ChemFOnt: Showing chemical card for stearoyl sphingomyelin (CFc000042971)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:46 UTC

Chemfont ID

CFc000042971

Molecule Identification

Common Name

stearoyl sphingomyelin

Definition

stearoyl sphingomyelin, also known as 2,3-(N-Steroylsphingosyl)-1-phosphocholine or 2,3-SPPC, is classified as a member of the Phosphosphingolipids. Phosphosphingolipids 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. stearoyl sphingomyelin is considered to be practically insoluble (in water) and acidic. stearoyl sphingomyelin is a phosphosphingolipid lipid molecule

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3R,4E)-3-Hydroxy-2-(stearoylamino)octadec-4-en-1-yl 2-(trimethylammonio)ethyl phosphate	ChEBI
2,3-(N-Steroylsphingosyl)-1-phosphocholine	ChEBI
2,3-SPPC	ChEBI
C18 Sphingomyelin	ChEBI
N-(Octadecanoyl)-sphing-4-enine-1-phosphocholine	ChEBI
N-Octadecanoylsphing-4-enine-1-phosphocholine	ChEBI
N-Octadecanoylsphingosine-1-phosphocholine	ChEBI
N-Stearoylsphing-4-enine-1-phosphocholine	ChEBI
Sphingomyelin (D18:1/18:0)	ChEBI
Stearoyl sphingomyelin	ChEBI
(2S,3R,4E)-3-Hydroxy-2-(stearoylamino)octadec-4-en-1-yl 2-(trimethylammonio)ethyl phosphoric acid	Generator
C18-Sphingomyelin	HMDB
N-Stearoyl-D-erythro-sphingosylphosphorylcholine	HMDB
N-Stearoylsphingomyelin	HMDB
N-Stearoylsphingosine-1-phosphocholine	HMDB
Sphingomyelin 18:0	HMDB
Stearoylsphingomyelin	HMDB
Sphingomyelin	MetBuilder
N-(Octadecanoyl)-1-phosphocholine-sphing-4-enine	MetBuilder
Sphingomyelin(D18:1/18:0)	MetBuilder
N-(Octadecanoyl)-1-phosphocholine-sphingosine	MetBuilder
N-(Octadecanoyl)-1-phosphocholine-D-erythro-sphingosine	MetBuilder
N-(Octadecanoyl)-1-phosphocholine-4-sphingenine	MetBuilder
N-(Octadecanoyl)-1-phosphocholine-D-sphingosine	MetBuilder
N-(Octadecanoyl)-1-phosphocholine-sphingenine	MetBuilder
N-(Octadecanoyl)-1-phosphocholine-erythro-4-sphingenine	MetBuilder
SM(D18:1/18:0)	HMDB, ChEBI

Chemical Formula

C₄₁H₈₃N₂O₆P

Average Molecular Weight

731.097

Monoisotopic Molecular Weight

730.598875399

IUPAC Name

(2-{[(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

58909-84-5

SMILES

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

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)/b34-32+/t39-,40+/m0/s1

InChI Key

LKQLRGMMMAHREN-YJFXYUILSA-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

sphingomyelin d18:1 (CHEBI:83358 )
sphingomyelin 36:1 (CHEBI:83358 )
Ceramide phosphocholines (sphingomyelins) (LMSP03010001 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062559)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.2e-05 g/L	ALOGPS
logP	5.47	ALOGPS
logP	7.87	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	-1.1	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	38	ChemAxon
Refractivity	223.14 m³·mol⁻¹	ChemAxon
Polarizability	93.1 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

HMDB0001348

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022570

KNApSAcK ID

Not Available

Chemspider ID

4956085

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6453725

PDB ID

Not Available

ChEBI ID

83358

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for stearoyl sphingomyelin (CFc000042971)

MOL for CFc000042971 (stearoyl sphingomyelin)

3D MOL for CFc000042971 (stearoyl sphingomyelin)

3D SDF for CFc000042971 (stearoyl sphingomyelin)

3D-SDF for CFc000042971 (stearoyl sphingomyelin)

PDB for CFc000042971 (stearoyl sphingomyelin)

3D PDB for CFc000042971 (stearoyl sphingomyelin)

SMILES for CFc000042971 (stearoyl sphingomyelin)

INCHI for CFc000042971 (stearoyl sphingomyelin)

Structure for CFc000042971 (stearoyl sphingomyelin)

3D Structure for CFc000042971 (stearoyl sphingomyelin)