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Punicic acid
- Family: Plantae - Cucurbitaceae
- Kingdom: Plantae
-
Class: Lipid
- Subclass: Fatty Acid
| Canonical Smiles | CCCC/C=C\C=C\C=C/CCCCCCCC(=O)O |
|---|---|
| InChI | InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5-,8-7+,10-9- |
| InChIKey | CUXYLFPMQMFGPL-BGDVVUGTSA-N |
| Formula | C18H30O2 |
| HBA | 1 |
| HBD | 1 |
| MW | 278.44 |
| Rotatable Bonds | 13 |
| TPSA | 37.3 |
| LogP | 5.66 |
| Number Rings | 0 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.61 |
| Exact Mass | 278.22 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ecballium elaterium | Cucurbitaceae | Plantae | 3679 |
Showing of synonyms
Punicic acid
Trichosanic acid
544-72-9
Trichosanoic acid
(9Z,11E,13Z)-octadeca-9,11,13-trienoic acid
9-cis,11-trans,13-cis-octadecatrienoic acid
Cis-9,trans-11,cis-13-Octadecatrienoic acid
UNII-VFQ03H211O
VFQ03H211O
9,11,13-Octadecatrienoic acid, (9Z,11E,13Z)-
9,11,13-Octadecatrienoic acid, (Z,Z,E)-
Cis,trans,cis-9,11,13-Octadecatrienoic acid
9Z,11E,13Z-octadeca-9,11,13-trienoic acid
9c,11t,13c-linolenic acid
CHEBI:8638
DTXSID10897463
Octadeca-9c,11t,13c-triensaeure
Octadeca-9c,11t,13c-trienoic acid
(9Z,11E,13Z)-octadecatrienoic acid
9cis,11trans,13cis-octadecatrienoic acid
(Z,E,Z)-octadeca-9,11,13-trienoic acid
Fatty Acid 18:3 n-5
DTXCID801326803
Cis,trans,cis-octadeca-9,11,13-trienoic acid
9(Z),11(E),13(Z)-OCTADECATRIENOIC ACID
9Z,11E,13Z-octadecatrienoic acid
Cis-9, trans-11, cis-13-octadecatrienoic acid
Punicinic acid
9c,11t,13c-18:3
C18:3 n-5 cis, 7 trans, 9 cis
SCHEMBL158967
CHEMBL5205249
LMFA01030146
PD088520
HY-139066
CS-0179308
C08364
Q201502
9(Z) pound not11(E) pound not13(Z)-Octadecatrienoic Acid
- Touihri I, Kallech-Ziri O, et al. (2019). Ecballium elaterium (L.) A. Rich. seed oil: Chemical composition and antiproliferative effect on human colonic adenocarcinoma and fibrosarcoma cancer cell lines. Arabian Journal of Chemistry, 2019, 12(8), 2347-2355. [View]
Pubchem:
5281126
Cas:
544-72-9
Zinc:
ZINC000016343346
Kegg Ligand:
C08364
Chebi:
8638
Nmrshiftdb2:
70000706
Metabolights:
MTBLC8638
Chembl:
CHEMBL5205249
Comptox:
DTXSID10897463
CPRiL:
68857
No scaffolds available.
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.68
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.27
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.88
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.37
- Plasma Protein Binding
- 60.33
- 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
- -1.27
- 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
- 1.21
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 3.86
- 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
- 2.35
- Rat (Acute)
- 1.77
- Rat (Chronic Oral)
- 2.39
- Fathead Minnow
- 4.11
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 360.68
- Hydration Free Energy
- -5.1
- Log(D) at pH=7.4
- 2.63
- Log(P)
- 6.48
- Log S
- -3.63
- Log(Vapor Pressure)
- -6.15
- Melting Point
- 51.69
- pKa Acid
- 7.12
- pKa Basic
- 7.66
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.9809 |
| thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.9750 |
| 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase | P9WNH5 | HSAD_MYCTU | Mycobacterium tuberculosis | 3 | 0.9605 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.9496 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8954 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8717 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.8188 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 3 | 0.8066 |
| Sodium/potassium-transporting ATPase subunit alpha | Q4H132 | Q4H132_SQUAC | Squalus acanthias | 2 | 0.7727 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7682 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7490 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 2 | 0.7489 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7482 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7480 |
| 12-oxophytodienoate reductase 1 | Q9XG54 | OPR1_SOLLC | Solanum lycopersicum | 2 | 0.7469 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7461 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 2 | 0.7429 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7420 |
| Geranyl diphosphate synthase large subunit | Q9SBR3 | Q9SBR3_MENPI | Mentha piperita | 3 | 0.7407 |
| Solanesyl diphosphate synthase 3, chloroplastic/mitochondrial | Q5HZ00 | SPS3_ARATH | Arabidopsis thaliana | 2 | 0.7375 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7373 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 2 | 0.7360 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7351 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7326 |
| Geranylgeranyl pyrophosphate synthase BTS1 | Q12051 | GGPPS_YEAST | Saccharomyces cerevisiae | 2 | 0.7307 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7255 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 2 | 0.7249 |
| Carboxyethyl-arginine beta-lactam-synthase | P0DJQ7 | BLS_STRCL | Streptomyces clavuligerus | 2 | 0.7215 |
| Glutamate receptor ionotropic, kainate 1 | P22756 | GRIK1_RAT | Rattus norvegicus | 2 | 0.7212 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7202 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 2 | 0.7181 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 2 | 0.7164 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7160 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7159 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7150 |
| Farnesyl pyrophosphate synthase | P14324 | FPPS_HUMAN | Homo sapiens | 2 | 0.7103 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 2 | 0.7047 |
| Pyrrolysine--tRNA ligase | Q8PWY1 | PYLS_METMA | Methanosarcina mazei | 2 | 0.7039 |
| Isopenicillin N synthase | P05326 | IPNS_EMENI | Emericella nidulans | 2 | 0.7031 |
| o-succinylbenzoate synthase | P29208 | MENC_ECOLI | Escherichia coli | 2 | 0.7026 |