SM(d18:1/18:0)

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SM(d18:1/18:0)
2D structure for SM(d18:1/18:0)
Chemical Name	2-[hydroxy-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]phosphoryl]oxyethyl-trimethyl-azanium
Chemical Formula	C₄₁H₈₄N₂O₆P
CAS Number	85187-10-6
Chemical Information	HMDB01348
Biochemical Taxonomy	Sphingolipids
Functional Taxonomy	Second Messenger
Nutritional Taxonomy	Not Available
Metabolic Pathways	Sphingolipid Metabolism
Biofluid Location	Blood Breast Milk
Tissue Location	Erythrocyte Liver Nervous Tissues Spleen Brain
Normal Biofluid Concentrations	Blood: 1145.0 +/- 67.0 uM Blood: 298.0 +/- 24.0 uM Breast Milk: 124 +/- 9 uM
Normal Tissue Concentrations	Not Available
Diseases / Conditions Related to Nutrition	Not Available
Other (Monogenic Disorders)	Not Available
Abnormal Biofluid Concentrations	Not Available
Abnormal Tissue Concentrations	Not Available
Physiological Processes	Not Available

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Introduction

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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.