Livestock Metabolome Database: Showing metabocard for SM(d18:0/22:2(13Z,16Z)(OH)) (LMDB00628)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:54:06 UTC

Update Date

2021-04-30 20:57:41 UTC

Lmdb

LMDB00628

Secondary Accession Numbers

None

Metabolite Identification

Common Name

SM(d18:0/22:2(13Z,16Z)(OH))

Description

Sphingomyelin (d18:0/22:2(13Z,16Z)(OH)) or SM(d18:0/22:2(13Z,16Z)(OH)) 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
C22:2-OH Sphingomyelin	ChEBI
Hydroxysphingomyeline C22:2	ChEBI
N-[(13Z,16Z)-3-Hydroxydocosa-13,16-enoyl]sphing-4-enine-1-phosphocholine	ChEBI
SM(D18:1/22:2(13Z,16Z)(OH))	ChEBI
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholine	HMDB
Sphingomyelin	MetBuilder
N-(3-Hydroxy-13Z,16Z-docosenoyl)-1-phosphocholine-sphinganine	MetBuilder
Sphingomyelin(D18:0/22:2(13Z,16Z)(OH))	MetBuilder
N-(3-Hydroxy-13Z,16Z-docosenoyl)-1-phosphocholine-dihydrosphingosine	MetBuilder
N-(3-Hydroxy-13Z,16Z-docosenoyl)-1-phosphocholine-D-erythro-sphinganine	MetBuilder

Chemical Formula

C₄₅H₈₇N₂O₇P

Average Molecular Weight

799.1552

Monoisotopic Molecular Weight

798.62508966

IUPAC Name

(2-{[(2S,3R,4E)-3-hydroxy-2-[(13Z,16Z)-3-hydroxydocosa-13,16-dienamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R,4E)-3-hydroxy-2-[(13Z,16Z)-3-hydroxydocosa-13,16-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)CC(O)CCCCCCCCC\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C45H87N2O7P/c1-6-8-10-12-14-16-18-20-21-22-23-25-26-28-30-32-34-36-42(48)40-45(50)46-43(41-54-55(51,52)53-39-38-47(3,4)5)44(49)37-35-33-31-29-27-24-19-17-15-13-11-9-7-2/h14,16,20-21,35,37,42-44,48-49H,6-13,15,17-19,22-34,36,38-41H2,1-5H3,(H-,46,50,51,52)/b16-14-,21-20-,37-35+/t42?,43-,44+/m0/s1

InChI Key

DRKCMBAZIYFIGX-ZWLRGCNFSA-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	5.48	ALOGPS
logP	7.69	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	128.15 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	245.3 m³·mol⁻¹	ChemAxon
Polarizability	98.78 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 (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0012-7011156900-59f57d1195e03f2c36a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-3262169200-e160ef1cde477bc1e9f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001r-9183012100-3720247adae3a413f2e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000001900-559fc5cc139f5f32636f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01p7-2046329800-16481575b3d31e9075d0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-8129003000-57feb73b7ccaa8c7653a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000000900-660cae17b4d35c24b5e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0012000900-83e7b7d1498d9989153f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002o-9053100000-0361dcc7ca7110485dfe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0600000900-30eed8331af5bacc2beb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-0600000900-30eed8331af5bacc2beb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000300-b40420bbdef3c1464c6c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000001190-dc352a899cda0a07b1a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ai0-0000009290-3b303ea7b058cdc54119	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0000019110-55eff114f0faed1ce593	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000001190-5779ca3e94feeaed7287	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e0-0000009290-9891327c4e39239d6046	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0000019110-f56ce78bf55ca621a041	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	1.7256 +/- 0.1388-1.9766+/-0.1388 uM	Not Available	Porcine	22492530	details
Plasma	Detected and Quantified	1.9865 +/- 0.1452-1.5705+/-0.1452 uM	Not Available	Porcine	22492530	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	20647382	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	22242129	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	0.002 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.006 uM	Not Available	Bovine	22959937	details
Serum	Detected and Quantified	3.3108 +/- 0.9954 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.3239 +/- 0.797 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.0357 +/- 1.9889 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.5676 +/- 1.4414 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.5008 +/- 1.1221 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.3875 +/- 0.8403 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.18 +/- 1.03 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	3.4394 +/- 0.7687 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.1742 +/- 0.5742 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.359 +/- 0.5162 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.3064 +/- 1.3219 uM	Normal	Ovine	Goldansaz et al.,...	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
Serum	Detected and Quantified	3.4222 +/- 0.797 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.5468 +/- 0.9721 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0013467

FooDB ID

FDB029467

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

Sphingomyelin

Chemspider ID

Not Available

ChEBI ID

90003

PubChem Compound ID

53481787

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(d18:0/22:2(13Z,16Z)(OH)) (LMDB00628)

Structure for LMDB00628 (SM(d18:0/22:2(13Z,16Z)(OH)))