Showing metabocard for CerP(d18:1/16:0) (BMDB0010700)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:12:07 UTC
Update Date2020-05-11 19:13:45 UTC
BMDB IDBMDB0010700
Secondary Accession Numbers
  • BMDB10700
Metabolite Identification
Common NameCerP(d18:1/16:0)
DescriptionCerP(d18:1/16:0), also known as N-hexadecanoyl-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(d18:1/16:0) is a colorless solid that consists of an unsaturated 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
N-Hexadecanoylsphing-4-enine-1-phosphateChEBI
N-Palmitoylsphing-4-enine-1-phosphateChEBI
N-Palmitoylsphingosine 1-phosphateChEBI
N-Hexadecanoylsphing-4-enine-1-phosphoric acidGenerator
N-Palmitoylsphing-4-enine-1-phosphoric acidGenerator
N-Palmitoylsphingosine 1-phosphoric acidGenerator
Ceramide phosphateMetBuilder
N-(Hexadecanoyl)-1-phosphate-sphing-4-enineMetBuilder
Ceramide phosphate(D18:1/16:0)MetBuilder
N-(Hexadecanoyl)-1-phosphate-sphingosineMetBuilder
N-(Hexadecanoyl)-1-phosphate-D-erythro-sphingosineMetBuilder
N-(Hexadecanoyl)-1-phosphate-4-sphingenineMetBuilder
N-(Hexadecanoyl)-1-phosphate-D-sphingosineMetBuilder
N-(Hexadecanoyl)-1-phosphate-sphingenineMetBuilder
N-(Hexadecanoyl)-1-phosphate-erythro-4-sphingenineMetBuilder
N-(Hexadecanoyl)-sphing-4-enine-1-phosphateHMDB
[(e,2S,3R)-2-(hexadecanoylamino)-3-Hydroxyoctadec-4-enyl] dihydrogen phosphateHMDB
Chemical FormulaC34H68NO6P
Average Molecular Weight617.8806
Monoisotopic Molecular Weight617.478425425
IUPAC Name{[(2S,3R,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid
Traditional NameC16 CerP
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(=O)(O)O)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C34H68NO6P/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/h27,29,32-33,36H,3-26,28,30-31H2,1-2H3,(H,35,37)(H2,38,39,40)/b29-27+/t32-,33+/m0/s1
InChI KeyUNRULDRRONAKLU-TURZORIXSA-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
logP8.24ALOGPS
logP10.58ChemAxon
logS-6.8ALOGPS
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 Count32ChemAxon
Refractivity176.65 m³·mol⁻¹ChemAxon
Polarizability78.06 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, Positivesplash10-022a-9114256000-70029283243742b63ffcView 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(d18:1/16:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2000009000-9b49d4a6a5e50d9a0bfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-9000007000-da48a526484a4a6e0f26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-0000197000-ca8198b56f63cdf30089View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0010092000-ee5db710d22114fccbecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-4590000000-a35ff7a144ee7bc18e02View 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 IDHMDB0010700
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027850
KNApSAcK IDNot Available
Chemspider ID4446694
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283581
PDB ID1PX
ChEBI ID73145
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available