Target type: biologicalprocess
The chemical reactions and pathways resulting in the formation of 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 biosynthesis is a crucial metabolic pathway that generates sphingosine, a fundamental component of sphingolipids, a diverse class of lipids with vital roles in cell signaling, membrane structure, and immune function. The process begins with the condensation of palmitoyl-CoA, a long-chain fatty acyl-CoA, with serine, catalyzed by serine palmitoyltransferase (SPT). This reaction forms 3-ketodihydrosphingosine, which is then reduced to dihydrosphingosine by 3-ketodihydrosphingosine reductase (KDSR). Dihydrosphingosine undergoes desaturation by dihydroceramide desaturase (DES1) to yield sphingosine. This essential building block is then utilized in the synthesis of various sphingolipid species, including ceramides, sphingomyelins, and glycosphingolipids, through distinct pathways involving the attachment of different head groups. Notably, the biosynthesis of ceramide, a central sphingolipid intermediate, involves the condensation of sphingosine with a fatty acid, catalyzed by ceramide synthases. Ceramide can be further modified to produce other sphingolipids, including sphingomyelin, through the addition of phosphocholine, and glycosphingolipids, through the addition of sugars. This complex and intricate process of sphingosine biosynthesis is tightly regulated by various factors, including nutritional status, cellular stress, and hormonal signals, ensuring the precise production of essential sphingolipids that play vital roles in maintaining cellular function and mediating diverse biological processes.'
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Protein | Definition | Taxonomy |
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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) |
Alkaline ceramidase 2 | An alkaline ceramidase 2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q5QJU3] | Homo sapiens (human) |
Acid ceramidase | An acid ceramidase that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q13510] | Homo sapiens (human) |
Lysosomal acid glucosylceramidase | A lysosomal acid glucosylceramidase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P04062] | Homo sapiens (human) |
Serine palmitoyltransferase 2 | A serine palmitoyltransferase 2 that is encoded in the genome of human. [PRO:CNA] | Homo sapiens (human) |
Serine palmitoyltransferase 1 | A serine palmitoyltransferase 1 that is encoded in the genome of human. [PRO:CNA] | Homo sapiens (human) |
Compound | Definition | Classes | Roles |
---|---|---|---|
ambroxol | Ambroxol: A metabolite of BROMHEXINE that stimulates mucociliary action and clears the air passages in the respiratory tract. It is usually administered as the hydrochloride. | aromatic amine | |
carmofur | organohalogen compound; pyrimidines | ||
beta-glucono-1,5-lactone | beta-glucono-1,5-lactone: structure D-glucono-1,5-lactone : An aldono-1,5-lactone obtained from D-gluconic acid. | aldono-1,5-lactone; gluconolactone | animal metabolite; mouse metabolite |
1-deoxynojirimycin | 1-deoxy-nojirimycin: structure in first source duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration. | 2-(hydroxymethyl)piperidine-3,4,5-triol; piperidine alkaloid | anti-HIV agent; anti-obesity agent; bacterial metabolite; EC 3.2.1.20 (alpha-glucosidase) inhibitor; hepatoprotective agent; hypoglycemic agent; plant metabolite |
miglustat | miglustat : A hydroxypiperidine that is deoxynojirimycin in which the amino hydrogen is replaced by a butyl group. miglustat: a glucosylceramide synthase inhibitor | piperidines; tertiary amino compound | anti-HIV agent; EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor |
n-phenylphthalimide | N-phenylphthalimide: structure given in first source | ||
N-Benzylphthalimide | isoindoles | ||
1-(10h-phenothiazin-2-yl)ethanone | 1-(10H-phenothiazin-2-yl)ethanone: structure in first source | phenothiazines | |
mor-14 | N-methyldeoxynojirimycin: glucosidase inhibitor | hydroxypiperidine; piperidine alkaloid; tertiary amino compound | anti-HIV agent; cardioprotective agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite |
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 |
1,2,3,4-tetrahydroxy-nor-tropane | calystegine B(2): RN given for (2-endo,3-exo,4-endo)-isomer; structure in first source | ||
2-(n-myristoylamino)-1-phenyl-1-propanol | 2-(N-myristoylamino)-1-phenyl-1-propanol: ceramidase inhibitor; RN given for ((R*,S*)-(+-))-isomer; structure in first source | alkylbenzene | |
homonojirimycin | homonojirimycin: inhibits alpha-glucosidase; RN given for (2R-(2alpha,3alpha,4beta,5alpha,6beta))-isomer; structure in first source | ||
cyclophellitol | cyclophellitol: structure given in first source; isolated from Phellinus sp. | ||
calystegine a3 | calystegine A3: also inhibits beta-xylosidase; structure in first source | ||
miglitol | piperidines | ||
isofagomine | piperidines | ||
n-nonyl-1-deoxynojirimycin | N-nonyldeoxynojirimycin : A hydroxypiperidine that is deoxynojirimycin (duvoglustat) in which the amino hydrogen is replaced by a nonyl group. | hydroxypiperidine; tertiary amino compound | antiviral agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; EC 3.2.1.45 (glucosylceramidase) inhibitor |
1-(1-benzimidazolyl)-3-(1-cyclohex-3-enylmethoxy)-2-propanol | benzimidazoles | ||
4-(4-(4-chloro-phenyl)thiazol-2-ylamino)phenol | substituted aniline | ||
2-(2-phenylethylthio)-3-pyridinecarboxylic acid | aromatic carboxylic acid; pyridines | ||
4-(2-furanylmethyl)-3-(phenylmethyl)-1H-1,2,4-triazole-5-thione | benzenes | ||
2-[[4-(4-chloroanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol | dialkylarylamine; tertiary amino compound | ||
4-(benzenesulfonamido)-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzamide | sulfonamide | ||
tamoxifen | stilbenoid; tertiary amino compound | angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator | |
4-oxido-3-(4-phenoxyphenyl)-4a,5,6,7,8,8a-hexahydroquinoxalin-1-ium 1-oxide | aromatic ether | ||
safingol | safingol: RN given refers to the (R-(R*,S*))-isomer | amino alcohol | |
2-[[4-(3-methylanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol | dialkylarylamine; tertiary amino compound | ||
N-(1-benzylpiperidin-4-yl)-2-(pyridin-3-yl)quinazolin-4-amine | N-(1-benzylpiperidin-4-yl)-2-(pyridin-3-yl)quinazolin-4-amine : A member of the class of quinazolines that is quinazoline which is substituted by a pyridin-3-yl group and a (1-benzylpiperidin-4-yl)nitrilo group at positions 2 and 4, respectively. | aromatic amine; piperidines; pyridines; quinazolines; secondary amino compound; tertiary amino compound | |
N-[4-methyl-2-(4-morpholinyl)-6-quinolinyl]cyclohexanecarboxamide | aminoquinoline | ||
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 |
n-oleoylethanolamine | N-oleoylethanolamine: ceramidase inhibitor oleoyl ethanolamide : An N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide. | endocannabinoid; N-(long-chain-acyl)ethanolamine; N-acylethanolamine 18:1 | EC 3.5.1.23 (ceramidase) inhibitor; geroprotector; PPARalpha agonist |
thermozymocidin | thermozymocidin: a serine palmitoyltransferase inhibitor; FTY720 is an analog | alpha-amino fatty acid; hydroxy monocarboxylic acid; non-proteinogenic alpha-amino acid; sphingoid | antifungal agent; antimicrobial agent; antineoplastic agent; apoptosis inducer; EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor; fungal metabolite; immunosuppressive agent |
n-(5-adamantane-1-yl-methoxy-pentyl)deoxynojirimycin | |||
ogt2378 | sinbaglustat: an antineopl agent; structure in first source | ||
nnc 26-9100 | NNC 26-9100: structure in first source | aminopyridine | |
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 |
3-(4-chlorophenyl)-adamantane-1-carboxylic acid (pyridin-4-ylmethyl)amide | organochlorine compound | ||
2-[[4-[2-[(2-methylpropan-2-yl)oxy]anilino]-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol | aromatic ether | ||
2-[[4-(5-chloro-2-methoxyanilino)-6-(1-piperidinyl)-1,3,5-triazin-2-yl]amino]ethanol | methoxybenzenes; substituted aniline | ||
2-[[4-(4-methylanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol | dialkylarylamine; tertiary amino compound | ||
2-[[4-(2-chloroanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol | dialkylarylamine; tertiary amino compound | ||
2-[[4-(2-methoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol | methoxybenzenes; substituted aniline | ||
2-[[4-(3-methoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol | methoxybenzenes; substituted aniline | ||
2-[[4-(4-methoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol | methoxybenzenes; substituted aniline | ||
2-[[4-(2-hydroxyethylamino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]phenol | dialkylarylamine; tertiary amino compound | ||
2-[[4-(2-phenoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol | aromatic ether | ||
2-[[4-(1-pyrrolidinyl)-6-[2-(trifluoromethoxy)anilino]-1,3,5-triazin-2-yl]amino]ethanol | aromatic ether | ||
2-[[4-(5-chloro-2-ethoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol | aromatic ether | ||
2-[[4-(5-chloro-2-propan-2-yloxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol | aromatic ether | ||
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 |