Livestock Metabolome Database: Showing metabocard for SM(d18:0/20:2(11Z,14Z)) (LMDB00626)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:54:03 UTC

Update Date

2021-04-30 20:57:40 UTC

Lmdb

LMDB00626

Secondary Accession Numbers

None

Metabolite Identification

Common Name

SM(d18:0/20:2(11Z,14Z))

Description

Sphingomyelin (d18:0/20:2(11Z,14Z)) or SM(d18:0/20:2(11Z,14Z)) 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
C20:2 Sphingomyelin	HMDB
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholine	HMDB
Sphingomyelin	MetBuilder
N-(11Z,14Z-Eicosadienoyl)-1-phosphocholine-sphinganine	MetBuilder
Sphingomyelin(D18:0/20:2(11Z,14Z))	MetBuilder
N-(11Z,14Z-Eicosadienoyl)-1-phosphocholine-dihydrosphingosine	MetBuilder
N-(11Z,14Z-Eicosadienoyl)-1-phosphocholine-D-erythro-sphinganine	MetBuilder

Chemical Formula

C₄₃H₈₃N₂O₆P

Average Molecular Weight

755.1027

Monoisotopic Molecular Weight

754.59887491

IUPAC Name

(2-{[(2S,3R,4E)-3-hydroxy-2-[(11Z,14Z)-icosa-11,14-dienamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R,4E)-3-hydroxy-2-[(11Z,14Z)-icosa-11,14-dienamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C43H83N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-43(47)44-41(40-51-52(48,49)50-39-38-45(3,4)5)42(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h14,16,20-21,34,36,41-42,46H,6-13,15,17-19,22-33,35,37-40H2,1-5H3,(H-,44,47,48,49)/b16-14-,21-20-,36-34+/t41-,42+/m0/s1

InChI Key

YVTVVJRJLRHYSJ-XJRFMCMQSA-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

Not Available

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	5.69	ALOGPS
logP	8.03	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	234.58 m³·mol⁻¹	ChemAxon
Polarizability	93.99 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fe0-6030190400-e1cd9c340396d5aee996	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ff0-2170190000-d9a5758314b21de9a818	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001r-6090012000-499a2a6b0911f909e839	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0010004900-34ad350060a9c02e2af0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2042149200-22954dd9b4e7633677d6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-9156020000-102abadcbd7864cff6aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a59-0600000900-dc42603a724a9eb0c1b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000900-dc42603a724a9eb0c1b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000300-de00bbcb18c90984ee96	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000010900-eedbacdb9e9769fb0f51	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03i0-0000070900-5ceafb7cbeb694c72b21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0000090200-17e838484947b3b991e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000010900-321a312f19fcc6c19312	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004o-0000070900-168a78dd16ed90eb8d0a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0000090200-e5b8b37576de2eb6d4f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000900-ceda67b68e8515475c4d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0000003900-0a67b009b5a29699b31f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9010301000-45294c6a5b8f2e54e91e	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 and Quantified	3.44 +/- 1.52 uM	Not Available	Bovine	25875852	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	20647382	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24630653	details
Ruminal Fluid	Detected and Quantified	0.001 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.001 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.001 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.003 uM	Not Available	Bovine	22959937	details
Serum	Detected and Quantified	0.2738 +/- 0.0996 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2496 +/- 0.089 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2995 +/- 0.1857 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2552 +/- 0.0843 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2562 +/- 0.1239 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2866 +/- 0.1071 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.34 +/- 0.11 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	0.2942 +/- 0.0954 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.217 +/- 0.0605 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2666 +/- 0.0697 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2376 +/- 0.1052 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.253 +/- 0.0862 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2305 +/- 0.0709 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0013465

FooDB ID

FDB029465

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

90009

PubChem Compound ID

53481783

Kegg Compound ID

C00550

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for SM(d18:0/20:2(11Z,14Z)) (LMDB00626)

Structure for LMDB00626 (SM(d18:0/20:2(11Z,14Z)))