Details of the Drug

General Information of Drug (ID: DM54O1Z)

Drug Name

OLEIC ACID

Synonyms

oleic acid; 112-80-1; cis-9-Octadecenoic acid; cis-Oleic acid; Elaidoic acid; oleate; Glycon wo; Wecoline OO; Pamolyn 100; Glycon RO; (Z)-Octadec-9-enoic acid; Metaupon; Oelsauere; Vopcolene 27; Groco 5l; Groco 2; Groco 4; Groco 6; Tego-oleic 130; Emersol 211; Z-9-Octadecenoic acid; Industrene 206; Industrene 105; Pamolyn; Industrene 205; Oleinic acid; Emersol 213; Emersol 210; L'Acide oleique; cis-Octadec-9-enoic acid; Century cd fatty acid; Emersol 6321; Extraolein 90; Oleine 7503; 9-Octadecenoic acid (Z)-; Emersol 205; Emersol 233LL

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

282.5

Logarithm of the Partition Coefficient (xlogp)

6.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 15.6 h [2]
Elimination: Less than 10% of total oleic acid was found to be eliminated via fecal excretion [2]
Metabolism: The drug is metabolized via the beta-oxidation and tricarboxylic acid cycle pathways of catabolism [2]

Chemical Identifiers

Formula: C18H34O2
IUPAC Name: (Z)-octadec-9-enoic acid
Canonical SMILES: CCCCCCCC/C=C\\CCCCCCCC(=O)O
InChI: InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
InChIKey: ZQPPMHVWECSIRJ-KTKRTIGZSA-N

Cross-matching ID

PubChem CID: 445639
ChEBI ID: CHEBI:16196
CAS Number: 112-80-1
UNII: 4837010H8C
DrugBank ID: DB04224
TTD ID: D0A4EA
VARIDT ID: DR00152

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Fatty acid-binding protein 1 (FABP1)	TTIV96N	FABPL_HUMAN	Inhibitor	[3]
Fatty acid-binding protein 4 (FABP4)	TTHWMFZ	FABP4_HUMAN	Inhibitor	[4]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Fatty acid transport protein 1 (SLC27A1)	DTKDTML	S27A1_HUMAN	Substrate	[5]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
1-acyl-sn-glycerol-3-phosphate acyltransferase beta (AGPAT2)	OT5I4Y9K	PLCB_HUMAN	Gene/Protein Processing	[6]
3-ketoacyl-CoA thiolase, mitochondrial (ACAA2)	OTGLVWOP	THIM_HUMAN	Gene/Protein Processing	[6]
Acetyl-CoA carboxylase 1 (ACACA)	OT5CQPZY	ACACA_HUMAN	Gene/Protein Processing	[7]
Acetyl-coenzyme A thioesterase (ACOT12)	OTN4RQK8	ACO12_HUMAN	Gene/Protein Processing	[6]
Actin, aortic smooth muscle (ACTA2)	OTEDLG8E	ACTA_HUMAN	Gene/Protein Processing	[8]
Aflatoxin B1 aldehyde reductase member 4 (AKR7L)	OTV1WM0N	ARK74_HUMAN	Gene/Protein Processing	[9]
Albumin (ALB)	OTVMM513	ALBU_HUMAN	Protein Interaction/Cellular Processes	[10]
Aldehyde dehydrogenase 1A1 (ALDH1A1)	OTCUWZKB	AL1A1_HUMAN	Gene/Protein Processing	[11]
Apolipoprotein A-IV (APOA4)	OT466POQ	APOA4_HUMAN	Gene/Protein Processing	[11]
Apolipoprotein A-V (APOA5)	OTEVKLVA	APOA5_HUMAN	Gene/Protein Processing	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1054).
2	OLEIC ACID - National Library of Medicine HSDB Database - Toxnet
3	Characterization of the drug binding specificity of rat liver fatty acid binding protein. J Med Chem. 2008 Jul 10;51(13):3755-64.
4	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.
5	The blood-brain barrier fatty acid transport protein 1 (FATP1/SLC27A1) supplies docosahexaenoic acid to the brain, and insulin facilitates transport. J Neurochem. 2017 May;141(3):400-412.
6	Farnesol induces fatty acid oxidation and decreases triglyceride accumulation in steatotic HepaRG cells. Toxicol Appl Pharmacol. 2019 Feb 15;365:61-70.
7	Lambda-cyhalothrin induces lipid accumulation in mouse liver is associated with AMPK inactivation. Food Chem Toxicol. 2023 Feb;172:113563. doi: 10.1016/j.fct.2022.113563. Epub 2022 Dec 15.
8	Sorafenib reduces steatosis-induced fibrogenesis in a human 3D co-culture model of non-alcoholic fatty liver disease. Environ Toxicol. 2021 Feb;36(2):168-176. doi: 10.1002/tox.23021. Epub 2020 Sep 12.
9	Exposure to dietary fatty acids oleic and palmitic acid alters structure and mechanotransduction of intestinal cells in vitro. Arch Toxicol. 2023 Jun;97(6):1659-1675. doi: 10.1007/s00204-023-03495-3. Epub 2023 Apr 29.
10	Quercetin ameliorate insulin resistance and up-regulates cellular antioxidants during oleic acid induced hepatic steatosis in HepG2 cells. Toxicol In Vitro. 2013 Mar;27(2):945-53.
11	A cellular model to study drug-induced liver injury in nonalcoholic fatty liver disease: application to acetaminophen. Toxicol Appl Pharmacol. 2016 Feb 1;292:40-55.