2,3-dimethoxy-6-[(6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methyl]benzaldehyde

Details

• Internal ID: dcaa77fe-3c35-4816-8819-51b8bb42cac6
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: 2,3-dimethoxy-6-[(6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methyl]benzaldehyde
• InChI: InChI=1S/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(22)8-13-4-5-18(24-2)21(25-3)16(13)11-23/h4-5,9-11,17H,6-8,12H2,1-3H3
• InChI Key: ROAHDZJDHGLGBA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.40 g/mol
• Exact Mass: 369.15762283 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.02
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• (S)-(+)-Canadaline
• 2,3-dimethoxy-6-[(6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methyl]benzaldehyde
• NSC272358
• (.+-.)-Canadaline
• Canadalin
• (+-)-Canadaline
• CHEMBL1968299
• SCHEMBL17934785
• CCA80127
• NSC279521
• NSC-272358
• NSC-279521
• 62475-57-4
• NCI60_002224

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9412	94.12%
Caco-2	+	0.8652	86.52%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.3965	39.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9072	90.72%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8567	85.67%
P-glycoprotein inhibitior	+	0.8861	88.61%
P-glycoprotein substrate	-	0.7129	71.29%
CYP3A4 substrate	+	0.6370	63.70%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	+	0.4337	43.37%
CYP3A4 inhibition	+	0.5487	54.87%
CYP2C9 inhibition	-	0.7362	73.62%
CYP2C19 inhibition	+	0.5196	51.96%
CYP2D6 inhibition	-	0.5730	57.30%
CYP1A2 inhibition	-	0.8458	84.58%
CYP2C8 inhibition	-	0.6870	68.70%
CYP inhibitory promiscuity	-	0.5721	57.21%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5860	58.60%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9808	98.08%
Skin irritation	-	0.8208	82.08%
Skin corrosion	-	0.9550	95.50%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7384	73.84%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8691	86.91%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6102	61.02%
Acute Oral Toxicity (c)	III	0.7785	77.85%
Estrogen receptor binding	+	0.7655	76.55%
Androgen receptor binding	-	0.5306	53.06%
Thyroid receptor binding	-	0.5487	54.87%
Glucocorticoid receptor binding	+	0.8207	82.07%
Aromatase binding	-	0.6112	61.12%
PPAR gamma	+	0.7016	70.16%
Honey bee toxicity	-	0.8097	80.97%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9500	95.00%

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	98.27%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.13%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.53%	95.56%
CHEMBL261	P00915	Carbonic anhydrase I	94.69%	96.76%
CHEMBL2581	P07339	Cathepsin D	93.15%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.85%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.51%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.22%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.92%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.83%	89.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.79%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.90%	93.40%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.26%	89.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.25%	92.62%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.37%	82.38%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.58%	80.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.40%	94.00%
CHEMBL4040	P28482	MAP kinase ERK2	81.99%	83.82%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	81.54%	96.86%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.08%	96.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.63%	82.67%
CHEMBL4208	P20618	Proteasome component C5	80.54%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.49%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.31%	89.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.06%	90.95%

Plants that contains it

• Hydrastis canadensis

Cross-Links

• PubChem: 321459
• NPASS: NPC27887
• LOTUS: LTS0019994
• wikiData: Q104667351