Page last updated: 2024-10-24

sphingosine metabolic process

Definition

Target type: biologicalprocess

The chemical reactions and pathways involving sphingosine (sphing-4-enine), trans-D-erytho-2-amino-octadec-4-ene-1,3-diol, a long chain amino diol sphingoid base that occurs in most sphingolipids in animal tissues. [GOC:ma, ISBN:0198506732]

Sphingosine metabolic process is a critical pathway involved in the synthesis and degradation of sphingolipids, a class of lipids that play diverse roles in cell signaling, membrane structure, and immune function. The process begins with the condensation of palmitoyl-CoA and serine to form 3-ketodihydrosphingosine, which is then reduced to dihydrosphingosine. Dihydrosphingosine undergoes a desaturation reaction to form sphingosine, the precursor to all sphingolipids. Sphingosine can be further metabolized through various pathways, including phosphorylation to form sphingosine-1-phosphate (S1P), a potent signaling molecule involved in cell survival, proliferation, and migration. Sphingosine can also be acylated to form ceramides, the major structural component of sphingolipid membranes. Ceramides can be further processed to form sphingomyelins, glycosphingolipids, and other complex sphingolipids. The degradation of sphingolipids occurs via various hydrolases that cleave specific bonds in the molecule, leading to the release of fatty acids and other metabolites. The sphingosine metabolic pathway is tightly regulated by a complex network of enzymes and transcription factors, ensuring proper cellular function and response to various stimuli. Dysregulation of sphingosine metabolism has been implicated in various diseases, including cancer, neurodegenerative disorders, and cardiovascular diseases. Therefore, understanding the intricate details of this pathway is crucial for developing novel therapeutic strategies.'
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Proteins (3)

ProteinDefinitionTaxonomy
Sphingosine kinase 1A sphingosine kinase 1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9NYA1]Homo sapiens (human)
Sphingosine kinase 2A sphingosine kinase 2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9NRA0]Homo sapiens (human)
N-acylethanolamine-hydrolyzing acid amidaseAn N-acylethanolamine-hydrolyzing acid amidase that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q02083]Homo sapiens (human)

Compounds (21)

CompoundDefinitionClassesRoles
cannabinolCannabinol: A physiologically inactive constituent of Cannabis sativa L.dibenzopyran
diacereindiacerein: chelates with bivalent metals; a quinone which possesses redox properties; metabolized to active rhein; proposed mechanisms include inhibiting IL1 and metalloproteinases; called a slow acting symptomatic drug in osteoarthritis; no effect of cyclooxygenase;anthraquinone
cannabichromene1-benzopyran
(6ar-trans)-isomer of tetrahydrocannabivarin 9
delta(9)-tetrahydrocannabinolic acidDelta(9)-tetrahydrocannabinolic acid : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant.benzochromene;
diterpenoid;
hydroxy monocarboxylic acid;
phytocannabinoid;
polyketide
anti-inflammatory agent;
biomarker;
metabolite;
neuroprotective agent
fingolimod hydrochloridefingolimod hydrochloride : The hydrochloride salt of 2-amino-2-[2-(4-octylphenyl) ethyl]-1,3-propanediol (fingolimod).

Fingolimod Hydrochloride: A sphingosine-derivative and IMMUNOSUPPRESSIVE AGENT that blocks the migration and homing of LYMPHOCYTES to the CENTRAL NERVOUS SYSTEM through its action on SPHINGOSINE 1-PHOSPHATE RECEPTORS. It is used in the treatment of MULTIPLE SCLEROSIS.
hydrochlorideimmunosuppressive agent;
prodrug;
sphingosine-1-phosphate receptor agonist
cannabidiolic acidcannabidiolic acid : A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a 3-p-mentha-1,8-dien-3-yl (limonene) group.

cannabidiolic acid: structure
dihydroxybenzoic acid;
phytocannabinoid;
polyketide;
resorcinols
sc 58272SC 58272: inhibits myristoyl-CoA:protein N-myristoyltransferase; structure given in first source
cannabidiolcannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.

Cannabidiol: Compound isolated from Cannabis sativa extract.
olefinic compound;
phytocannabinoid;
resorcinols
antimicrobial agent;
plant metabolite
4-(4-(4-chloro-phenyl)thiazol-2-ylamino)phenolsubstituted aniline
safingolsafingol: RN given refers to the (R-(R*,S*))-isomeramino alcohol
sphingosine2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.

sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.

sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.

sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.
sphing-4-eninehuman metabolite;
mouse metabolite
n,n-dimethylsphingenineN,N-dimethylsphingosine : A sphingoid that is sphingosine in which the two amino hydrogens are replaced by methyl groups.

N,N-dimethylsphingosine: a sphingosine kinase inhibitor
aminodiol;
sphingoid;
tertiary amino compound
EC 2.7.1.91 (sphingosine kinase) inhibitor;
metabolite
cannabigerolcannabigerol : A member of the class of resorcinols that is resorcinol which is substituted by a (2E)-3,7-dimethylocta-2,6-dien-1-yl group at position 2 and by a pentyl group at position 5. It is a natural product found in Cannabis sativa and Helichrysum species.

cannabigerol: RN given refers to (E)-isomer; structure given in first source
phytocannabinoid;
resorcinols
anti-inflammatory agent;
antibacterial agent;
antioxidant;
appetite enhancer;
cannabinoid receptor agonist;
neuroprotective agent;
plant metabolite
cannabigerolic acidcannabigerolic acid : A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant.

cannabigerolic acid: structure in first source
dihydroxybenzoic acid;
diterpenoid;
phytocannabinoid;
polyketide;
resorcinols
es-2851-deoxysphinganine : A bioactive sphingoid, sphinganine, in which the terminal hydroxy group has been replaced by a hydrogen.

spisulosine: from marine organism, Spisula polynyma; structure in first source
amino alcohol;
sphingoid
antineoplastic agent
cannabidivarincannabidivarin: from Cannabis sativamonoterpenoid
3-(4-chlorophenyl)-adamantane-1-carboxylic acid (pyridin-4-ylmethyl)amideorganochlorine compound
bml 258
pf-543PF-543: Sphingosine Kinase 1 Selective Inhibitor; structure in first sourcesulfonamide
rome(2R)-2-amino-2-(methoxymethyl)-4-(4-octylphenyl)butan-1-ol : A 2-amino-2-(methoxymethyl)-4-(4-octylphenyl)butan-1-ol that has R-configuration. It is a sphingosine kinase-2 inhibitor.

Rome: The capital city of Italy.
2-amino-2-(methoxymethyl)-4-(4-octylphenyl)butan-1-olEC 2.7.1.91 (sphingosine kinase) inhibitor