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9,12,13-trihydroxyoctadecadienoic acid
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
- Class: Fatty Acid
Canonical Smiles | CCCCCC(C(CCC(CCC/C=C/C=C/C(=O)O)O)O)O |
---|---|
InChI | InChI=1S/C18H32O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h4,6,9,12,15-17,19-21H,2-3,5,7-8,10-11,13-14H2,1H3,(H,22,23)/b6-4+,12-9+ |
InChIKey | CIIIRTKAWCRSFV-ISVYGWFVSA-N |
Formula | C18H32O5 |
HBA | 4 |
HBD | 4 |
MW | 328.45 |
Rotatable Bonds | 14 |
TPSA | 97.99 |
LogP | 2.8 |
Number Rings | 0 |
Number Aromatic Rings | 0 |
Heavy Atom Count | 23 |
Formal Charge | 0 |
Fraction CSP3 | 0.72 |
Exact Mass | 328.22 |
Number of Lipinski Rule Violations | 0 |
# | Species | Family | Kingdom | NCBI Taxonomy ID |
---|---|---|---|---|
1 | Ammoides atlantica | Apiaceae | Plantae | 386050 |
2 | Rosmarinuseriocalyx | Lamiaceae | Plantae | — |
Showing of synonyms
9,12,13-trihydroxyoctadecadienoic acid
- Benteldjoune M, Boudiar T, et al. (2021). Antioxidant activity and characterization of flavonoids and phenolic acids of Ammoides atlantica by RP–UHPLC– ESI–QTOF–MS. Nat Prod Res, 2021, 35(10), 1639-1643.. [View] [PubMed]
- Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]
No compound-protein relationship available.
No scaffolds available.
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.54
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.85
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.64
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.63
- Plasma Protein Binding
- 14.32
- 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
- 1.91
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -1.6
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.96
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.33
- 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
- 4.12
- Rat (Acute)
- 1.73
- Rat (Chronic Oral)
- 3.01
- Fathead Minnow
- 4.04
- 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
- 388.8
- Hydration Free Energy
- -9.75
- Log(D) at pH=7.4
- -0.13
- Log(P)
- 2.64
- Log S
- -2.74
- Log(Vapor Pressure)
- -8.88
- Melting Point
- 84.33
- pKa Acid
- 5.78
- pKa Basic
- 5.8
Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
---|---|---|---|---|---|
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.9474 |
Bile salt hydrolase/transferase | P54965 | CBH_CLOPE | Clostridium perfringens | 3 | 0.9269 |
Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9053 |
Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.8959 |
Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 3 | 0.8892 |
Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8845 |
Iota toxin component Ia | Q46220 | Q46220_CLOPF | Clostridium perfringens | 3 | 0.8728 |
Regulatory protein SdiA | P07026 | SDIA_ECOLI | Escherichia coli | 4 | 0.8711 |
Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8699 |
4-alpha-glucanotransferase | O87172 | MALQ_THETH | Thermus thermophilus | 3 | 0.8630 |
Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 3 | 0.8535 |
Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.8526 |
Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 3 | 0.8481 |
Glycogen synthase | P0A6U8 | GLGA_ECOLI | Escherichia coli | 3 | 0.8405 |
Alpha/beta hydrolase fold protein | D2J2T6 | D2J2T6_9RHIZ | Ochrobactrum sp. T63 | 3 | 0.8402 |
Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.8362 |
Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8328 |
Beta-glucosidase A | Q08638 | BGLA_THEMA | Thermotoga maritima | 3 | 0.8270 |
Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8233 |
Glycogenin-1 | P46976 | GLYG_HUMAN | Homo sapiens | 3 | 0.8197 |
Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.8185 |
beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.8078 |
Phenolphthiocerol/phthiocerol polyketide synthase subunit C | P96202 | PPSC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8074 |
Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.8064 |
Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.8020 |
Beta-glucosidase | Q8T0W7 | Q8T0W7_9NEOP | Neotermes koshunensis | 3 | 0.8015 |
Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 4 | 0.7961 |
ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7868 |
Beta-glucosidase 1A | Q25BW5 | BGL1A_PHACH | Phanerodontia chrysosporium | 3 | 0.7864 |
Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7850 |
Fluoroacetyl-CoA thioesterase | Q1EMV2 | FLK_STRCT | Streptantibioticus cattleyicolor | 3 | 0.7841 |
Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7778 |
Lysosomal acid glucosylceramidase | P04062 | GLCM_HUMAN | Homo sapiens | 3 | 0.7770 |
Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7746 |
Glucosidase II subunit alpha | Q9STC1 | Q9STC1_GRALE | Gracilariopsis lemaneiformis | 3 | 0.7731 |
Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7725 |
Lactose operon repressor | P03023 | LACI_ECOLI | Escherichia coli | 3 | 0.7700 |
Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7694 |
Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7651 |
Ascorbate-specific PTS system EIIC component | P39301 | ULAA_ECOLI | Escherichia coli | 3 | 0.7650 |
Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7630 |
Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7588 |
Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7584 |
Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.7571 |
Fatty acid-binding protein 2, liver | P81400 | FABP2_AMBME | Ambystoma mexicanum | 3 | 0.7548 |
Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7474 |
Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7406 |
Regucalcin | Q64374 | RGN_MOUSE | Mus musculus | 3 | 0.7382 |
Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7320 |
Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7313 |
11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7300 |
Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 2 | 0.7294 |
Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7283 |
TamL | D3Y1I2 | D3Y1I2_9ACTN | Streptomyces sp. 307-9 | 2 | 0.7202 |
Glucosidase II subunit alpha | Q9STC1 | Q9STC1_GRALE | Gracilariopsis lemaneiformis | 3 | 0.7194 |
thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.7178 |
Reaction center protein L chain | P0C0Y8 | RCEL_RHOSH | Rhodobacter sphaeroides | 3 | 0.7172 |
Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7160 |
Raucaffricine-O-beta-D-glucosidase | Q9SPP9 | RG1_RAUSE | Rauvolfia serpentina | 3 | 0.7142 |
Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7140 |
Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7140 |
Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7120 |
Carnitine O-acetyltransferase | P47934 | CACP_MOUSE | Mus musculus | 2 | 0.7117 |
Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7100 |
Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7095 |
Sodium/potassium-transporting ATPase subunit alpha | Q4H132 | Q4H132_SQUAC | Squalus acanthias | 2 | 0.7063 |
N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7051 |
Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7029 |
Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7000 |