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Identification
YMDB IDYMDB00762
NamePhytosphingosine 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPhytosphingosine 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
SynonymsNot Available
CAS numberNot Available
WeightAverage: 397.4871
Monoisotopic: 397.259324529
InChI KeyAYGOSKULTISFCW-KSZLIROESA-N
InChIInChI=1S/C18H40NO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(20)18(21)16(19)15-25-26(22,23)24/h16-18,20-21H,2-15,19H2,1H3,(H2,22,23,24)/t16-,17+,18-/m0/s1
IUPAC Name{[(2S,3S,4R)-2-amino-3,4-dihydroxyoctadecyl]oxy}phosphonic acid
Traditional IUPAC Namephytosphingosine 1-phosphate
Chemical FormulaC18H40NO6P
SMILESCCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)COP(O)(O)=O
Chemical Taxonomy
DescriptionThis compound 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
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • 1,3-aminoalcohol
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP3.01ALOGPS
logP2.56ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)9.37ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area133.24 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity103.16 m³·mol⁻¹ChemAxon
Polarizability45.65 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 PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
Phytosphingosine 1-phosphate2-hydroxyhexadecanal + O-Phosphoethanolamine
Phytosphingosine 1-phosphate + waterPhytosphingosine + phosphate
Adenosine triphosphate + PhytosphingosinePhytosphingosine 1-phosphate + hydron + 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
  • 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
  • Cowart, L. A., Shotwell, M., Worley, M. L., Richards, A. J., Montefusco, D. J., Hannun, Y. A., Lu, X. (2010). "Revealing a signaling role of phytosphingosine-1-phosphate in yeast." Mol Syst Biol 6:349.20160710
  • Dickson, R. C., Sumanasekera, C., Lester, R. L. (2006). "Functions and metabolism of sphingolipids in Saccharomyces cerevisiae." Prog Lipid Res 45:447-465.16730802
  • 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:Not Available
External Links:
ResourceLink
CHEBI ID46970
HMDB IDNot Available
Pubchem Compound ID10883829
Kegg IDNot Available
ChemSpider ID9059097
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

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