2,3-Dimethoxy-6-methyl-5,7,8,15-tetrahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[c]azecin-14(6H)-one

Details

• Internal ID: 056e72ac-2b7c-4cd1-9dea-aca1ca4dd1d5
• Taxonomy: Alkaloids and derivatives > Protopine alkaloids
• IUPAC Name: 6,7-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.04,9.016,20]henicosa-1(21),4,6,8,14,16(20)-hexaen-2-one
• SMILES (Canonical): CN1CCC2=CC3=C(C=C2C(=O)CC4=CC(=C(C=C4C1)OC)OC)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C=C2C(=O)CC4=CC(=C(C=C4C1)OC)OC)OCO3
• InChI: InChI=1S/C21H23NO5/c1-22-5-4-13-7-20-21(27-12-26-20)10-16(13)17(23)6-14-8-18(24-2)19(25-3)9-15(14)11-22/h7-10H,4-6,11-12H2,1-3H3
• InChI Key: AGSOWAZSCZVVDU-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

• SCHEMBL16970984
• SR-01000216887
• SR-01000216887-1
• 2,3-Dimethoxy-6-methyl-5,7,8,15-tetrahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[c]azecin-14(6H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9779	97.79%
Caco-2	+	0.9159	91.59%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Lysosomes	0.5083	50.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9317	93.17%
OATP1B3 inhibitior	+	0.9454	94.54%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.8173	81.73%
P-glycoprotein inhibitior	+	0.8302	83.02%
P-glycoprotein substrate	-	0.5997	59.97%
CYP3A4 substrate	+	0.5587	55.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4730	47.30%
CYP3A4 inhibition	+	0.6555	65.55%
CYP2C9 inhibition	-	0.8857	88.57%
CYP2C19 inhibition	+	0.8455	84.55%
CYP2D6 inhibition	+	0.8623	86.23%
CYP1A2 inhibition	-	0.9054	90.54%
CYP2C8 inhibition	-	0.9292	92.92%
CYP inhibitory promiscuity	-	0.6979	69.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5555	55.55%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.8892	88.92%
Skin irritation	-	0.8283	82.83%
Skin corrosion	-	0.9505	95.05%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3928	39.28%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8547	85.47%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5933	59.33%
Acute Oral Toxicity (c)	III	0.6982	69.82%
Estrogen receptor binding	+	0.6606	66.06%
Androgen receptor binding	-	0.6121	61.21%
Thyroid receptor binding	-	0.5700	57.00%
Glucocorticoid receptor binding	+	0.6679	66.79%
Aromatase binding	-	0.6129	61.29%
PPAR gamma	+	0.6963	69.63%
Honey bee toxicity	-	0.8001	80.01%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9497	94.97%

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	99.37%	96.77%
CHEMBL2581	P07339	Cathepsin D	97.12%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.39%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.44%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.94%	93.40%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	90.83%	90.95%
CHEMBL4208	P20618	Proteasome component C5	90.81%	90.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	90.64%	96.86%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	89.08%	82.38%
CHEMBL2056	P21728	Dopamine D1 receptor	89.04%	91.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.63%	86.33%
CHEMBL2535	P11166	Glucose transporter	87.99%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.29%	93.99%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.00%	82.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.58%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.55%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.06%	85.14%
CHEMBL5747	Q92793	CREB-binding protein	85.99%	95.12%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	83.76%	92.38%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	83.48%	94.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.99%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.81%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.84%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.38%	99.23%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.35%	89.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.00%	89.00%

Plants that contains it

• Zanthoxylum coco

Cross-Links

• PubChem: 15559220
• LOTUS: LTS0264047
• wikiData: Q104912017