingenineHMDB
[R-[R*,s*-(e)]]-2-amino-4-octadecene-1,3-diolHMDB
Chemical FormulaC18H37NO2
Average Molecular Weight299.4919
Monoisotopic Molecular Weight299.282429433
IUPAC Name(4E)-2-aminooctadec-4-ene-1,3-diol
Traditional Namesphingosine
CAS Registry Number123-78-4
SMILES
CCCCCCCCCCCCC\C=C\C(O)C(N)CO
InChI Identifier
InChI=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+
InChI KeyWWUZIQQURGPMPG-CCEZHUSRSA-N
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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-9260000000-2ff04e0afd9e8b2f0851Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-003r-8915100000-51f94df9cbd9e00dbf76Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0090000000-67307f0b7f6f858af400Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9010000000-e66065dfabaedfa9a7f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0api-9000000000-a5c7c01555839f61ab3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0092000000-c0188d9e3166e42d0a72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ai-2390000000-23fd78f38dca1695f653Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-6940000000-bd71a7546dbbc9a6e83bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-310f8ec2f529dd63e5b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07d4-4090000000-3ec929924c6bbc7293e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9030000000-c344fe4fe9af07abf710Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0000252
FooDB IDFDB021919
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID34606
BioCyc IDNot Available
METLIN ID392
PDB IDNot Available
Wikipedia LinkSphingosine
Chemspider ID4510275
ChEBI ID16393
PubChem Compound ID5353955
Kegg Compound IDC00319
YMDB IDYMDB00190
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available