Berberastine

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Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	52ffc71e-e27f-457b-b2fc-5a4b14774753
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-octaen-11-ol
SMILES (Canonical)	COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4C(C3)O)OCO5)OC
SMILES (Isomeric)	COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4C(C3)O)OCO5)OC
InChI	InChI=1S/C20H18NO5/c1-23-17-4-3-11-5-15-12-6-18-19(26-10-25-18)7-13(12)16(22)9-21(15)8-14(11)20(17)24-2/h3-8,16,22H,9-10H2,1-2H3/q+1
InChI Key	VFCGRXCCUHLLIP-UHFFFAOYSA-N
Popularity	0 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₀H₁₈NO₅+
Molecular Weight	352.40 g/mol
Exact Mass	352.11849767 g/mol
Topological Polar Surface Area (TPSA)	61.00 Å²
XlogP	2.50
Atomic LogP (AlogP)	2.59
H-Bond Acceptor	5
H-Bond Donor	1
Rotatable Bonds	2

Synonyms

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2435-73-6

C09360

Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-5-hydroxy-9,10-dimethoxy-

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-octaen-11-ol

AC1L9CE2

CHEBI:3065

C20H18NO5

DTXSID40947203

C20-H18-N-O5

Q27105935

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6469	64.69%
Caco-2	+	0.8568	85.68%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.4480	44.80%
OATP2B1 inhibitior	-	0.8849	88.49%
OATP1B1 inhibitior	+	0.9249	92.49%
OATP1B3 inhibitior	+	0.9428	94.28%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8003	80.03%
P-glycoprotein inhibitior	-	0.4607	46.07%
P-glycoprotein substrate	-	0.7034	70.34%
CYP3A4 substrate	+	0.5728	57.28%
CYP2C9 substrate	-	0.7992	79.92%
CYP2D6 substrate	-	0.7477	74.77%
CYP3A4 inhibition	-	0.6631	66.31%
CYP2C9 inhibition	-	0.8008	80.08%
CYP2C19 inhibition	+	0.6146	61.46%
CYP2D6 inhibition	+	0.7945	79.45%
CYP1A2 inhibition	+	0.8434	84.34%
CYP2C8 inhibition	+	0.5664	56.64%
CYP inhibitory promiscuity	+	0.6789	67.89%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4356	43.56%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9317	93.17%
Skin irritation	-	0.7988	79.88%
Skin corrosion	-	0.9465	94.65%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8105	81.05%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8577	85.77%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7198	71.98%
Acute Oral Toxicity (c)	III	0.7192	71.92%
Estrogen receptor binding	+	0.8725	87.25%
Androgen receptor binding	+	0.6992	69.92%
Thyroid receptor binding	+	0.7268	72.68%
Glucocorticoid receptor binding	+	0.8424	84.24%
Aromatase binding	-	0.5499	54.99%
PPAR gamma	+	0.7532	75.32%
Honey bee toxicity	-	0.8656	86.56%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	-	0.7755	77.55%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	96.34%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.78%	96.77%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	94.69%	89.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.75%	91.11%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	92.27%	83.57%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.30%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.68%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.50%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.42%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.87%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.68%	94.45%
CHEMBL2535	P11166	Glucose transporter	84.77%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.75%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.62%	89.00%
CHEMBL2581	P07339	Cathepsin D	84.44%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.82%	95.89%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	82.09%	85.49%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	82.02%	82.67%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.66%	92.38%
CHEMBL3438	Q05513	Protein kinase C zeta	81.07%	88.48%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.01%	96.00%
CHEMBL261	P00915	Carbonic anhydrase I	80.80%	96.76%
CHEMBL5747	Q92793	CREB-binding protein	80.67%	95.12%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.25%	99.17%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.07%	89.44%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.