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Juniperonic acid
- Family: Plantae - Cupressaceae
- Kingdom: Plantae
-
Class: Lipid
- Subclass: Unsaturated Fatty Acid
| Canonical Smiles | CC/C=C\C/C=C\C/C=C\CCCC/C=C\CCCC(=O)O |
|---|---|
| InChI | InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,15-16H,2,5,8,11-14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,16-15- |
| InChIKey | JDKIKEYFSJUYJZ-OUJQXAOTSA-N |
| Formula | C20H32O2 |
| HBA | 1 |
| HBD | 1 |
| MW | 304.47 |
| Rotatable Bonds | 14 |
| TPSA | 37.3 |
| LogP | 6.22 |
| Number Rings | 0 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.55 |
| Exact Mass | 304.24 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Juniperus phoenicea | Cupressaceae | Plantae | 61308 |
Showing of synonyms
Juniperonic acid
(5Z,11Z,14Z,17Z)-icosatetraenoic acid
C20:4n-3,6,9,15
(5Z,11Z,14Z,17Z)-icosa-5,11,14,17-tetraenoic acid
CHEBI:82835
(5Z,11Z,14Z,17Z)-5,11,14,17-Eicosatetraenoic Acid
5Z,11Z,14Z,17Z-Eicosatetraenoate
(all-Z)-5,11,14,17-Eicosatetraenoic acid
FA(20:4(5Z,11Z,14Z,17Z))
5Z,11Z,14Z,17Z-eicosatetraenoic acid
18016-45-0
All-cis-5,11,14,17-eicosatetraenoic acid
LMFA01030394
SCHEMBL6119205
5(Z),11(Z),14(Z),17(Z)-EICOSATETRAENOIC ACID
HY-W718408
(5Z,11Z,14Z,17Z)-eicosatetraenoic acid
All-cis-5,11,14,17-icosatetraenoic acid
NS00116320
Q27156397
- Nasri N, Tlili N, et al. (2011). Chemical compounds from Phoenician juniper berries (Juniperus phoenicea). Natural Product Research,2011,25(18),1733-1742. [View]
Pubchem:
5312543
Cas:
18016-45-0
Zinc:
ZINC000033822161
Chebi:
82835
Nmrshiftdb2:
60059230
Metabolights:
MTBLC82835
CPRiL:
84975
No scaffolds available.
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.64
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.42
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.98
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.48
- Plasma Protein Binding
- 69.4
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- 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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- -1.78
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.3
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.89
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.49
- 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
- 0.2
- Rat (Acute)
- 1.44
- Rat (Chronic Oral)
- 2.42
- Fathead Minnow
- 4.39
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Toxic
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 369.15
- Hydration Free Energy
- -4.87
- Log(D) at pH=7.4
- 2.54
- Log(P)
- 7.07
- Log S
- -3.89
- Log(Vapor Pressure)
- -6.25
- Melting Point
- -34.89
- pKa Acid
- 6.74
- pKa Basic
- 7.93
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 3 | 0.9804 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 3 | 0.9804 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.9789 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.9789 |
| thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.9477 |
| thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.9477 |
| 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase | P9WNH5 | HSAD_MYCTU | Mycobacterium tuberculosis | 3 | 0.9233 |
| 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase | P9WNH5 | HSAD_MYCTU | Mycobacterium tuberculosis | 3 | 0.9233 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8799 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8799 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7830 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7830 |
| Sodium/potassium-transporting ATPase subunit alpha | Q4H132 | Q4H132_SQUAC | Squalus acanthias | 2 | 0.7763 |
| Sodium/potassium-transporting ATPase subunit alpha | Q4H132 | Q4H132_SQUAC | Squalus acanthias | 2 | 0.7763 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7511 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7511 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 2 | 0.7486 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 2 | 0.7486 |
| 12-oxophytodienoate reductase 1 | Q9XG54 | OPR1_SOLLC | Solanum lycopersicum | 2 | 0.7410 |
| 12-oxophytodienoate reductase 1 | Q9XG54 | OPR1_SOLLC | Solanum lycopersicum | 2 | 0.7410 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7358 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7358 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7347 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7347 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7343 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7343 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7341 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7341 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7310 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7310 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 2 | 0.7298 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 2 | 0.7298 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7258 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7258 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7242 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7242 |
| Solanesyl diphosphate synthase 3, chloroplastic/mitochondrial | Q5HZ00 | SPS3_ARATH | Arabidopsis thaliana | 2 | 0.7228 |
| Solanesyl diphosphate synthase 3, chloroplastic/mitochondrial | Q5HZ00 | SPS3_ARATH | Arabidopsis thaliana | 2 | 0.7228 |
| Geranyl diphosphate synthase large subunit | Q9SBR3 | Q9SBR3_MENPI | Mentha piperita | 3 | 0.7184 |
| Geranyl diphosphate synthase large subunit | Q9SBR3 | Q9SBR3_MENPI | Mentha piperita | 3 | 0.7184 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7140 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7140 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7130 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7130 |
| Geranylgeranyl pyrophosphate synthase BTS1 | Q12051 | GGPPS_YEAST | Saccharomyces cerevisiae | 2 | 0.7119 |
| Geranylgeranyl pyrophosphate synthase BTS1 | Q12051 | GGPPS_YEAST | Saccharomyces cerevisiae | 2 | 0.7119 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7035 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7035 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7027 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7027 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7023 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7023 |
| Glutamate receptor ionotropic, kainate 1 | P22756 | GRIK1_RAT | Rattus norvegicus | 2 | 0.7017 |
| Glutamate receptor ionotropic, kainate 1 | P22756 | GRIK1_RAT | Rattus norvegicus | 2 | 0.7017 |