FComEx: Sphinganine (PC000448)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:46 UTC

Update date

2017-01-19 02:36:24 UTC

FoodComEx ID

PC000448

FoodDB Record

FDB021924

Chemical Information

Name

Sphinganine

Description

Sphinganine, also known as D18:0 or safingol, 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; which is mediated by the enzyme 3-ketodihydrosphingosine reductase. In addition, sphinganine can be converted into sphinganine 1-phosphate; which is catalyzed by the enzyme sphingosine kinase 2. In humans, sphinganine is involved in the metabolic disorder called the fabry disease pathway. Outside of the human body, Sphinganine has been detected, but not quantified in, several different foods, such as beech nuts, docks, citrus, watercress, and brazil nuts. This could make sphinganine a potential biomarker for the consumption of these foods. A Sphinganine having (2S,3R)-configuration.

CAS Number

764-22-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2S,3R)-2-amino-1,3-Octadecanediol	ChEBI
(2S,3R)-2-Aminooctadecane-1,3-diol	ChEBI
(R-(R,s))-2-aminooctadecane-1,3-diol	ChEBI
[R-(R,S)]-2-amino-1,3-Octadecanediol	hmdb
2-amino-1,3-Dihydroxyoctadecane	ChEBI
2-amino-D-erythro-1,3-Octadecanediol	hmdb
C18-dihydro-Sphingosine	hmdb
C18-Dihydrosphingosine	hmdb
C18-Sphinganine	ChEBI
D-erythro-1,3-Dihydroxy-2-aminooctadecane	hmdb
D-erythro-2-Amino-1,3-octadecanediol	hmdb
D-erythro-C18-Dihydrosphingosine	hmdb
D-erythro-Sphinganine	hmdb
D18:0	ChEBI
Dihydro-C18-sphingosine	hmdb
Dihydrosphingosine	hmdb
erythro-Sphinganine	hmdb
Octadecasphinganine	hmdb
Safingol	ChEBI
Sphinganine	hmdb

Chemical Formula

C18H39NO2

IUPAC name

(2S,3R)-2-aminooctadecane-1,3-diol

InChI Identifier

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

InChI Key

OTKJDMGTUTTYMP-ZWKOTPCHSA-N

Isomeric SMILES

CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO

Average Molecular Weight

301.5078

Monoisotopic Molecular Weight

301.298079497

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

1,2-aminoalcohols

Alternative Parents

Substituents