16,17-Dimethoxy-6-tritio-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene

Details

• Internal ID: 4de2bd6e-3032-438d-bb8c-0fd683a86ca2
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 16,17-dimethoxy-6-tritio-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene
• SMILES (Canonical): COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC
• SMILES (Isomeric): [3H]C1OC2=C(O1)C=C3C(=C2)CC[N+]4=C3C=C5C=CC(=C(C5=C4)OC)OC
• InChI: InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1/i11T
• InChI Key: YBHILYKTIRIUTE-KNWSOFMKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈NO₄+
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.13180730 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	+	0.7454	74.54%
Caco-2	+	0.8763	87.63%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4894	48.94%
OATP2B1 inhibitior	-	0.8861	88.61%
OATP1B1 inhibitior	+	0.9226	92.26%
OATP1B3 inhibitior	+	0.9458	94.58%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.5348	53.48%
BSEP inhibitior	+	0.6988	69.88%
P-glycoprotein inhibitior	+	0.6072	60.72%
P-glycoprotein substrate	-	0.5997	59.97%
CYP3A4 substrate	+	0.5905	59.05%
CYP2C9 substrate	-	0.8153	81.53%
CYP2D6 substrate	-	0.7038	70.38%
CYP3A4 inhibition	-	0.5873	58.73%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.7463	74.63%
CYP2D6 inhibition	+	0.8933	89.33%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.9003	90.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4717	47.17%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9679	96.79%
Skin irritation	-	0.7800	78.00%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6361	63.61%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.5428	54.28%
skin sensitisation	-	0.8664	86.64%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8246	82.46%
Acute Oral Toxicity (c)	III	0.6360	63.60%
Estrogen receptor binding	+	0.9155	91.55%
Androgen receptor binding	+	0.7921	79.21%
Thyroid receptor binding	+	0.6767	67.67%
Glucocorticoid receptor binding	+	0.7652	76.52%
Aromatase binding	-	0.5683	56.83%
PPAR gamma	+	0.6037	60.37%
Honey bee toxicity	-	0.8386	83.86%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	-	0.5793	57.93%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	100 nM	IC50	via Super-PRED
CHEMBL4878	Q16678	Cytochrome P450 1B1	44 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.52%	96.77%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	93.51%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.47%	91.11%
CHEMBL261	P00915	Carbonic anhydrase I	92.69%	96.76%
CHEMBL5747	Q92793	CREB-binding protein	92.67%	95.12%
CHEMBL1951	P21397	Monoamine oxidase A	92.43%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.55%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.43%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.88%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.20%	92.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.94%	93.99%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.75%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.27%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.03%	94.45%
CHEMBL2581	P07339	Cathepsin D	85.98%	98.95%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.30%	95.78%
CHEMBL2535	P11166	Glucose transporter	85.19%	98.75%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.19%	82.67%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	85.13%	94.03%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.86%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.32%	100.00%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.58%	92.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.97%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	81.93%	83.82%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.45%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.39%	99.17%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.33%	90.95%

Plants that contains it

• Argemone mexicana
• Berberis amurensis
• Berberis fortunei
• Berberis japonica
• Berberis julianae
• Berberis thunbergii
• Chelidonium majus
• Coptis chinensis
• Coptis deltoidea
• Coptis omeiensis
• Coptis teeta
• Corydalis turtschaninovii
• Corydalis yanhusuo
• Fibraurea recisa
• Hydrastis canadensis
• Magnolia biondii
• Meconopsis punicea
• Phellodendron amurense
• Phellodendron chinense
• Stephania tetrandra
• Thalictrum atriplex
• Thalictrum faberi
• Thalictrum foliolosum
• Thalictrum glandulosissimum
• Thalictrum microgynum
• Thalictrum petaloideum
• Thalictrum simplex
• Zanthoxylum bungeanum
• Ziziphus jujuba

Cross-Links

• PubChem: 10246509
• NPASS: NPC183485