(13aR)-12-[[(6aS)-1,2,3,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-9-yl]oxy]-2,3,10,11-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline

Details

• Internal ID: e659b6d1-70e8-448c-8518-6b21cbfc272f
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (13aR)-12-[[(6aS)-1,2,3,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-9-yl]oxy]-2,3,10,11-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
• SMILES (Canonical): CN1CCC2=C3C1CC4=CC(=C(C=C4C3=C(C(=C2OC)OC)OC)OC)OC5=C6CC7C8=CC(=C(C=C8CCN7CC6=CC(=C5OC)OC)OC)OC
• SMILES (Isomeric): CN1CCC2=C3[C@@H]1CC4=CC(=C(C=C4C3=C(C(=C2OC)OC)OC)OC)OC5=C6C[C@@H]7C8=CC(=C(C=C8CCN7CC6=CC(=C5OC)OC)OC)OC
• InChI: InChI=1S/C42H48N2O9/c1-43-12-11-25-36-30(43)14-23-16-34(33(47-4)20-27(23)37(36)41(51-8)42(52-9)38(25)49-6)53-39-28-18-29-26-19-32(46-3)31(45-2)15-22(26)10-13-44(29)21-24(28)17-35(48-5)40(39)50-7/h15-17,19-20,29-30H,10-14,18,21H2,1-9H3/t29-,30+/m1/s1
• InChI Key: AFLFUXQTWZZMDX-IHLOFXLRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₄₈N₂O₉
• Molecular Weight: 724.80 g/mol
• Exact Mass: 724.33598111 g/mol
• Topological Polar Surface Area (TPSA): 89.60 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 6.96
• H-Bond Acceptor: 11
• H-Bond Donor: 0
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9293	92.93%
Caco-2	-	0.6772	67.72%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.4766	47.66%
OATP2B1 inhibitior	-	0.7020	70.20%
OATP1B1 inhibitior	+	0.8746	87.46%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9946	99.46%
P-glycoprotein inhibitior	+	0.9269	92.69%
P-glycoprotein substrate	+	0.5794	57.94%
CYP3A4 substrate	+	0.7068	70.68%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8198	81.98%
CYP3A4 inhibition	-	0.8225	82.25%
CYP2C9 inhibition	-	0.9728	97.28%
CYP2C19 inhibition	-	0.9563	95.63%
CYP2D6 inhibition	-	0.8766	87.66%
CYP1A2 inhibition	-	0.8517	85.17%
CYP2C8 inhibition	+	0.6469	64.69%
CYP inhibitory promiscuity	-	0.9442	94.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6363	63.63%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9275	92.75%
Skin irritation	-	0.7789	77.89%
Skin corrosion	-	0.9466	94.66%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9272	92.72%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.6199	61.99%
skin sensitisation	-	0.9016	90.16%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6697	66.97%
Acute Oral Toxicity (c)	III	0.7427	74.27%
Estrogen receptor binding	+	0.8162	81.62%
Androgen receptor binding	+	0.7034	70.34%
Thyroid receptor binding	+	0.6003	60.03%
Glucocorticoid receptor binding	+	0.8276	82.76%
Aromatase binding	+	0.6703	67.03%
PPAR gamma	+	0.7319	73.19%
Honey bee toxicity	-	0.7534	75.34%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.7500	75.00%
Fish aquatic toxicity	+	0.8553	85.53%

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	98.84%	96.09%
CHEMBL217	P14416	Dopamine D2 receptor	98.28%	95.62%
CHEMBL5747	Q92793	CREB-binding protein	97.32%	95.12%
CHEMBL2056	P21728	Dopamine D1 receptor	96.81%	91.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	95.96%	91.79%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.73%	93.40%
CHEMBL240	Q12809	HERG	94.29%	89.76%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	93.37%	91.03%
CHEMBL4302	P08183	P-glycoprotein 1	91.54%	92.98%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	91.25%	83.14%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	91.14%	96.86%
CHEMBL2581	P07339	Cathepsin D	90.83%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.20%	97.25%
CHEMBL4208	P20618	Proteasome component C5	90.03%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.67%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.34%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.04%	89.62%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	87.65%	95.34%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.64%	93.99%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.46%	82.38%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	86.78%	92.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.76%	95.89%
CHEMBL284	P27487	Dipeptidyl peptidase IV	84.85%	95.69%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.46%	95.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.26%	85.14%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	83.90%	95.53%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	83.28%	95.70%
CHEMBL2535	P11166	Glucose transporter	83.26%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.80%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.74%	99.17%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.50%	90.95%
CHEMBL1907	P15144	Aminopeptidase N	81.49%	93.31%
CHEMBL5319	Q08345	Epithelial discoidin domain-containing receptor 1	81.49%	90.30%
CHEMBL1938212	Q9UPP1	Histone lysine demethylase PHF8	81.00%	98.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.87%	89.50%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.36%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	80.04%	83.82%

Plants that contains it

• Thalictrum wangii

Cross-Links

• PubChem: 162843190
• LOTUS: LTS0036427
• wikiData: Q104911304