8-Trichloromethyldihydroberberine

Details

• Internal ID: 50b68e84-bd8e-4105-be0a-26b6293902bc
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaene
• InChI: InChI=1S/C21H18Cl3NO4/c1-26-15-4-3-12-7-14-13-9-17-16(28-10-29-17)8-11(13)5-6-25(14)20(21(22,23)24)18(12)19(15)27-2/h3-4,7-9,20H,5-6,10H2,1-2H3
• InChI Key: CAGHPRDTHLKFCW-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈Cl₃NO₄
• Molecular Weight: 454.70 g/mol
• Exact Mass: 453.030141 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 5.21
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 8-Trichloromethyldihydroberberine
• NSC269192
• dimethoxy(trichloromethyl)[?]
• CHEMBL396263
• SCHEMBL12329060
• DTXSID80313347
• NSC-269192
• 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8-dihydro-9,10-dimethoxy-8-(trichloromethyl)-
• NCI60_002194
• TRICHLOROMETHYLDIHYDROBERBRINE, 8-
• 9,10-Dimethoxy-8-(trichloromethyl)-5,8-dihydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9780	97.80%
Caco-2	+	0.7551	75.51%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5467	54.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9230	92.30%
OATP1B3 inhibitior	+	0.9467	94.67%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6098	60.98%
BSEP inhibitior	+	0.9301	93.01%
P-glycoprotein inhibitior	+	0.6834	68.34%
P-glycoprotein substrate	-	0.6038	60.38%
CYP3A4 substrate	+	0.6425	64.25%
CYP2C9 substrate	-	0.5905	59.05%
CYP2D6 substrate	+	0.5456	54.56%
CYP3A4 inhibition	+	0.7708	77.08%
CYP2C9 inhibition	-	0.6357	63.57%
CYP2C19 inhibition	+	0.5795	57.95%
CYP2D6 inhibition	+	0.6072	60.72%
CYP1A2 inhibition	+	0.7156	71.56%
CYP2C8 inhibition	+	0.4519	45.19%
CYP inhibitory promiscuity	+	0.9373	93.73%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.4287	42.87%
Eye corrosion	-	0.9821	98.21%
Eye irritation	-	0.9667	96.67%
Skin irritation	-	0.7711	77.11%
Skin corrosion	-	0.9220	92.20%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6634	66.34%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.5966	59.66%
skin sensitisation	-	0.8244	82.44%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6722	67.22%
Acute Oral Toxicity (c)	III	0.5960	59.60%
Estrogen receptor binding	+	0.8921	89.21%
Androgen receptor binding	+	0.6644	66.44%
Thyroid receptor binding	+	0.7990	79.90%
Glucocorticoid receptor binding	+	0.8594	85.94%
Aromatase binding	+	0.6147	61.47%
PPAR gamma	+	0.8247	82.47%
Honey bee toxicity	-	0.8130	81.30%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9291	92.91%

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	97.38%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.86%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.35%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	95.15%	89.62%
CHEMBL2581	P07339	Cathepsin D	93.11%	98.95%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	92.61%	82.67%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	91.65%	95.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.46%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.99%	95.89%
CHEMBL5747	Q92793	CREB-binding protein	90.81%	95.12%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.60%	91.11%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.25%	92.62%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	89.11%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.10%	93.40%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.35%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.45%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.34%	94.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	87.23%	96.86%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.00%	97.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.40%	93.99%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	85.31%	94.78%
CHEMBL4208	P20618	Proteasome component C5	84.56%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.39%	94.45%
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	83.85%	92.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.31%	89.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.15%	90.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.93%	100.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.81%	100.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.49%	90.24%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.06%	96.25%
CHEMBL2535	P11166	Glucose transporter	81.33%	98.75%

Plants that contains it

• Berberis integerrima
• Berberis lycium

Cross-Links

• PubChem: 320713
• LOTUS: LTS0240019
• wikiData: Q82064327