2,9-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline-3,10-diol

Details

• Internal ID: 0d583216-cbf1-4bb8-8dd4-8ba98712395f
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (13aS)-2,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-3,10-diol
• SMILES (Canonical): COC1=C(C=C2CCN3CC4=C(CC3C2=C1)C=CC(=C4OC)O)O
• SMILES (Isomeric): COC1=C(C=C2CCN3CC4=C(C[C@H]3C2=C1)C=CC(=C4OC)O)O
• InChI: InChI=1S/C19H21NO4/c1-23-18-9-13-12(8-17(18)22)5-6-20-10-14-11(7-15(13)20)3-4-16(21)19(14)24-2/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
• InChI Key: OPLHOPJAFJJLPX-HNNXBMFYSA-N
• Popularity: 3 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): 62.20 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.77
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• BDBM50130338
• (S)-2,9-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline-3,10-diol
• 2,9-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline-3,10-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7394	73.94%
Caco-2	+	0.8770	87.70%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7876	78.76%
OATP2B1 inhibitior	-	0.8510	85.10%
OATP1B1 inhibitior	+	0.9416	94.16%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.5832	58.32%
P-glycoprotein inhibitior	-	0.6611	66.11%
P-glycoprotein substrate	-	0.5886	58.86%
CYP3A4 substrate	+	0.5900	59.00%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.8667	86.67%
CYP2C9 inhibition	-	0.9373	93.73%
CYP2C19 inhibition	+	0.6996	69.96%
CYP2D6 inhibition	+	0.8204	82.04%
CYP1A2 inhibition	+	0.8037	80.37%
CYP2C8 inhibition	-	0.5804	58.04%
CYP inhibitory promiscuity	-	0.7737	77.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6510	65.10%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9022	90.22%
Skin irritation	-	0.7453	74.53%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6684	66.84%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8909	89.09%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7303	73.03%
Acute Oral Toxicity (c)	III	0.4885	48.85%
Estrogen receptor binding	+	0.5828	58.28%
Androgen receptor binding	+	0.5211	52.11%
Thyroid receptor binding	+	0.7430	74.30%
Glucocorticoid receptor binding	+	0.7616	76.16%
Aromatase binding	-	0.6579	65.79%
PPAR gamma	-	0.5190	51.90%
Honey bee toxicity	-	0.8712	87.12%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.3973	39.73%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL229	P35348	Alpha-1a adrenergic receptor	630 nM	Ki	via Super-PRED
CHEMBL2056	P21728	Dopamine D1 receptor	200 nM	Ki	via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	113 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.63%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.39%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.91%	93.40%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	94.24%	91.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.81%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.45%	94.45%
CHEMBL2535	P11166	Glucose transporter	91.33%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.49%	89.62%
CHEMBL3438	Q05513	Protein kinase C zeta	90.14%	88.48%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.95%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.89%	85.14%
CHEMBL5747	Q92793	CREB-binding protein	86.85%	95.12%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.30%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.85%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.33%	91.03%
CHEMBL4208	P20618	Proteasome component C5	84.62%	90.00%
CHEMBL2581	P07339	Cathepsin D	84.34%	98.95%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.32%	82.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.80%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.16%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.68%	93.99%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.10%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.43%	90.71%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	80.28%	95.70%

Plants that contains it

• Annona leptopetala
• Artabotrys maingayi
• Duguetia moricandiana
• Fissistigma glaucescens
• Guatteria discolor
• Meiogyne monosperma
• Mitrella kentii
• Polyalthia parviflora
• Xylopia buxifolia
• Xylopia discreta

Cross-Links

• PubChem: 14378574
• LOTUS: LTS0265029
• wikiData: Q105370334