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Record Information
Version3.6
Creation Date2008-09-26 14:11:34 UTC
Update Date2016-02-11 01:19:59 UTC
HMDB IDHMDB10699
Secondary Accession NumbersNone
Metabolite Identification
Common NameCerP(d18:1/12:0)
DescriptionCerP(d18:1/12:0) or N-(dodecanoyl)-sphing-4-enine-1-phosphate 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.
Structure
Thumb
Synonyms
ValueSource
N-(Dodecanoyl)sphing-4-enine-1-phosphateChEBI
N-Dodecanoylsphing-4-enine-1-phosphateChEBI
N-Lauroylceramide-1-phosphateChEBI
N-Lauroylsphing-4-enine-1-phosphateChEBI
N-Lauroylsphingosine 1-phosphateChEBI
N-(Dodecanoyl)sphing-4-enine-1-phosphoric acidGenerator
N-Dodecanoylsphing-4-enine-1-phosphoric acidGenerator
N-Lauroylceramide-1-phosphoric acidGenerator
N-Lauroylsphing-4-enine-1-phosphoric acidGenerator
N-Lauroylsphingosine 1-phosphoric acidGenerator
N-(Dodecanoyl)-sphing-4-enine-1-phosphateHMDB
N-Lauroyl-ceramide-1-phosphateHMDB
Chemical FormulaC30H60NO6P
Average Molecular Weight561.7743
Monoisotopic Molecular Weight561.415825169
IUPAC Name{[(2S,3R,4E)-2-dodecanamido-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid
Traditional Name[(2S,3R,4E)-2-dodecanamido-3-hydroxyoctadec-4-en-1-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C\[C@@]([H])(O)[C@]([H])(COP(=O)(O)O)NC(=O)CCCCCCCCCCC
InChI Identifier
InChI=1S/C30H60NO6P/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-29(32)28(27-37-38(34,35)36)31-30(33)26-24-22-20-17-12-10-8-6-4-2/h23,25,28-29,32H,3-22,24,26-27H2,1-2H3,(H,31,33)(H2,34,35,36)/b25-23+/t28-,29+/m0/s1
InChI KeyInChIKey=KXEMZGPJXBKYJP-VARSQMIESA-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
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-acyl-amine
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
Water Solubility0.000184 mg/mLALOGPS
logP7.11ALOGPS
logP8.8ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)1.53ChemAxon
pKa (Strongest Basic)0.00068ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.09 Å2ChemAxon
Rotatable Bond Count28ChemAxon
Refractivity158.24 m3·mol-1ChemAxon
Polarizability69.42 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • All Tissues
Pathways
NameSMPDB LinkKEGG Link
Fabry diseaseSMP00525Not Available
Gaucher DiseaseSMP00349Not Available
Globoid Cell LeukodystrophySMP00348Not Available
Krabbe diseaseSMP00526Not Available
Metachromatic Leukodystrophy (MLD)SMP00347Not Available
Sphingolipid MetabolismSMP00034map00500
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027849
KNApSAcK IDNot Available
Chemspider ID4446693
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10699
Metagene LinkHMDB10699
METLIN IDNot Available
PubChem Compound5283580
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available