ChemFOnt: Showing chemical card for CerP(d18:1/22:0) (CFc000006709)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:46 UTC

Chemfont ID

CFc000006709

Molecule Identification

Common Name

CerP(d18:1/22:0)

Definition

CerP(d18:1/22:0) 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(Docosanoyl)sphing-4-enine 1-phosphate	ChEBI
N-(Docosanoyl)sphing-4-enine 1-phosphoric acid	Generator
Ceramide phosphate	MetBuilder
N-(Docosanoyl)-1-phosphate-sphing-4-enine	MetBuilder
Ceramide phosphate(D18:1/22:0)	MetBuilder
N-(Docosanoyl)-1-phosphate-sphingosine	MetBuilder
N-(Docosanoyl)-1-phosphate-D-erythro-sphingosine	MetBuilder
N-(Docosanoyl)-1-phosphate-4-sphingenine	MetBuilder
N-(Docosanoyl)-1-phosphate-D-sphingosine	MetBuilder
N-(Docosanoyl)-1-phosphate-sphingenine	MetBuilder
N-(Docosanoyl)-1-phosphate-erythro-4-sphingenine	MetBuilder
N-(Docosanoyl)-sphing-4-enine-1-phosphate	HMDB
[(e,2S,3R)-2-(docosanoylamino)-3-Hydroxyoctadec-4-enyl] dihydrogen phosphate	HMDB

Chemical Formula

C₄₀H₈₀NO₆P

Average Molecular Weight

702.0401

Monoisotopic Molecular Weight

701.572325809

IUPAC Name

{[(2S,3R,4E)-2-docosanamido-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid

Traditional Name

C22 CerP

CAS Registry Number

None

SMILES

CCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(=O)(O)O)[C@]([H])(O)\C=C\CCCCCCCCCCCCC

InChI Identifier

InChI=1S/C40H80NO6P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-40(43)41-38(37-47-48(44,45)46)39(42)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h33,35,38-39,42H,3-32,34,36-37H2,1-2H3,(H,41,43)(H2,44,45,46)/b35-33+/t38-,39+/m0/s1

InChI Key

ZRTZYMMYLZPKEQ-GLQCRSEXSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Phosphosphingolipids

Direct Parent

Phosphosphingolipids

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 Framework

Aliphatic acyclic compounds

External Descriptors

N-acylsphingosine 1-phosphate (CHEBI:73138 )
Ceramide 1-phosphates (LMSP02050006 )

Functional Ontology

Physiological effect

Organoleptic effect

Touch

Smooth (HMDB: HMDB0010703)

Disposition

Biological location

Cellular substructure

Tissue

All Tissues (HMDB: HMDB0010703)
All Tissues (HMDB: HMDB0010703)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0010703)

Source

Endogenous

Endogenous (HMDB: HMDB0010703)

Animal

Animal (HMDB: HMDB0010703)

Exogenous

Food

Food (HMDB: HMDB0010703)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0010703)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0010703)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0010703)

Lipid metabolism pathway (HMDB: HMDB0010703)

Cellular process

Cell signaling (HMDB: HMDB0010703)

Biochemical process

Lipid transport (HMDB: HMDB0010703)

Role

Biological role

Energy source (HMDB: HMDB0010703)

Industrial application

Food and nutrition

Food additive (HMDB: HMDB0010703)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0010703)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.1e-05 g/L	ALOGPS
logP	9.35	ALOGPS
logP	13.25	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	1.53	ChemAxon
pKa (Strongest Basic)	0.00068	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.09 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	204.25 m³·mol⁻¹	ChemAxon
Polarizability	90.78 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0010703

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027853

KNApSAcK ID

Not Available

Chemspider ID

4446698

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283585

PDB ID

Not Available

ChEBI ID

73138

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for CerP(d18:1/22:0) (CFc000006709)

MOL for CFc000006709 (CerP(d18:1/22:0))

3D MOL for CFc000006709 (CerP(d18:1/22:0))

3D SDF for CFc000006709 (CerP(d18:1/22:0))

3D-SDF for CFc000006709 (CerP(d18:1/22:0))

PDB for CFc000006709 (CerP(d18:1/22:0))

3D PDB for CFc000006709 (CerP(d18:1/22:0))

SMILES for CFc000006709 (CerP(d18:1/22:0))

INCHI for CFc000006709 (CerP(d18:1/22:0))

Structure for CFc000006709 (CerP(d18:1/22:0))

3D Structure for CFc000006709 (CerP(d18:1/22:0))