Page last updated: 2024-10-24

unsaturated fatty acid metabolic process

Definition

Target type: biologicalprocess

The chemical reactions and pathways involving an unsaturated fatty acid, any fatty acid containing one or more double bonds between carbon atoms. [GOC:mah]

Unsaturated fatty acid metabolic process is a critical biochemical pathway essential for maintaining cellular structure, function, and signaling. It encompasses the synthesis, breakdown, and interconversion of unsaturated fatty acids, which contain one or more double bonds in their hydrocarbon chains. These fatty acids play diverse roles in biological systems, including:

- **Membrane structure:** Unsaturated fatty acids are key components of cell membranes, contributing to fluidity and permeability. Their double bonds introduce kinks in the fatty acid chains, preventing tight packing and maintaining membrane flexibility.

- **Hormone and signaling molecule synthesis:** Unsaturated fatty acids are precursors to important signaling molecules, such as prostaglandins, leukotrienes, and thromboxanes, involved in inflammation, blood clotting, and other physiological processes.

- **Energy metabolism:** Unsaturated fatty acids can be broken down for energy production through beta-oxidation, a process that occurs in the mitochondria.

- **Gene regulation:** Unsaturated fatty acids can influence gene expression by interacting with transcription factors and modifying chromatin structure.

**Key steps in unsaturated fatty acid metabolism:**

1. **Synthesis:** Unsaturated fatty acids are synthesized from saturated fatty acids by enzymes called desaturases. These enzymes introduce double bonds into the fatty acid chain.

2. **Elongation:** Fatty acids can be elongated by adding two-carbon units to their chains.

3. **Desaturation:** Desaturases can further increase the number of double bonds in unsaturated fatty acids.

4. **Beta-oxidation:** Unsaturated fatty acids are broken down into acetyl-CoA units through beta-oxidation, a process that releases energy.

**Regulation of unsaturated fatty acid metabolism:**

Unsaturated fatty acid metabolism is tightly regulated by various factors, including:

- **Hormones:** Hormones such as insulin and glucagon influence the activity of enzymes involved in fatty acid metabolism.

- **Dietary intake:** The composition of dietary fats affects the synthesis and breakdown of unsaturated fatty acids.

- **Cellular demand:** The needs of individual cells and tissues determine the rate of unsaturated fatty acid metabolism.

**Disruptions in unsaturated fatty acid metabolism can lead to various health problems, including:**

- **Cardiovascular disease:** Elevated levels of certain saturated fatty acids and reduced levels of essential unsaturated fatty acids are linked to increased risk of heart disease.

- **Metabolic disorders:** Disruptions in fatty acid metabolism can contribute to obesity, diabetes, and other metabolic disorders.

- **Neurological disorders:** Imbalances in fatty acid metabolism have been implicated in neurological disorders such as Alzheimer's disease and Parkinson's disease.

Understanding the intricacies of unsaturated fatty acid metabolism is crucial for comprehending human health and developing strategies to prevent and treat related diseases.'
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Proteins (1)

ProteinDefinitionTaxonomy
Polyunsaturated fatty acid lipoxygenase ALOX12A polyunsaturated fatty acid lipoxygenase ALOX12 that is encoded in the genome of human. [PRO:DNx, UniProtKB:P18054]Homo sapiens (human)

Compounds (41)

CompoundDefinitionClassesRoles
chloroxinechloroxine : A monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 have been substituted by chlorine. A synthetic antibacterial prepared by chlorination of quinolin-8-ol, it is used for the treatment of dandruff and seborrhoeic dermatitis of the scalp.monohydroxyquinoline;
organochlorine compound
antibacterial agent;
antifungal drug;
antiseborrheic
hexylresorcinolresorcinols
4-(dimethylamino)-n-(7-(hydroxyamino)-7-oxoheptyl)benzamide4-(dimethylamino)-N-(7-(hydroxyamino)-7-oxoheptyl)benzamide: structure in first source

4-(dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]benzamide : A benzamide resulting from the formal condensation of the carboxy group of 4-(dimethylamino)benzoic acid with the amino group of 7-amino-N-hydroxyheptanamide. It is a potent inhibitor of histone deacetylases and induces cell cycle arrest and apoptosis in several human cancer cell lines.
benzamides;
hydroxamic acid;
secondary carboxamide;
tertiary amino compound
antineoplastic agent;
apoptosis inducer;
EC 3.5.1.98 (histone deacetylase) inhibitor
masoprocolnordihydroguaretic acid: antioxidant compound found in the creosote bush (Larrea tridentata)catechols;
lignan;
tetrol
antioxidant;
ferroptosis inhibitor;
geroprotector;
plant metabolite
vorinostatvorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).

Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.
dicarboxylic acid diamide;
hydroxamic acid
antineoplastic agent;
apoptosis inducer;
EC 3.5.1.98 (histone deacetylase) inhibitor
tetrabromobisphenol a3,3',5,5'-tetrabromobisphenol A : A bromobisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups and the phenyl rings are substituted by bromo groups at positions 2, 2', 6 and 6'. It is a brominated flame retardant.

tetrabromobisphenol A: a brominated flame retardant
brominated flame retardant;
bromobisphenol
phenidonephenidone: photographic developer; RN given refers to parent cpd; structure
2-bromophenolbromophenol : A halophenol that is any phenol containing one or more covalently bonded bromine atoms.bromophenolmarine metabolite
4-bromophenol4-bromophenol : A bromophenol containing only hydroxy and bromo substituents that are para to one another.bromophenolhuman urinary metabolite;
human xenobiotic metabolite;
marine metabolite;
mouse metabolite;
persistent organic pollutant;
rat metabolite
3-hydroxyflavone3-hydroxyflavone: structure given in first source

flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.
flavonols;
monohydroxyflavone
3-bromophenol
2,6-dibromophenol2,6-dibromophenol : A dibromophenol that is phenol in which both of the hydrogens that are ortho to the phenolic hydroxy group have been replaced by bromines.bromohydrocarbon;
dibromophenol
marine metabolite
2,4-dibromophenol2,4-dibromophenol : A bromophenol that is phenol in which the hydrogens at positions 2 and 4 have been replaced by bromines.brominated flame retardant;
bromophenol;
dibromobenzene
marine metabolite
zileuton1-benzothiophenes;
ureas
anti-asthmatic drug;
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor;
ferroptosis inhibitor;
leukotriene antagonist;
non-steroidal anti-inflammatory drug
6-hydroxyflavone6-hydroxyflavone: antioxidant; structure in first sourcehydroxyflavonoid
puupehenone
moracin cbenzofurans
3,6-dihydroxyflavone3,6-dihydroxyflavone: induces apoptosis in leukemia HL-60 cells; structure in first source
N-[(5-chloro-8-hydroxy-7-quinolinyl)-(2-furanyl)methyl]acetamidehydroxyquinoline
1-phenyl-2-[[4-(trifluoromethyl)phenyl]methylthio]imidazoleimidazoles
quercetin7-hydroxyflavonol;
pentahydroxyflavone
antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
15-keto-5,8,11,13-eicosatetraenoic acid15-keto-5,8,11,13-eicosatetraenoic acid: RN given refers to (E,Z,Z,Z)-isomer; RN for cpd without isomeric designation not available 3/88

15-oxo-ETE : An oxoicosatetraenoic acid having (5Z,8Z,11Z,13E) double bond stereochemistry, and an oxo group in position 15.
oxoicosatetraenoic acidhuman metabolite
baicaleintrihydroxyflavoneangiogenesis inhibitor;
anti-inflammatory agent;
antibacterial agent;
anticoronaviral agent;
antifungal agent;
antineoplastic agent;
antioxidant;
apoptosis inducer;
EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
EC 4.1.1.17 (ornithine decarboxylase) inhibitor;
ferroptosis inhibitor;
geroprotector;
hormone antagonist;
plant metabolite;
prostaglandin antagonist;
radical scavenger
fisetin3'-hydroxyflavonoid;
7-hydroxyflavonol;
tetrahydroxyflavone
anti-inflammatory agent;
antioxidant;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
metabolite;
plant metabolite
mangostinalpha-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities.

mangostin: xanthone from rind of Garcinia mangostana Linn. fruit
aromatic ether;
phenols;
xanthones
antimicrobial agent;
antineoplastic agent;
antioxidant;
plant metabolite
morusinmorusin : An extended flavonoid that is flavone substituted by hydroxy groups at positions 5, 2' and 4', a prenyl group at position 3 and a 2,2-dimethyl pyran group across positions 7 and 8.

morusin: from Morus root bark; structure given in first source
extended flavonoid;
trihydroxyflavone
antineoplastic agent;
plant metabolite
daidzein7-hydroxyisoflavonesantineoplastic agent;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
phytoestrogen;
plant metabolite
7-hydroxyflavone7-hydroxyflavone : A hydroxyflavonoid in which the flavone nucleus is substituted at position 7 by a hydroxy group.hydroxyflavonoid
5-oxo-6,8,11,14-eicosatetraenoic acid5-ketoeicosatetraenoic acid: a nonenzymatic rearrangement product of leukotriene A4; structure given in first source

5-oxo-ETE : An oxoicosatetraenoic acid having a 5-oxo group; and (6E)-, (8Z), (11Z)- and (14Z)-double bonds.
oxoicosatetraenoic acidhuman metabolite;
immunomodulator;
mouse metabolite
6,7,4'-trihydroxyisoflavone4',6,7-trihydroxyisoflavone : A hydroxyisoflavone that is daidzein bearing an additional hydroxy substituent at position 6.

6,7,4'-trihydroxyisoflavone: structure in first source
7-hydroxyisoflavonesanti-inflammatory agent;
antimutagen;
EC 1.14.18.1 (tyrosinase) inhibitor;
metabolite;
PPARalpha agonist;
PPARgamma agonist
7-hydroxyisoflavone7-hydroxyisoflavone : The simplest member of the class of 7-hydroxyisoflavones that is isoflavone with a hydroxy substituent at position 7.

7-hydroxyisoflavone: effective against, Enterovirus 71; structure in first source
7-hydroxyisoflavonesEC 1.14.14.14 (aromatase) inhibitor;
metabolite
3,7-dihydroxyflavone3,7-dihydroxyflavone: structure in first source

7-hydroxyflavonol : Any flavonol carrying a 7-hydroxy substituent.
hydroxyflavan
13-oxo-9,11-octadecadienoic acid13-oxo-9Z,11E-ODE : An oxooctadecadienoic acid that consists of 9Z,11E-octadecadienoic acid bearing an additional 13-keto substituent. In addtion it has been found as a natural product found in Carthamus oxyacantha.13-oxo-9,11-octadecadienoic acidmetabolite;
mouse metabolite
dysidenindysidenin : A secondary carboxamide resulting from the formal condensation of the carboxy group of (4S)-5,5,5-trichloro-N-methyl-N-[(3S)-4,4,4-trichloro-3-methylbutanoyl]-L-leucine with the amino group of (1S)-1-(1,3-thiazol-2-yl)ethanamine. It is a marine metabolite initially isolated from the sponge dysidea herbacea.

dysidenin: structure given in first source; from the sponge Dysidea herbacea; RN given refers to (2S-(N(R*),2R*(R*),4R*))-isomer; RN for cpd without isomeric designation not avail 5/90
1,3-thiazoles;
organochlorine compound;
secondary carboxamide;
tertiary carboxamide
animal metabolite;
marine metabolite;
toxin
jaspaquinoljaspaquinol: structure in first source
N-[(5-chloro-8-hydroxy-7-quinolinyl)-cyclopropylmethyl]acetamidehydroxyquinoline
N-[(5-fluoro-8-hydroxy-7-quinolinyl)-thiophen-2-ylmethyl]acetamidehydroxyquinoline
N-[(5-bromo-8-hydroxy-7-quinolinyl)-(2-furanyl)methyl]propanamidehydroxyquinoline
N-[(5-bromo-8-hydroxy-7-quinolinyl)-thiophen-2-ylmethyl]acetamidehydroxyquinoline
ML355ML355 : A sulfonamide resulting from the formal condensation of the amino group of 2-aminobenzothiazole with the sulfo group of 4-[(2-hydroxy-3-methoxybenzyl)amino]benzenesulfonic acid. It is an inhibitor of 12-lipoxygenase, being developed by Veralox Therapeutics for the treatment of heparin-induced thrombocytopenia and thrombosis.

ML355: 12-Lipoxygenase inhibitor
benzothiazoles;
monomethoxybenzene;
phenols;
secondary amino compound;
substituted aniline;
sulfonamide
EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor;
platelet aggregation inhibitor
hydrazinocurcuminhydrazinocurcumin : A pyrazole obtained by cyclocodensation of the two carbonyl groups of curcumin with hydrazine.

hydrazinocurcumin: structure in first source
aromatic ether;
olefinic compound;
polyphenol;
pyrazoles
angiogenesis modulating agent;
antineoplastic agent;
EC 2.3.1.48 (histone acetyltransferase) inhibitor;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor