2,9,10-Trimethoxy-4a,8,11,13a-tetrahydro-5H-isoquinolino[2,3-a]quinolin-3-ol

Details

• Internal ID: 2c368186-eb58-489a-bf7b-f6057e2271b9
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Hydropyridines > Tetrahydropyridines
• IUPAC Name: 2,9,10-trimethoxy-5,8,11,13a-tetrahydro-4aH-isoquinolino[2,3-a]quinolin-3-ol
• SMILES (Canonical): COC1=C(CC2=CN3C4C=C(C(=CC4CC=C3C=C2C1)O)OC)OC
• SMILES (Isomeric): COC1=C(CC2=CN3C4C=C(C(=CC4CC=C3C=C2C1)O)OC)OC
• InChI: InChI=1S/C20H23NO4/c1-23-18-10-16-12(7-17(18)22)4-5-15-6-13-8-19(24-2)20(25-3)9-14(13)11-21(15)16/h5-7,10-12,16,22H,4,8-9H2,1-3H3
• InChI Key: WWVOQNBJYPKUTR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.40 g/mol
• Exact Mass: 341.16270821 g/mol
• Topological Polar Surface Area (TPSA): 51.20 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 3.67
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 2,9,10-Trimethoxy-4a,8,11,13a-tetrahydro-5H-isoquinolino[2,3-a]quinolin-3-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9418	94.18%
Caco-2	+	0.8649	86.49%
Blood Brain Barrier	+	0.6070	60.70%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5343	53.43%
OATP2B1 inhibitior	-	0.8645	86.45%
OATP1B1 inhibitior	+	0.8989	89.89%
OATP1B3 inhibitior	+	0.9504	95.04%
MATE1 inhibitior	-	0.6833	68.33%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8942	89.42%
P-glycoprotein inhibitior	-	0.5467	54.67%
P-glycoprotein substrate	-	0.6700	67.00%
CYP3A4 substrate	+	0.5494	54.94%
CYP2C9 substrate	-	0.5954	59.54%
CYP2D6 substrate	-	0.7555	75.55%
CYP3A4 inhibition	-	0.5271	52.71%
CYP2C9 inhibition	-	0.8050	80.50%
CYP2C19 inhibition	-	0.6278	62.78%
CYP2D6 inhibition	+	0.5000	50.00%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.6018	60.18%
CYP inhibitory promiscuity	+	0.5693	56.93%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4632	46.32%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.9649	96.49%
Skin irritation	-	0.7331	73.31%
Skin corrosion	-	0.9332	93.32%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4710	47.10%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	+	0.5216	52.16%
skin sensitisation	-	0.8549	85.49%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6623	66.23%
Acute Oral Toxicity (c)	III	0.6452	64.52%
Estrogen receptor binding	+	0.6564	65.64%
Androgen receptor binding	-	0.5097	50.97%
Thyroid receptor binding	+	0.7380	73.80%
Glucocorticoid receptor binding	+	0.6551	65.51%
Aromatase binding	-	0.4903	49.03%
PPAR gamma	+	0.6709	67.09%
Honey bee toxicity	-	0.8965	89.65%
Biodegradation	-	1.0000	100.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	-	0.4311	43.11%

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	94.27%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.09%	96.09%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	88.33%	92.68%
CHEMBL2581	P07339	Cathepsin D	87.97%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.92%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.38%	86.33%
CHEMBL4208	P20618	Proteasome component C5	82.57%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.80%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.29%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.57%	94.08%

Plants that contains it

• Berberis julianae
• Corydalis incisa
• Corydalis yanhusuo
• Uncaria macrophylla

Cross-Links

• PubChem: 3083926
• NPASS: NPC198462