ChemFOnt: Showing chemical card for SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)) (CFc000270108)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:11:06 UTC

Chemfont ID

CFc000270108

Molecule Identification

Common Name

SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S))

Definition

SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)) is a type of oxidized sphingolipid found in animal cell membranes. It usually consists of phosphorylcholine and ceramide. SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)) consists of a sphingosine backbone and a 5(S),15(S)-Dihydroxyeicosatetraenoyl chain. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SM 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 localize 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

Not Available

Chemical Formula

C₄₃H₇₇N₂O₈P

Average Molecular Weight

781.069

Monoisotopic Molecular Weight

780.541754445

IUPAC Name

(2-{[(2S,3R,4E,14Z)-2-[(5S,6E,8Z,11Z,13E,15R)-5,15-dihydroxyicosa-6,8,11,13-tetraenamido]-3-hydroxyoctadeca-4,14-dien-1-yl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R,4E,14Z)-2-[(5S,6E,8Z,11Z,13E,15R)-5,15-dihydroxyicosa-6,8,11,13-tetraenamido]-3-hydroxyoctadeca-4,14-dien-1-yl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

[H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCC[C@H](O)\C=C\C=C/C\C=C/C=C/[C@H](O)CCCCC)[C@H](O)\C=C\CCCCCCCC\C=C/CCC

InChI Identifier

InChI=1S/C43H77N2O8P/c1-6-8-10-11-12-13-14-15-16-17-21-24-28-34-42(48)41(38-53-54(50,51)52-37-36-45(3,4)5)44-43(49)35-29-33-40(47)32-27-23-20-18-19-22-26-31-39(46)30-25-9-7-2/h10-11,19-20,22-23,26-28,31-32,34,39-42,46-48H,6-9,12-18,21,24-25,29-30,33,35-38H2,1-5H3,(H-,44,49,50,51)/b11-10-,22-19-,23-20-,31-26+,32-27+,34-28+/t39-,40-,41+,42-/m1/s1

InChI Key

UWXMTSKRUCPOBY-SEGQVVKRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Phosphocholines

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

All cells and tissues (HMDB: HMDB0290592)

Cellular substructure

Organelle

Endoplasmic reticulum (PMID: 9009829)

Cell membrane (PMID: 9009829)
Golgi apparatus membrane (PMID: 11062253)

Source

Endogenous

Endogenous (HMDB: HMDB0290592)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (PMID: 8086039)

Role

Biological role

Nutrient (PMID: 23684760)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.1e-05 g/L	ALOGPS
logP	4.25	ALOGPS
logP	4.48	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	148.38 Å²	ChemAxon
Rotatable Bond Count	35	ChemAxon
Refractivity	240.96 m³·mol⁻¹	ChemAxon
Polarizability	92.97 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

HMDB0290592

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156998529

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)) (CFc000270108)

MOL for CFc000270108 (SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)))

3D MOL for CFc000270108 (SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)))

3D SDF for CFc000270108 (SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)))

3D-SDF for CFc000270108 (SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)))

PDB for CFc000270108 (SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)))

3D PDB for CFc000270108 (SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)))

SMILES for CFc000270108 (SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)))

INCHI for CFc000270108 (SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)))

Structure for CFc000270108 (SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)))

3D Structure for CFc000270108 (SM(d18:2(4E,14Z)/20:4(6E,8Z,11Z,13E)-2OH(5S,15S)))