Bovine Metabolome Database: Showing metabocard for LysoSM(d18:1) (BMDB0006482)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:22:23 UTC

Update Date

2020-04-22 15:17:33 UTC

BMDB ID

BMDB0006482

Secondary Accession Numbers

BMDB06482

Metabolite Identification

Common Name

LysoSM(d18:1)

Description

LysoSM(d18:1), also known as lysosphingomyelin, belongs to the class of organic compounds known as sphingosylphosphorylcholines. These are sphingolipids containing a sphingosine attached to the phosphate group of a phosphocholine. Based on a literature review very few articles have been published on LysoSM(d18:1).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Sphing-4-enine-1-phosphocholine	ChEBI
Sphingosyl-phosphocholine	ChEBI
Sphingosylphosphocholine	ChEBI
Lysosphingomyelin	MeSH
Sphingosine phosphorylcholine	MeSH
C18-Sphingosine phosphocholine	HMDB
D-erythro-Sphingosylphosphorylcholine	HMDB
SM(D18:1/0:0)	HMDB
Sphingenyl-1-phosphorylcholine	HMDB
Sphingomyelin(D18:1/0:0)	HMDB
Sphingosylphosphorylcholine	MeSH, HMDB

Chemical Formula

C₂₃H₅₀N₂O₅P

Average Molecular Weight

465.6273

Monoisotopic Molecular Weight

465.345734232

IUPAC Name

{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid

Traditional Name

lysosphingomyelin

CAS Registry Number

1670-26-4

SMILES

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

InChI Identifier

InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/p+1/b18-17+/t22-,23+/m0/s1

InChI Key

JLVSPVFPBBFMBE-HXSWCURESA-O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as sphingosylphosphorylcholines. These are sphingolipids containing a sphingosine attached to the phosphate group of a phosphocholine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Phosphosphingolipids

Direct Parent

Sphingosylphosphorylcholines

Alternative Parents

Substituents

Sphingosylphosphorylcholine
Phosphocholine
Phosphoethanolamine
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary alcohol
Alcohol
Amine
Organic salt
Hydrocarbon derivative
Primary amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:52897 )
phosphocholines (CHEBI:52897 )
phosphosphingolipid (CHEBI:52897 )
Lysosphingomyelins and lysoglycosphingolipids (C03640 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Endosome
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.3	ALOGPS
logP	-0.24	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	9.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	102.01 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	141.18 m³·mol⁻¹	ChemAxon
Polarizability	55.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ej-9782140000-24f3d9fcbb4a3475e571	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0104900000-a7aeccafba8588e15456	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001r-0900200000-b7b9a408b9290c492481	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9800000000-f089839fe08ca8c6e6f6	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Endosome
Membrane

Biospecimen Locations

Blood

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24888604	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24630653	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Hepatic lipidosis	PMID: 24888604	details

External Links

HMDB ID

HMDB0006482

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023932

KNApSAcK ID

Not Available

Chemspider ID

4444221

KEGG Compound ID

C03640

BioCyc ID

Not Available

BiGG ID

2704995

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280613

PDB ID

SPU

ChEBI ID

52897

References

Synthesis Reference

Sphingomyelin, intermediates thereof and methods for preparation of same. Rochlin, Elimelech; Hildesheim, Jean; Berlin, Alisa. (Biolab Ltd., Israel). PCT Int. Appl. (2005), 39 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for LysoSM(d18:1) (BMDB0006482)

Structure for BMDB0006482 (LysoSM(d18:1))