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Showing Compound Sphingosine (FDB021919)

Record Information
Version1.0
Creation date2011-09-21 00:05:10 UTC
Update date2019-11-26 03:21:00 UTC
Primary IDFDB021919
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSphingosine
DescriptionA 18-carbon amino alcohol with a long unsaturated hydrocarbon chain. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. (Dorland, 28th ed.) Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid. [HMDB]. Sphingosine is found in many foods, some of which are alaska blueberry, watercress, redcurrant, and rowanberry.
CAS Number123-78-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-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
(-)-D-erythro-Sphingosinehmdb
[R-[R*,S*-(E)]]-2-amino-4-Octadecene-1,3-diolhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H37NO2
IUPAC name(4E)-2-aminooctadec-4-ene-1,3-diol
InChI IdentifierInChI=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
Isomeric SMILESCCCCCCCCCCCCC\C=C\C(O)C(N)CO
Average Molecular Weight299.4919
Monoisotopic Molecular Weight299.282429433
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSphingosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dr-9260000000-2ff04e0afd9e8b2f0851Spectrum
Predicted GC-MSSphingosine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-003r-8915100000-51f94df9cbd9e00dbf76Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0090000000-67307f0b7f6f858af4002012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9010000000-e66065dfabaedfa9a7f22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0api-9000000000-a5c7c01555839f61ab3d2012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0092000000-c0188d9e3166e42d0a722016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ai-2390000000-23fd78f38dca1695f6532016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-6940000000-bd71a7546dbbc9a6e83b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-310f8ec2f529dd63e5b72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07d4-4090000000-3ec929924c6bbc7293e02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9030000000-c344fe4fe9af07abf7102016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID4510275
ChEMBL IDNot Available
KEGG Compound IDC00319
Pubchem Compound ID5353955
Pubchem Substance IDNot Available
ChEBI ID16393
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00252
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34606
KNApSAcK IDNot Available
HET ID1SX6
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSphingosine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Acid ceramidaseASAH1Q13510
Putative neutral ceramidase CASAH2CP0C7U2
Alkaline ceramidase 2ACER2Q5QJU3
Neutral ceramidaseASAH2Q9NR71
Alkaline ceramidase 1ACER1Q8TDN7
Ganglioside GM2 activatorGM2AP17900
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylasePIGLQ9Y2B2
Phosphatidylinositol N-acetylglucosaminyltransferase subunit QPIGQQ9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit APIGAP37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit HPIGHQ14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit PPIGPP57054
Phosphatidylinositol N-acetylglucosaminyltransferase subunit CPIGCQ92535
T-cell surface glycoprotein CD1e, membrane-associatedCD1EP15812
Epididymal secretory protein E1NPC2P61916
Ceramide synthase 1CERS1P27544
Antigen-presenting glycoprotein CD1dCD1DP15813
GPI mannosyltransferase 1PIGMQ9H3S5
Phosphatidylinositol-glycan biosynthesis class W proteinPIGWQ7Z7B1
Phosphatidylinositol-glycan biosynthesis class X proteinPIGXQ8TBF5
GPI mannosyltransferase 4PIGZQ86VD9
Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferaseB3GNT5Q9BYG0
Beta-1,3-galactosyltransferase 5B3GALT5Q9Y2C3
GPI mannosyltransferase 3PIGBQ92521
Phosphatidylinositol-glycan biosynthesis class F proteinPIGFQ07326
GPI ethanolamine phosphate transferase 2PIGGQ5H8A4
GPI ethanolamine phosphate transferase 1PIGNO95427
GPI ethanolamine phosphate transferase 3PIGOQ8TEQ8
GPI transamidase component PIG-SPIGSQ96S52
GPI transamidase component PIG-TPIGTQ969N2
Phosphatidylinositol glycan anchor biosynthesis class U proteinPIGUQ9H490
GPI mannosyltransferase 2PIGVQ9NUD9
Phosphatidylinositol N-acetylglucosaminyltransferase subunit YPIGYQ3MUY2
Non-lysosomal glucosylceramidaseGBA2Q9HCG7
GPI-anchor transamidasePIGKQ92643
Sphingosine-1-phosphate phosphatase 2SGPP2Q8IWX5
Sphingosine kinase 1SPHK1Q96GK1
Sphingosine 1-phosphate receptor 4S1PR4O95977
Sphingosine 1-phosphate receptor 2S1PR2O95136
Sphingosine 1-phosphate receptor 1S1PR1P21453
Sphingosine 1-phosphate receptor 5S1PR5Q9H228
Pathways
NameSMPDB LinkKEGG Link
Sphingolipid MetabolismSMP00034 map00500
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference