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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-04-16 20:46:41 UTC
Update Date2018-05-20 18:56:46 UTC
HMDB IDHMDB0061712
Secondary Accession Numbers
  • HMDB61712
Metabolite Identification
Common NamePalmitoyl sphingomyelin
DescriptionPalmitoyl sphingomyelin is a common form of sphingomyelin. Sphingomyelins are complex membrane lipids composed of phosphorylcholine, sphingosine, and an acylated group, such as a fatty acid. Palmitoyl sphingomyelin is a form of sphingomyelin containing palmitate (16:0) at the variable acylation position. It is the most common form of sphingomyelin found in eggs and is less abundant in the brain and milk. Palmitoyl sphingomyelin interacts with cholesterol in ordered lipid domains (lipid rafts). Sphingomyelinases remove phosphorylcholine from palmitoyl sphingomyelin to produce C-16 ceramide. While ceramides commonly induce apoptosis, ceramides with different fatty acid chain lengths might direct distinct functions and, in some cases, reduce apoptosis. (Reference: https://www.caymanchem.com/app/template/Product.vm/catalog/10007946
Structure
Thumb
Synonyms
ValueSource
(2S,3R,4E)-2-(palmitoylamino)-3-Hydroxyoctadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphateChEBI
(2S,3R,4E)-3-Hydroxy-2-(palmitoylamino)octadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphateChEBI
C16 SphingomyelinChEBI
C16-SphingomyelinChEBI
Hexadecanoyl sphingomyelinChEBI
N-(Hexadecanoyl)-sphing-4-enine-1-phosphocholineChEBI
N-Hexadecanoylsphing-4-enine-1-phosphocholineChEBI
N-HexadecanoylsphingomyelinChEBI
N-Palmitoyl-D-erythro-sphingosylphosphorylcholineChEBI
N-Palmitoylsphing-4-enine-1-phosphocholineChEBI
N-PalmitoylsphingomyelinChEBI
N-Palmitoylsphingosine-1-phosphocholineChEBI
Palmitoyl sphingomyelinChEBI
Palmitoyl sphingomyelin (D18:1/16:0)ChEBI
PalmitoylsphingomyelinChEBI
SM(18:1/16:0)ChEBI
Sphingomyelin (D18:1/16:0)ChEBI
Sphingomyelin D18:1/16:0ChEBI
Sphingomyelin(D18:1/16:0)ChEBI
(2S,3R,4E)-2-(palmitoylamino)-3-Hydroxyoctadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphoric acidGenerator
(2S,3R,4E)-3-Hydroxy-2-(palmitoylamino)octadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphoric acidGenerator
Chemical FormulaC39H79N2O6P
Average Molecular Weight703.0281
Monoisotopic Molecular Weight702.567574782
IUPAC Name(2-{[(2S,3R,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
Traditional NameC16 sphingomyelin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/b32-30+/t37-,38+/m0/s1
InChI KeyRWKUXQNLWDTSLO-GWQJGLRPSA-N
Chemical Taxonomy
DescriptionThis compound 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
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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
Water Solubility3.3e-05 g/LALOGPS
logP5.12ALOGPS
logP8.07ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)0.012ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area107.92 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity213.94 m³·mol⁻¹ChemAxon
Polarizability89.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD66-42
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9939941
PDB IDNot Available
ChEBI ID78646
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
  7. Hannun YA: The sphingomyelin cycle and the second messenger function of ceramide. J Biol Chem. 1994 Feb 4;269(5):3125-8. [PubMed:8106344 ]
  8. de Jong A, Cheng TY, Huang S, Gras S, Birkinshaw RW, Kasmar AG, Van Rhijn I, Pena-Cruz V, Ruan DT, Altman JD, Rossjohn J, Moody DB: CD1a-autoreactive T cells recognize natural skin oils that function as headless antigens. Nat Immunol. 2014 Feb;15(2):177-85. doi: 10.1038/ni.2790. Epub 2013 Dec 22. [PubMed:24362891 ]
  9. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.