Details of Metabolite

General Information of MET (ID: META00222)
Name Sphingosine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(-)-D-erythro-Sphingosine; (-)-Sphingosine; (2S,3R)-(e)-2-Amino-1,3-dihydroxy-4-octadecene; (2S,3R)-Sphingosine; (2S,3R,4E)-2-Amino-3-hydroxyoctadec-4-ene-1-ol; (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol; (2S,3R,e)-2-Aminooctadec-4-ene-1,3-diol; (4E)-Sphing-4-enine; (4E)-Sphingenine; (e)-2-Amino-4-octadecan-1,3-diol; (e)-D-Erythro-4-octadecene-1,3-diol; 2-Amino-4-octadecene-1,3-diol; 4 Sphingenine; 4-Sphingenine; 4-trans-Sphingenine; C18 Sphingosine; C18-Sphingosine; D-(+)-Erythro-1,3-dihydroxy-2-amino-4-trans-octadecene; D-(+)-erythro-4-trans-Sphingenine; D-Erythro-sphingosine; D-Sphingosine; D-erythro-C18-Sphingosine; Erythrosphingosine; SP(d18:1); Sph; Sphing-4-enine; Sphingenine; Sphingoid; Sphingosin; Sphingosine; Sphingosine D18:1; erythro-4-Sphingenine; erythro-C18-Sphingosine; trans-4-Sphingenine; trans-D-Erythro-2-amino-4-octadecene-1,3-diol
Source Aliphatic acyclic compounds
Structure Type   Amines  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic nitrogen compounds
Organonitrogen compounds
Amines
PubChem CID
5280335
HMDB ID
HMDB0000252
Formula
C18H37NO2
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00319
DrugBank ID
DB03203
ChEBI ID
16393
FooDB ID
FDB021919
ChemSpider ID
4444047
Physicochemical Properties Molecular Weight 299.5 Topological Polar Surface Area 66.5
XlogP 5.3 Complexity 231
Heavy Atom Count 21 Rotatable Bond Count 15
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Function
Sphingosine is a 18-carbon amino alcohol with a long unsaturated hydrocarbon chain. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. (Dorland, 28th ed.). Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Bone morphogenic antagonist (BMA)
            DAN domain family member 5 (DAND5) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockdown (siRNA) of DAND5
                      Induced Change Sphingosine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockdown of DAND5 leads to the decrease of sphingosine levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockdown (siRNA) of DAND5
                      Induced Change Sphingosine concentration: increase (FC = 1.82)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockdown of DAND5 leads to the increase of sphingosine levels compared with control group.
      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 [2]
                      Introduced Variation Knockout of Acer1
                      Induced Change Sphingosine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Acer1 leads to the increase of sphingosine 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 [3]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Sphingosine concentration: increase (FC = 5.08)
                      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 sphingosine levels compared with control group.
      Transmembrane protein (TMEM)
            ORM1-like protein 3 (ORMDL3) 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 [4]
                      Introduced Variation Knockout of Ormdl3
                      Induced Change Sphingosine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status White matter disorders [ICD-11: 8A45]
                      Details It is reported that knockout of Ormdl3 leads to the increase of sphingosine levels compared with control group.
References
1 Golgi alkaline ceramidase regulates cell proliferation and survival by controlling levels of sphingosine and S1P. FASEB J. 2006 Sep;20(11):1813-25.
2 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.
3 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
4 The Ormdl genes regulate the sphingolipid synthesis pathway to ensure proper myelination and neurologic function in mice. Elife. 2019 Dec 27;8:e51067.

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