[13s,13Ar,(+)]-5,8,13,13a-tetrahydro-2,9-dimethoxy-13-methyl-6H-dibenzo[a,g]quinolizine-3,10-diol

Details

• Internal ID: 6241c512-d547-4c93-8f07-dd2c0b25574f
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (13S,13aR)-2,9-dimethoxy-13-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-3,10-diol
• InChI: InChI=1S/C20H23NO4/c1-11-13-4-5-16(22)20(25-3)15(13)10-21-7-6-12-8-17(23)18(24-2)9-14(12)19(11)21/h4-5,8-9,11,19,22-23H,6-7,10H2,1-3H3/t11-,19+/m0/s1
• InChI Key: GWIIAEUJSONJQC-JEOXALJRSA-N
• Popularity: 2 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): 62.20 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.33
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• SCHEMBL20764619
• [13s,13Ar,(+)]-5,8,13,13a-tetrahydro-2,9-dimethoxy-13-methyl-6H-dibenzo[a,g]quinolizine-3,10-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6167	61.67%
Caco-2	+	0.9096	90.96%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7395	73.95%
OATP2B1 inhibitior	-	0.8522	85.22%
OATP1B1 inhibitior	+	0.9465	94.65%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.5286	52.86%
P-glycoprotein inhibitior	-	0.5632	56.32%
P-glycoprotein substrate	-	0.5572	55.72%
CYP3A4 substrate	+	0.6017	60.17%
CYP2C9 substrate	-	0.5942	59.42%
CYP2D6 substrate	+	0.7968	79.68%
CYP3A4 inhibition	-	0.7779	77.79%
CYP2C9 inhibition	-	0.8791	87.91%
CYP2C19 inhibition	+	0.5086	50.86%
CYP2D6 inhibition	+	0.7871	78.71%
CYP1A2 inhibition	+	0.6917	69.17%
CYP2C8 inhibition	+	0.4475	44.75%
CYP inhibitory promiscuity	-	0.7973	79.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6157	61.57%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9380	93.80%
Skin irritation	-	0.7648	76.48%
Skin corrosion	-	0.9411	94.11%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7915	79.15%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8964	89.64%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8362	83.62%
Acute Oral Toxicity (c)	III	0.5438	54.38%
Estrogen receptor binding	+	0.6504	65.04%
Androgen receptor binding	-	0.5050	50.50%
Thyroid receptor binding	+	0.7646	76.46%
Glucocorticoid receptor binding	+	0.7616	76.16%
Aromatase binding	-	0.6055	60.55%
PPAR gamma	+	0.5416	54.16%
Honey bee toxicity	-	0.8561	85.61%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	-	0.5393	53.93%

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	98.29%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.09%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.26%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.90%	93.99%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.72%	93.40%
CHEMBL2535	P11166	Glucose transporter	91.58%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.26%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.31%	95.56%
CHEMBL217	P14416	Dopamine D2 receptor	89.94%	95.62%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	89.44%	100.00%
CHEMBL2056	P21728	Dopamine D1 receptor	88.01%	91.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.62%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.27%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.68%	94.45%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	85.99%	91.79%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.49%	92.94%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.58%	91.03%
CHEMBL4208	P20618	Proteasome component C5	83.93%	90.00%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	83.88%	95.70%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.76%	97.21%
CHEMBL2581	P07339	Cathepsin D	83.64%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.28%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.37%	90.71%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.24%	82.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.40%	97.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.11%	80.78%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	80.01%	96.86%

Plants that contains it

• Corydalis nobilis

Cross-Links

• PubChem: 10427420
• LOTUS: LTS0064967
• wikiData: Q105022421