(13aS)-3-(hydroxymethyl)-10-methoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol

Details

• Internal ID: 6f61ecad-1381-484d-98e6-2a0488960238
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (13aS)-3-(hydroxymethyl)-10-methoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol
• SMILES (Canonical): COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)CO)O)C=C1)O
• SMILES (Isomeric): COC1=C(C2=C(C[C@H]3C4=CC(=C(C=C4CCN3C2)CO)O)C=C1)O
• InChI: InChI=1S/C19H21NO4/c1-24-18-3-2-11-7-16-14-8-17(22)13(10-21)6-12(14)4-5-20(16)9-15(11)19(18)23/h2-3,6,8,16,21-23H,4-5,7,9-10H2,1H3/t16-/m0/s1
• InChI Key: WQHQWBLCZPRPBJ-INIZCTEOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.40 g/mol
• Exact Mass: 327.14705815 g/mol
• Topological Polar Surface Area (TPSA): 73.20 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.25
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8264	82.64%
Caco-2	+	0.6221	62.21%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5710	57.10%
OATP2B1 inhibitior	-	0.5733	57.33%
OATP1B1 inhibitior	+	0.9229	92.29%
OATP1B3 inhibitior	+	0.9362	93.62%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.5609	56.09%
P-glycoprotein inhibitior	-	0.8131	81.31%
P-glycoprotein substrate	+	0.6524	65.24%
CYP3A4 substrate	+	0.6157	61.57%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	+	0.7692	76.92%
CYP3A4 inhibition	-	0.8822	88.22%
CYP2C9 inhibition	-	0.8085	80.85%
CYP2C19 inhibition	-	0.6779	67.79%
CYP2D6 inhibition	+	0.5435	54.35%
CYP1A2 inhibition	+	0.6445	64.45%
CYP2C8 inhibition	-	0.6143	61.43%
CYP inhibitory promiscuity	-	0.7092	70.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6717	67.17%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8555	85.55%
Skin irritation	-	0.7348	73.48%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7138	71.38%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.5935	59.35%
skin sensitisation	-	0.8801	88.01%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7384	73.84%
Acute Oral Toxicity (c)	III	0.6288	62.88%
Estrogen receptor binding	+	0.6061	60.61%
Androgen receptor binding	+	0.5387	53.87%
Thyroid receptor binding	+	0.6905	69.05%
Glucocorticoid receptor binding	+	0.6794	67.94%
Aromatase binding	-	0.5455	54.55%
PPAR gamma	+	0.5867	58.67%
Honey bee toxicity	-	0.8949	89.49%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5149	51.49%
Fish aquatic toxicity	-	0.6840	68.40%

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	99.29%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.40%	91.11%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	94.47%	91.79%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.34%	93.99%
CHEMBL217	P14416	Dopamine D2 receptor	93.67%	95.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.44%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.72%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.54%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.35%	95.89%
CHEMBL2581	P07339	Cathepsin D	91.50%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.86%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.82%	95.56%
CHEMBL2535	P11166	Glucose transporter	87.21%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.15%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.13%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.39%	99.17%
CHEMBL3438	Q05513	Protein kinase C zeta	85.92%	88.48%
CHEMBL2056	P21728	Dopamine D1 receptor	85.71%	91.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.65%	92.94%
CHEMBL4208	P20618	Proteasome component C5	84.03%	90.00%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	83.94%	96.25%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.00%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.91%	94.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.30%	90.95%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.04%	89.05%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.34%	82.38%

Plants that contains it

• Glaucium fimbrilligerum

Cross-Links

• PubChem: 162879760
• LOTUS: LTS0131142
• wikiData: Q105310721