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Toussaintine D
- Family: Plantae - Annonaceae
- Kingdom: Plantae
-
Class: Amide
- Subclass: N-Cinnamoyltetraketide
| Canonical Smiles | O=C(N[C@@H]1O[C@@H]2[C@](C1)(O)C=CC(=O)C2)/C=C/c1ccccc1 |
|---|---|
| InChI | InChI=1S/C17H17NO4/c19-13-8-9-17(21)11-16(22-14(17)10-13)18-15(20)7-6-12-4-2-1-3-5-12/h1-9,14,16,21H,10-11H2,(H,18,20)/b7-6+/t14-,16+,17-/m0/s1 |
| InChIKey | DPHMUUPBVSFDQB-YZHNWMQMSA-N |
| Formula | C17H17NO4 |
| HBA | 4 |
| HBD | 2 |
| MW | 299.33 |
| Rotatable Bonds | 3 |
| TPSA | 75.63 |
| LogP | 1.19 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 299.12 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Toussaintia orientalis | Annonaceae | Plantae | 489350 |
| 2 | Toussaintia orientalis | Annonaceae | Plantae | 489350 |
Showing of synonyms
Toussaintine D
- Nyandoro SS, Ndanu J, et al. (2015). N-Cinnamoyltetraketide derivatives from the leaves of Toussaintia orientalis. Journal of Natural Products,2015,78(8),2045-2050. [View] [PubMed]
- Samwel S, Odalo JO, et al. (2011). Toussaintines A-E: antimicrobial indolidinoids, a cinnamoylhydrobenzofuranoid and a cinnamoylcyclohexenoid from Toussaintia orientalis leaves. Phytochemistry,2011,72(14-15),1826-1832. [View] [PubMed]
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)NC(C2)OC(C23)CC(=O)C=C3
Level: 1
Mol. Weight: 299.33 g/mol
SMILES: C1COC(C12)CC(=O)C=C2
Level: 0
Mol. Weight: 299.33 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 299.33 g/mol
Antibacterial
Antifungal
Antimycobacterial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.75
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.27
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.05
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.7
- Plasma Protein Binding
- 65.6
- 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
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-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
- 4.36
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.4
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.23
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.98
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Toxic
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -0.53
- Rat (Acute)
- 2.91
- Rat (Chronic Oral)
- 2.08
- Fathead Minnow
- 3.95
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 397.47
- Hydration Free Energy
- -14.38
- Log(D) at pH=7.4
- 1.31
- Log(P)
- 1.4
- Log S
- -2.94
- Log(Vapor Pressure)
- -9.05
- Melting Point
- 182.9
- pKa Acid
- 8.88
- pKa Basic
- 6.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.9608 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.9608 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.9553 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.9553 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.9110 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.9110 |
| Ascorbate-specific PTS system EIIC component | P39301 | ULAA_ECOLI | Escherichia coli | 3 | 0.8657 |
| Ascorbate-specific PTS system EIIC component | P39301 | ULAA_ECOLI | Escherichia coli | 3 | 0.8657 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.8591 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.8591 |
| Cyclin-dependent kinase 8 | P49336 | CDK8_HUMAN | Homo sapiens | 3 | 0.8585 |
| Cyclin-dependent kinase 8 | P49336 | CDK8_HUMAN | Homo sapiens | 3 | 0.8585 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8521 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8521 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 3 | 0.8485 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 3 | 0.8485 |
| Purine nucleoside phosphorylase DeoD-type | Q5EEL8 | DEOD_BACCE | Bacillus cereus | 3 | 0.8276 |
| Purine nucleoside phosphorylase DeoD-type | Q5EEL8 | DEOD_BACCE | Bacillus cereus | 3 | 0.8276 |
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 3 | 0.8219 |
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 3 | 0.8219 |
| Iota toxin component Ia | Q46220 | Q46220_CLOPF | Clostridium perfringens | 3 | 0.8161 |
| Iota toxin component Ia | Q46220 | Q46220_CLOPF | Clostridium perfringens | 3 | 0.8161 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7727 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7727 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7528 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7528 |
| Caffeoyl-CoA O-methyltransferase | Q40313 | CAMT_MEDSA | Medicago sativa | 3 | 0.7473 |
| Caffeoyl-CoA O-methyltransferase | Q40313 | CAMT_MEDSA | Medicago sativa | 3 | 0.7473 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 2 | 0.7447 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 2 | 0.7447 |
| Purine nucleoside phosphorylase DeoD-type | Q5EEL8 | DEOD_BACCE | Bacillus cereus | 3 | 0.7418 |
| Purine nucleoside phosphorylase DeoD-type | Q5EEL8 | DEOD_BACCE | Bacillus cereus | 3 | 0.7418 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7415 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7415 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7362 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7362 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7348 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7348 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7336 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7336 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7192 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7192 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7175 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7175 |
| Polymerase basic protein 2 | P31345 | PB2_I75A3 | Influenza A virus | 2 | 0.7061 |
| Polymerase basic protein 2 | P31345 | PB2_I75A3 | Influenza A virus | 2 | 0.7061 |
| Multidrug efflux pump subunit AcrB | P31224 | ACRB_ECOLI | Escherichia coli | 3 | 0.7060 |
| Multidrug efflux pump subunit AcrB | P31224 | ACRB_ECOLI | Escherichia coli | 3 | 0.7060 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7032 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7032 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7032 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7032 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7029 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7029 |
| 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase | P9WNH5 | HSAD_MYCTU | Mycobacterium tuberculosis | 3 | 0.7024 |
| 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase | P9WNH5 | HSAD_MYCTU | Mycobacterium tuberculosis | 3 | 0.7024 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 3 | 0.7022 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 3 | 0.7022 |
| Type II methyltransferase M.HhaI | P05102 | MTH1_HAEPH | Haemophilus parahaemolyticus | 2 | 0.7004 |
| Type II methyltransferase M.HhaI | P05102 | MTH1_HAEPH | Haemophilus parahaemolyticus | 2 | 0.7004 |