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Record Information
StatusExpected but not Quantified
Creation Date2008-09-26 14:11:36 UTC
Update Date2019-07-23 05:55:09 UTC
Secondary Accession Numbers
  • HMDB10701
Metabolite Identification
Common NameCerP(d18:1/18:0)
DescriptionCerP(d18:1/18:0) is a ceramide 1-phosphate belonging to the sphingolipid class of molecules. Ceramides are amides of fatty acids with long-chain di- or trihydroxy bases, the commonest in animals being sphingosine and in plants phytosphingosine. The acyl group of ceramides is generally a long-chain saturated or monounsaturated fatty acid. The most frequent fatty acids found in animal ceramides are 18:0, 24:0 and 24:1(n-9). Ceramide 1-phosphates are produced by phosphorylation of ceramide by a specific ceramide kinase. Ceramide-1-phosphate was shown to be a specific and potent inducer of arachidonic acid and prostanoid synthesis in cells through the translocation and activation of the cytoplasmic phospholipase A2.
N-Octadecanoylsphing-4-enine 1-phosphateChEBI
N-Stearoylsphing-4-enine 1-phosphateChEBI
N-Stearoylsphingosine 1-phosphateChEBI
N-Octadecanoylsphing-4-enine 1-phosphoric acidGenerator
N-Stearoylsphing-4-enine 1-phosphoric acidGenerator
N-Stearoylsphingosine 1-phosphoric acidGenerator
[(e,2S,3R)-3-Hydroxy-2-(octadecanoylamino)octadec-4-enyl] dihydrogen phosphateHMDB
Chemical FormulaC36H72NO6P
Average Molecular Weight645.9337
Monoisotopic Molecular Weight645.509725553
IUPAC Name{[(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}phosphonic acid
Traditional NameC18 CerP
CAS Registry NumberNot Available
InChI Identifier
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
Sub ClassPhosphosphingolipids
Direct ParentPhosphosphingolipids
Alternative Parents
  • Sphingoid-1-phosphate or derivatives
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Fatty amide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physiological effect

Organoleptic effect:


Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility8.8e-05 g/LALOGPS
pKa (Strongest Acidic)1.53ChemAxon
pKa (Strongest Basic)0.00068ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.09 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity185.85 m³·mol⁻¹ChemAxon
Polarizability82.26 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • All Tissues
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027851
KNApSAcK IDNot Available
Chemspider ID4446696
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283583
PDB IDNot Available
ChEBI ID73144
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  2. 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 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.