3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol

Details

• Internal ID: 33aecf41-b916-48f2-b416-b39cd7f59616
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol
• SMILES (Canonical): COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
• SMILES (Isomeric): COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
• InChI: InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3
• InChI Key: JKPISQIIWUONPB-UHFFFAOYSA-N
• Popularity: 28 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

• 16562-14-4
• 3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol
• CHEMBL595489
• 6H-Dibenzo[a,g]quinolizine-2,10-diol, 5,8,13,13a-tetrahydro-3,9-dimethoxy-
• 13a-alpha-BERBINE-2,10-DIOL, 3,9-DIMETHOXY-
• Probes1_000256
• Probes2_000298
• SCHEMBL460434
• CHEBI:91837
• DTXSID00274461
• DTXSID70937112
• BDBM50152837
• HSCI1_000061
• AKOS030254427
• LS-43451
• FT-0628017
• FT-0674659
• J-010216
• Q7611023
• BRD-A71203467-001-01-5
• 3,9-Dimethoxy-5,6,13,13a-tetrahydro-8H-dibenzo[a,g]quinolizine-2,10-diol
• 3,9-Dimethoxy-5,8,13,13A-Tetrahydro-6H-Isoquino[3,2-A]Isoquinoline-2,10-Diol
• 3,9-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,10-diol
• 3,9-dimethoxy-5,8,13,13alpha-tetrahydro-6h-isoquinolino[3,2-a]isoquinoline-2,10-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7394	73.94%
Caco-2	+	0.7781	77.81%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7876	78.76%
OATP2B1 inhibitior	-	0.8542	85.42%
OATP1B1 inhibitior	+	0.9472	94.72%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.5560	55.60%
P-glycoprotein inhibitior	-	0.7128	71.28%
P-glycoprotein substrate	+	0.5055	50.55%
CYP3A4 substrate	+	0.5953	59.53%
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	-	0.5858	58.58%
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	-	0.9368	93.68%
Skin irritation	-	0.7453	74.53%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4738	47.38%
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	-	0.7410	74.10%
Acute Oral Toxicity (c)	III	0.4885	48.85%
Estrogen receptor binding	+	0.5807	58.07%
Androgen receptor binding	+	0.5211	52.11%
Thyroid receptor binding	+	0.6127	61.27%
Glucocorticoid receptor binding	+	0.7301	73.01%
Aromatase binding	-	0.6827	68.27%
PPAR gamma	+	0.5473	54.73%
Honey bee toxicity	-	0.8769	87.69%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	-	0.3973	39.73%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4081	P13726	Coagulation factor III	104.58 nM	IC50	via Super-PRED
CHEMBL2056	P21728	Dopamine D1 receptor	5.6 nM; 3.4 nM; 5.6 nM; 135 nM	Ki; Ki; Ki; Ki	PMID: 27032890; via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	115.5 nM; 11 nM; 115.5 nM	Ki; Ki; Ki	PMID: 27032890; via Super-PRED; via Super-PRED
CHEMBL234	P35462	Dopamine D3 receptor	101 nM; 101 nM; 30 nM	Ki; Ki; Ki	PMID: 27032890; via Super-PRED; via Super-PRED
CHEMBL1850	P21918	Dopamine D5 receptor	4.4 nM	Ki	via Super-PRED
CHEMBL287	Q99720	Sigma opioid receptor	269 nM; 269 nM	Ki; Ki	via Super-PRED; PMID: 27032890

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.59%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.17%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.82%	93.40%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	94.21%	91.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.01%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.76%	94.45%
CHEMBL2535	P11166	Glucose transporter	91.33%	98.75%
CHEMBL3438	Q05513	Protein kinase C zeta	90.53%	88.48%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.47%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.90%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.95%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.85%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.59%	85.14%
CHEMBL5747	Q92793	CREB-binding protein	85.45%	95.12%
CHEMBL2581	P07339	Cathepsin D	85.19%	98.95%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.85%	91.03%
CHEMBL4208	P20618	Proteasome component C5	84.62%	90.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.32%	82.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.80%	99.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.62%	93.99%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.04%	95.89%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.10%	100.00%

Plants that contains it

• Alphonsea lutea
• Annona glabra
• Cocculus laurifolius
• Desmos cochinchinensis
• Fibraurea recisa
• Liriodendron tulipifera
• Menispermum dauricum
• Pachygone ovata
• Sinomenium acutum

Cross-Links

• PubChem: 5290
• NPASS: NPC110416
• ChEMBL: CHEMBL595489
• LOTUS: LTS0242646
• wikiData: Q7611023