Showing metabocard for SM(d18:1/26:1(17Z)) (BMDB0109610)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-03-26 13:18:14 UTC
Update Date2020-04-22 20:21:36 UTC
BMDB IDBMDB0109610
Secondary Accession NumbersNone
Metabolite Identification
Common NameSM(d18:1/26:1(17Z))
DescriptionSM(d18:1/26:1(17Z)) 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(d18:1/26:1(17Z)) consists of an unsaturated 18-carbon sphingoid base with an attached unsaturated 17Z-hexacosenoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
C26:1 SphingomyelinChEBI
N-(17Z-Hexacosenoyl)-sphing-4-enine-1-phosphocholineChEBI
N-(Tricosanoyl)-sphing-4-enine-1-phosphocholineHMDB
SphingomyelinHMDB
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphing-4-enineMetBuilder
Sphingomyelin(D18:1/26:1(17Z))MetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-D-erythro-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-4-sphingenineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-D-sphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphingenineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-erythro-4-sphingenineMetBuilder
SM(D18:1/26:1(17Z))ChEBI
N-(17Z-Hexacosenoyl)-1-phosphocholine-sphinganineMetBuilder
Sphingomyelin(D18:0/26:1(17Z))MetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-dihydrosphingosineMetBuilder
N-(17Z-Hexacosenoyl)-1-phosphocholine-D-erythro-sphinganineMetBuilder
Chemical FormulaC49H97N2O6P
Average Molecular Weight841.278
Monoisotopic Molecular Weight840.708425358
IUPAC Name(2-{[(2S,3R,4E)-2-[(17Z)-hexacos-17-enamido]-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S,3R,4E)-2-[(17Z)-hexacos-17-enamido]-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C49H97N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-29-31-33-35-37-39-41-43-49(53)50-47(46-57-58(54,55)56-45-44-51(3,4)5)48(52)42-40-38-36-34-32-30-19-17-15-13-11-9-7-2/h20-21,40,42,47-48,52H,6-19,22-39,41,43-46H2,1-5H3,(H-,50,53,54,55)/b21-20-,42-40+/t47-,48+/m0/s1
InChI KeyYXEXWUZHFGYOHJ-UOJCCMJYSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassPhosphosphingolipids
Direct ParentPhosphosphingolipids
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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Axon
  • Cell membrane
  • Endosome
  • Membrane
  • Myelin sheath
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.53ALOGPS
logP11.06ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area107.92 ŲChemAxon
Rotatable Bond Count45ChemAxon
Refractivity261.07 m³·mol⁻¹ChemAxon
Polarizability108.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053l-6011109040-78d43e222f56260422feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0536-2142109100-86de838a540453f018fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001s-9166002300-ec56b7022d6302efcb2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000490-cb91e2cdfa0fc1ef0e53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2015004920-8dd85b3408ce46984d72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9128002000-1f1df5bc5b2e61edb1daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001190-852973a8181afd58aa19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dk-0000009290-2a89ec676a087342ac72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000009110-41d912ffebeab2f9e19cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000x-0600000090-f3afb84c3623381e151fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0600000090-f3afb84c3623381e151fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000030-ea80282a636c1f91d6e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-dbddecc32b1e8eef807dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000000390-a19ee8177a5c774ca039View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9001030100-33cf30aa4edf3e21f80cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001090-b6e3615b7d0d42bfc294View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03f0-0000007090-7266def15f5db339d557View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0000009020-fbc8eda2d3b38d2ae7b9View in MoNA
Biological Properties
Cellular Locations
  • Axon
  • Cell membrane
  • Endosome
  • Membrane
  • Myelin sheath
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0013461
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029461
KNApSAcK IDNot Available
Chemspider ID24846876
KEGG Compound IDC00550
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44260128
PDB IDNot Available
ChEBI ID84476
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available