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)
| Protein | Definition | Taxonomy |
|---|---|---|
| Sphingosine kinase 1 | A sphingosine kinase 1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9NYA1] | Homo sapiens (human) |
| Sphingosine kinase 2 | A sphingosine kinase 2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9NRA0] | Homo sapiens (human) |
| N-acylethanolamine-hydrolyzing acid amidase | An N-acylethanolamine-hydrolyzing acid amidase that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q02083] | Homo sapiens (human) |
Compounds (21)
| Compound | Definition | Classes | Roles |
|---|---|---|---|
| cannabinol | Cannabinol: A physiologically inactive constituent of Cannabis sativa L. | dibenzopyran | |
| diacerein | diacerein: 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 | |
| cannabichromene | 1-benzopyran | ||
| (6ar-trans)-isomer of tetrahydrocannabivarin 9 | |||
| delta(9)-tetrahydrocannabinolic acid | Delta(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 hydrochloride | fingolimod 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. | hydrochloride | immunosuppressive agent; prodrug; sphingosine-1-phosphate receptor agonist |
| cannabidiolic acid | cannabidiolic 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 58272 | SC 58272: inhibits myristoyl-CoA:protein N-myristoyltransferase; structure given in first source | ||
| cannabidiol | cannabidiol : 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)phenol | substituted aniline | ||
| safingol | safingol: RN given refers to the (R-(R*,S*))-isomer | amino alcohol | |
| sphingosine | 2-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-enine | human metabolite; mouse metabolite |
| n,n-dimethylsphingenine | N,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 |
| cannabigerol | cannabigerol : 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 acid | cannabigerolic 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-285 | 1-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 |
| cannabidivarin | cannabidivarin: from Cannabis sativa | monoterpenoid | |
| 3-(4-chlorophenyl)-adamantane-1-carboxylic acid (pyridin-4-ylmethyl)amide | organochlorine compound | ||
| bml 258 | |||
| pf-543 | PF-543: Sphingosine Kinase 1 Selective Inhibitor; structure in first source | sulfonamide | |
| 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-ol | EC 2.7.1.91 (sphingosine kinase) inhibitor |