(6aR)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-3,9-diol

Details

• Internal ID: d44af106-b5c3-4ff5-bd45-eab91d527d0d
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (6aR)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-3,9-diol
• SMILES (Canonical): CN1CCC2=C3C1CC4=CC(=C(C=C4C3=C(C(=C2O)OC)OC)OC)O
• SMILES (Isomeric): CN1CCC2=C3[C@H]1CC4=CC(=C(C=C4C3=C(C(=C2O)OC)OC)OC)O
• InChI: InChI=1S/C20H23NO5/c1-21-6-5-11-16-13(21)7-10-8-14(22)15(24-2)9-12(10)17(16)19(25-3)20(26-4)18(11)23/h8-9,13,22-23H,5-7H2,1-4H3/t13-/m1/s1
• InChI Key: QXYCMLRBKSSDAI-CYBMUJFWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₃NO₅
• Molecular Weight: 357.40 g/mol
• Exact Mass: 357.15762283 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.88
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8694	86.94%
Caco-2	+	0.8611	86.11%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5046	50.46%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.8808	88.08%
OATP1B3 inhibitior	+	0.9370	93.70%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.4523	45.23%
P-glycoprotein inhibitior	-	0.8787	87.87%
P-glycoprotein substrate	-	0.6530	65.30%
CYP3A4 substrate	+	0.6392	63.92%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.8855	88.55%
CYP2C9 inhibition	-	0.9013	90.13%
CYP2C19 inhibition	-	0.8664	86.64%
CYP2D6 inhibition	+	0.7346	73.46%
CYP1A2 inhibition	+	0.8785	87.85%
CYP2C8 inhibition	-	0.6033	60.33%
CYP inhibitory promiscuity	-	0.9660	96.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6960	69.60%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9091	90.91%
Skin irritation	-	0.7568	75.68%
Skin corrosion	-	0.9344	93.44%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6639	66.39%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.6199	61.99%
skin sensitisation	-	0.8911	89.11%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.9418	94.18%
Acute Oral Toxicity (c)	III	0.6311	63.11%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.5684	56.84%
Thyroid receptor binding	+	0.6404	64.04%
Glucocorticoid receptor binding	+	0.7667	76.67%
Aromatase binding	+	0.5554	55.54%
PPAR gamma	+	0.6476	64.76%
Honey bee toxicity	-	0.8924	89.24%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.8962	89.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.13%	96.09%
CHEMBL217	P14416	Dopamine D2 receptor	98.20%	95.62%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	96.57%	91.79%
CHEMBL2056	P21728	Dopamine D1 receptor	95.82%	91.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.32%	91.11%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	92.98%	91.03%
CHEMBL2581	P07339	Cathepsin D	92.93%	98.95%
CHEMBL4208	P20618	Proteasome component C5	92.90%	90.00%
CHEMBL5747	Q92793	CREB-binding protein	92.48%	95.12%
CHEMBL1951	P21397	Monoamine oxidase A	92.35%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.44%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.35%	93.40%
CHEMBL3438	Q05513	Protein kinase C zeta	89.95%	88.48%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.06%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.00%	95.89%
CHEMBL2535	P11166	Glucose transporter	88.95%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.60%	89.62%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.42%	82.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.74%	89.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	83.42%	96.86%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.41%	92.94%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	83.31%	95.70%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.11%	85.14%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	83.08%	95.34%
CHEMBL3474	P14555	Phospholipase A2 group IIA	83.04%	94.05%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.01%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.37%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.75%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.36%	89.50%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	80.23%	89.32%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.09%	90.71%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.00%	93.03%

Plants that contains it

• Delphinium dictyocarpum

Cross-Links

• PubChem: 162985664
• LOTUS: LTS0266411
• wikiData: Q105229964