ContaminantDB: SM(d18:0/12:0)

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

Record Information

Version

1.0

Creation Date

2016-05-27 00:13:00 UTC

Update Date

2016-11-09 01:22:17 UTC

Accession Number

CHEM040620

Identification

Common Name

SM(d18:0/12:0)

Class

Small Molecule

Description

SM(d18:0/12:0) (d18:0/12:0) or SM(d18:0/12:0)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 humans, SM(d18:0/12:0) 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 SM(d18:0/12:0) 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 SM(d18:0/12:0) pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down SM(d18:0/12:0) into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be SM(d18:0/12:0) present there. SM(d18:0/12:0) 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 SM(d18:0/12:0) 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 SM(d18:0/12:0) synthase.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
C12 Sphingomyelin	HMDB
N-(Dodecanoyl)-sphing-4-enine-1-phosphocholine	HMDB
Sphingomyelin	HMDB
Sphingomyelin (D18:0/12:0)	HMDB
N-(Dodecanoyl)-1-phosphocholine-sphinganine	HMDB
Sphingomyelin(D18:0/12:0)	HMDB
N-(Dodecanoyl)-1-phosphocholine-dihydrosphingosine	HMDB
N-(Dodecanoyl)-1-phosphocholine-D-erythro-sphinganine	HMDB

Chemical Formula

C₃₅H₇₅N₂O₆P

Average Molecular Mass

650.954 g/mol

Monoisotopic Mass

650.536 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2-{[(2S,3R)-3-hydroxy-2-[(1-hydroxydodecyl)amino]octadecyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R)-3-hydroxy-2-[(1-hydroxydodecyl)amino]octadecyl phosphonato]oxy}ethyl)trimethylazanium

SMILES

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

InChI Identifier

InChI=1S/C35H75N2O6P/c1-6-8-10-12-14-16-17-18-19-21-22-24-26-28-34(38)33(32-43-44(40,41)42-31-30-37(3,4)5)36-35(39)29-27-25-23-20-15-13-11-9-7-2/h33-36,38-39H,6-32H2,1-5H3/t33-,34+,35?/m0/s1

InChI Key

DBRCJAPVYYEHRO-GWDKEWMYSA-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
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Hemiaminal
Secondary alcohol
Secondary amine
Secondary aliphatic amine
Alkanolamine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Amine
Organic salt
Organic zwitterion
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	6.4e-05 g/L	ALOGPS
logP	3.76	ALOGPS
logP	4.44	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	1.82	ChemAxon
pKa (Strongest Basic)	9.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.08 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	195.69 m³·mol⁻¹	ChemAxon
Polarizability	82.78 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 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 (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("SM(d18:0/12:0),1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000009000-e464f2f77a5dab09d395	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0000039000-4a17ff4c872cf94c5cc8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9002010000-9f7d501363ae1ab8afba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-3100009000-b2b29ec1931796e71951	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2900001000-1c206cc6b9ceff19c8c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-7900000000-0eaacb075ecdf28009da	Spectrum