Showing metabocard for CerP(d18:0/16:0) (BMDB0010698)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:12:04 UTC
Update Date2020-05-11 19:13:44 UTC
BMDB IDBMDB0010698
Secondary Accession Numbers
  • BMDB10698
Metabolite Identification
Common NameCerP(d18:0/16:0)
DescriptionCerP(d18:0/16:0), also known as N-hexadecanoyl-sphinganine-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(d18:0/16:0) is a colorless solid that consists of a saturated 18-carbon sphingoid base with an attached saturated hexadecanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Ceramide phosphateMetBuilder
N-(Hexadecanoyl)-1-phosphate-sphinganineMetBuilder
Ceramide phosphate(D18:0/16:0)MetBuilder
N-(Hexadecanoyl)-1-phosphate-dihydrosphingosineMetBuilder
N-(Hexadecanoyl)-1-phosphate-D-erythro-sphinganineMetBuilder
N-(Hexadecanoyl)-sphinganine-1-phosphateHMDB
[(2S,3R)-2-(hexadecanoylamino)-3-Hydroxyoctadecyl] dihydrogen phosphateHMDB
Chemical FormulaC34H70NO6P
Average Molecular Weight619.8965
Monoisotopic Molecular Weight619.494075489
IUPAC Name{[(2S,3R)-2-hexadecanamido-3-hydroxyoctadecyl]oxy}phosphonic acid
Traditional NameC16DH CerP
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CCCCCCCCCCCCCCC)[C@]([H])(COP(O)(O)=O)NC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C34H70NO6P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(36)32(31-41-42(38,39)40)35-34(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h32-33,36H,3-31H2,1-2H3,(H,35,37)(H2,38,39,40)/t32-,33+/m0/s1
InChI KeyILHPMPAVRAZOJB-JHOUSYSJSA-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
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Endosome
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.01ALOGPS
logP10.79ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)1.54ChemAxon
pKa (Strongest Basic)0.014ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.09 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity175.69 m³·mol⁻¹ChemAxon
Polarizability78.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ea-9231754000-cf555a1257a1f7b50d2bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("CerP(d18:0/16:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1000059000-3e9390372389bf8b79f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-3012490000-95b46a4f07959f75808aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aos-6697010000-1136260e38882f00b703View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-7000009000-02c938f8dec4fee23cc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000002000-061652d035cb0f47a15dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d5aaca13a836cb9f1725View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010698
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027848
KNApSAcK IDNot Available
Chemspider ID4446695
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283582
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available