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Toussaintine A
- Family: Plantae - Annonaceae
- Kingdom: Plantae
-
Class: Amide
- Subclass: N-Cinnamoyltetraketide
| Canonical Smiles | O=C1C=C[C@]2([C@H](C1)N(C(=O)/C=C/c1ccccc1)C(=O)C2)O |
|---|---|
| InChI | InChI=1S/C17H15NO4/c19-13-8-9-17(22)11-16(21)18(14(17)10-13)15(20)7-6-12-4-2-1-3-5-12/h1-9,14,22H,10-11H2/b7-6+/t14-,17-/m0/s1 |
| InChIKey | QCYNQLVLOBLZFY-MFTLYIETSA-N |
| Formula | C17H15NO4 |
| HBA | 4 |
| HBD | 1 |
| MW | 297.31 |
| Rotatable Bonds | 2 |
| TPSA | 74.68 |
| LogP | 1.09 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.24 |
| Exact Mass | 297.1 |
| 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 A
CHEBI:232496
(3aR,7aS)-3a-hydroxy-1-[(E)-3-phenylprop-2-enoyl]-7,7a-dihydro-3H-indole-2,6-dione
- 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: C1=CC(=O)CC(C12)N(C(=O)C2)C(=O)C=Cc3ccccc3
Level: 1
Mol. Weight: 297.31 g/mol
SMILES: C1C(=O)NC(C12)CC(=O)C=C2
Level: 0
Mol. Weight: 297.31 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 297.31 g/mol
Antibacterial
Antifungal
Antimycobacterial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.47
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.320
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.57
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.540
- Plasma Protein Binding
- 68.42
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.800
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.120
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.950
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.290
- Micronucleos
- Toxic
- 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
- 0.430
- Rat (Acute)
- 2.550
- Rat (Chronic Oral)
- 2.330
- Fathead Minnow
- 4.110
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 384.970
- Hydration Free Energy
- -11.300
- Log(D) at pH=7.4
- 1.290
- Log(P)
- 1.19
- Log S
- -3.37
- Log(Vapor Pressure)
- -7.95
- Melting Point
- 174.09
- pKa Acid
- 8.84
- pKa Basic
- 5.9
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8446 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8446 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8402 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8402 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8066 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8066 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 3 | 0.7899 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 3 | 0.7899 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7809 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7809 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7728 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7728 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 | O88703 | HCN2_MOUSE | Mus musculus | 3 | 0.7589 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 | O88703 | HCN2_MOUSE | Mus musculus | 3 | 0.7589 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7441 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7441 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7359 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7359 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7352 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7352 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7346 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7346 |
| Lethal factor | P15917 | LEF_BACAN | Bacillus anthracis | 3 | 0.7338 |
| Lethal factor | P15917 | LEF_BACAN | Bacillus anthracis | 3 | 0.7338 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7333 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7333 |
| AcsD | Q93AT8 | Q93AT8_DICCH | Dickeya chrysanthemi | 3 | 0.7316 |
| AcsD | Q93AT8 | Q93AT8_DICCH | Dickeya chrysanthemi | 3 | 0.7316 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7313 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7313 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7308 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7308 |
| Nucleoside diphosphate kinase | Q9U1E1 | Q9U1E1_LEIMA | Leishmania major | 3 | 0.7285 |
| Nucleoside diphosphate kinase | Q9U1E1 | Q9U1E1_LEIMA | Leishmania major | 3 | 0.7285 |
| Non-receptor tyrosine-protein kinase TYK2 | P29597 | TYK2_HUMAN | Homo sapiens | 2 | 0.7279 |
| Non-receptor tyrosine-protein kinase TYK2 | P29597 | TYK2_HUMAN | Homo sapiens | 2 | 0.7279 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7181 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7181 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 2 | 0.7172 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 2 | 0.7172 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7169 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7169 |
| Alanine racemase | Q180W0 | Q180W0_CLOD6 | Clostridioides difficile | 2 | 0.7162 |
| Alanine racemase | Q180W0 | Q180W0_CLOD6 | Clostridioides difficile | 2 | 0.7162 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 2 | 0.7143 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 2 | 0.7143 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7141 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7141 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7086 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7086 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7085 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7085 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 2 | 0.7042 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 2 | 0.7042 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7041 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7041 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7040 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7040 |
| Polymerase basic protein 2 | P31345 | PB2_I75A3 | Influenza A virus | 2 | 0.7037 |
| Polymerase basic protein 2 | P31345 | PB2_I75A3 | Influenza A virus | 2 | 0.7037 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7024 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7024 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7017 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7017 |
| Pyruvate:ferredoxin oxidoreductase | P94692 | PFOR_DESAF | Desulfocurvibacter africanus | 3 | 0.7001 |
| Pyruvate:ferredoxin oxidoreductase | P94692 | PFOR_DESAF | Desulfocurvibacter africanus | 3 | 0.7001 |