Thalirabine

Details

• Internal ID: 82bbef9a-438b-480d-aa6b-6eb2666e4770
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: (1S)-6,7-dimethoxy-1-[[4-methoxy-3-[4-[[(5S)-9-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methyl]phenoxy]phenyl]methyl]-2,2-dimethyl-3,4-dihydro-1H-isoquinolin-2-ium-5-ol
• SMILES (Canonical): CN1CCC2=C(C3=C(C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=CC(=C(C(=C7CC[N+]6(C)C)O)OC)OC)OC)OCO3)OC
• SMILES (Isomeric): CN1CCC2=C(C3=C(C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)C[C@H]6C7=CC(=C(C(=C7CC[N+]6(C)C)O)OC)OC)OC)OCO3)OC
• InChI: InChI=1S/C40H46N2O8/c1-41-16-14-28-29(21-36-40(38(28)46-6)49-23-48-36)31(41)18-24-8-11-26(12-9-24)50-34-20-25(10-13-33(34)44-4)19-32-30-22-35(45-5)39(47-7)37(43)27(30)15-17-42(32,2)3/h8-13,20-22,31-32H,14-19,23H2,1-7H3/p+1/t31-,32-/m0/s1
• InChI Key: QQJYBIOINVHLKO-ACHIHNKUSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₇N₂O₈+
• Molecular Weight: 683.80 g/mol
• Exact Mass: 683.33324146 g/mol
• Topological Polar Surface Area (TPSA): 88.10 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 6.64
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 10

Synonyms

• 67624-63-9
• DTXSID90986980
• 5-Hydroxy-6,7-dimethoxy-1-[(4-methoxy-3-{4-[(9-methoxy-6-methyl-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methyl]phenoxy}phenyl)methyl]-2,2-dimethyl-1,2,3,4-tetrahydroisoquinolin-2-ium

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9597	95.97%
Caco-2	-	0.7687	76.87%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.3710	37.10%
OATP2B1 inhibitior	+	0.5788	57.88%
OATP1B1 inhibitior	+	0.8851	88.51%
OATP1B3 inhibitior	+	0.9237	92.37%
MATE1 inhibitior	+	0.5800	58.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.9804	98.04%
P-glycoprotein inhibitior	+	0.9041	90.41%
P-glycoprotein substrate	+	0.5344	53.44%
CYP3A4 substrate	+	0.7125	71.25%
CYP2C9 substrate	-	0.6056	60.56%
CYP2D6 substrate	+	0.3992	39.92%
CYP3A4 inhibition	-	0.6576	65.76%
CYP2C9 inhibition	-	0.9034	90.34%
CYP2C19 inhibition	-	0.8725	87.25%
CYP2D6 inhibition	-	0.7526	75.26%
CYP1A2 inhibition	-	0.9169	91.69%
CYP2C8 inhibition	+	0.8135	81.35%
CYP inhibitory promiscuity	-	0.8681	86.81%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6131	61.31%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9251	92.51%
Skin irritation	-	0.8025	80.25%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9136	91.36%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8701	87.01%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.9321	93.21%
Acute Oral Toxicity (c)	III	0.6916	69.16%
Estrogen receptor binding	+	0.7700	77.00%
Androgen receptor binding	+	0.7438	74.38%
Thyroid receptor binding	+	0.6278	62.78%
Glucocorticoid receptor binding	+	0.7960	79.60%
Aromatase binding	+	0.6502	65.02%
PPAR gamma	+	0.6482	64.82%
Honey bee toxicity	-	0.7486	74.86%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9562	95.62%

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	99.15%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.96%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.25%	96.77%
CHEMBL3192	Q9BY41	Histone deacetylase 8	96.71%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.95%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.65%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.55%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.42%	94.45%
CHEMBL261	P00915	Carbonic anhydrase I	94.75%	96.76%
CHEMBL4208	P20618	Proteasome component C5	94.68%	90.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	94.41%	97.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.89%	95.89%
CHEMBL5747	Q92793	CREB-binding protein	93.59%	95.12%
CHEMBL2581	P07339	Cathepsin D	93.24%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.32%	92.62%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	92.19%	92.68%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.93%	86.33%
CHEMBL2535	P11166	Glucose transporter	90.13%	98.75%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.33%	95.78%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.02%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.94%	99.17%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.02%	93.40%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.59%	95.17%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	83.05%	85.49%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.76%	89.44%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.74%	97.25%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.09%	82.38%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.03%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.60%	97.09%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.67%	90.95%
CHEMBL240	Q12809	HERG	80.03%	89.76%

Plants that contains it

• Thalictrum lucidum
• Thalictrum podocarpum

Cross-Links

• PubChem: 181902
• NPASS: NPC205948