Sphinganine

{{Chembox | Name = Sphinganine | ImageFile = Sphinganine.svg | ImageSize = 250px | OtherNames = {{Unbulleted list|Dihydrospingosine|DL-erythro-Dihydrosphingosine|2-Amino-1,3-dihydroxyoctadecane|[R-(R*,S*)]-2-aminooctadecane-1,3-diol}} | IUPACName = Sphinganine | PIN = Sphinganine | SystematicName = (2''S'',3''R'')-2-Aminooctadecane-1,3-diol | Section1 = {{Chembox Identifiers |CASNo=764-22-7 |ChemSpiderID=82609 |ChEBI=16566 |ChEMBL=448741 |DrugBank = DB11924 |EC_number=212-116-0 |KEGG=C00836 |IUPHAR_ligand = 2453 |PubChem=91486 |UNII=YT0ZSD64HM |SMILES=C(CCCCCCCCCCCCCC)[C@H]([C@H](CO)N)O |InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1 |InChIKey=OTKJDMGTUTTYMP-ZWKOTPCHSA-N}} | Section2 = {{Chembox Properties | C = 18 | H = 39 | N = 1 |O = 2 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section9 = {{Chembox Related|OtherCompounds=Safingol|OtherFunction_label=sphingolipids|OtherFunction={{unbulleted list|Sulfatide|Ceramide|Sphingosine|Phytosphingosine|Sphingosine-1-phosphate}}}} }}

'''Sphinganine''' is a chemical compound of the sphingolipid class with molecular formula {{chem2|C18H39NO2}}. Via the action of sphingosine kinase enzymes, it is converted to dihydrosphingosine 1-phosphate (sphinganine 1-phosphate), which has a variety of biological functions.<ref>{{cite web | url = https://www.lipidmaps.org/databases/lmsd/LMSP01020001 | title = Sphinganine | work = Lipid Maps Structure Database }}</ref>

Sphinganine is one of many sphingoid bases (long-chain bases) besides sphingosine, which are backbones of sphingolipids.<ref>{{Cite journal |last=Merrill |first=Alfred H. |date=2025-01-14 |title=Don't Be Surprised When These Surprise You: Some Infrequently Studied Sphingoid Bases, Metabolites, and Factors That Should Be Kept in Mind During Sphingolipidomic Studies |journal=International Journal of Molecular Sciences |language=en |volume=26 |issue=2 |pages=650 |doi=10.3390/ijms26020650 |doi-access=free |issn=1422-0067 |pmc=11765627 |pmid=39859363}}</ref> It is made by dehydrogenating 3-ketosphinganine, which is produced by condensation reaction of serine with palmitate. It is an intermediate in the biosynthesis of ceramide.<ref>{{Cite journal |last1=Abed Rabbo |first1=Muna |last2=Khodour |first2=Yara |last3=Kaguni |first3=Laurie S. |last4=Stiban |first4=Johnny |date=2021-05-03 |title=Sphingolipid lysosomal storage diseases: from bench to bedside |journal=Lipids in Health and Disease |volume=20 |issue=1 |pages=44 |doi=10.1186/s12944-021-01466-0 |issn=1476-511X |pmc=8094529 |pmid=33941173 |doi-access=free}}</ref>

Sphinganine is a diastereomer of safingol.

==References== {{reflist}}

== Further reading == * {{Cite journal |last1=Qu |first1=Linkai |last2=Wang |first2=Lei |last3=Ji |first3=Hao |last4=Fang |first4=Yimeng |last5=Lei |first5=Pengyu |last6=Zhang |first6=Xingxing |last7=Jin |first7=Libo |last8=Sun |first8=Da |last9=Dong |first9=Hao |date=2022-03-01 |title=Toxic Mechanism and Biological Detoxification of Fumonisins |journal=Toxins |language=en |volume=14 |issue=3 |pages=182 |doi=10.3390/toxins14030182 |doi-access=free |issn=2072-6651 |pmc=8954241 |pmid=35324679}}

Category:Amines Category:Diols