ContaminantDB: SM(d17:1/24:0)

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 20:36:40 UTC

Update Date

2016-11-09 01:22:15 UTC

Accession Number

CHEM040422

Identification

Common Name

SM(d17:1/24:0)

Class

Small Molecule

Description

SM(d17:1/24:0) or SM(d17:1/24:0) is a sphingomyelin. Sphingomyelin (SM or SPH) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. SM(18:1/16:0) consists of oleic acid attached to the C1 position and palmitic acid attached to the C2 position. 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.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
SPH(D17:1/24:0)	HMDB
Sphingomyelin (D17:1/24:0)	HMDB

Chemical Formula

C₄₆H₉₄N₂O₆P

Average Molecular Mass

802.222 g/mol

Monoisotopic Mass

801.685 g/mol

CAS Registry Number

Not Available

IUPAC Name

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

Traditional Name

[(2S,3R,4E)-3-hydroxy-2-tetracosanamidoheptadec-4-en-1-yl]oxy(2-(trimethylammonio)ethoxy)phosphinic acid

SMILES

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

InChI Identifier

InChI=1S/C46H93N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-30-32-34-36-38-40-46(50)47-44(43-54-55(51,52)53-42-41-48(3,4)5)45(49)39-37-35-33-31-29-19-17-15-13-11-9-7-2/h37,39,44-45,49H,6-36,38,40-43H2,1-5H3,(H-,47,50,51,52)/p+1/b39-37+/t44-,45+/m0/s1

InChI Key

NBEKBSIOEMQZTN-NMIJJABPSA-O

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.2e-05 g/L	ALOGPS
logP	6.19	ALOGPS
logP	11.18	ChemAxon
logS	-7.4	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	3	ChemAxon
Polar Surface Area	105.09 Å²	ChemAxon
Rotatable Bond Count	43	ChemAxon
Refractivity	247.27 m³·mol⁻¹	ChemAxon
Polarizability	103.92 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uyr-6021319410-cbacd799a19b61f7c0c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-3162209100-ee02a772befac1fefa15	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01bi-9077002100-9d1dc446ba89d19037db	Spectrum