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Showing Compound Sphingosine 1-phosphate (FDB021927)

Record Information
Version1.0
Creation date2011-09-21 00:05:21 UTC
Update date2018-05-02 12:56:49 UTC
Primary IDFDB021927
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSphingosine 1-phosphate
DescriptionSphingosine 1-phosphate (S1P) is a phosphorylated sphingolipid metabolite with potent bioactive actions in the Sphingolipid metabolism, Calcium signaling pathway and Neuroactive ligand-receptor interaction. Generated by sphingosine kinases and ceramide kinase, S1P control numerous aspects of cell physiology, including cell survival and mammalian inflammatory responses. S1P is involved in cyclooxygenase-2 induction (COX-2), and regulate production of eicosanoids (important inflammatory mediators). S1P functions mainly via G-protein-coupled receptors and probably also has intracellular targets. (PMID 16219683) [HMDB]
CAS Number26993-30-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Sphingosine 1-phosphoric acidGenerator
(2S,3R,4E)-1-(Dihydrogen phosphate)2-amino-4-octadecene-1,3-diolHMDB
C18-Sphingosine 1-phosphateHMDB
D-erythro-Sphingosine-1-phosphateHMDB
(2S,3R,4e)-1-(Dihydrogen ate)2-amino-4-octadecene-1,3-diolHMDB
(2S,3R,4E)-1-(dihydrogen phosphate)2-amino-4-Octadecene-1,3-diolhmdb
C18-Sphingosine 1-ateHMDB
D-erythro-Sphingosine-1-ateHMDB
Sphingosine 1-phosphic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0065 g/LALOGPS
logP3.73ALOGPS
logP3.43ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area113.01 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity102.76 m³·mol⁻¹ChemAxon
Polarizability44.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H38NO5P
IUPAC name{[(4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid
InChI IdentifierInChI=1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+
InChI KeyDUYSYHSSBDVJSM-CCEZHUSRSA-N
Isomeric SMILESCCCCCCCCCCCCC\C=C\C(O)C(N)COP(O)(O)=O
Average Molecular Weight379.4718
Monoisotopic Molecular Weight379.248759843
Classification
Description Belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassPhosphosphingolipids
Direct ParentPhosphosphingolipids
Alternative Parents
Substituents
  • Sphingoid-1-phosphate or derivatives
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Secondary alcohol
  • Amine
  • Organic oxygen compound
  • Primary amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Primary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
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 1-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000f-4931000000-4b3c540de3fc7400424bSpectrum
Predicted GC-MSSphingosine 1-phosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dj-6391200000-9cd841cb00505ed223b7Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0196000000-5eea23195b7b99ec34e52016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-1291000000-1adf6b535316debf2e132016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r7-6890000000-139c79c466e4d15fe2cc2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-8019000000-fec1176b1adea0fec76c2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-44f97efcca84f202d4282016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-2eea77084e3b7f68590a2016-09-14View Spectrum
NMRNot Available
ChemSpider ID4510276
ChEMBL IDNot Available
KEGG Compound IDC06124
Pubchem Compound ID5353956
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00277
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID47453
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSphingosine 1-phosphate
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
Ganglioside GM2 activatorGM2AP17900
Sphingosine-1-phosphate lyase 1SGPL1O95470
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
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
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