Showing metabocard for SM(d18:0/24:1(15Z)(OH)) (LMDB00630)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:54:08 UTC
Update Date2021-04-30 20:57:41 UTC
LmdbLMDB00630
Secondary Accession NumbersNone
Metabolite Identification
Common NameSM(d18:0/24:1(15Z)(OH))
DescriptionSphingomyelin (d18:0/24:1(15Z)(OH))or SM(d18:0/24:1(15Z)(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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
C24:1-OH SphingomyelinChEBI
Hydroxysphingomyeline C24:1ChEBI
N-[(15Z)-3-Hydroxytetracos-15-enoyl]sphing-4-enine-1-phosphocholineChEBI
SM(D18:1/24:1(15Z)(OH))ChEBI
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholineHMDB
SphingomyelinMetBuilder
N-(3-Hydroxy-15Z-tetracosenoyl)-1-phosphocholine-sphinganineMetBuilder
Sphingomyelin(D18:0/24:1(15Z)(OH))MetBuilder
N-(3-Hydroxy-15Z-tetracosenoyl)-1-phosphocholine-dihydrosphingosineMetBuilder
N-(3-Hydroxy-15Z-tetracosenoyl)-1-phosphocholine-D-erythro-sphinganineMetBuilder
Chemical FormulaC47H93N2O7P
Average Molecular Weight829.2243
Monoisotopic Molecular Weight828.672039852
IUPAC Name(2-{[(2S,3R,4E)-3-hydroxy-2-[(15Z)-3-hydroxytetracos-15-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S,3R,4E)-3-hydroxy-2-[(15Z)-3-hydroxytetracos-15-enamido]octadec-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)CC(O)CCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C47H93N2O7P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-28-30-32-34-36-38-44(50)42-47(52)48-45(43-56-57(53,54)55-41-40-49(3,4)5)46(51)39-37-35-33-31-29-26-19-17-15-13-11-9-7-2/h20-21,37,39,44-46,50-51H,6-19,22-36,38,40-43H2,1-5H3,(H-,48,52,53,54)/b21-20-,39-37+/t44?,45-,46+/m0/s1
InChI KeyIOOMOQUTKQGEFH-BSZNTFKYSA-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 DescriptorsNot Available
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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
logP5.81ALOGPS
logP8.94ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.15 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity253.38 m³·mol⁻¹ChemAxon
Polarizability104.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01u9-5011109240-f45aa83673aaedd9b0e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003s-1131109100-6ee25eea1e94d73daadbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-9173002300-42f818b95026245bfd6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001000490-2592f8fea67f74bbabedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-1026103920-ea9f4b2bfa57ca6b4c1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-7119002000-f70cbc7f0bbf017e71c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000001190-6d740e1e58d8dbb46607Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0vi0-0000009290-50bbb33a1cae45260dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0000009110-7a6b14cc52f5095d3876Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000001190-1e5e29d2dddefa955f56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue0-0000009290-623e50f0c5f51f505554Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0000009110-8a16f4d508ac5473a45fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-0600000090-6f462a4e6af316089153Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0600000090-6f462a4e6af316089153Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000030-79679eccf6c21dad24abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000090-5bf2bfc8f2db1f55a5ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0002000390-e8a76791ef98e8d8e329Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-8009010000-5b89f28202b8b8c5e49eSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Ruminal FluidDetected and Quantified0.002 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified0.002 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified0.002 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified0.003 uMNot AvailableBovine details
SerumDetected and Quantified0.8705 +/- 0.3423 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified0.8772 +/- 0.2486 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified1.0017 +/- 0.3777 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified0.899 +/- 0.3554 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified0.9534 +/- 0.4224 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified0.7333 +/- 0.3467 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified1.09 +/- 0.36 uMNot AvailableOvine
    • Candidate serum m...
 details
SerumDetected and Quantified0.7466 +/- 0.3499 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified0.8698 +/- 0.1804 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified0.6878 +/- 0.29 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified0.9265 +/- 0.406 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected and Quantified0.8754 +/- 0.2714 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified0.9612 +/- 0.3514 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
DrugBank IDNot Available
HMDB IDHMDB0013469
FooDB IDFDB029469
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSphingomyelin
Chemspider IDNot Available
ChEBI ID90006
PubChem Compound ID53481791
Kegg Compound IDC00550
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available