Oleic acid - Compound Card

Oleic acid

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Oleic acid

Structure
Zoomed Structure
  • Family: Plantae - Myrsinaceae
  • Kingdom: Plantae
  • Class: Lipid
    • Subclass: Fatty Acid
Canonical Smiles CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
InChI 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
Formula C18H32O2
HBA 1
HBD 1
MW 280.45
Rotatable Bonds 14
TPSA 37.3
LogP 5.88
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 280.24
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pergularia tomentosa Apocynaceae Plantae 264979
2 Hyphaene thebaica Arecaceae Plantae 115479
3 Euphorbia helioscopia Euphorbiaceae Plantae 154990
4 Apium graveolens Apiaceae Plantae 4045
5 Juniperus phoenicea Cupressaceae Plantae 61308
6 Chrysanthemum macrocarpum Asteraceae Plantae 13422
7 Warburgia ugandensis Canellaceae Plantae 549619
8 Vernonia galamensis Asteraceae Plantae 83960
9 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]
  • Nasri N, Tlili N, et al. (2011). Chemical compounds from Phoenician juniper berries (Juniperus phoenicea). Natural Product Research,2011,25(18),1733-1742. [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]
  • 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]
  • Wube AA, Bucar F, et al. (2005). Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. Phytochemistry,2005,66(19),2309-2315. [View] [PubMed]
  • Babaamer ZY, Sakhri L, et al. (2012). Two new taraxasterol-type triterpenes from Pergularia tomentosa growing wild in Algeria. Journal of Asian Natural Products Research,2012,14(12),1137-1143. [View] [PubMed]
  • MacLeod AJ, MacLeod G, et al. (1988). Volatile aroma constituents of celery. Phytochemistry,1988,27(2),373-375. [View]
Pubchem: 445639
Kegg Ligand: C00712
Chebi: 16196
Nmrshiftdb2: 10008720
Metabolights: MTBLC16196
Chembl: CHEMBL8659
Pdb Ligand: OLA
Bindingdb: 50150484
CPRiL: 309

No scaffolds available.

Anthelmintic
Antimycobacterial

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.21
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.36
Plasma Protein Binding
54.17
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
-1.13
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.37
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.43
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.68
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
Toxic
NR-TR
Safe
T. Pyriformis
2.59
Rat (Acute)
1.36
Rat (Chronic Oral)
2.31
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
356.16
Hydration Free Energy
-4.72
Log(D) at pH=7.4
3.01
Log(P)
6.8
Log S
-4.03
Log(Vapor Pressure)
-5.9
Melting Point
12.57
pKa Acid
5.4
pKa Basic
8.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 3 0.9885
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 3 0.9885
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.9697
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.9697
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9402
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9402
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 3 0.9394
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 3 0.9394
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8346
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8346
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7728
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7728
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7630
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7630
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7579
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7579
12-oxophytodienoate reductase 1 Q9XG54 OPR1_SOLLC Solanum lycopersicum 2 0.7566
12-oxophytodienoate reductase 1 Q9XG54 OPR1_SOLLC Solanum lycopersicum 2 0.7566
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7479
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7479
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7472
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7472
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7422
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7422
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7384
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7384
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7334
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7334
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7333
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7333
Geranylgeranyl pyrophosphate synthase BTS1 Q12051 GGPPS_YEAST Saccharomyces cerevisiae 2 0.7323
Geranylgeranyl pyrophosphate synthase BTS1 Q12051 GGPPS_YEAST Saccharomyces cerevisiae 2 0.7323
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7265
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7265
Solanesyl diphosphate synthase 3, chloroplastic/mitochondrial Q5HZ00 SPS3_ARATH Arabidopsis thaliana 2 0.7240
Solanesyl diphosphate synthase 3, chloroplastic/mitochondrial Q5HZ00 SPS3_ARATH Arabidopsis thaliana 2 0.7240
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7156
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7156
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7153
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7153
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7140
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7140
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7131
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7131
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7097
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7097
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7071
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7071
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7069
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7069
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7062
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7062
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7057
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7057
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7034
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7034
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7032
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7032
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7027
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7027
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7022
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7022
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7000
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7000

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