(13S)-2,3,9-trimethoxy-13-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-10-ol

Details

• Internal ID: 6cdf3350-c580-457c-bfc2-db8040325672
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (13S)-2,3,9-trimethoxy-13-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-10-ol
• SMILES (Canonical): CC1C2C3=CC(=C(C=C3CCN2CC4=C1C=CC(=C4OC)O)OC)OC
• SMILES (Isomeric): C[C@@H]1C2C3=CC(=C(C=C3CCN2CC4=C1C=CC(=C4OC)O)OC)OC
• InChI: InChI=1S/C21H25NO4/c1-12-14-5-6-17(23)21(26-4)16(14)11-22-8-7-13-9-18(24-2)19(25-3)10-15(13)20(12)22/h5-6,9-10,12,20,23H,7-8,11H2,1-4H3/t12-,20?/m0/s1
• InChI Key: PVYYNJAXBCIMNG-SVZXGPMESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.40 g/mol
• Exact Mass: 355.17835828 g/mol
• Topological Polar Surface Area (TPSA): 51.20 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.63
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7453	74.53%
Caco-2	+	0.9249	92.49%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7026	70.26%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.9487	94.87%
OATP1B3 inhibitior	+	0.9443	94.43%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	+	0.5595	55.95%
P-glycoprotein inhibitior	+	0.5868	58.68%
P-glycoprotein substrate	+	0.5347	53.47%
CYP3A4 substrate	+	0.6069	60.69%
CYP2C9 substrate	-	0.5942	59.42%
CYP2D6 substrate	+	0.7968	79.68%
CYP3A4 inhibition	-	0.6935	69.35%
CYP2C9 inhibition	-	0.8825	88.25%
CYP2C19 inhibition	-	0.6090	60.90%
CYP2D6 inhibition	+	0.7220	72.20%
CYP1A2 inhibition	+	0.6197	61.97%
CYP2C8 inhibition	-	0.5785	57.85%
CYP inhibitory promiscuity	-	0.8286	82.86%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6226	62.26%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9445	94.45%
Skin irritation	-	0.7537	75.37%
Skin corrosion	-	0.9408	94.08%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7683	76.83%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8985	89.85%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8254	82.54%
Acute Oral Toxicity (c)	III	0.5705	57.05%
Estrogen receptor binding	+	0.7125	71.25%
Androgen receptor binding	-	0.5105	51.05%
Thyroid receptor binding	+	0.6804	68.04%
Glucocorticoid receptor binding	+	0.7162	71.62%
Aromatase binding	-	0.7306	73.06%
PPAR gamma	+	0.5403	54.03%
Honey bee toxicity	-	0.8667	86.67%
Biodegradation	-	1.0000	100.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.5594	55.94%

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	97.83%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.71%	93.99%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.69%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.91%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.95%	93.40%
CHEMBL2535	P11166	Glucose transporter	92.79%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.86%	92.94%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	90.64%	91.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.51%	95.56%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	89.44%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.44%	89.62%
CHEMBL217	P14416	Dopamine D2 receptor	89.09%	95.62%
CHEMBL2056	P21728	Dopamine D1 receptor	87.71%	91.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.31%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.77%	91.03%
CHEMBL4208	P20618	Proteasome component C5	83.93%	90.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.74%	97.21%
CHEMBL2581	P07339	Cathepsin D	83.71%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.18%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.12%	85.14%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	82.90%	95.70%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.12%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.74%	99.15%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.04%	82.38%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	80.33%	96.86%

Plants that contains it

• Corydalis ophiocarpa
• Corydalis yanhusuo
• Dioscorea tokoro

Cross-Links

• PubChem: 11291216
• NPASS: NPC101715