Livestock Metabolome Database: Showing metabocard for SM(d18:0/16:1(9Z)(OH)) (LMDB00780)

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

Record Information

Version

1.0

Creation Date

2016-07-30 18:18:01 UTC

Update Date

2021-04-30 20:57:40 UTC

Lmdb

LMDB00780

Secondary Accession Numbers

None

Metabolite Identification

Common Name

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

Description

SM(d18:0/16:1(9Z)(OH)) is a sphingomyelin (SM). Sphingomyelins are members of the class of compounds known as sphingolipids (SPs), or glycosylceramides. SPs are lipids containing a backbone of sphingoid bases (e.g. sphingosine or sphinganine) that are often covalently bound to a fatty acid derivative through N-acylation. SPs are found in cell membranes, particularly in peripheral nerve cells and the cells found in the central nervous system (including the brain and spinal cord). Sphingolipids are extremely versatile molecules that have functions controlling fundamental cellular processes such as cell division, differentiation, and cell death. Impairments associated with sphingolipid metabolism are associated with many common human diseases such as diabetes, various cancers, microbial infections, diseases of the cardiovascular and respiratory systems, Alzheimer’s disease and other neurological syndromes. The biosynthesis and catabolism of sphingolipids involves a large number of intermediate metabolites where many different enzymes are involved. Simple sphingolipids, which include the sphingoid bases and ceramides, make up the early products of the sphingolipid synthetic pathways, while complex sphingolipids may be formed by the addition of head groups to the ceramide template (Wikipedia). SM is the major sphingolipid in mammals it is found in animal cell membranes, especially in the membranous myelin sheath that surrounds some nerve cell axons. It usually consists of phosphocholine and ceramide, or a phosphoethanolamine head group. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. SM 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. In terms of its appearance and structure, SM(d18:0/16:1(9Z)(OH)) consists of a saturated 18-carbon sphingoid base with an attached unsaturated 3-hydroxy-9Z-hexadecenoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
C16:1-OH Sphingomyelin	ChEBI
Hydroxysphingomyeline C16:1	ChEBI
N-[(9Z)-3-Hydroxyhexadec-9-enoyl]sphing-4-enine-1-phosphocholine	ChEBI
SM(D18:1/16:1(9Z)(OH))	ChEBI
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholine	HMDB
Sphingomyelin	MetBuilder
N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-sphinganine	MetBuilder
Sphingomyelin(D18:0/16:1(9Z)(OH))	MetBuilder
N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-dihydrosphingosine	MetBuilder
N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-D-erythro-sphinganine	MetBuilder

Chemical Formula

C₃₉H₇₇N₂O₇P

Average Molecular Weight

717.0116

Monoisotopic Molecular Weight

716.54683934

IUPAC Name

(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]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)CCCCC\C=C/CCCCCC

InChI Identifier

InChI=1S/C39H77N2O7P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(43)37(35-48-49(45,46)47-33-32-41(3,4)5)40-39(44)34-36(42)30-28-26-24-22-20-17-15-13-11-9-7-2/h17,20,29,31,36-38,42-43H,6-16,18-19,21-28,30,32-35H2,1-5H3,(H-,40,44,45,46)/b20-17-,31-29+/t36?,37-,38+/m0/s1

InChI Key

LPHMSPONPQCKTL-FKUNDBCPSA-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	4.38	ALOGPS
logP	5.38	ChemAxon
logS	-7.2	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	35	ChemAxon
Refractivity	216.57 m³·mol⁻¹	ChemAxon
Polarizability	87.13 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 (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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00m1-5020195100-75c4428f308b70e492a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-2140191000-1a1ed63feed3f152dcdb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001r-8190032000-c1f385095a959e7e14be	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0010004900-03516550d63a4b14a21d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02u0-1172149200-27f568a6bfc192cf91f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-9183120000-1d21406c331bfb554143	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000011900-4aa51f66c591f10a45d0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a50-0000092900-3dc7f7c1babd46a42d93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0000091100-d0b9a75fac9ff500e6c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000900-282d41e16428007043d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0020003900-41188580822b70887c3a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9282000000-d0383bad10de3658c4d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000011900-913b25a99091d7742381	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00do-0000092900-807f48801e76940db556	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0000091100-11de640103dd3b340f84	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0600000900-a4544d9a891eec8a2b0e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0600000900-a4544d9a891eec8a2b0e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900001100-59b07f8576eaafa65901	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 but not Quantified	Not Applicable	Not Available	Ovine	22242129	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24630653	details
Ruminal Fluid	Detected and Quantified	0.006 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.006 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.007 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.01 uM	Not Available	Bovine	22959937	details
Serum	Detected and Quantified	4.7502 +/- 1.3581 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.153 +/- 1.3362 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.6371 +/- 3.2145 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.0397 +/- 1.877 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.0057 +/- 1.4713 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.339 +/- 1.6671 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.3124 +/- 1.2723 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.47 +/- 2.12 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	4.6734 +/- 1.4132 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.1466 +/- 1.0 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.6752 +/- 1.8714 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.9407 +/- 1.4691 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.9512 +/- 1.3263 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0013463

FooDB ID

FDB029463

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

90007

PubChem Compound ID

53481779

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)(OH)) (LMDB00780)

Structure for LMDB00780 (SM(d18:0/16:1(9Z)(OH)))