Livestock Metabolome Database: Showing metabocard for SM(d18:0/16:1(9Z)) (LMDB00625)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:54:02 UTC

Update Date

2021-04-30 20:58:24 UTC

Lmdb

LMDB00625

Secondary Accession Numbers

None

Metabolite Identification

Common Name

SM(d18:0/16:1(9Z))

Description

Sphingomyelin (d18:0/16:1(9Z)) or SM(d18:0/16:1(9Z)) 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
C16:1 Sphingomyelin	HMDB
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholine	HMDB
Sphingomyelin	MetBuilder
N-(9Z-Hexadecenoyl)-1-phosphocholine-sphinganine	MetBuilder
Sphingomyelin(D18:0/16:1(9Z))	MetBuilder
N-(9Z-Hexadecenoyl)-1-phosphocholine-dihydrosphingosine	MetBuilder
N-(9Z-Hexadecenoyl)-1-phosphocholine-D-erythro-sphinganine	MetBuilder

Chemical Formula

C₃₉H₇₉N₂O₆P

Average Molecular Weight

703.0281

Monoisotopic Molecular Weight

702.567574782

IUPAC Name

(2-{[(2S,3R)-2-[(9Z)-hexadec-9-enamido]-3-hydroxyoctadecyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R)-2-[(9Z)-hexadec-9-enamido]-3-hydroxyoctadecyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCC[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCC\C=C/CCCCCC

InChI Identifier

InChI=1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h17,19,37-38,42H,6-16,18,20-36H2,1-5H3,(H-,40,43,44,45)/b19-17-/t37-,38+/m0/s1

InChI Key

CGVOQSQIYSUXAT-PPLFXBRHSA-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	5.04	ALOGPS
logP	7.91	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	36	ChemAxon
Refractivity	214.1 m³·mol⁻¹	ChemAxon
Polarizability	88.13 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	splash10-0fe0-6020193100-cb8ec240bfaa94c069f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ul9-2060191000-693d2600958ae42f2646	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001r-8190032000-991c41643b2704ff9c3f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000013900-6dcf2092ee87df42f97e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uy1-2062096200-5655783b8aaa759a8654	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-9183030000-80a3338885d153b40444	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000011900-1d22b33527aec6c2bac2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a90-0000092900-aacf4f47e4b1b3216788	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0000091100-0e83614fafb2fa889b08	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-0600000900-be758d36e1a256cac4a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-0600000900-be758d36e1a256cac4a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900001100-94967dd8d4d77f7fa445	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000011900-c5d2f234e24c0a593f9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004o-0000092900-3c7e0616c8e11bafdb0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0000091100-ec927235531ec4f37fc5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000900-6cd0aa91f5b1a16397c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0000002900-d2f6b3b3d48fafc8b8e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9002000000-a2b51a23065d1bc1a338	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
Serum	Detected and Quantified	3.0303 +/- 1.068 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.2218 +/- 1.0601 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.7025 +/- 2.0778 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.2043 +/- 1.3624 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.1257 +/- 0.8806 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.2548 +/- 0.9488 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.3873 +/- 1.0467 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.8939 +/- 0.7632 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.3572 +/- 0.9145 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.8899 +/- 1.115 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.2252 +/- 1.1867 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.0471 +/- 0.7271 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0013464

FooDB ID

FDB029464

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

90008

PubChem Compound ID

53481781

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(d18:0/16:1(9Z)) (LMDB00625)

Structure for LMDB00625 (SM(d18:0/16:1(9Z)))