Page last updated: 2024-10-24

monoacylglycerol catabolic process

Definition

Target type: biologicalprocess

The chemical reactions and pathways resulting in the breakdown of monoacylglycerol, any ester of glycerol in which any one of its hydroxyl groups has been acylated with a fatty acid, the other being non-esterified. [PMID:25290914]

Monoacylglycerol catabolic process involves the breakdown of monoacylglycerols, which are simple lipids composed of a glycerol molecule linked to a single fatty acid. This process is crucial for the digestion and absorption of dietary fats and plays a role in various metabolic pathways.

The primary enzyme responsible for monoacylglycerol catabolism is **monoacylglycerol lipase (MAG lipase)**. This enzyme hydrolyzes the ester bond between the fatty acid and glycerol, generating free fatty acids and glycerol.

**Here's a detailed breakdown of the process:**

1. **Dietary Fat Digestion:** When dietary fats enter the small intestine, they are emulsified by bile salts, forming smaller droplets.
2. **Pancreatic Lipase Activity:** Pancreatic lipase, an enzyme secreted by the pancreas, acts on these emulsified fat droplets, breaking down triglycerides into diacylglycerols, monoacylglycerols, and free fatty acids.
3. **Monoacylglycerol Lipase Activity:** Monoacylglycerol lipase, located in the intestinal brush border membrane, further hydrolyzes monoacylglycerols into glycerol and free fatty acids.
4. **Absorption:** The liberated glycerol and fatty acids are then absorbed into the intestinal epithelial cells.
5. **Re-esterification:** Within the intestinal cells, the glycerol and fatty acids can be re-esterified to form triglycerides, which are packaged into chylomicrons and transported to the bloodstream.

**Beyond digestion, monoacylglycerol catabolism plays roles in:**

* **Lipid signaling:** Monoacylglycerols can act as signaling molecules, influencing processes like inflammation and cell growth.
* **Energy production:** The breakdown of monoacylglycerols provides energy for various cellular processes.
* **Fatty acid metabolism:** Monoacylglycerol catabolism is interconnected with other fatty acid metabolic pathways, contributing to the overall regulation of lipid homeostasis.

**In summary, monoacylglycerol catabolic process is an essential step in dietary fat digestion and absorption. It also contributes to various metabolic functions, including lipid signaling, energy production, and fatty acid metabolism.'
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Proteins (5)

ProteinDefinitionTaxonomy
Monoacylglycerol lipase ABHD6A monoacylglycerol lipase ABHD6 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9BV23]Homo sapiens (human)
Monoglyceride lipaseA monoglyceride lipase that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q99685]Homo sapiens (human)
Lysophosphatidylserine lipase ABHD12A lysophosphatidylserine lipase ABHD12 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q8N2K0]Homo sapiens (human)
Phosphatidylserine lipase ABHD16AA phosphatidylserine lipase ABHD16A that is encoded in the genome of human. [PRO:DNx, UniProtKB:O95870]Homo sapiens (human)
Fatty-acid amide hydrolase 1A fatty-acid amide hydrolase 1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:O00519]Homo sapiens (human)

Compounds (72)

CompoundDefinitionClassesRoles
benzo(b)thiophene-2-boronic acidbenzo(b)thiophene-2-boronic acid: inhibits AmpC beta-lactamase; structure in first source
disulfiramorganic disulfide;
organosulfur acaricide
angiogenesis inhibitor;
antineoplastic agent;
apoptosis inducer;
EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor;
EC 3.1.1.1 (carboxylesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
ferroptosis inducer;
fungicide;
NF-kappaB inhibitor
ethylmaleimideEthylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.maleimidesanticoronaviral agent;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.1.1 (hexokinase) inhibitor
phenylmethylsulfonyl fluoridephenylmethanesulfonyl fluoride : An acyl fluoride with phenylmethanesulfonyl as the acyl group.

Phenylmethylsulfonyl Fluoride: An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.
acyl fluorideserine proteinase inhibitor
propofolpropofol : A phenol resulting from the formal substitution of the hydrogen at the 2 position of 1,3-diisopropylbenzene by a hydroxy group.

Propofol: An intravenous anesthetic agent which has the advantage of a very rapid onset after infusion or bolus injection plus a very short recovery period of a couple of minutes. (From Smith and Reynard, Textbook of Pharmacology, 1992, 1st ed, p206). Propofol has been used as ANTICONVULSANTS and ANTIEMETICS.
phenolsanticonvulsant;
antiemetic;
intravenous anaesthetic;
radical scavenger;
sedative
1,6-bis(cyclohexyloximinocarbonyl)hexane1,6-bis(cyclohexyloximinocarbonyl)hexane: selective inhibitor of canine platelet diglyceride lipasecarbamate ester;
organonitrogen compound
thiramthiram : An organic disulfide that results from the formal oxidative dimerisation of N,N-dimethyldithiocarbamic acid. It is widely used as a fungicidal seed treatment.

Thiram: A dithiocarbamate chemical, used commercially in the rubber processing industry and as a fungicide. In vivo studies indicate that it inactivates the enzyme GLUTATHIONE REDUCTASE. It has mutagenic activity and may induce chromosomal aberrations.
organic disulfideantibacterial drug;
antifungal agrochemical;
antiseptic drug
carbarylcarbaryl : A carbamate ester obtained by the formal condensation of 1-naphthol with methylcarbamic acid.

Carbaryl: A carbamate insecticide and parasiticide. It is a potent anticholinesterase agent belonging to the carbamate group of reversible cholinesterase inhibitors. It has a particularly low toxicity from dermal absorption and is used for control of head lice in some countries.
carbamate ester;
naphthalenes
acaricide;
agrochemical;
carbamate insecticide;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant growth retardant
bis(1-piperidylthiocarbonyl)disulfidebis(1-piperidylthiocarbonyl)disulfide: indicator for analysis of copper; structure
tetramethylthiuram monosulfide
4,4'-dithiodimorpholine4,4'-dithiodimorpholine: rubber vulcanizing agent causing occupational dermatitis; structure
benzilbenzil : An alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively.

benzil: structure
alpha-diketone;
aromatic ketone
phenyl trifluoromethyl ketonephenyl trifluoromethyl ketone: converted to trifluoroacetic acid in water
hydratropic acidhydratropic acid : A 2-arylpropionic acid carrying a phenyl group at position 2. It is a metabolite of alpha-methylstyrene (AMS), a volatile hydrocarbon.

hydratropic acid: RN given refers to cpd without isomeric designation; structure
2-arylpropionic acidhuman xenobiotic metabolite
methyl diethyldithiocarbamate
diphenyl disulfidebenzenes
n-phenylmaleimideN-phenylmaleimide: structure in Merck Index, 9th ed, #7104
dronabinolDelta(9)-tetrahydrocannabinol : 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. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.

Dronabinol: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.
benzochromene;
diterpenoid;
phytocannabinoid;
polyketide
cannabinoid receptor agonist;
epitope;
hallucinogen;
metabolite;
non-narcotic analgesic
1,6-bismaleimidohexane
phenmediphamphenmedipham : A carbamate ester that is (3-methylphenyl)carbamic acid in which the hydrogen of the hydroxy group has been replaced by a 3-[(methoxycarbonyl)amino]phenyl group.

phenmedipham: minor descriptor (72-84); on-line search CARBAMATES (72-84); Index Medicus search HERBICIDES, CARBAMATE (75-84), CARBAMATES (72-75)
carbamate esterenvironmental contaminant;
herbicide;
xenobiotic
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
phenylethane boronic acid
n-methylmaleimideN-methylmaleimide: structure in first source
amperozideamperozide : A member of the class of ureas that is urea in which three of the four hydrogens are replaced by ethyl and 4-[4,4-bis(4-fluorophenyl)butyl]piperazin-1-yl groups. An atypical antipsychotic which was in clinical development for the treatment of schizophrenia and substance-related disorders. It is a potent 5-HT2A antagonist and used in veterinary medicine because of its sedative effect on pigs.diarylmethane;
monofluorobenzenes;
N-alkylpiperazine;
secondary carboxamide;
ureas
anxiolytic drug;
dopamine uptake inhibitor;
geroprotector;
second generation antipsychotic;
serotonergic antagonist
n-benzylmaleimide
n,n'-4-phenylenedimaleimide
n-(2-methoxyphenyl)maleimideN-(2-methoxyphenyl)maleimide: structure given in first source
n-(4-bromophenyl)maleimideN-(4-bromophenyl)maleimide: structure given in first source
3-octylthio-1,1,1-trifluoro-2-propanone3-octylthio-1,1,1-trifluoro-2-propanone: a pesticide synergist; inhibits juvenile hormone esterase
1,1'-biphenyl-4-yl-boronic acid
4-methoxyphenylboronic acid4-methoxyphenylboronic acid: structure in first source
arachidonic acidarachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.

icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.
icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid
Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite
oleic acidoleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.

Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed)
octadec-9-enoic acidantioxidant;
Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
Escherichia coli metabolite;
mouse metabolite;
plant metabolite;
solvent
urb 597cyclohexyl carbamic acid 3'-carbamoylbiphenyl-3-yl ester: a fatty acid amide hydrolase inhibitor; structure in first sourcebiphenyls
jnj-1661010N-arylpiperazine
orlistatorlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.

Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.
beta-lactone;
carboxylic ester;
formamides;
L-leucine derivative
anti-obesity agent;
bacterial metabolite;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor
2-octyl-gamma-bromoacetoacetate2-octyl-gamma-bromoacetoacetate: RN given refers to (D)-isomer; structure
arachidonyltrifluoromethaneAACOCF3 : A fatty acid derivative that is arachidonic acid in which the OH part of the carboxy group has been replaced by a trifluoromethyl group

arachidonyltrifluoromethane: structure given in first source; inhibits 85-kDa phospholipase A2
fatty acid derivative;
ketone;
olefinic compound;
organofluorine compound
EC 3.1.1.4 (phospholipase A2) inhibitor
anandamideanandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.endocannabinoid;
N-acylethanolamine 20:4
human blood serum metabolite;
neurotransmitter;
vasodilator agent
glyceryl 2-arachidonate2-arachidonoylglycerol : An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.

glyceryl 2-arachidonate: binds to cannabinoid receptors; structure in first source
2-acylglycerol 20:4;
endocannabinoid
human metabolite
oleylamidealiphatic amide : A carboxamide in which the amide linkage is bonded directly to an aliphatic system.

oleamide : A fatty amide derived from oleic acid.

oleylamide: plastic additive; can cause contact urticaria; RN given refers to (Z)-isomer; a sleep inducing factor
primary fatty amidehuman metabolite;
plant metabolite
n-arachidonylglycineN-arachidonoylglycine : Biologically active derivative of anandamide

N-arachidonylglycine: structure in first source
fatty amide;
N-acylglycine
N-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoylethanolamineN-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoylethanolamine : An N-acylethanolamine 22:6 that is the ethanolamide of (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid.

synaptamide: structurally similar to the endocannabinoid N-arachidonoylethanolamine (anandamide)
endocannabinoid;
N-acylethanolamine 22:6
[2-(1-piperidinyl)-1,3-benzothiazol-6-yl]-[4-(2-pyridinyl)-1-piperazinyl]methanonepiperazines;
pyridines
arachidonyl-2-chloroethylamidearachidonyl-2-chloroethylamide: a potent and selective agonist of the neuronal cannabinoid receptor; structure in first source

arachidonyl-2'-chloroethylamide : A fatty amide obtained by the formal condensation of arachidonic acid with 2-chloroethanamine. It is a potent agonist of the CB1 receptor (Ki = 1.4 nM) and also has a low affinity for the CB2 receptor (Ki = 3100 nM).
fatty amide;
organochlorine compound;
secondary carboxamide;
synthetic cannabinoid
CB1 receptor agonist;
CB2 receptor agonist;
neuroprotective agent
6-(bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2h-pyran-2-one6-(bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2H-pyran-2-one: structure given in first source; potent irreversible, mechanism-based inhibitor of myocardial calcium-independent phospholipase A2naphthalenes
guineensineguineensine: an Acyl-CoA: cholesterol acyltransferase inhibitor, from the fruits of Piper longum; structure in first sourcbenzodioxoles
omdm-2 cpdOMDM-2 cpd: structure in first source
cay 10499carbamate ester
CAY10435oxazolopyridine
arachidonoylserotoninarachidonoylserotonin: an NSAID with antinociceptive activity; fatty acid amide hydrolase inhibitor; structure in first source

N-arachidonoylserotonin : An N-acylserotonin obtained by formal condensation of the carboxy group of arachidonic acid with the primary amino group of serotonin.
N-acylserotonin;
phenols
anti-inflammatory agent;
anticonvulsant;
antioxidant;
capsaicin receptor antagonist;
EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor;
human metabolite;
signalling molecule
urb 524
ol-135
methyl arachidonylfluorophosphonatephosphonic ester
urb602URB602: inhibitor of 2-arachidonoylglycerol (2-AG)-deactivating enzyme, monoacylglycerol lipase, structure in first source
n-benzylhexadecanamideN-benzylhexadecanamide : A macamide resulting from the formal condensation of the carboxy group of hexadecanoic acid with benzylamine. A moderate inhibitor of fatty acid amide hydrolase.

N-benzylhexadecanamide: isolated from Lepidium meyenii; structure in first source
macamide;
secondary carboxamide
EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor;
neuroprotective agent;
plant metabolite
ly2183240LY2183240: structure in first sourcebiphenyls
methylphenidateN-phenyl-4-(quinolin-2-ylmethyl)piperazine-1-carboxamide: a fatty acid amide hydrolase inhibitor; structure in first source
1-(4-chlorophenyl)-3-(3-(6-pyrrolidin-1-ylpyridin-2-yl)phenyl)urea1-(4-chlorophenyl)-3-(3-(6-pyrrolidin-1-ylpyridin-2-yl)phenyl)urea: structure in first source
omdm 169OMDM 169: has antinociceptive activity; structure in first source
4-(4-(3-adamantan-1-ylureido)cyclohexyloxy)benzoic acid
t-tucb
pf 04457845
am 6701
jzl 184JZL 184: inhibits monoacylglycerol lipase; structure in first sourcebenzodioxoles
pf 3845PF 3845: inhibits fatty acid amide hydrolasepiperidines
pf 750N-phenyl-4-(quinolin-3-ylmethyl)piperidine-1-carboxamide: a fatty acid amide hydrolase inhibitor; structure in first sourcequinolines
azd7687AZD7687: structure in first source
palmostatin bpalmostatin B: inhibits acyl protein thioesterase 1; structure in first source
jzl195JZL195: inhibits both ​fatty-acid amide hydrolase 1 and ​monoglyceride lipase; structure in first source
sar127303SAR127303: inhibits monoacylglycerol lipase; structure in first source
mjn110MJN110: structure in first source