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Identification
YMDB IDYMDB00299
NameSphinganine 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSphinganine 1-phosphate (dihydrosphingosine 1-phosphate) is an intermediate in sphingolipid metabolism pathway. Sphingolipids are essential components of the plasma membrane in all eukaryotic cells. S. cerevisiae cells make three complex sphingolipids: inositol-phosphoceramide (IPC), mannose-inositol-phosphoceramide (MIPC), and mannosyl-diinositol-phosphorylceramide (M(IP)2C). Sphingolipid long chain bases (LCBs) - dihydrosphingosine (DHS) and phytosphingosine (PHS) - are implicated as secondary messengers in vital signaling pathways. [Biocyc SPHINGOLIPID-SYN-PWY]
Structure
Thumb
Synonyms
  • 2-amino-3-hydroxyoctadecyl dihydrogen phosphate
  • Dihydrosphingosine 1-phosphate
  • dihydrosphingosine-1-phosphate
  • Sphinganine 1-phosphate
  • Sphinganine 1-phosphic acid
  • (2S,3R)-2-Amino-3-hydroxyoctadecyl dihydrogen phosphate
  • (2S,3R)-2-Amino-3-hydroxyoctadecyl dihydrogen phosphoric acid
  • Dihydrosphingosine 1-phosphoric acid
  • Dihydrosphingosine-1-phosphoric acid
  • Sphinganine 1-phosphoric acid
CAS number19794-97-9
WeightAverage: 381.4877
Monoisotopic: 381.264409907
InChI KeyYHEDRJPUIRMZMP-ZWKOTPCHSA-N
InChIInChI=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
IUPAC Name{[(2S,3R)-2-amino-3-hydroxyoctadecyl]oxy}phosphonic acid
Traditional IUPAC Namedihydrosphingosine 1-phosphate
Chemical FormulaC18H40NO5P
SMILES[H]O[C@]([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@@]([H])(N([H])[H])C([H])([H])OP(=O)(O[H])O[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0057 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
Organoleptic PropertiesNot Available
SMPDB Pathways
Sphingolipid metabolismPW002479 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Sphingolipid metabolismec00600 Map00600
SMPDB Reactions
Adenosine triphosphate + SphinganineADP + Sphinganine 1-phosphate
Sphinganine 1-phosphate + ADPSphinganine + Adenosine triphosphate
Sphinganine 1-phosphate + waterSphinganine + phosphate
Sphinganine 1-phosphateO-Phosphoethanolamine + Palmitaldehyde
KEGG Reactions
Sphinganine 1-phosphatePalmitaldehyde + O-Phosphoethanolamine
water + Sphinganine 1-phosphateSphinganine + phosphate
Sphinganine + Adenosine triphosphatehydron + Sphinganine 1-phosphate + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Mao, C., Xu, R., Bielawska, A., Szulc, Z. M., Obeid, L. M. (2000). "Cloning and characterization of a Saccharomyces cerevisiae alkaline ceramidase with specificity for dihydroceramide." J Biol Chem 275:31369-31378.10900202
Synthesis Reference:Schick, Andreas; Kolter, Thomas; Giannis, Athanassios; Sandhoff, Konrad. Synthesis of phosphoramide analogs of sphinganine-1-phosphate. Tetrahedron (1996), 52(8), 2945-56.
External Links:
ResourceLink
CHEBI ID16893
HMDB IDHMDB01383
Pubchem Compound ID520
Kegg IDC01120
ChemSpider ID23169036
FOODB IDFDB022594
Wikipedia IDNot Available
BioCyc IDCPD-649

Enzymes

General function:
Involved in diacylglycerol kinase activity
Specific function:
Catalyzes the phosphorylation of the sphingoid long chain bases dihydrosphingosine (DHS or sphinganine) and phytosphingosine (PHS) to form dihydrosphingosine 1-phosphate (DHS-1P) and phytosphingosine 1-phosphate (PHS-1P) respectively. Involved in the biosynthesis of sphingolipids and ceramides. Required with LCB3 for an effective incorporation of DHS into ceramides through a phosphorylation-dephosphorylation cycle. Involved in heat-induced transient cell cycle arrest. Accumulation of phosphorylated sphingoid long chain bases (LCBPs) stimulates calcium influx and activates calcineurin signaling. Involved in heat-stress resistance
Gene Name:
LCB4
Uniprot ID:
Q12246
Molecular weight:
69638.60156
Reactions
ATP + sphinganine → ADP + sphinganine 1-phosphate.
ATP + phytosphingosine → ADP + phytosphingosine 1-phosphate.
General function:
Involved in diacylglycerol kinase activity
Specific function:
Catalyzes the phosphorylation of the sphingoid long chain bases dihydrosphingosine (DHS or sphinganine) and phytosphingosine (PHS) to form dihydrosphingosine 1-phosphate (DHS-1P) and phytosphingosine 1-phosphate (PHS-1P) respectively. Redundant to LCB4, is only responsible for few percent of the total activity. Involved in the biosynthesis of sphingolipids and ceramides. Involved in heat-induced transient cell cycle arrest. Accumulation of phosphorylated sphingoid long chain bases (LCBPs) stimulates calcium influx and activates calcineurin signaling. Involved in heat-stress resistance
Gene Name:
LCB5
Uniprot ID:
Q06147
Molecular weight:
77564.60156
Reactions
ATP + sphinganine → ADP + sphinganine 1-phosphate.
ATP + phytosphingosine → ADP + phytosphingosine 1-phosphate.
General function:
Involved in carboxy-lyase activity
Specific function:
Cleaves phosphorylated sphingoid bases (PSBs), such as sphingosine-1-phosphate, into fatty aldehydes and phosphoethanolamine
Gene Name:
DPL1
Uniprot ID:
Q05567
Molecular weight:
65565.10156
Reactions
Sphinganine 1-phosphate → phosphoethanolamine + palmitaldehyde.
General function:
Involved in catalytic activity
Specific function:
Dihydrosphingosine 1-phosphate phosphatase required for efficient ceramide synthesis from exogenous sphingoid bases. Involved in endocytosis and calcium-mediated signaling
Gene Name:
LCB3
Uniprot ID:
P47013
Molecular weight:
47371.30078
Reactions
General function:
Involved in catalytic activity
Specific function:
Dihydrosphingosine 1-phosphate phosphatase required for efficient ceramide synthesis from exogenous sphingoid bases. Involved in endocytosis and calcium-mediated signaling
Gene Name:
YSR3
Uniprot ID:
P23501
Molecular weight:
46487.69922
Reactions