Showing metabocard for Sphingosine 1-phosphate (BMDB0000277)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:44 UTC
Update Date2020-05-21 16:27:10 UTC
BMDB IDBMDB0000277
Secondary Accession Numbers
  • BMDB00277
Metabolite Identification
Common NameSphingosine 1-phosphate
DescriptionSphingosine 1-phosphate, also known as S1P, 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. Based on a literature review a significant number of articles have been published on Sphingosine 1-phosphate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2-Amino-3-hydroxy-octadec-4-enoxy)phosphonic acidChEBI
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(dihydrogen phosphate)ChEBI
C18-Sphingosine 1-phosphateChEBI
D-Erythro-sphingosine 1-phosphateChEBI
S1PChEBI
Sphing-4-enine 1-phosphateChEBI
Sphingosine 1-phosphic acidChEBI
Sphingosine-1-phosphateChEBI
(2-Amino-3-hydroxy-octadec-4-enoxy)phosphonateGenerator
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(dihydrogen phosphoric acid)Generator
C18-Sphingosine 1-phosphoric acidGenerator
D-Erythro-sphingosine 1-phosphoric acidGenerator
Sphing-4-enine 1-phosphoric acidGenerator
Sphingosine 1-phosphoric acidGenerator
Sphingosine-1-phosphoric acidGenerator
Sphingosine 1-phosphateGenerator
S1p CompoundMeSH, HMDB
Chemical FormulaC18H38NO5P
Average Molecular Weight379.4718
Monoisotopic Molecular Weight379.248759843
IUPAC Name{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid
Traditional Namesphingosine 1-phosphate
CAS Registry Number26993-30-6
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O
InChI Identifier
InChI=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+/t17-,18+/m0/s1
InChI KeyDUYSYHSSBDVJSM-KRWOKUGFSA-N
Chemical Taxonomy
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 Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Endosome
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability43.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01oy-9704000000-01cb22ce1e9a3c960e45View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-708280c66eba879f3760View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-b7ef97202b0963c529afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-5e7a9cfe6021f7ce34f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2009000000-6702a746f1f83cd2f7e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e1f5b79920ef4f1ff109View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1179000000-a20f05ceee2f0e373891View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1190000000-533e39f252437099592aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apl-9110000000-71e07136e3b122e68a29View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Endosome
  • Membrane
Biospecimen Locations
  • Fibroblasts
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0062531
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00053795
Chemspider ID4446673
KEGG Compound IDC06124
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSphingosine-1-phosphate
METLIN IDNot Available
PubChem Compound5283560
PDB IDNot Available
ChEBI ID37550
References
Synthesis ReferenceMorigaki, Eiji; Miura, Yoshie; Takahata, Kyoya; Tada, Mikiro; Nakajima, Shuhei; Baba, Naomichi. Enzymic preparation of sphingosine 1-phosphate. Journal of Chemical Research, Synopses (1998), (12), 774-775.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. SGPL1 protein
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
SGPL1
Uniprot ID:
A5D788
Molecular weight:
63567.0
Reactions
Sphingosine 1-phosphate → O-Phosphoethanolamine + Palmitaldehydedetails
Enzyme Details
2. Sphingosine 1-phosphate receptor 1
General function:
Involved in lysosphingolipid and lysophosphatidic acid
Specific function:
G-protein coupled receptor for the bioactive lysosphingolipid sphingosine 1-phosphate (S1P) that seems to be coupled to the G(i) subclass of heteromeric G proteins. Signaling leads to the activation of RAC1, SRC, PTK2/FAK1 and MAP kinases. Plays an important role in cell migration, probably via its role in the reorganization of the actin cytoskeleton and the formation of lamellipodia in response to stimuli that increase the activity of the sphingosine kinase SPHK1. Required for normal chemotaxis toward sphingosine 1-phosphate. Required for normal embryonic heart development and normal cardiac morphogenesis. Plays an important role in the regulation of sprouting angiogenesis and vascular maturation. Inhibits sprouting angiogenesis to prevent excessive sprouting during blood vessel development. Required for normal egress of mature T-cells from the thymus into the blood stream and into peripheral lymphoid organs. Plays a role in the migration of osteoclast precursor cells, the regulation of bone mineralization and bone homeostasis. Plays a role in responses to oxidized 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine by pulmonary endothelial cells and in the protection against ventilator-induced lung injury (By similarity).
Gene Name:
S1PR1
Uniprot ID:
Q5E9P3
Molecular weight:
42949.0