| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2009-04-06 10:22:15 -0600 |
| Update Date |
2013-02-08 17:28:41 -0700 |
| HMDB ID |
HMDB12280 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Phytosphingosine-1-P |
| Description |
Phytosphingosine-1-P is an intermediate in sphingolipid metabolism pathway. It is the enzymatic oxidation product of 4-hydroxysphinganine. 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) [ Dickson02 ]. In the yeast plasma membrane sphingolipids concentrate with ergosterol to form lipid rafts, specialized membrane microdomains implicated in a variety of cellular processes, including sorting of membrane proteins and lipids, as well as organizing and regulating signaling cascades [ Bagnat02 ]. Intermediates in sphingolipid biosynthesis have been shown to play important roles as signaling molecules and growth regulators. Sphingolipid long chain bases (LCBs), dihydrosphingosine (DHS) and phytosphingosine (PHS), have been implicated as secondary messengers in signaling pathways that regulate heat stress response. Other intermediates, phytoceramide and long-chain base phosphates (LCBPs), have been shown to be components of tightly-controlled ceramide/LCBP rheostat, which regulates cell growth. Since phosphoinositol-containing sphingolipids are unique to fungi, the sphingolipid biosynthesis pathway is considered a target for antifungal drugs. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- PHS-1-Phosphate
|
| Chemical Formula |
C18H40NO6P |
| Average Molecular Weight |
397.4871 |
| Monoisotopic Molecular Weight |
397.259324529 |
| IUPAC Name |
{[(2R,3R,4R)-2-amino-3,4-dihydroxyoctadecyl]oxy}phosphonic acid |
| Traditional IUPAC Name |
[(2R,3R,4R)-2-amino-3,4-dihydroxyoctadecyl]oxyphosphonic acid |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCCCCCCCCCCC[C@@H](O)[C@H](O)[C@H](N)COP(O)(O)=O |
| InChI Identifier |
InChI=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-/m1/s1 |
| InChI Key |
AYGOSKULTISFCW-KZNAEPCWSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Sphingolipids |
| Sub Class |
N/A |
| Other Descriptors |
- Aliphatic Acyclic Compounds
|
| Substituents |
- 1,2 Aminoalcohol
- 1,2 Diol
- 1,3 Aminoalcohol
- Organic Hypophosphite
- Organic Phosphite
- Phosphoethanolamine
- Phosphoric Acid Ester
- Primary Aliphatic Amine (Alkylamine)
- Secondary Alcohol
|
| Direct Parent |
Sphingolipids |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
Not Available
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB028911 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
Not Available |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
PHTYOSPHINGOSINE-1-P  |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB12280 |
| Metagene Link |
HMDB12280 |
| METLIN ID |
Not Available |
| PubChem Compound |
53481399 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |
