5,7,8,15-Tetrahydro-4-hydroxy-3-methoxy-6-methyl[1,3]benzodioxolo[5,6-e][2]benzazecin-14(6H)-one

Details

• Internal ID: a2268f9b-e2ab-4878-b705-1ca62f3fd0a3
• Taxonomy: Alkaloids and derivatives > Protopine alkaloids
• IUPAC Name: 8-hydroxy-7-methoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.04,9.016,20]henicosa-1(21),4(9),5,7,14,16(20)-hexaen-2-one
• InChI: InChI=1S/C20H21NO5/c1-21-6-5-13-8-18-19(26-11-25-18)9-14(13)16(22)7-12-3-4-17(24-2)20(23)15(12)10-21/h3-4,8-9,23H,5-7,10-11H2,1-2H3
• InChI Key: RSMSJQDBPYSXHH-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁NO₅
• Molecular Weight: 355.40 g/mol
• Exact Mass: 355.14197277 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 490-52-8
• 5,7,8,15-Tetrahydro-4-hydroxy-3-methoxy-6-methyl[1,3]benzodioxolo[5,6-e][2]benzazecin-14(6H)-one
• EINECS 207-711-7
• 5,7,8,15-Tetrahydro-4-hydroxy-3-methoxy-6-methyl(1,3)benzodioxolo(5,6-e)(2)benzazecin-14(6H)-one
• 8-hydroxy-7-methoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.04,9.016,20]henicosa-1(21),4(9),5,7,14,16(20)-hexaen-2-one
• Benzo(e)(1,3)dioxolo(4,5-k)(3)benzazecin-14(6H)-one, 5,7,8,15-tetrahydro-4-hydroxy-3-methoxy-6-methyl-
• ST048766
• S9TC6BMK2V
• Oprea1_819797
• MEGxp0_001728
• SCHEMBL3368057
• ACon1_000791
• DTXSID90197655
• RSMSJQDBPYSXHH-UHFFFAOYSA-N
• AKOS024281760
• FH66061
• NS00031848
• BRD-K24867927-001-01-7
• [1,3]Benzodioxolo[5,6-e][2]benzazecin-14(6H)-one, 5,7,8,15-tetrahydro-4-hydroxy-3-methoxy-6-methyl-
• 30334-59-9
• 4-hydroxy-3-methoxy-6-methyl-5H,7H,8H,11H,15H-benzo[1'',2''-8',9']azecino[5',4 '-2,1]benzo[4,5-d]1,3-dioxolen-14-one
• 5,7,8,15-Tetrahydro-4-hydroxy-3-methoxy-6-methylbenzo[c][1,3]benzodioxolo[5,6-g]azecin-14(6H)-one
• Benzo[c][1,3]benzodioxolo[5,6-g]azecin-14(6H)-one, 5,7,8,15-tetrahydro-4-hydroxy-3-methoxy-6-methyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9606	96.06%
Caco-2	+	0.8454	84.54%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4865	48.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9191	91.91%
OATP1B3 inhibitior	+	0.9328	93.28%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.7010	70.10%
P-glycoprotein inhibitior	-	0.5680	56.80%
P-glycoprotein substrate	-	0.6466	64.66%
CYP3A4 substrate	+	0.6034	60.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4345	43.45%
CYP3A4 inhibition	+	0.5298	52.98%
CYP2C9 inhibition	-	0.8970	89.70%
CYP2C19 inhibition	+	0.6809	68.09%
CYP2D6 inhibition	+	0.7267	72.67%
CYP1A2 inhibition	-	0.6897	68.97%
CYP2C8 inhibition	-	0.8422	84.22%
CYP inhibitory promiscuity	-	0.8164	81.64%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5811	58.11%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9142	91.42%
Skin irritation	-	0.7935	79.35%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6013	60.13%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8664	86.64%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.6340	63.40%
Acute Oral Toxicity (c)	III	0.6717	67.17%
Estrogen receptor binding	+	0.6873	68.73%
Androgen receptor binding	+	0.5293	52.93%
Thyroid receptor binding	-	0.6239	62.39%
Glucocorticoid receptor binding	+	0.6882	68.82%
Aromatase binding	+	0.5757	57.57%
PPAR gamma	+	0.6552	65.52%
Honey bee toxicity	-	0.8736	87.36%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9456	94.56%

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	98.99%	96.77%
CHEMBL2581	P07339	Cathepsin D	96.93%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.84%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.38%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.82%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.66%	91.11%
CHEMBL4208	P20618	Proteasome component C5	94.18%	90.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.60%	93.40%
CHEMBL2056	P21728	Dopamine D1 receptor	92.74%	91.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.47%	86.33%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	91.35%	90.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.30%	95.89%
CHEMBL2535	P11166	Glucose transporter	90.21%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.83%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.35%	90.71%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	88.34%	82.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.87%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.59%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	86.64%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.63%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.62%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.04%	99.23%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.59%	96.25%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.32%	82.67%

Plants that contains it

• Argemone albiflora
• Dactylicapnos torulosa
• Eschscholzia californica
• Hunnemannia fumariifolia
• Hypecoum procumbens
• Larix decidua
• Swertia mussotii

Cross-Links

• PubChem: 1275589
• NPASS: NPC91878
• LOTUS: LTS0240248
• wikiData: Q83070457