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N-acylsphingosine amidohydrolase activity

Definition

Target type: molecularfunction

Catalysis of the reaction: N-acylsphingosine + H2O = a fatty acid + sphingosine. [EC:3.5.1.23]

N-acylsphingosine amidohydrolase activity refers to the enzymatic hydrolysis of N-acylsphingosines (ceramides), a class of lipids that are crucial components of cell membranes. This hydrolysis reaction breaks the amide bond between the fatty acid and the sphingosine base, yielding a free fatty acid and a sphingosine molecule. This enzymatic activity plays a significant role in the regulation of cellular sphingolipid metabolism, which is essential for various cellular processes, including cell signaling, membrane structure, and apoptosis. N-acylsphingosine amidohydrolase activity is also implicated in various pathological conditions, including cancer and neurodegenerative disorders. The enzyme responsible for this activity is known as ceramidase, and it exists in multiple isoforms with distinct substrate specificities and cellular localization. The hydrolysis of ceramides by ceramidases leads to the production of sphingosine and fatty acids, which act as signaling molecules and participate in various cellular processes. For instance, sphingosine is involved in the activation of the sphingosine kinase pathway, which leads to the production of sphingosine-1-phosphate, a potent bioactive lipid that regulates cell growth, survival, and migration. Fatty acids released from ceramides can also act as signaling molecules and contribute to various cellular functions. Overall, N-acylsphingosine amidohydrolase activity is a crucial enzymatic function that regulates sphingolipid metabolism and plays a significant role in various cellular processes and disease states.'
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Proteins (4)

ProteinDefinitionTaxonomy
Alkaline ceramidase 2An alkaline ceramidase 2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q5QJU3]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)
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 (14)

CompoundDefinitionClassesRoles
cannabinolCannabinol: A physiologically inactive constituent of Cannabis sativa L.dibenzopyran
carmofurorganohalogen compound;
pyrimidines
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
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
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
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
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
cannabidivarincannabidivarin: from Cannabis sativamonoterpenoid