General Information of MET (ID: META00228) |
Name |
Sphinganine
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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
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Source |
Endogenous;Yeast Metabolite;Sphingolipids;Food;Cosmetic;Microbial
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Structure Type |
Amines (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic nitrogen compounds
Organonitrogen compounds
Amines
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PubChem CID |
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HMDB ID |
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Formula |
C18H39NO2
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Structure |
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3D MOL is unavailable
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2D MOL
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Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
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KEGG ID |
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ChEBI ID |
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FooDB ID |
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ChemSpider ID |
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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.
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Regulatory Network
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