6-Hydroxy-5-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

Details

• Internal ID: 84351275-db42-4a38-9716-836edc3eef36
• Taxonomy: Alkaloids and derivatives > Protopine alkaloids
• IUPAC Name: 6-hydroxy-5-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
• SMILES (Canonical): CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C=CC(=C4OC)O)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C=CC(=C4OC)O)OCO3
• InChI: InChI=1S/C20H21NO5/c1-21-6-5-12-7-18-19(26-11-25-18)9-14(12)17(23)8-15-13(10-21)3-4-16(22)20(15)24-2/h3-4,7,9,22H,5-6,8,10-11H2,1-2H3
• InChI Key: CHHDMEBAPJTZDW-UHFFFAOYSA-N
• Popularity: 0 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

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9239	92.39%
Caco-2	+	0.8909	89.09%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Lysosomes	0.4648	46.48%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.9328	93.28%
OATP1B3 inhibitior	+	0.9362	93.62%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.6741	67.41%
P-glycoprotein inhibitior	-	0.6454	64.54%
P-glycoprotein substrate	-	0.7599	75.99%
CYP3A4 substrate	+	0.5831	58.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4345	43.45%
CYP3A4 inhibition	+	0.7119	71.19%
CYP2C9 inhibition	-	0.9192	91.92%
CYP2C19 inhibition	+	0.5953	59.53%
CYP2D6 inhibition	+	0.7396	73.96%
CYP1A2 inhibition	-	0.7195	71.95%
CYP2C8 inhibition	-	0.8463	84.63%
CYP inhibitory promiscuity	-	0.7442	74.42%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5866	58.66%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8467	84.67%
Skin irritation	-	0.8041	80.41%
Skin corrosion	-	0.9435	94.35%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4574	45.74%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8655	86.55%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6231	62.31%
Acute Oral Toxicity (c)	III	0.6627	66.27%
Estrogen receptor binding	+	0.8117	81.17%
Androgen receptor binding	-	0.5168	51.68%
Thyroid receptor binding	-	0.7093	70.93%
Glucocorticoid receptor binding	+	0.7984	79.84%
Aromatase binding	+	0.7375	73.75%
PPAR gamma	+	0.5470	54.70%
Honey bee toxicity	-	0.8447	84.47%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9473	94.73%

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	99.29%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.96%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.08%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.65%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.39%	95.56%
CHEMBL4208	P20618	Proteasome component C5	94.80%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.53%	96.09%
CHEMBL2056	P21728	Dopamine D1 receptor	91.89%	91.00%
CHEMBL2535	P11166	Glucose transporter	90.91%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.85%	99.15%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.70%	93.99%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	90.51%	80.78%
CHEMBL1951	P21397	Monoamine oxidase A	90.01%	91.49%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	88.01%	90.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.03%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.99%	94.45%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.44%	82.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.57%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.42%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.21%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.09%	90.71%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	82.41%	82.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.95%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.64%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.46%	99.17%

Plants that contains it

• Argemone mexicana

Cross-Links

• PubChem: 162989715
• LOTUS: LTS0232788
• wikiData: Q104958769