16,19-Dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,13,15,17,19-octaene

Details

• Internal ID: 1a971f6c-a4f3-4c1f-a809-d5aa7dad49b5
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 16,19-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,13,15,17,19-octaene
• SMILES (Canonical): COC1=C2C=C3C4=CC5=C(C=C4CC[N+]3=CC2=C(C=C1)OC)OCO5
• SMILES (Isomeric): COC1=C2C=C3C4=CC5=C(C=C4CC[N+]3=CC2=C(C=C1)OC)OCO5
• InChI: InChI=1S/C20H18NO4/c1-22-17-3-4-18(23-2)15-10-21-6-5-12-7-19-20(25-11-24-19)9-13(12)16(21)8-14(15)17/h3-4,7-10H,5-6,11H2,1-2H3/q+1
• InChI Key: PGMNLULLZKOMNY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈NO₄+
• Molecular Weight: 336.40 g/mol
• Exact Mass: 336.12358306 g/mol
• Topological Polar Surface Area (TPSA): 40.80 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 4
• 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	+	0.7747	77.47%
Caco-2	+	0.9690	96.90%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4952	49.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9332	93.32%
OATP1B3 inhibitior	+	0.9417	94.17%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.5598	55.98%
BSEP inhibitior	+	0.7640	76.40%
P-glycoprotein inhibitior	+	0.7186	71.86%
P-glycoprotein substrate	-	0.7479	74.79%
CYP3A4 substrate	+	0.5351	53.51%
CYP2C9 substrate	-	0.8153	81.53%
CYP2D6 substrate	-	0.7038	70.38%
CYP3A4 inhibition	-	0.6442	64.42%
CYP2C9 inhibition	-	0.9082	90.82%
CYP2C19 inhibition	-	0.7919	79.19%
CYP2D6 inhibition	+	0.8873	88.73%
CYP1A2 inhibition	+	0.9143	91.43%
CYP2C8 inhibition	-	0.7124	71.24%
CYP inhibitory promiscuity	+	0.8830	88.30%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4870	48.70%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.8679	86.79%
Skin irritation	-	0.7782	77.82%
Skin corrosion	-	0.9468	94.68%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4531	45.31%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8626	86.26%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5763	57.63%
Acute Oral Toxicity (c)	III	0.6252	62.52%
Estrogen receptor binding	+	0.9504	95.04%
Androgen receptor binding	+	0.8330	83.30%
Thyroid receptor binding	+	0.6595	65.95%
Glucocorticoid receptor binding	+	0.8620	86.20%
Aromatase binding	-	0.5620	56.20%
PPAR gamma	+	0.6631	66.31%
Honey bee toxicity	-	0.8154	81.54%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	-	0.6879	68.79%

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	97.84%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.83%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.80%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.45%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.34%	93.99%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.18%	94.80%
CHEMBL1951	P21397	Monoamine oxidase A	89.98%	91.49%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	89.95%	82.67%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.55%	89.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.23%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.19%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.98%	92.62%
CHEMBL5747	Q92793	CREB-binding protein	85.66%	95.12%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.25%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.98%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.03%	96.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.72%	90.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.67%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.25%	86.33%
CHEMBL2535	P11166	Glucose transporter	81.73%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.44%	100.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.22%	95.78%

Plants that contains it

• Atriplex muricata
• Chromolaena laevigata
• Crinum asiaticum
• Crotalaria crispata
• Haplopappus deserticola
• Hesperocyparis arizonica
• Seriphidium junceum
• Viburnum lantana

Cross-Links

• PubChem: 25051817
• NPASS: NPC201092