Livestock Metabolome Database: Showing metabocard for SM(d18:0/18:0) (LMDB00569)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:52:45 UTC

Update Date

2021-04-30 20:57:40 UTC

Lmdb

LMDB00569

Secondary Accession Numbers

None

Metabolite Identification

Common Name

SM(d18:0/18:0)

Description

Sphingomyelin (d18:0/18:0) or SM(d18:0/18:0) 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
C18 Sphingomyelin	HMDB
N-(Octadecanoyl)-sphinganine-1-phosphocholine	HMDB
Sphingomyelin	HMDB
Sphingomyelin (D18:0/18:0)	HMDB
N-(Octadecanoyl)-1-phosphocholine-sphinganine	HMDB
Sphingomyelin(D18:0/18:0)	HMDB
N-(Octadecanoyl)-1-phosphocholine-dihydrosphingosine	HMDB
N-(Octadecanoyl)-1-phosphocholine-D-erythro-sphinganine	HMDB

Chemical Formula

C₄₁H₈₅N₂O₆P

Average Molecular Weight

733.0972

Monoisotopic Molecular Weight

732.614524974

IUPAC Name

(2-{[(2S,3R)-3-hydroxy-2-octadecanamidooctadecyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

C18DH sphingomyelin

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)CCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C41H85N2O6P/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/h39-40,44H,6-38H2,1-5H3,(H-,42,45,46,47)/t39-,40+/m0/s1

InChI Key

JCELSEVNSMXGKA-IOLBBIBUSA-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

Ceramide phosphocholines (sphingomyelins) (LMSP03010020 )

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	5.44	ALOGPS
logP	9.16	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	0.025	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	39	ChemAxon
Refractivity	222.18 m³·mol⁻¹	ChemAxon
Polarizability	94.08 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	splash10-001r-6030190400-b4c2ebf67bd2270d22a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2070191000-99bc8c00c06f3a1ef708	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-6090022000-a691638f2890eb559cff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000004900-3487ec5451edeb775e7f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1051039200-dcc56efdec76291dd9e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-9182020000-3f4a4245401d08fc5fe6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000011900-0da3c6ff6e67cc4dfd99	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ai0-0000092900-67c9cd9dc0e1f20ae87f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0000091100-7e39e49790d8800bac48	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0600000900-7983d9dafb007fa90dce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-7983d9dafb007fa90dce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000300-a15c99ce6b59e1aec7ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000011900-9fb101a7fb8faef1e09f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a50-0000092900-eee822a518fa9cf3f69a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0000091100-f7447776d7d5898fad1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-d877867268040bb1f5a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0000003900-9f056f6eae0fb2a47279	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000001000-9a12743542dba50f983b	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	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
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	22242129	details
Serum	Detected and Quantified	5.9622 +/- 1.4163 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.4105 +/- 1.5693 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	7.263 +/- 4.1477 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.4465 +/- 2.7947 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.2355 +/- 1.4544 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.9858 +/- 2.3353 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	24888604	details
Serum	Detected and Quantified	6.52 +/- 2.15 uM	Not Available	Ovine	Candidate serum m...	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
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected and Quantified	6.8117 +/- 1.8913 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.7923 +/- 1.3561 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	7.0712 +/- 1.9139 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.824 +/- 2.296 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.5418 +/- 1.8321 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.115 +/- 1.3153 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0012087

FooDB ID

FDB028754

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

ChEBI ID

PubChem Compound ID

Kegg Compound ID

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(d18:0/18:0) (LMDB00569)

Structure for LMDB00569 (SM(d18:0/18:0))