General Information of MET (ID: META00536)
Name Phytosphingosine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(+)-D-Ribo-phytosphingosine; (2S,3S,4R)-2-Amino-1,3,4-octadecanetriol; (2S,3S,4R)-2-Amino-1,3,4-trihydroxyoctadecane; 4-D-Hydroxy-sphinganine; 4-D-Hydroxysphinganine; 4-R-Hydroxyoctadecasphinganine; 4D-Hydroxysphinganine; 8-(Z-e)-C18-Phytosphingenine; C18-Phytosphingosine; D-Ribo-1,3,4-trihydroxy-2-aminooctadecane; D-Ribo-2-amino-1,3,4-octadecanetriol; D-ribo-Phytosphingosine; Phytosphingosine; SP(t18:0); [2S-(2R*,3R*,4S*)]-2-amino-1,3,4-octadecanetriol
Source Endogenous;Yeast Metabolite;Sphingolipids;Food;Cosmetic;Microbial
Structure Type   Amines  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic nitrogen compounds
Organonitrogen compounds
Amines
PubChem CID
122121
HMDB ID
HMDB0004610
Formula
C18H39NO3
Structure
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3D MOL is unavailable 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C12144
ChEBI ID
46961
FooDB ID
FDB023381
ChemSpider ID
108921
METLIN ID
7066
Physicochemical Properties Molecular Weight 317.5 Topological Polar Surface Area 86.7
XlogP 4.6 Complexity 226
Heavy Atom Count 22 Rotatable Bond Count 16
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 4
Function
Phytosphingosine is a phospholipid. Phospholipids are a class of lipids and a major component of all biological membranes; sphingolipid metabolites, such as sphingosine and ceramide, are highly bioactive compounds and are involved in diverse cell processes, including cell-cell interaction, cell proliferation, differentiation, and apoptosis. Phytosphingosine is also one of the most widely distributed natural sphingoid bases, which is abundant in fungi and plants, and also found in animals including humans. Phytosphingosine is structurally similar to sphingosine; phytosphingosine possesses a hydroxyl group at C-4 of the sphingoid long-chain base. The physiological roles of phytosphingosine are largely unknown. Phytosphingosine induces apoptosis in human T-cell lymphoma and non-small cell lung cancer cells, and induces caspase-independent cytochrome c release from mitochondria. In the presence of caspase inhibitors, phytosphingosine-induced apoptosis is almost completely suppressed, suggesting that phytosphingosine-induced apoptosis is largely dependent on caspase activities.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Alkaline ceramidase 1 (ACER1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of Acer1
                      Induced Change Phytosphingosine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Acer1 leads to the increase of phytosphingosine levels compared with control group.
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Phytosphingosine concentration: increase (FC = 4.09 / 5.76)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of phytosphingosine levels compared with control group.
References
1 Alkaline Ceramidase 1 Protects Mice from Premature Hair Loss by Maintaining the Homeostasis of Hair Follicle Stem Cells. Stem Cell Reports. 2017 Nov 14;9(5):1488-1500.
2 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.

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