Toussaintine A

Details

• Internal ID: 398db406-6603-4de9-8bda-3bf61f97e451
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives
• IUPAC Name: (3aR,7aS)-3a-hydroxy-1-[(E)-3-phenylprop-2-enoyl]-7,7a-dihydro-3H-indole-2,6-dione
• 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
• InChI Key: QCYNQLVLOBLZFY-MFTLYIETSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₅NO₄
• Molecular Weight: 297.30 g/mol
• Exact Mass: 297.10010796 g/mol
• Topological Polar Surface Area (TPSA): 74.70 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.09
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• CHEBI:232496
• (3aR,7aS)-3a-hydroxy-1-[(E)-3-phenylprop-2-enoyl]-7,7a-dihydro-3H-indole-2,6-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	-	0.5259	52.59%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6143	61.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9348	93.48%
OATP1B3 inhibitior	+	0.9429	94.29%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.8273	82.73%
P-glycoprotein substrate	-	0.8328	83.28%
CYP3A4 substrate	+	0.5256	52.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8330	83.30%
CYP3A4 inhibition	-	0.8990	89.90%
CYP2C9 inhibition	-	0.8603	86.03%
CYP2C19 inhibition	-	0.8677	86.77%
CYP2D6 inhibition	-	0.9255	92.55%
CYP1A2 inhibition	-	0.8819	88.19%
CYP2C8 inhibition	-	0.7721	77.21%
CYP inhibitory promiscuity	-	0.9017	90.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4997	49.97%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.8983	89.83%
Skin irritation	-	0.7574	75.74%
Skin corrosion	-	0.9389	93.89%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5285	52.85%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	-	0.5731	57.31%
skin sensitisation	-	0.8815	88.15%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.5516	55.16%
Acute Oral Toxicity (c)	III	0.5664	56.64%
Estrogen receptor binding	+	0.6938	69.38%
Androgen receptor binding	+	0.7376	73.76%
Thyroid receptor binding	-	0.6260	62.60%
Glucocorticoid receptor binding	-	0.4810	48.10%
Aromatase binding	+	0.6348	63.48%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9428	94.28%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.8311	83.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.38%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.12%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.13%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.23%	86.33%
CHEMBL2581	P07339	Cathepsin D	89.09%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.68%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.50%	94.62%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.72%	94.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.71%	89.00%
CHEMBL5028	O14672	ADAM10	83.15%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.13%	94.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.98%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.63%	93.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.38%	85.14%

Plants that contains it

• Toussaintia orientalis

Cross-Links

• PubChem: 54578251
• LOTUS: LTS0056886
• wikiData: Q105218664