Details of the Drug Inactive Ingredient (DIG)

General Information of DIG (ID: E00WOC)
DIG Name
Linoleic acid
Synonyms    Click to Show/Hide the Synonyms of This DIG
linoleic acid; 60-33-3; Linolic acid; Telfairic acid; cis,cis-Linoleic acid; (9Z,12Z)-octadeca-9,12-dienoic acid; Linoleate; cis,cis-9,12-Octadecadienoic acid; Grape seed oil; cis-9,cis-12-Octadecadienoic acid; 9Z,12Z-Linoleic acid; Emersol 315; (Z,Z)-9,12-Octadecadienoic acid; 9,12-Linoleic acid; Unifac 6550; 9Z,12Z-octadecadienoic acid; Extra Linoleic 90; 9-cis,12-cis-Linoleic acid; Emersol 310; Polylin 515; all-cis-9,12-Octadecadienoic acid; Polylin No. 515; 9,12-Octadecadienoic acid (9Z,12Z)-; Linoleic; acide linoleique; 9,12-Octadecadienoic acid; Linoleic acid, pure; 9,12-Octadecadienoic acid (Z,Z)-; acido linoleico; Leinoleic acid; (9Z,12Z)-Octadecadienoic acid; UNII-9KJL21T0QJ; 9-cis,12-cis-Octadecadienoic acid; alpha-Linoleic acid; acide cis-linoleique; 9,12-Octadecadienoic acid, (Z,Z)-; (9Z,12Z)-9,12-octadecadienoic acid; CHEBI:17351; cis-9, cis-12-octadecadienoic acid; MFCD00064241; cis-Delta(9,12)-octadecadienoic acid; 9KJL21T0QJ; CHEMBL267476; 9-cis,12-cis-Octadecadienoate; C18:2; Oils, grape; NSC-281243; Linoleic acid, 99%; cis,cis-linoleate; NCGC00091049-04; VESPULA PENSYLVANICA B708568K063; DSSTox_CID_5505; DSSTox_RID_77814; DSSTox_GSID_25505; Linoleic acid, 60%, tech.; 2197-37-7; 506-21-8; Oils, grape seed; CAS-60-33-3; CCRIS 650; 14C-Linoleic acid; HSDB 5200; (14C)-Linoleic acid; SR-01000944790; cis-delta9,12-Octadecadienoic acid; UNII-7552P0K6PN; EINECS 200-470-9; NSC 281243; (14C)alpha-Linolenic acid; 7552P0K6PN; Linolate; grapeseed oil; linoleic-acid; Leinolic acid; AI3-11132; trans-9,trans-12-Octadecadienoic acid; linoleic acid group; 9,12-Octadecadienoic acid, (9E,12E)-; 9Z,12Z-Linoleate; Linoleic Acid 315; 8024-22-4; n-6,9 all-cis; Linoleic acid, 95%; 9Z,12Z-Octadecadienoate; 9-cis,12-cis-Linoleate; Linoleic acid, >=95%; Linoleic acid, >=99%; bmse000497; bmse000604; Epitope ID:117705; linoleic and linolenic acids; SCHEMBL7067; cis,12-Octadecadienoic acid; Pamolyn 125 (Salt/Mix); cis-D9,12-Octadecadienoate; BSPBio_001374; CCRIS 652; all-cis-9,12-Octadecadienoate; BML3-C03; cis-9,cis-12-Octadecadienoate; GTPL1052; Linoleic acid, >=95%, FG; Linoleic acid, puriss., 90%; delta9,12-Octadecadienoic acid; (Z,Z)-9,12-Octadecadienoate; DTXSID2025505; ACon1_000270; BDBM22231; C18:2, n-6,9 all-cis; cis-D9,12-Octadecadienoic acid; Linoleic acid, >=93% (GC); CHEBI:137735; 9,12-Octadecadienoic acid, (Z,Z)-, labeled with carbon-14; HMS1361E16; HMS1791E16; HMS1989E16; HMS3402E16; HMS3649F07; HMS3886F05; Linoleic acid, analytical standard; 9,12-Octadecadienoic acid (VAN); HY-N0729; ZINC4474613; 9,12-Octadecadienoic acid, (Z)-; Tox21_111067; Tox21_202171; Tox21_303080; (9Z,12Z)-9,12-Octadecadienoate; C18:2 9c; cis,cis-octadeca-9,12-dienoic acid; cis-9,cis-12-Octadecadienoic acid,; LMFA01030120; NSC281243; s5821; (Z,Z)-Octadeca-9, 12-dienoic acid; 9,12-Octadecadienoic acid, (E,E)-; 9,12-Octadecadienoic acid, cis,cis-; AKOS015951293; ACN-045515; DB14104; rans, trans-9,12-octadecadienoic acid; (9Z,12Z)octadeca-9,12-dienoic acid; 9-(Z), 12-(Z)-Octadecadienoic acid; cis-.DELTA.9,12-Octadecadienoic acid; IDI1_033844; NCGC00091049-01; NCGC00091049-02; NCGC00091049-03; NCGC00091049-05; NCGC00091049-06; NCGC00091049-07; NCGC00257024-01; NCGC00259720-01; 12c omega6 todos cis-9,12-octadienoico; 80969-37-5; AS-12672; FEMA NO. 3380, LINOLEIC ACID-; ST098723; Linoleic acid, technical, 60-74% (GC); Octadeca-9,12-dienoic acid, (cis,cis)-; AI3-36448; 9,Z)-; CS-0009742; L0053; L0124; A-8680; C01595; 9, (Z)-; Q407426; SR-01000944790-1; SR-01000944790-3; BRD-K08973992-001-03-9; C18:2 9c, 12c omega6 todos cis-9,12-octadienoico; 5CE5E1F3-8859-4C5B-9AFE-E44A7076DF6E; UNII-0JXR8F0V1Q component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-116Z6MZN1M component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-44NH37HHP9 component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-5U9XZ261ER component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-96GS7P39SN component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-9B22238JYI component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-B6G0Y5Z616 component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-F85N2YHE4E component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-HBA528N3PW component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-ODL221H4AM component OYHQOLUKZRVURQ-HZJYTTRNSA-N; UNII-V1PY73ZXPE component OYHQOLUKZRVURQ-HZJYTTRNSA-N; Linoleic acid, liquid, BioReagent, suitable for cell culture; UNII-79P21R4317 component OYHQOLUKZRVURQ-HZJYTTRNSA-N; Linoleic acid, 2.0 mg/mL in ethanol, certified reference material; Linoleic acid, PharmaGrade, Manufactured under appropriate controls for use as a raw material in pharma or biopharmaceutical production
DIG Function
Emulsifying agent; Penetration agent; Solubilizing agent
PubChem CID
5280450
Formula
C18H32O2
Canonical SMILES
CCCCC/C=C\\C/C=C\\CCCCCCCC(=O)O
InChI
1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
InChIKey
OYHQOLUKZRVURQ-HZJYTTRNSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This DIG
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=5280450"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 280.4 Topological Polar Surface Area 37.3
XlogP 6.8 Complexity 267
Heavy Atom Count 20 Rotatable Bond Count 14
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Full List of Active Pharmaceutical Ingredients (APIs) Co-administrated with This DIG
       ICD Disease Classification 06 Mental/behavioural/neurodevelopmental disorder Click to Show/Hide
Chlordiazepoxide
 API Info
Anxiety disorder [ICD-11: 6B00]
 [1]
Full List of Biological Targets of DIG (DBTs) Regulated by This DIG
      G-protein coupled receptor (GPCR)
            DBT Name: Adenosine receptor A1 (AA1R) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 65000 nM (tested by experiment) [2]
                    Tested Species Rattus norvegicus (Rat)
                    UniProt ID AA1R_RAT
            DBT Name: Free fatty acid receptor 1 (FFAR1) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity EC50 = 540 nM (tested by experiment) [3]
                    Tested Species Homo sapiens (Human)
                    UniProt ID FFAR1_HUMAN
            DBT Name: Free fatty acid receptor 4 (FFAR4) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity EC50 = 316.23 nM (tested by experiment) [4]
                    Tested Species Homo sapiens (Human)
                    UniProt ID FFAR4_HUMAN
      Oxidoreductase (ORase)
            DBT Name: Aromatase (ARO1) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 48000 nM (tested by experiment) [5]
                    Tested Species Homo sapiens (Human)
                    UniProt ID CP19A_HUMAN
            DBT Name: Prostaglandin G/H synthase 1 (COX-1) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 170000 nM (tested by experiment) [6]
                    Tested Species Bos taurus (Bovine)
                    UniProt ID PGH1_BOVIN
            DBT Name: Prostaglandin G/H synthase 2 (COX-2) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 94000 nM (tested by experiment) [6]
                    Tested Species Ovis aries (Sheep)
                    UniProt ID PGH2_SHEEP
      Hydrolase (HDase)
            DBT Name: Proconvertin-TF complex (F7-F3) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 41000 nM (tested by experiment) [7]
                    Tested Species Homo sapiens (Human)
                    UniProt ID FA7_HUMAN ; TF_HUMAN
            DBT Name: Vaccinia H1 phosphatase (VHR) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 > 100000 nM (tested by experiment) [8]
                    Tested Species Homo sapiens (Human)
                    UniProt ID DUS3_HUMAN
            DBT Name: Trypsin (PRSS) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 > 200000 nM (tested by experiment) [7]
                    Tested Species Sus scrofa (Pig)
                    UniProt ID TRYP_PIG
            DBT Name: Protein-tyrosine phosphatase 7 (PTPN7) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 > 100000 nM (tested by experiment) [8]
                    Tested Species Homo sapiens (Human)
                    UniProt ID PTN7_HUMAN
      Nuclear receptor (NR)
            DBT Name: PPAR-alpha (PPARA) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 1100 nM (tested by experiment) [9]
                    Tested Species Homo sapiens (Human)
                    UniProt ID PPARA_HUMAN
            DBT Name: PPAR-delta (PPARD) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 10000 nM (tested by experiment) [10]
                    Tested Species Homo sapiens (Human)
                    UniProt ID PPARD_HUMAN
            DBT Name: PPAR-gamma (PPARG) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 6200 nM (tested by experiment) [10]
                    Tested Species Homo sapiens (Human)
                    UniProt ID PPARG_HUMAN
      Other protein families (OPF)
            DBT Name: Adipocyte lipid-binding protein (ALBP) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 1000 nM (tested by experiment) [11]
                    Tested Species Homo sapiens (Human)
                    UniProt ID FABP4_HUMAN
            DBT Name: Heart lipid-binding protein (H-FABP) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 1000 nM (tested by experiment) [12]
                    Tested Species Homo sapiens (Human)
                    UniProt ID FABPH_HUMAN
References
1 FDA label for approved chlordiazepoxide from the official website of the U.S. Food and Drug Administration.
2 Interference of linoleic acid fraction in some receptor binding assays. J Nat Prod. 1999 Jun; 62(6):912-4.
3 Discovery of diacylphloroglucinols as a new class of GPR40 (FFAR1) agonists. Bioorg Med Chem Lett. 2008 Dec 15; 18(24):6357-61.
4 Identification of diarylsulfonamides as agonists of the free fatty acid receptor 4 (FFA4/GPR120). Bioorg Med Chem Lett. 2014 Jul 15; 24(14):3100-3.
5 Interference by naturally occurring fatty acids in a noncellular enzyme-based aromatase bioassay. J Nat Prod. 2006 Apr; 69(4):700-3.
6 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun; 64(6):745-9.
7 Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex. J Nat Prod. 1998 Nov; 61(11):1352-5.
8 Fatty acids as natural specific inhibitors of the proto-oncogenic protein Shp2. Bioorg Med Chem Lett. 2011 Nov 15; 21(22):6833-7.
9 Molecular recognition of long chain fatty acids by peroxisome proliferator-activated receptor. Med Chem Res (2009) 18:8-19.
10 Molecular properties of fatty acids related to PPAR binding and metabolic diseases. Med Chem Res (2013) 22:3126-3133.
11 Discovery of highly selective inhibitors of human fatty acid binding protein 4 (FABP4) by virtual screening. Bioorg Med Chem Lett. 2010 Jun 15; 20(12):3675-9.
12 Novel fatty acid binding protein 4 (FABP4) inhibitors: virtual screening, synthesis and crystal structure determination. Eur J Med Chem. 2015 Jan 27; 90:241-50.

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