2-[(6aS)-2,9-dihydroxy-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-yl]acetonitrile

Details

• Internal ID: fb1f66ea-42ce-4822-9845-76d8d8b94b8c
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: 2-[(6aS)-2,9-dihydroxy-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-yl]acetonitrile
• SMILES (Canonical): COC1=C(C=C2CC3C4=C(C2=C1)C(=C(C=C4CCN3CC#N)O)OC)O
• SMILES (Isomeric): COC1=C(C=C2C[C@H]3C4=C(C2=C1)C(=C(C=C4CCN3CC#N)O)OC)O
• InChI: InChI=1S/C20H20N2O4/c1-25-17-10-13-12(9-15(17)23)7-14-18-11(3-5-22(14)6-4-21)8-16(24)20(26-2)19(13)18/h8-10,14,23-24H,3,5-7H2,1-2H3/t14-/m0/s1
• InChI Key: GITOUTAPMZCUDL-AWEZNQCLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀N₂O₄
• Molecular Weight: 352.40 g/mol
• Exact Mass: 352.14230712 g/mol
• Topological Polar Surface Area (TPSA): 86.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.76
• 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	+	0.6972	69.72%
Caco-2	+	0.6523	65.23%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7756	77.56%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.8929	89.29%
OATP1B3 inhibitior	+	0.9413	94.13%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.6480	64.80%
P-glycoprotein inhibitior	-	0.7626	76.26%
P-glycoprotein substrate	-	0.6683	66.83%
CYP3A4 substrate	+	0.6104	61.04%
CYP2C9 substrate	+	0.5955	59.55%
CYP2D6 substrate	+	0.7919	79.19%
CYP3A4 inhibition	-	0.9133	91.33%
CYP2C9 inhibition	-	0.8814	88.14%
CYP2C19 inhibition	-	0.6841	68.41%
CYP2D6 inhibition	-	0.5249	52.49%
CYP1A2 inhibition	+	0.5673	56.73%
CYP2C8 inhibition	+	0.4866	48.66%
CYP inhibitory promiscuity	-	0.6763	67.63%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6900	69.00%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9386	93.86%
Skin irritation	-	0.7606	76.06%
Skin corrosion	-	0.9533	95.33%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5580	55.80%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.9047	90.47%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8392	83.92%
Acute Oral Toxicity (c)	III	0.6596	65.96%
Estrogen receptor binding	+	0.6934	69.34%
Androgen receptor binding	-	0.5143	51.43%
Thyroid receptor binding	+	0.6634	66.34%
Glucocorticoid receptor binding	+	0.8767	87.67%
Aromatase binding	+	0.5527	55.27%
PPAR gamma	+	0.7861	78.61%
Honey bee toxicity	-	0.8111	81.11%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5051	50.51%
Fish aquatic toxicity	-	0.3709	37.09%

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	99.35%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.92%	91.11%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	95.66%	91.79%
CHEMBL217	P14416	Dopamine D2 receptor	95.32%	95.62%
CHEMBL2581	P07339	Cathepsin D	94.91%	98.95%
CHEMBL2535	P11166	Glucose transporter	91.22%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.08%	92.94%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	90.30%	96.25%
CHEMBL5747	Q92793	CREB-binding protein	89.10%	95.12%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.98%	86.33%
CHEMBL4208	P20618	Proteasome component C5	88.27%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.70%	89.62%
CHEMBL3438	Q05513	Protein kinase C zeta	87.59%	88.48%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.43%	99.17%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.33%	91.03%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.96%	82.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.62%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.70%	89.00%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	81.39%	89.32%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.02%	92.38%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.59%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.29%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.20%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.01%	92.62%

Plants that contains it

• Alseodaphne perakensis

Cross-Links

• PubChem: 162869381
• LOTUS: LTS0019238
• wikiData: Q105009201