1,2-Dimethoxy-7-methyl-5H,6H,8H,11H,14H-benzo[1'',2''-4',5']azecino[9',8'-2,1]benzo[4,5-d]1,3-dioxolan-15-one

Details

• Internal ID: 88044f10-aeb3-4559-9785-5b4977f7dfcb
• Taxonomy: Alkaloids and derivatives > Protopine alkaloids
• IUPAC Name: 5,6-dimethoxy-12-methyl-17,19-dioxa-12-azatetracyclo[12.7.0.04,9.016,20]henicosa-1(21),4(9),5,7,14,16(20)-hexaen-3-one
• SMILES (Canonical): CN1CCC2=C(C(=O)CC3=CC4=C(C=C3C1)OCO4)C(=C(C=C2)OC)OC
• SMILES (Isomeric): CN1CCC2=C(C(=O)CC3=CC4=C(C=C3C1)OCO4)C(=C(C=C2)OC)OC
• InChI: InChI=1S/C21H23NO5/c1-22-7-6-13-4-5-17(24-2)21(25-3)20(13)16(23)8-14-9-18-19(27-12-26-18)10-15(14)11-22/h4-5,9-10H,6-8,11-12H2,1-3H3
• InChI Key: IQMNEXSNDKWUSQ-UHFFFAOYSA-N
• Popularity: 1 reference 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: 2.90
• Atomic LogP (AlogP): 2.85
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9780	97.80%
Caco-2	+	0.9434	94.34%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Lysosomes	0.5056	50.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9498	94.98%
OATP1B3 inhibitior	+	0.9429	94.29%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7528	75.28%
P-glycoprotein inhibitior	+	0.8730	87.30%
P-glycoprotein substrate	-	0.7781	77.81%
CYP3A4 substrate	+	0.5722	57.22%
CYP2C9 substrate	-	0.8284	82.84%
CYP2D6 substrate	+	0.4303	43.03%
CYP3A4 inhibition	+	0.5995	59.95%
CYP2C9 inhibition	-	0.8480	84.80%
CYP2C19 inhibition	+	0.7434	74.34%
CYP2D6 inhibition	+	0.7348	73.48%
CYP1A2 inhibition	-	0.9120	91.20%
CYP2C8 inhibition	-	0.8427	84.27%
CYP inhibitory promiscuity	-	0.7556	75.56%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5403	54.03%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9159	91.59%
Skin irritation	-	0.8310	83.10%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7884	78.84%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.5303	53.03%
skin sensitisation	-	0.8467	84.67%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5646	56.46%
Acute Oral Toxicity (c)	III	0.7136	71.36%
Estrogen receptor binding	+	0.8016	80.16%
Androgen receptor binding	-	0.4819	48.19%
Thyroid receptor binding	-	0.5964	59.64%
Glucocorticoid receptor binding	+	0.7562	75.62%
Aromatase binding	+	0.5306	53.06%
PPAR gamma	+	0.6035	60.35%
Honey bee toxicity	-	0.8654	86.54%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9437	94.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.79%	96.77%
CHEMBL4040	P28482	MAP kinase ERK2	97.96%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.60%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.96%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.93%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.60%	98.95%
CHEMBL4208	P20618	Proteasome component C5	94.50%	90.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.55%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.95%	86.33%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	91.86%	82.38%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	89.87%	96.86%
CHEMBL2056	P21728	Dopamine D1 receptor	89.81%	91.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.36%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.29%	93.40%
CHEMBL2535	P11166	Glucose transporter	88.28%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.99%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.38%	95.89%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.96%	82.67%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.77%	94.80%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.37%	99.17%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.19%	90.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.42%	92.62%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.05%	92.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.54%	89.00%

Plants that contains it

• Argemone mexicana

Cross-Links

• PubChem: 503963
• NPASS: NPC284428
• LOTUS: LTS0069123
• wikiData: Q105118018