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Oleic acid

Family: Plantae - Myrsinaceae
Kingdom: Fungi, Plantae
Class: Lipid
- Subclass: Fatty 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
Formula	C₁₈H₃₄O₂
HBA	1
HBD	1
MW	282.47
Rotatable Bonds	15
TPSA	37.3
LogP	6.11
Number Rings	0
Number Aromatic Rings	0
Heavy Atom Count	20
Formal Charge	0
Fraction CSP3	0.83
Exact Mass	282.26
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Agave decipiens	Agavaceae	Plantae	2695036
2	Hyphaene thebaica	Arecaceae	Plantae	115479
3	Euphorbia helioscopia	Euphorbiaceae	Plantae	154990
4	Nigrospora sphaerica	Trichosphaeriaceae	Fungi	114231
5	Apium graveolens	Apiaceae	Plantae	4045
6	Bunium incrassatum	Apiaceae	Plantae	1094602
7	Juniperus phoenicea	Cupressaceae	Plantae	61308
8	Chrysanthemum macrocarpum	Asteraceae	Plantae	13422
9	Mkilua fragrans	Annonaceae	Plantae	49754
10	Vernonia galamensis	Asteraceae	Plantae	83960
11	Embelia schimperi	Myrsinaceae	Plantae	2595069

Showing of synonyms

Tessema EN, Neubert R, et al. (2018). Anthelmintic activity-guided fractionation and GC-MS analysis of extracts from Embelia schimperi fruits. International Journal of Applied Research in Natural Products,2018,11(1),11-16.. [View] [PubMed]
Baraza LD, Nkunya MH, et al. (2006). C18 tetraynoic fatty acids and essential oil composition of Mkilua fragrans. Natural Product Research,2006,20(2),187-193. [View] [PubMed]
Nasri N, Tlili N, et al. (2011). Chemical compounds from Phoenician juniper berries (Juniperus phoenicea). Natural Product Research,2011,25(18),1733-1742. [View]
Bousetla A, Zellagui A, et al. (2015). Chemical constituents of the roots of Algerian Bunium incrassatum and evaluation of its antimicrobial activity. Arabian Journal of Chemistry,2015,8,313-316. [View]
Boutaghane N, Kabouche A, et al. (2008). Composition of the essential oil of Chrysanthemum macrocarpum from Algeria. Chemistry of Natural Compounds,2008,44(6),817-818. [View]
Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]
Abdel-Gawad MM, El-Sayed MM and Abdel-Hameed ES. (1999). Molluscicidal steroidal saponins and lipid content of Agave decipiens. Fitoterapia,1999,70,371-381. [View]
Metwaly AM, Kadry HA, et al. (2014). Nigrosphaerin A a new isochromene derivative from the endophytic fungus Nigrospora sphaerica. Phytochemistry Letters,2014,7,1-5. [View]
Bedemo B, Fiseha A, et al. (2006). Phytochemical investigation on the seeds of Vernonia galamensis. M.Sc. Thesis-1, Addis Ababa University, Ethiopia,2006. [View] [PubMed]
Eldahshan OA, Ayoub NA, et al. (2008). Potential superoxide anion radical scavenging activity of doum palm (Hyphaene thebaica L.) leaves extract. Records of Natural Products,2008,2(3),83-93. [View]
MacLeod AJ, MacLeod G, et al. (1988). Volatile aroma constituents of celery. Phytochemistry,1988,27(2),373-375. [View]

Pubchem: 445639

Cas: 112-80-1

Gnps: CCMSLIB00005750505

Zinc: ZINC000006845860

Kegg Ligand: C00712

Chebi: 16196

Nmrshiftdb2: 10008720

Metabolights: MTBLC16196

Chembl: CHEMBL8659

Comptox: DTXSID1025809

Pdb Ligand: OLA

Bindingdb: 50150484

CPRiL: 309

No scaffolds available.

Anthelmintic

Absorption

Caco-2 (logPapp): -4.8
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.09
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.82

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.4
Plasma Protein Binding: 46.09
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: -0.78
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.34
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Toxic
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.89
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 3.28
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 4.82
Rat (Acute): 1.4
Rat (Chronic Oral): 2.34
Fathead Minnow: 3.92
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 360.01
Hydration Free Energy: -4.65
Log(D) at pH=7.4: 3.44
Log(P): 7.41
Log S: -4.54
Log(Vapor Pressure): -6.15
Melting Point: 50.25
pKa Acid: 4.93
pKa Basic: 8.74

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
thiamine diphosphokinase	Q82ZE3	Q82ZE3_ENTFA	Enterococcus faecalis	3	0.9914
thiamine diphosphokinase	Q82ZE3	Q82ZE3_ENTFA	Enterococcus faecalis	3	0.9914
Phospholipase A2	P00593	PA21B_BOVIN	Bos taurus	3	0.8401
Phospholipase A2	P00593	PA21B_BOVIN	Bos taurus	3	0.8401
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.8395
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.8395
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	3	0.8371
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	3	0.8371
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7764
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7764
Geranyl diphosphate synthase large subunit	Q9SBR3	Q9SBR3_MENPI	Mentha piperita	3	0.7620
Geranyl diphosphate synthase large subunit	Q9SBR3	Q9SBR3_MENPI	Mentha piperita	3	0.7620
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7429
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7429
12-oxophytodienoate reductase 1	Q9XG54	OPR1_SOLLC	Solanum lycopersicum	2	0.7246
12-oxophytodienoate reductase 1	Q9XG54	OPR1_SOLLC	Solanum lycopersicum	2	0.7246
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7196
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7196
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7161
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7161
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7126
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7126
Quorum-sensing transcriptional activator	Q8XBD0	Q8XBD0_ECO57	Escherichia coli O157:H7	2	0.7099
Quorum-sensing transcriptional activator	Q8XBD0	Q8XBD0_ECO57	Escherichia coli O157:H7	2	0.7099
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	2	0.7049
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	2	0.7049
Glutamate receptor 4	P19493	GRIA4_RAT	Rattus norvegicus	2	0.7041
Glutamate receptor 4	P19493	GRIA4_RAT	Rattus norvegicus	2	0.7041
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7039
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7039
Isopenicillin N synthase	P05326	IPNS_EMENI	Emericella nidulans	2	0.7032
Isopenicillin N synthase	P05326	IPNS_EMENI	Emericella nidulans	2	0.7032
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7017
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7017

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