Livestock Metabolome Database: Showing metabocard for SM(d18:1/24:1(15Z)) (LMDB00570)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:52:46 UTC

Update Date

2016-09-23 18:45:37 UTC

Lmdb

LMDB00570

Secondary Accession Numbers

None

Metabolite Identification

Common Name

SM(d18:1/24:1(15Z))

Description

Sphingomyelin (d18:1/24:1(15Z)) or SM(d18:1/24:1(15Z)) 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. In animals, 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
C24:1 Sphingomyelin	ChEBI
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholine	ChEBI
N-(15Z-Tetracosenoyl)sphing-4-enine-1-phosphocholine	ChEBI
Sphingomyelin	HMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-sphing-4-enine	HMDB
Sphingomyelin(D18:1/24:1(15Z))	HMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-sphingosine	HMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-D-erythro-sphingosine	HMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-4-sphingenine	HMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-D-sphingosine	HMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-sphingenine	HMDB
N-(15Z-Tetracosenoyl)-1-phosphocholine-erythro-4-sphingenine	HMDB
SM D18:1/24:1(15Z)	HMDB
Sphingomyelin (D18:1,C24:1(15Z))	HMDB
Sphingomyelin (D18:1/24:1(15Z))	HMDB
SM(D18:1/24:1(15Z))	ChEBI

Chemical Formula

C₄₇H₉₃N₂O₆P

Average Molecular Weight

813.2249

Monoisotopic Molecular Weight

812.67712523

IUPAC Name

(2-{[(2S,3R,4E)-3-hydroxy-2-[(15Z)-tetracos-15-enamido]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

C24:1 sphingomyelin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C47H93N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-29-31-33-35-37-39-41-47(51)48-45(44-55-56(52,53)54-43-42-49(3,4)5)46(50)40-38-36-34-32-30-28-19-17-15-13-11-9-7-2/h20-21,38,40,45-46,50H,6-19,22-37,39,41-44H2,1-5H3,(H-,48,51,52,53)/b21-20-,40-38+/t45-,46+/m0/s1

InChI Key

WKZHECFHXLTOLJ-QYKFWSDSSA-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:74535 )
sphingomyelin 42:2 (CHEBI:74535 )
N-tetracosenoylsphingosine-1-phosphocholine (CHEBI:74535 )
Ceramide phosphocholines (sphingomyelins) (LMSP03010007 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	6.3	ALOGPS
logP	11.26	ChemAxon
logS	-7.5	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	2	ChemAxon
Polar Surface Area	107.92 Å²	ChemAxon
Rotatable Bond Count	43	ChemAxon
Refractivity	251.87 m³·mol⁻¹	ChemAxon
Polarizability	103.75 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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01qj-6011109310-e55f9a9b7fe1fa074f2a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-2142109100-042e69121044cc723425	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-008i-9166003200-491572fa5edbe8ee5512	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000490-a68aba8c44804dba30ec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08i0-2015104920-3eb8b1ec9c81fa6a1560	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fr-9128002000-95b79a4f5adbce3d07b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-0600000090-139550ecb3809eb4819f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0600000090-139550ecb3809eb4819f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000110-5abb18835ee1db626837	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000001190-723e05c52172cf4b8083	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue0-0000009290-b3f9f3329970da774224	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0000009110-3e0915ce1af8e9733cfc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000090-fd44e397a6bdccec75d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0000000390-a4ffc25b99b9424b0a4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9001300100-de705bb79d2d2a50b172	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000001190-469667d89771f34fe9cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0150-0000009290-7720669a8b116abc32be	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0000009110-45ca65e6e07937c41807	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24630653	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	22242129	details
Plasma	Detected and Quantified	17.51 +/- 1.40-21.14+/-1.40 uM	Not Available	Porcine	22492530	details
Plasma	Detected and Quantified	18.8 +/- 1.46-16.74+/-1.46 uM	Not Available	Porcine	22492530	details
Ruminal Fluid	Detected and Quantified	0.01 +/- 0.005 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.02 +/- 0.07 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.03 +/- 0.06 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.04 +/- 0.01 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.04 +/- 0.01 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.006 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.009 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.024 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.034 uM	Not Available	Bovine	22959937	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	24888604	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	24888604	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details