General Information of MET (ID: META00228)
Name Sphinganine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S,3R)-2-Amino-1,3-octadecanediol; (2S,3R)-2-Aminooctadecane-1,3-diol; (2S,3R)-Sphinganine; (R-(R*,s*))-2-aminooctadecane-1,3-diol; 2-Amino-1,3-dihydroxyoctadecane; 2-Aminooctadecane-1,3-diol; 2-amino-D-erythro-1,3-Octadecanediol; C18-Dihydrosphingosine; C18-Sphinganine; C18-dihydro-Sphingosine; D-Erythro-1,3-dihydroxy-2-aminooctadecane; D-Erythro-2-amino-1,3-octadecanediol; D-Erythro-C18-dihydrosphingosine; D-erythro-Dihydrosphingosine; D-erythro-Sphinganine; D18:0; Dihydrosphingosine; Erythro-D-sphinganine; Octadecasphinganine; SP(d18:0); Safingol; Sphinganine; Threo-dihydrosphingosine; [R-(R*,s*)]-2-amino-1,3-octadecanediol; dihydro-C18-Sphingosine; erythro-Sphinganine
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
91486
HMDB ID
HMDB0000269
Formula
C18H39NO2
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
C00836
ChEBI ID
16566
FooDB ID
FDB030824
ChemSpider ID
82609
Physicochemical Properties Molecular Weight 301.5 Topological Polar Surface Area 66.5
XlogP 5.8 Complexity 200
Heavy Atom Count 21 Rotatable Bond Count 16
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Function
Sphinganine belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Thus, sphinganine is considered to be a sphingoid base lipid molecule. Sphinganine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sphinganine exists in all living species, ranging from bacteria to humans. Within humans, sphinganine participates in a number of enzymatic reactions. In particular, sphinganine can be converted into 3-dehydrosphinganine through its interaction with the enzyme 3-ketodihydrosphingosine reductase. In addition, sphinganine can be converted into sphinganine 1-phosphate; which is catalyzed by the enzyme sphingosine kinase 2. Outside of the human body, sphinganine has been detected, but not quantified in, several different foods, such as Mexican oregano, jostaberries, winter squash, angelica, and epazotes. This could make sphinganine a potential biomarker for the consumption of these foods. Sphinganine blocks postlysosomal cholesterol transport by inhibiting low-density lipoprotein-induced esterification of cholesterol and causing unesterified cholesterol to accumulate in perinuclear vesicles. It has been suggested that endogenous sphinganine may inhibit cholesterol transport in Niemann-Pick Type C (NPC) disease.
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 Sphinganine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Acer1 leads to the increase of sphinganine 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 [2]
                      Introduced Variation Knockout of Ormdl3
                      Induced Change Sphinganine 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 sphinganine 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 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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