(13aS)-3-(hydroxymethyl)-9,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-2-ol

Details

• Internal ID: 16747fb2-e2ab-4fb9-9c65-d22c69528f53
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (13aS)-3-(hydroxymethyl)-9,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-2-ol
• InChI: InChI=1S/C20H23NO4/c1-24-19-4-3-12-8-17-15-9-18(23)14(11-22)7-13(15)5-6-21(17)10-16(12)20(19)25-2/h3-4,7,9,17,22-23H,5-6,8,10-11H2,1-2H3/t17-/m0/s1
• InChI Key: GUYGHGTULHWCTK-KRWDZBQOSA-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: 2.60
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 5
• 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	+	0.8441	84.41%
Caco-2	+	0.7161	71.61%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5864	58.64%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	+	0.9301	93.01%
OATP1B3 inhibitior	+	0.9294	92.94%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.6123	61.23%
P-glycoprotein inhibitior	-	0.7170	71.70%
P-glycoprotein substrate	+	0.6027	60.27%
CYP3A4 substrate	+	0.6189	61.89%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	+	0.7692	76.92%
CYP3A4 inhibition	-	0.8446	84.46%
CYP2C9 inhibition	-	0.8657	86.57%
CYP2C19 inhibition	-	0.6781	67.81%
CYP2D6 inhibition	+	0.5308	53.08%
CYP1A2 inhibition	-	0.5445	54.45%
CYP2C8 inhibition	-	0.5815	58.15%
CYP inhibitory promiscuity	-	0.7308	73.08%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6938	69.38%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9561	95.61%
Skin irritation	-	0.7748	77.48%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6459	64.59%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8699	86.99%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8046	80.46%
Acute Oral Toxicity (c)	III	0.6364	63.64%
Estrogen receptor binding	+	0.7138	71.38%
Androgen receptor binding	+	0.5450	54.50%
Thyroid receptor binding	+	0.7075	70.75%
Glucocorticoid receptor binding	+	0.7363	73.63%
Aromatase binding	-	0.6098	60.98%
PPAR gamma	+	0.5823	58.23%
Honey bee toxicity	-	0.8970	89.70%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5149	51.49%
Fish aquatic toxicity	-	0.6489	64.89%

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	99.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.67%	91.11%
CHEMBL217	P14416	Dopamine D2 receptor	96.01%	95.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.60%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.17%	86.33%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	91.98%	91.79%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.42%	89.62%
CHEMBL2535	P11166	Glucose transporter	91.17%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.39%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.76%	93.40%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.74%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.41%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.26%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.03%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.88%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.37%	92.62%
CHEMBL2056	P21728	Dopamine D1 receptor	85.97%	91.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.56%	85.14%
CHEMBL3438	Q05513	Protein kinase C zeta	84.90%	88.48%
CHEMBL5747	Q92793	CREB-binding protein	84.84%	95.12%
CHEMBL4208	P20618	Proteasome component C5	84.77%	90.00%
CHEMBL261	P00915	Carbonic anhydrase I	83.75%	96.76%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.36%	82.38%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.59%	89.05%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.59%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.50%	94.00%
CHEMBL4302	P08183	P-glycoprotein 1	81.60%	92.98%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	80.29%	96.25%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.11%	92.94%

Plants that contains it

• Glaucium fimbrilligerum

Cross-Links

• PubChem: 154620537
• LOTUS: LTS0200485
• wikiData: Q105342770