Record Information
Version1.0
Creation date2011-09-21 01:30:55 UTC
Update date2015-07-21 06:59:15 UTC
Primary IDFDB027851
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCerP(d18:1/18:0)
DescriptionCerP(d18:1/18:0), also known as N-octadecanoyl-sphing-4-enine-1-phosphate, is a ceramide phosphate (CerP). Ceramide phosphates 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). In humans, ceramide phosphate are formed from ceramides by the action of a specific ceramide kinase (CerK) and can be dephosphorylated by phosphatidate phosphatase back to the ceramide. CerPs are an important metabolite of ceramide as it acts as a mediator of the inflammatory response. CerPs are also known to have a dual regulatory capacity acting as intracellular second messengers to regulate cell survival, or as extracellular receptor ligands to stimulate chemotaxis. Moreover, CerPs have been shown to be specific and potent inducers of arachidonic acid and prostanoid synthesis in cells through the translocation and activation of cytoplasmic phospholipase A2. In terms of its appearance and structure, CerP(d18:1/18:0) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached saturated octadecanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481).
CAS NumberNot Available
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility8.8e-05 g/LALOGPS
logP8.68ALOGPS
logP11.47ChemAxon
logS-6.9ALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC36H72NO6P
IUPAC name{[(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}phosphonic acid
InChI IdentifierInChI=1S/C36H72NO6P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(39)37-34(33-43-44(40,41)42)35(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38H,3-28,30,32-33H2,1-2H3,(H,37,39)(H2,40,41,42)/b31-29+/t34-,35+/m0/s1
InChI KeyZQQLMECVOXKFJK-NXCSZAMKSA-N
Isomeric SMILESCCCCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(=O)(O)O)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
Average Molecular Weight645.9337
Monoisotopic Molecular Weight645.509725553
Classification
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
  • 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
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

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Process

Naturally occurring process:

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Industrial application:

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Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCerP(d18:1/18:0), TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCerP(d18:1/18:0), TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCerP(d18:1/18:0), TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCerP(d18:1/18:0), TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCerP(d18:1/18:0), TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCerP(d18:1/18:0), TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCerP(d18:1/18:0), "CerP(d18:1/18:0),1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000197000-a4d61ca5d6c47d158f832021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-1100092000-64bcd7b593825ba2a80f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-8690000000-bdfc25d87221744804612021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2000009000-8300713cd59c69f96d372021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9000007000-0f5db15f8caea78936e22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-22View Spectrum
NMRNot Available
ChemSpider ID4446696
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5283583
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10701
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference