16-Methoxy-12-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-17-ol

Details

• Internal ID: 75ff6e06-b7b9-43c9-86f7-f464a92e5755
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 16-methoxy-12-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-17-ol
• SMILES (Canonical): CC1C2C3=CC(=C(C=C3CCN2CC4=C1C=CC5=C4OCO5)O)OC
• SMILES (Isomeric): CC1C2C3=CC(=C(C=C3CCN2CC4=C1C=CC5=C4OCO5)O)OC
• InChI: InChI=1S/C20H21NO4/c1-11-13-3-4-17-20(25-10-24-17)15(13)9-21-6-5-12-7-16(22)18(23-2)8-14(12)19(11)21/h3-4,7-8,11,19,22H,5-6,9-10H2,1-2H3
• InChI Key: IHNKNZSIZUBHCB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.40 g/mol
• Exact Mass: 339.14705815 g/mol
• Topological Polar Surface Area (TPSA): 51.20 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.35
• H-Bond Acceptor: 5
• 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	+	0.7986	79.86%
Caco-2	+	0.8913	89.13%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5678	56.78%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.9309	93.09%
OATP1B3 inhibitior	+	0.9336	93.36%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.7232	72.32%
P-glycoprotein inhibitior	-	0.4546	45.46%
P-glycoprotein substrate	-	0.6106	61.06%
CYP3A4 substrate	+	0.6179	61.79%
CYP2C9 substrate	-	0.6036	60.36%
CYP2D6 substrate	+	0.6404	64.04%
CYP3A4 inhibition	+	0.7406	74.06%
CYP2C9 inhibition	-	0.9146	91.46%
CYP2C19 inhibition	+	0.8760	87.60%
CYP2D6 inhibition	+	0.8910	89.10%
CYP1A2 inhibition	+	0.8819	88.19%
CYP2C8 inhibition	-	0.5778	57.78%
CYP inhibitory promiscuity	+	0.6798	67.98%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5842	58.42%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9716	97.16%
Skin irritation	-	0.7827	78.27%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7296	72.96%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6120	61.20%
Acute Oral Toxicity (c)	III	0.5244	52.44%
Estrogen receptor binding	+	0.6234	62.34%
Androgen receptor binding	-	0.4903	49.03%
Thyroid receptor binding	+	0.6232	62.32%
Glucocorticoid receptor binding	+	0.7324	73.24%
Aromatase binding	-	0.5896	58.96%
PPAR gamma	+	0.6013	60.13%
Honey bee toxicity	-	0.7850	78.50%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.7554	75.54%

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	98.20%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.24%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.07%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.06%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.25%	94.45%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	93.41%	82.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.16%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.43%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.72%	95.89%
CHEMBL2581	P07339	Cathepsin D	90.38%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.96%	96.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.50%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.97%	89.62%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	88.11%	100.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.08%	93.99%
CHEMBL2535	P11166	Glucose transporter	87.01%	98.75%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	85.52%	96.86%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	85.38%	91.79%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.36%	82.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.52%	100.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	84.48%	90.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.33%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.02%	97.09%
CHEMBL2056	P21728	Dopamine D1 receptor	83.91%	91.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.91%	95.89%
CHEMBL4208	P20618	Proteasome component C5	83.23%	90.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.07%	89.05%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.43%	90.24%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.26%	95.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.84%	94.00%

Plants that contains it

• Corydalis cava

Cross-Links

• PubChem: 85133911
• LOTUS: LTS0149825
• wikiData: Q105113146