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Showing Compound SM(d17:1/24:0) (FDB028381)

Record Information
Version1.0
Creation date2011-09-21 01:38:53 UTC
Update date2015-07-21 06:59:24 UTC
Primary IDFDB028381
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSM(d17:1/24:0)
DescriptionSphingomyelin (d17:1/24:0) or SM(d17:1/24:0) is a sphingomyelin. Sphingomyelin (SM or SPH) 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. SM(18:1/16:0) consists of oleic acid attached to the C1 position and palmitic acid attached to the C2 position. In humans, 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility3.2e-05 g/LALOGPS
logP6.19ALOGPS
logP11.18ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)0.012ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.09 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity247.27 m³·mol⁻¹ChemAxon
Polarizability103.92 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC46H94N2O6P
IUPAC name{[(2S,3R,4E)-3-hydroxy-2-tetracosanamidoheptadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid
InChI IdentifierInChI=1S/C46H93N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-30-32-34-36-38-40-46(50)47-44(43-54-55(51,52)53-42-41-48(3,4)5)45(49)39-37-35-33-31-29-19-17-15-13-11-9-7-2/h37,39,44-45,49H,6-36,38,40-43H2,1-5H3,(H-,47,50,51,52)/p+1/b39-37+/t44-,45+/m0/s1
InChI KeyNBEKBSIOEMQZTN-NMIJJABPSA-O
Isomeric SMILESCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(O)(=O)OCC[N+](C)(C)C)[C@]([H])(O)\C=C\CCCCCCCCCCCC
Average Molecular Weight802.2221
Monoisotopic Molecular Weight801.684950262
Classification
Description Belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentPhosphocholines
Alternative Parents
Substituents
  • Phosphocholine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty amide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Amine
  • Alcohol
  • Organic oxide
  • Organic salt
  • Hydrocarbon derivative
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Organoleptic effect:

Disposition

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Process

Naturally occurring process:

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Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uyr-6021319410-cbacd799a19b61f7c0c32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-3162209100-ee02a772befac1fefa152017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bi-9077002100-9d1dc446ba89d19037db2017-09-01View Spectrum
NMRNot Available
ChemSpider ID24768060
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID52931214
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11695
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference