ChemFOnt: Showing chemical card for SM(d18:1/12:0) (CFc000007658)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:05 UTC

Chemfont ID

CFc000007658

Molecule Identification

Common Name

SM(d18:1/12:0)

Definition

Sphingomyelin (d18:1/12:0) or SM(d18:1/12:0) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
C12 Sphingomyelin	HMDB
N-(Dodecanoyl)-sphing-4-enine-1-phosphocholine	HMDB
N-Lauroyl-D-erythro-sphingosylphosphoryl choline	HMDB
Sphingomyelin	HMDB
N-(Dodecanoyl)-1-phosphocholine-sphing-4-enine	HMDB
Sphingomyelin(D18:1/12:0)	HMDB
N-(Dodecanoyl)-1-phosphocholine-sphingosine	HMDB
N-(Dodecanoyl)-1-phosphocholine-D-erythro-sphingosine	HMDB
N-(Dodecanoyl)-1-phosphocholine-4-sphingenine	HMDB
N-(Dodecanoyl)-1-phosphocholine-D-sphingosine	HMDB
N-(Dodecanoyl)-1-phosphocholine-sphingenine	HMDB
N-(Dodecanoyl)-1-phosphocholine-erythro-4-sphingenine	HMDB

Chemical Formula

C₃₅H₇₁N₂O₆P

Average Molecular Weight

646.9218

Monoisotopic Molecular Weight

646.504974526

IUPAC Name

(2-{[(2S,3R,4E)-2-dodecanamido-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R,4E)-2-dodecanamido-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

None

SMILES

CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCC

InChI Identifier

InChI=1S/C35H71N2O6P/c1-6-8-10-12-14-16-17-18-19-21-22-24-26-28-34(38)33(32-43-44(40,41)42-31-30-37(3,4)5)36-35(39)29-27-25-23-20-15-13-11-9-7-2/h26,28,33-34,38H,6-25,27,29-32H2,1-5H3,(H-,36,39,40,41)/b28-26+/t33-,34+/m0/s1

InChI Key

HZCLJRFPXMKWHR-FEBLJDHQSA-N

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

Substituents

Sphingoid-1-phosphate or derivatives
Phosphocholine
Phosphoethanolamine
Dialkyl phosphate
Fatty amide
N-acyl-amine
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organic zwitterion
Alcohol
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Ceramide phosphocholines (sphingomyelins) (LMSP03010002 )

Functional Ontology

All cells and tissues (HMDB: HMDB0012096)

Cellular substructure

Membrane (HMDB: HMDB0012096)
Endosome (HMDB: HMDB0012096)
Extracellular (HMDB: HMDB0012096)
Cell membrane (PMID: 9009829)
Golgi apparatus membrane (PMID: 11062253)
Myelin sheath (HMDB: HMDB0012096)
Cell membrane (HMDB: HMDB0012096)
Axon (HMDB: HMDB0012096)

Organelle

Endoplasmic reticulum (PMID: 9009829)

Nervous system (HMDB: HMDB0012096)

Organ

Brain (HMDB: HMDB0012096)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012096)

Source

Endogenous

Endogenous (HMDB: HMDB0012096)

Animal

Animal (HMDB: HMDB0012096)

Exogenous

Food

Food (HMDB: HMDB0012096)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0012096)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012096)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012096)

Lipid metabolism pathway (HMDB: HMDB0012096)

Cellular process

Cell signaling (HMDB: HMDB0012096)
Cell signaling (PMID: 8086039)

Biochemical process

Lipid transport (HMDB: HMDB0012096)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.6e-05 g/L	ALOGPS
logP	4.25	ALOGPS
logP	6.29	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	0.012	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	107.92 Å²	ChemAxon
Rotatable Bond Count	32	ChemAxon
Refractivity	195.54 m³·mol⁻¹	ChemAxon
Polarizability	79.96 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012096

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028763

KNApSAcK ID

Not Available

Chemspider ID

24846872

KEGG Compound ID

C00550

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44260123

PDB ID

Not Available

ChEBI ID

17636

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for SM(d18:1/12:0) (CFc000007658)

MOL for CFc000007658 (SM(d18:1/12:0))

3D MOL for CFc000007658 (SM(d18:1/12:0))

3D SDF for CFc000007658 (SM(d18:1/12:0))

3D-SDF for CFc000007658 (SM(d18:1/12:0))

PDB for CFc000007658 (SM(d18:1/12:0))

3D PDB for CFc000007658 (SM(d18:1/12:0))

SMILES for CFc000007658 (SM(d18:1/12:0))

INCHI for CFc000007658 (SM(d18:1/12:0))

Structure for CFc000007658 (SM(d18:1/12:0))

3D Structure for CFc000007658 (SM(d18:1/12:0))