Showing metabocard for Sphinganine 1-phosphate (BMDB0001383)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:45:06 UTC
Update Date2020-05-21 16:28:58 UTC
BMDB IDBMDB0001383
Secondary Accession Numbers
  • BMDB01383
Metabolite Identification
Common NameSphinganine 1-phosphate
DescriptionSphinganine 1-phosphate 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. Sphinganine 1-phosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,3R)-2-Amino-3-hydroxyoctadecyl dihydrogen phosphateChEBI
Dihydrosphingosine 1-phosphateChEBI
Dihydrosphingosine-1-phosphateChEBI
(2S,3R)-2-Amino-3-hydroxyoctadecyl dihydrogen phosphoric acidGenerator
Dihydrosphingosine 1-phosphoric acidGenerator
Dihydrosphingosine-1-phosphoric acidGenerator
Sphinganine 1-phosphoric acidGenerator
2-Amino-3-hydroxyoctadecyl dihydrogen phosphateHMDB
Chemical FormulaC18H40NO5P
Average Molecular Weight381.4877
Monoisotopic Molecular Weight381.264409907
IUPAC Name{[(2S,3R)-2-amino-3-hydroxyoctadecyl]oxy}phosphonic acid
Traditional Namedihydrosphingosine 1-phosphate
CAS Registry Number19794-97-9
SMILES
CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)COP(O)(O)=O
InChI Identifier
InChI=1S/C18H40NO5P/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/h17-18,20H,2-16,19H2,1H3,(H2,21,22,23)/t17-,18+/m0/s1
InChI KeyYHEDRJPUIRMZMP-ZWKOTPCHSA-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
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • 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
logP3.8ALOGPS
logP3.64ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.52ChemAxon
pKa (Strongest Basic)9.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area113.01 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity101.8 m³·mol⁻¹ChemAxon
Polarizability45.32 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 (Non-derivatized) - 70eV, Positivesplash10-0006-4910000000-711eb3339b5799f5551fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9712000000-d3f905278b0c98d96e21View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0092000000-c380cef639a76f98b5d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0091000000-cd799d86547cdbc576fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0092000000-ca0e502c70b5513a4d0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ai-0096000000-dbafed0491e9c794b653View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-1191000000-8eba0bc6a08b306ade37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-6980000000-5d1a644d3395595f3a2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003s-8019000000-89a5c40259a01d528cfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-c58d4e7b8dd266ebb800View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-67c93080b619a8be70dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2009000000-f0dd423d086ac14ad6d6View 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-2179000000-80cef27c29d75c429aa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2190000000-46af6fd14fe789f145f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9110000000-3a5962a17ce1beb8cda7View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Endosome
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001383
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022594
KNApSAcK IDC00007541
Chemspider ID559277
KEGG Compound IDC01120
BioCyc IDCPD-649
BiGG ID1485322
Wikipedia LinkNot Available
METLIN ID3512
PubChem Compound644260
PDB IDNot Available
ChEBI ID16893
References
Synthesis ReferenceSchick, Andreas; Kolter, Thomas; Giannis, Athanassios; Sandhoff, Konrad. Synthesis of phosphoramide analogs of sphinganine-1-phosphate. Tetrahedron (1996), 52(8), 2945-56.
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
Sphinganine 1-phosphate → O-Phosphoethanolamine + Palmitaldehydedetails
Enzyme Details
2. Phospholipid phosphatase 2
General function:
Not Available
Specific function:
Magnesium-independent phospholipid phosphatase that catalyzes the dephosphorylation of a variety of glycerolipid and sphingolipid phosphate esters including phosphatidate/PA, lysophosphatidate/LPA, sphingosine 1-phosphate/S1P and ceramide 1-phosphate/C1P. Has no apparent extracellular phosphatase activity and therefore most probably acts intracellularly. Also acts on N-oleoyl ethanolamine phosphate/N-(9Z-octadecenoyl)-ethanolamine phosphate, a potential physiological compound. Through dephosphorylation of these bioactive lipid mediators produces new bioactive compounds and may regulate signal transduction in different cellular processes (By similarity). Indirectly regulates, for instance, cell cycle G1/S phase transition through its phospholipid phosphatase activity (By similarity).
Gene Name:
PLPP2
Uniprot ID:
Q2HJ61
Molecular weight:
32328.0
Reactions
Sphinganine 1-phosphate + Water → Sphinganine + Hydrogen phosphatedetails
Enzyme Details
3. Sphingosine kinase 2
General function:
Not Available
Specific function:
Not Available
Gene Name:
SPHK2
Uniprot ID:
E1BJM1
Molecular weight:
69343.0
Reactions
Adenosine triphosphate + Sphinganine → ADP + Sphinganine 1-phosphatedetails
Enzyme Details
4. Sphingosine-1-phosphate phosphatase 2
General function:
Not Available
Specific function:
Not Available
Gene Name:
SGPP2
Uniprot ID:
G3MXX9
Molecular weight:
44782.0
Reactions
Sphinganine 1-phosphate + ADP → Sphinganine + Adenosine triphosphatedetails