CID 6426334

Details

• Internal ID: e9461fdf-38ce-4525-bab6-f7b234685118
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 16,17-dimethoxy-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;chloride
• SMILES (Canonical): COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.[Cl-]
• SMILES (Isomeric): COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.[Cl-]
• InChI: InChI=1S/C20H18NO4.ClH/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;1H/q+1;/p-1
• InChI Key: VKJGBAJNNALVAV-UHFFFAOYSA-M
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈ClNO₄
• Molecular Weight: 371.80 g/mol
• Exact Mass: 371.0924357 g/mol
• Topological Polar Surface Area (TPSA): 40.80 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.10
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• ILTRWWGSIZFEIW-UHFFFAOYSA-N
• Berbinium, 7,8,13,13a-tetradehydro-9.10-dimethoxy-2,3-(methylene dioxy)-, chloride

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8727	87.27%
Caco-2	+	0.9418	94.18%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Lysosomes	0.4132	41.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.5098	50.98%
BSEP inhibitior	+	0.8318	83.18%
P-glycoprotein inhibitior	+	0.6872	68.72%
P-glycoprotein substrate	-	0.6924	69.24%
CYP3A4 substrate	+	0.5449	54.49%
CYP2C9 substrate	-	0.8114	81.14%
CYP2D6 substrate	-	0.7718	77.18%
CYP3A4 inhibition	-	0.5297	52.97%
CYP2C9 inhibition	-	0.8576	85.76%
CYP2C19 inhibition	-	0.6263	62.63%
CYP2D6 inhibition	+	0.7986	79.86%
CYP1A2 inhibition	+	0.8831	88.31%
CYP2C8 inhibition	+	0.4443	44.43%
CYP inhibitory promiscuity	+	0.9059	90.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.4585	45.85%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.9157	91.57%
Skin irritation	-	0.7778	77.78%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7260	72.60%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8519	85.19%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6951	69.51%
Acute Oral Toxicity (c)	III	0.6389	63.89%
Estrogen receptor binding	+	0.9240	92.40%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.6855	68.55%
Glucocorticoid receptor binding	+	0.8556	85.56%
Aromatase binding	-	0.6449	64.49%
PPAR gamma	+	0.6935	69.35%
Honey bee toxicity	-	0.8583	85.83%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	-	0.4699	46.99%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	610 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.44%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.52%	91.11%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	93.75%	96.09%
CHEMBL5747	Q92793	CREB-binding protein	93.32%	95.12%
CHEMBL1951	P21397	Monoamine oxidase A	93.00%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.63%	89.62%
CHEMBL261	P00915	Carbonic anhydrase I	91.33%	96.76%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.88%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.43%	92.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.28%	93.99%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.00%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.75%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.63%	95.56%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	87.59%	94.03%
CHEMBL2581	P07339	Cathepsin D	87.43%	98.95%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.20%	82.67%
CHEMBL4040	P28482	MAP kinase ERK2	86.15%	83.82%
CHEMBL2535	P11166	Glucose transporter	85.54%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.50%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.32%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.62%	95.78%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.16%	96.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.35%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.88%	100.00%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.55%	92.38%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.05%	90.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.18%	89.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	80.28%	80.96%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6426334
• NPASS: NPC296482
• ChEMBL: CHEMBL12089