Page last updated: 2024-10-24

sphingosine biosynthetic process

Definition

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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Proteins (7)

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)
Alkaline ceramidase 2An alkaline ceramidase 2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q5QJU3]Homo sapiens (human)
Acid ceramidaseAn acid ceramidase that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q13510]Homo sapiens (human)
Lysosomal acid glucosylceramidaseA lysosomal acid glucosylceramidase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P04062]Homo sapiens (human)
Serine palmitoyltransferase 2A serine palmitoyltransferase 2 that is encoded in the genome of human. [PRO:CNA]Homo sapiens (human)
Serine palmitoyltransferase 1A serine palmitoyltransferase 1 that is encoded in the genome of human. [PRO:CNA]Homo sapiens (human)

Compounds (54)

CompoundDefinitionClassesRoles
ambroxolAmbroxol: 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
carmofurorganohalogen compound;
pyrimidines
beta-glucono-1,5-lactonebeta-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-deoxynojirimycin1-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
miglustatmiglustat : 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-phenylphthalimideN-phenylphthalimide: structure given in first source
N-Benzylphthalimideisoindoles
1-(10h-phenothiazin-2-yl)ethanone1-(10H-phenothiazin-2-yl)ethanone: structure in first sourcephenothiazines
mor-14N-methyldeoxynojirimycin: glucosidase inhibitorhydroxypiperidine;
piperidine alkaloid;
tertiary amino compound
anti-HIV agent;
cardioprotective agent;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
plant metabolite
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
1,2,3,4-tetrahydroxy-nor-tropanecalystegine B(2): RN given for (2-endo,3-exo,4-endo)-isomer; structure in first source
2-(n-myristoylamino)-1-phenyl-1-propanol2-(N-myristoylamino)-1-phenyl-1-propanol: ceramidase inhibitor; RN given for ((R*,S*)-(+-))-isomer; structure in first sourcealkylbenzene
homonojirimycinhomonojirimycin: inhibits alpha-glucosidase; RN given for (2R-(2alpha,3alpha,4beta,5alpha,6beta))-isomer; structure in first source
cyclophellitolcyclophellitol: structure given in first source; isolated from Phellinus sp.
calystegine a3calystegine A3: also inhibits beta-xylosidase; structure in first source
miglitolpiperidines
isofagominepiperidines
n-nonyl-1-deoxynojirimycinN-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-propanolbenzimidazoles
4-(4-(4-chloro-phenyl)thiazol-2-ylamino)phenolsubstituted aniline
2-(2-phenylethylthio)-3-pyridinecarboxylic acidaromatic carboxylic acid;
pyridines
4-(2-furanylmethyl)-3-(phenylmethyl)-1H-1,2,4-triazole-5-thionebenzenes
2-[[4-(4-chloroanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanoldialkylarylamine;
tertiary amino compound
4-(benzenesulfonamido)-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzamidesulfonamide
tamoxifenstilbenoid;
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-oxidearomatic ether
safingolsafingol: RN given refers to the (R-(R*,S*))-isomeramino alcohol
2-[[4-(3-methylanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanoldialkylarylamine;
tertiary amino compound
N-(1-benzylpiperidin-4-yl)-2-(pyridin-3-yl)quinazolin-4-amineN-(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]cyclohexanecarboxamideaminoquinoline
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
n-oleoylethanolamineN-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
thermozymocidinthermozymocidin: a serine palmitoyltransferase inhibitor; FTY720 is an analogalpha-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
ogt2378sinbaglustat: an antineopl agent; structure in first source
nnc 26-9100NNC 26-9100: structure in first sourceaminopyridine
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
3-(4-chlorophenyl)-adamantane-1-carboxylic acid (pyridin-4-ylmethyl)amideorganochlorine compound
2-[[4-[2-[(2-methylpropan-2-yl)oxy]anilino]-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanolaromatic ether
2-[[4-(5-chloro-2-methoxyanilino)-6-(1-piperidinyl)-1,3,5-triazin-2-yl]amino]ethanolmethoxybenzenes;
substituted aniline
2-[[4-(4-methylanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanoldialkylarylamine;
tertiary amino compound
2-[[4-(2-chloroanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanoldialkylarylamine;
tertiary amino compound
2-[[4-(2-methoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanolmethoxybenzenes;
substituted aniline
2-[[4-(3-methoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanolmethoxybenzenes;
substituted aniline
2-[[4-(4-methoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanolmethoxybenzenes;
substituted aniline
2-[[4-(2-hydroxyethylamino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]phenoldialkylarylamine;
tertiary amino compound
2-[[4-(2-phenoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanolaromatic ether
2-[[4-(1-pyrrolidinyl)-6-[2-(trifluoromethoxy)anilino]-1,3,5-triazin-2-yl]amino]ethanolaromatic ether
2-[[4-(5-chloro-2-ethoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanolaromatic ether
2-[[4-(5-chloro-2-propan-2-yloxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanolaromatic ether
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