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Vernolic acid
- Family: Plantae - Asteraceae
- Kingdom: Plantae
- Class: Glyceride
| Canonical Smiles | CCCCC[C@H]1O[C@H]1C/C=C\CCCCCCCC(=O)O |
|---|---|
| InChI | InChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m1/s1 |
| InChIKey | CCPPLLJZDQAOHD-GJGKEFFFSA-N |
| Formula | C18H32O3 |
| HBA | 2 |
| HBD | 1 |
| MW | 296.45 |
| Rotatable Bonds | 14 |
| TPSA | 49.83 |
| LogP | 5.1 |
| Number Rings | 1 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.83 |
| Exact Mass | 296.24 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Vernonia galamensis | Asteraceae | Plantae | 83960 |
Showing of synonyms
Vernolic acid
(+)-vernolic acid
Vernoleate
Leukotoxin B
17966-13-1
Vernolic acid (+)-form
503-07-1
Isoleukotoxin
Cis-12-Epoxyoctadeca-cis-9-enoate
UNII-FR42854EPW
12S,13R-EpOME
Cis-12,13-Epoxyoleic acid
Cis-12-Epoxyoctadeca-cis-9-enoic acid
FR42854EPW
Vernolic acid, cis-(+/-)-
(9Z)-(12S,13R)-12,13-Epoxyoctadecenoic acid
4S5JF40ZOQ
(Z)-11-[(2S,3R)-3-pentyloxiran-2-yl]undec-9-enoic acid
12S,13R-epoxy-9Z-octadecenoic acid
(+/-)12(13)-EpOME
Cis-12,13-epoxy-9(z)-octadecenoic acid
9-Undecenoic acid, 11-((2R,3S)-3-pentyl-2-oxiranyl)-, (9Z)-rel-
9-Undecenoic acid, 11-(3-pentyloxiranyl)-, (2S-(2alpha(Z),3alpha))-
UNII-4S5JF40ZOQ
Vernolic acid, cis-(+)-
(Z)-11-[(2R,3S)-3-pentyloxiran-2-yl]undec-9-enoic acid
(?)12(13)-EpOME
Iso-Leukotoxin
(+)-Vernolsaeure
(+)-leukotoxin B
VERNOLEIC ACID
Cis-(+)-vernolic acid
(+/-)-Vernolic Acid
SCHEMBL55116
(+/-)-cis-12,13-Epoxy-9(Z)-octadecenoic acid
CHEBI:27706
DTXSID40895851
CCPPLLJZDQAOHD-GJGKEFFFSA-N
HY-W782236A
9-Undecenoic acid, 11-(3-pentyloxiranyl)-, (2alpha(Z),3alpha)-
LMFA02000282
(+)-12(S),13(R)-vernolic acid
HY-W782236
VERNOLIC ACID (+)-FORM [MI]
12(S),13(R)-Epoxy-9(Z)-octadecenoic acid
12S,13R-Epoxy-oleic Acid
SR-01000946972
(+)-12,13-EPOXY-9-CIS-OCTADECENOIC ACID
SR-01000946972-1
Q28530676
CIS-(+)-12,13-EPOXYOCTADEC-CIS-9-ENOIC ACID
OCTADEC-CIS-(+)-12,13-EPOXY-CIS-9-ENOIC ACID
OLEIC ACID, 12,13-EPOXY-, (12S,13R)-(+)-
(9Z)-11-[(2S,3R)-3-pentyloxiran-2-yl]undec-9-enoic acid
9-UNDECENOIC ACID, 11-((2S,3R)-3-PENTYL-2-OXIRANYL)-, (9Z)-
9-UNDECENOIC ACID, 11-(3-PENTYLOXIRANYL)-, (2.ALPHA.(Z),3.ALPHA.)-
Pubchem:
6449780
Cas:
17966-13-1
Zinc:
ZINC000004726635
Chebi:
27706
Nmrshiftdb2:
70129100
Metabolights:
MTBLC27706
Comptox:
DTXSID40895851
CPRiL:
53657
SMILES: C1CO1
Level: 0
Mol. Weight: 296.45 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.91
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.34
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.05
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.81
- Plasma Protein Binding
- 52.25
- 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
- 5.84
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.29
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.39
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.09
- 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
- 2.03
- Rat (Acute)
- 1.63
- Rat (Chronic Oral)
- 2.12
- Fathead Minnow
- 3.95
- 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
- 379.55
- Hydration Free Energy
- -5.3
- Log(D) at pH=7.4
- 2.14
- Log(P)
- 5.86
- Log S
- -4.83
- Log(Vapor Pressure)
- -6.13
- Melting Point
- 7.62
- pKa Acid
- 5.14
- pKa Basic
- 7.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.9121 |
| thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.9121 |
| 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase | P9WNH5 | HSAD_MYCTU | Mycobacterium tuberculosis | 3 | 0.8663 |
| 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase | P9WNH5 | HSAD_MYCTU | Mycobacterium tuberculosis | 3 | 0.8663 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8056 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8056 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7805 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7805 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7767 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7767 |
| Sodium/potassium-transporting ATPase subunit alpha | Q4H132 | Q4H132_SQUAC | Squalus acanthias | 2 | 0.7718 |
| Sodium/potassium-transporting ATPase subunit alpha | Q4H132 | Q4H132_SQUAC | Squalus acanthias | 2 | 0.7718 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7685 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7685 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 2 | 0.7676 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 2 | 0.7676 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 2 | 0.7633 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 2 | 0.7633 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 2 | 0.7627 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 2 | 0.7627 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7602 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7602 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7578 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7578 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7562 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7562 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7560 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7560 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 2 | 0.7530 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 2 | 0.7530 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 2 | 0.7507 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 2 | 0.7507 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7457 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7457 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 2 | 0.7448 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 2 | 0.7448 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7427 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7427 |
| Carnitine O-acetyltransferase | P47934 | CACP_MOUSE | Mus musculus | 2 | 0.7385 |
| Carnitine O-acetyltransferase | P47934 | CACP_MOUSE | Mus musculus | 2 | 0.7385 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7382 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7382 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7350 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7350 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7345 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7345 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 2 | 0.7307 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 2 | 0.7307 |
| Alpha/beta hydrolase fold protein | D2J2T6 | D2J2T6_9RHIZ | Ochrobactrum sp. T63 | 2 | 0.7292 |
| Alpha/beta hydrolase fold protein | D2J2T6 | D2J2T6_9RHIZ | Ochrobactrum sp. T63 | 2 | 0.7292 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 2 | 0.7273 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 2 | 0.7273 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7256 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7256 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7078 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7078 |
| 12-oxophytodienoate reductase 1 | Q9XG54 | OPR1_SOLLC | Solanum lycopersicum | 2 | 0.7055 |
| 12-oxophytodienoate reductase 1 | Q9XG54 | OPR1_SOLLC | Solanum lycopersicum | 2 | 0.7055 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 2 | 0.7050 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 2 | 0.7050 |