Showing chemical card for SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)) (CFc000269811)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:10:32 UTC

Chemfont ID

CFc000269811

Molecule Identification

Common Name

SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R))

Definition

SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)) is a type of oxidized sphingolipid found in animal cell membranes. It usually consists of phosphorylcholine and ceramide. SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)) consists of a sphingosine backbone and a 11,12-epoxyeicosatrienoyl 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

SMILES for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

[H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCC\C=C/C\C=C/CC1OC1C\C=C/CCCCC)[C@H](O)\C=C\CC\C=C/CCCCCCC

Download

INCHI for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

InChI=1S/C41H73N2O7P/c1-6-8-10-12-14-15-16-17-19-22-26-30-38(44)37(36-49-51(46,47)48-35-34-43(3,4)5)42-41(45)33-29-25-21-18-20-24-28-32-40-39(50-40)31-27-23-13-11-9-7-2/h16-18,21,23-24,26-28,30,37-40,44H,6-15,19-20,22,25,29,31-36H2,1-5H3,(H-,42,45,46,47)/b17-16-,21-18-,27-23-,28-24-,30-26+/t37-,38+,39?,40?/m0/s1

Download

Structure for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

Download

3D Structure for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

Synonyms

Not Available

Chemical Formula

C₄₁H₇₃N₂O₇P

Average Molecular Weight

737.016

Monoisotopic Molecular Weight

736.515539697

IUPAC Name

(2-{[(2S,3R,4E,8Z)-3-hydroxy-2-[(5Z,8Z)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamido]hexadeca-4,8-dien-1-yl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R,4E,8Z)-3-hydroxy-2-[(5Z,8Z)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamido]hexadeca-4,8-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=C/C\C=C/CC1OC1C\C=C/CCCCC)[C@H](O)\C=C\CC\C=C/CCCCCCC

InChI Identifier

InChI=1S/C41H73N2O7P/c1-6-8-10-12-14-15-16-17-19-22-26-30-38(44)37(36-49-51(46,47)48-35-34-43(3,4)5)42-41(45)33-29-25-21-18-20-24-28-32-40-39(50-40)31-27-23-13-11-9-7-2/h16-18,21,23-24,26-28,30,37-40,44H,6-15,19-20,22,25,29,31-36H2,1-5H3,(H-,42,45,46,47)/b17-16-,21-18-,27-23-,28-24-,30-26+/t37-,38+,39?,40?/m0/s1

InChI Key

DBCQGBGZIIQEDM-JQTKMIEDSA-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

Phosphoethanolamines
Dialkyl phosphates
N-acyl amines
Tetraalkylammonium salts
Secondary carboxylic acid amides
Secondary alcohols
Oxacyclic compounds
Epoxides
Dialkyl ethers
Organopnictogen compounds
Organic zwitterions
Organic salts
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
Amines

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
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organic zwitterion
Organooxygen compound
Carbonyl group
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Health effect

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (PMID: 30310470)

Vascular disorder

Atherosclerosis (PMID: 17963772)

Nervous system disorder

Central nervous system disorder

Pick's disease (PMID: 32310589)

Endocrine system disorder

Diabetes mellitus type 2 (PMID: 30310470)
Diabetes mellitus type 1 (PMID: 30310470)

Metabolic disorder

Metabolic syndrome (PMID: 21844222)

Disposition

Biological location

Cell

All cells and tissues (HMDB: HMDB0290295)

Cellular substructure

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

Organelle

Endoplasmic reticulum (PMID: 9009829)

Source

Endogenous

Endogenous (HMDB: HMDB0290295)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (PMID: 8086039)

Role

Biological role

Nutrient (PMID: 23684760)

Industrial application

Pharmaceutical industry

Biomarker

Pick's disease ()
Diabetes mellitus type 2 ()
Cardiovascular disease ()
Insulin resistance ()
Atherosclerosis ()

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.0e-05 g/L	ALOGPS
logP	4.62	ALOGPS
logP	5.12	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	120.45 Å²	ChemAxon
Rotatable Bond Count	33	ChemAxon
Refractivity	227.13 m³·mol⁻¹	ChemAxon
Polarizability	87.11 Å³	ChemAxon
Number of Rings	1	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

HMDB0290295

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

156997935

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)) (CFc000269811)

MOL for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

3D MOL for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

3D SDF for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

3D-SDF for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

PDB for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

3D PDB for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

SMILES for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

INCHI for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

Structure for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))

3D Structure for CFc000269811 (SM(d16:2(4E,8Z)/20:3(5Z,8Z,14Z)-O(11S,12R)))