Details of Metabolite

General Information of MET (ID: META00087)
Name Oleic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(9Z)-9-Octadecenoate; (9Z)-9-Octadecenoic acid; (9Z)-Octadecenoate; (9Z)-Octadecenoic acid; (Z)-9-Octadecanoate; (Z)-9-Octadecanoic acid; (Z)-Octadec-9-enoate; (Z)-Octadec-9-enoic acid; 18:1 N-9; 18:1DElta9cis; 9 Octadecenoic acid; 9,10-Octadecenoate; 9,10-Octadecenoic acid; 9-(Z)-Octadecenoate; 9-(Z)-Octadecenoic acid; 9-Octadecenoate; 9-Octadecenoic acid; Acid, 9-octadecenoic; Acid, cis-9-octadecenoic; Acid, oleic; C18:1 N-9; Century CD fatty acid; Distoline; Emersol 210; Emersol 211; Emersol 213; Emersol 220 white oleate; Emersol 220 white oleic acid; Emersol 221 low titer white oleate; Emersol 221 low titer white oleic acid; Emersol 233LL; Emersol 6321; Emersol 6333 NF; Emersol 7021; FA 18:1; FA(18:1(9Z)); FA(18:1n9); Glycon ro; Glycon wo; Groco 2; Groco 4; Groco 5l; Groco 6; Industrene 104; Industrene 105; Industrene 205; Industrene 206', L'acide oleique, 'Metaupon; Octadec-9-enoate; Octadec-9-enoic acid; Oelsaeure; Oelsauere; Oleate; Oleic acid extra pure; Oleinate; Oleinic acid; Pamolyn; Pamolyn 100; Pamolyn 100 FG; Pamolyn 100 FGK; Pamolyn 125; Priolene 6900; Red oil; Tego-oleic 130; Vopcolene 27; Wecoline oo; Z-9-Octadecenoate; Z-9-Octadecenoic acid; cis 9 Octadecenoic acid; cis-9-Octadecenoate; cis-9-Octadecenoic acid; cis-Delta(9)-Octadecenoic acid; cis-Octadec-9-enoate; cis-Octadec-9-enoic acid; cis-Oleate; cis-Oleic acid
Source Endogenous;Yeast Metabolite;Fatty acyls;Food;Toxins/Pollutant;Cosmetic;Food additives;TCM Ingredients;Microbial
Structure Type   Fatty acids and conjugates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Fatty acids and conjugates
PubChem CID
445639
HMDB ID
HMDB0000207
Formula
C18H34O2
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00712
ChEBI ID
16196
FooDB ID
FDB012858
ChemSpider ID
393217
METLIN ID
190
Physicochemical Properties Molecular Weight 282.5 Topological Polar Surface Area 37.3
XlogP 6.5 Complexity 234
Heavy Atom Count 20 Rotatable Bond Count 15
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Function
Oleic acid is 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). Biological source: Major constituent of plant oils e.g. olive oil (about 80%), almond oil (about 80%) and many others, mainly as glyceride. Constituent of tall oil and present in fruits Use/Importance: Food additive. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. Emulsifying agent in foods and pharmaceuticals. Biological Use/Importance: Skin penetrant. Herbicide, insecticide, fungicide (Dictionary of Organic Compounds). Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colourless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The term "oleic" means related to, or derived from, oil or olive, the oil that is predominantly composed of oleic acid. Oleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      Cytokine receptor (CytR)
            Apoptosis mediating antigen FAS (CD95) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Oleic acid addition (24 hours)
                      Induced Change FAS protein expression levels: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Hepatocellular carcinoma [ICD-11: 2C12]
                      Details It is reported that oleic acid addition causes the decrease of FAS protein expression compared with control group.
      GPCR rhodopsin (GPCR-1)
            G-protein coupled receptor 120 (GPR120) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Oleic acid addition (40.08 hours)
                      Induced Change FFAR4 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that oleic acid addition causes the increase of FFAR4 protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Group 3 secretory phospholipase A2 (PLA2G3) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Knockout of Pla2g3
                      Induced Change Oleic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colorectal cancer [ICD-11: 2B91]
                      Details It is reported that knockout of Pla2g3 leads to the increase of oleic acid levels compared with control group.
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Oleic acid concentration: increase (FC = 2.22 / 2.70)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of oleic acid levels compared with control group.
      Transcription factor (TF)
            Hypoxia-inducible factor 1-alpha (HIF1A) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [5]
                      Introduced Variation Knockout of HIF1A
                      Induced Change Oleic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colorectal cancer [ICD-11: 2B91]
                      Details It is reported that knockout of HIF1A leads to the increase of oleic acid levels compared with control group.
References
1 Tetrahydrocurcumin ameliorates free fatty acid-induced hepatic steatosis and improves insulin resistance in HepG2 cells. J Food Drug Anal. 2018 Jul;26(3):1075-1085.
2 Differential signaling by splice variants of the human free fatty acid receptor GPR120. Mol Pharmacol. 2012 May;81(5):631-42.
3 Group III phospholipase A 2 promotes colitis and colorectal cancer. Sci Rep. 2017 Sep 25;7(1):12261.
4 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
5 Hypoxia induces a lipogenic cancer cell phenotype via HIF1-dependent and -independent pathways. Oncotarget. 2015 Feb 10;6(4):1920-41.

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