ChemFOnt: Showing chemical card for Sphingosine 1-phosphate (CFc000000188)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:31 UTC

Chemfont ID

CFc000000188

Molecule Identification

Common Name

Sphingosine 1-phosphate

Definition

Sphingosine 1-phosphate (S1P), also known as sphing-4-enine-1-phosphate, is classified as a member of the phosphosphingolipids. Phosphosphingolipids 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. S1P is a compound with potent bioactive actions in sphingolipid metabolism, the calcium signalling pathway, and neuroactive ligand-receptor interaction. Generated by sphingosine kinases and ceramide kinase, S1P control numerous aspects of cell physiology, including cell survival and mammalian inflammatory responses. S1P is involved in cyclooxygenase-2 induction (COX-2) and regulates the production of eicosanoids (important inflammatory mediators). S1P functions mainly via G-protein-coupled receptors and probably also has intracellular targets (PMID: 16219683 ). S1P is considered to be practically insoluble (in water) and acidic.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Sphingosine 1-phosphoric acid	Generator
(2S,3R,4E)-1-(Dihydrogen phosphate)2-amino-4-octadecene-1,3-diol	HMDB
C18-Sphingosine 1-phosphate	HMDB
D-erythro-Sphingosine-1-phosphate	HMDB

Chemical Formula

C₁₈H₃₈NO₅P

Average Molecular Weight

379.4718

Monoisotopic Molecular Weight

379.248759843

IUPAC Name

{[(4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid

Traditional Name

[(4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxyphosphonic acid

CAS Registry Number

26993-30-6

SMILES

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

InChI Identifier

InChI=1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+

InChI Key

DUYSYHSSBDVJSM-CCEZHUSRSA-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
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Secondary alcohol
Amine
Organic oxygen compound
Primary amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Primary aliphatic amine
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Organoleptic effect

Touch

Smooth (HMDB: HMDB0000277)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17085324)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000277)

Cell

Fibroblasts (HMDB: HMDB0000277)

Hematocyte

Platelet (HMDB: HMDB0000277)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000277)

Source

Endogenous

Endogenous (HMDB: HMDB0000277)

Animal

Animal (HMDB: HMDB0000277)

Exogenous

Food

Food (HMDB: HMDB0000277)

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: HMDB0000277)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000277)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000277)
Sphingolipid Metabolism (PathBank: SMP0002378)
Sphingolipid Metabolism (PathBank: SMP0063667)

Disease pathway

Globoid Cell Leukodystrophy (PathBank: SMP0120702)
Metachromatic Leukodystrophy (MLD) (PathBank: SMP0120738)
Krabbe Disease (PathBank: SMP0120810)
Gaucher Disease (PathBank: SMP0120481)
Fabry Disease (PathBank: SMP0120809)

Lipid metabolism pathway (HMDB: HMDB0000277)

Biochemical process

Lipid transport (HMDB: HMDB0000277)

Role

Biological role

Energy source (HMDB: HMDB0000277)

Industrial application

Food and nutrition

Food additive (HMDB: HMDB0000277)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000277)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0065 g/L	ALOGPS
logP	3.73	ALOGPS
logP	3.43	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	113.01 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	102.76 m³·mol⁻¹	ChemAxon
Polarizability	44.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021927

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sphingosine-1-phosphate

METLIN ID

Not Available

PubChem Compound

5353956

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Morigaki, Eiji; Miura, Yoshie; Takahata, Kyoya; Tada, Mikiro; Nakajima, Shuhei; Baba, Naomichi. Enzymic preparation of sphingosine 1-phosphate. Journal of Chemical Research, Synopses (1998), (12), 774-775.

Showing chemical card for Sphingosine 1-phosphate (CFc000000188)

MOL for CFc000000188 (Sphingosine 1-phosphate)

3D MOL for CFc000000188 (Sphingosine 1-phosphate)

3D SDF for CFc000000188 (Sphingosine 1-phosphate)

3D-SDF for CFc000000188 (Sphingosine 1-phosphate)

PDB for CFc000000188 (Sphingosine 1-phosphate)

3D PDB for CFc000000188 (Sphingosine 1-phosphate)

SMILES for CFc000000188 (Sphingosine 1-phosphate)

INCHI for CFc000000188 (Sphingosine 1-phosphate)

Structure for CFc000000188 (Sphingosine 1-phosphate)

3D Structure for CFc000000188 (Sphingosine 1-phosphate)