FComEx: SM(d18:1/18:0) (PC000268)

Record Information

Version

1.0

Creation date

2015-10-09 22:29:35 UTC

Update date

2017-01-19 02:36:18 UTC

FoodComEx ID

PC000268

FoodDB Record

FDB022570

Chemical Information

Name

SM(d18:1/18:0)

Description

Sphingomyelin (d18:1/18:0) or SM(d18:1/18:0) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. SM(18:1/18:0) consists of oleic acid attached to the C1 position and stearic acid attached to the C2 position. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of Sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase. [HMDB]

CAS Number

85187-10-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
N-(Octadecanoyl)-sphing-4-enine-1-ocholine	HMDB
N-(octadecanoyl)-sphing-4-enine-1-phosphocholine	hmdb
N-Acyl-4-sphingenyl-1-O-orylcholine	HMDB
N-Acyl-D-sphingosine-1-ocholine	HMDB
Sphingomyelin (d18:1/18:0)	hmdb

Chemical Formula

C41H84N2O6P

IUPAC name

{[(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid

InChI Identifier

InChI=1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/p+1/b34-32+/t39-,40+/m0/s1

InChI Key

LKQLRGMMMAHREN-YJFXYUILSA-O

Isomeric SMILES

CCCCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(O)(=O)OCC[N+](C)(C)C)[C@]([H])(O)\C=C\CCCCCCCCCCCCC

Average Molecular Weight

732.0892

Monoisotopic Molecular Weight

731.606699942

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Phosphosphingolipids

Direct Parent

Phosphosphingolipids

Alternative Parents