9,10-Dimethoxy-2,3-(methylenedioxy)-13,13a-didehydro-8-berbinol

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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	8c229cdb-bce8-4df5-b140-03b28ffcc218
Taxonomy	Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name	16,17-dimethoxy-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-heptaen-14-ol
SMILES (Canonical)	COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2O)OCO5)OC
SMILES (Isomeric)	COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2O)OCO5)OC
InChI	InChI=1S/C20H19NO5/c1-23-15-4-3-12-7-14-13-9-17-16(25-10-26-17)8-11(13)5-6-21(14)20(22)18(12)19(15)24-2/h3-4,7-9,20,22H,5-6,10H2,1-2H3
InChI Key	ZRBGFWOXAQPDTH-UHFFFAOYSA-N
Popularity	2 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₀H₁₉NO₅
Molecular Weight	353.40 g/mol
Exact Mass	353.12632271 g/mol
Topological Polar Surface Area (TPSA)	60.40 Å²
XlogP	3.00
Atomic LogP (AlogP)	2.79
H-Bond Acceptor	6
H-Bond Donor	1
Rotatable Bonds	2

Synonyms

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10134-52-8

Berberinol

16,17-dimethoxy-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-heptaen-14-ol

8-BERBINOL, 13,13a-DIDEHYDRO-9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)-

SCHEMBL13328184

DTXSID50906068

9,10-Dimethoxy-5,8-dihydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-8-ol

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	+	0.9160	91.60%
Caco-2	+	0.8894	88.94%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7226	72.26%
OATP2B1 inhibitior	-	0.8740	87.40%
OATP1B1 inhibitior	+	0.9238	92.38%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8654	86.54%
P-glycoprotein inhibitior	+	0.6424	64.24%
P-glycoprotein substrate	-	0.6617	66.17%
CYP3A4 substrate	+	0.6088	60.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3459	34.59%
CYP3A4 inhibition	+	0.5101	51.01%
CYP2C9 inhibition	-	0.7786	77.86%
CYP2C19 inhibition	-	0.7580	75.80%
CYP2D6 inhibition	+	0.5156	51.56%
CYP1A2 inhibition	-	0.5584	55.84%
CYP2C8 inhibition	-	0.6560	65.60%
CYP inhibitory promiscuity	+	0.6076	60.76%
UGT catelyzed	-	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4946	49.46%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.9282	92.82%
Skin irritation	-	0.7601	76.01%
Skin corrosion	-	0.9305	93.05%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6722	67.22%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8438	84.38%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6991	69.91%
Acute Oral Toxicity (c)	III	0.6021	60.21%
Estrogen receptor binding	+	0.7509	75.09%
Androgen receptor binding	+	0.5983	59.83%
Thyroid receptor binding	+	0.7299	72.99%
Glucocorticoid receptor binding	+	0.7271	72.71%
Aromatase binding	-	0.6189	61.89%
PPAR gamma	+	0.6317	63.17%
Honey bee toxicity	-	0.8660	86.60%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5551	55.51%
Fish aquatic toxicity	+	0.7466	74.66%

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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.39%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.68%	96.77%
CHEMBL1951	P21397	Monoamine oxidase A	95.59%	91.49%
CHEMBL2581	P07339	Cathepsin D	93.88%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.35%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.03%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.06%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.35%	95.89%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	89.65%	82.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.01%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.69%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.60%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.68%	92.62%
CHEMBL5747	Q92793	CREB-binding protein	86.67%	95.12%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.60%	94.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.53%	95.78%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.54%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.54%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.05%	100.00%
CHEMBL4208	P20618	Proteasome component C5	83.63%	90.00%
CHEMBL2535	P11166	Glucose transporter	82.95%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.75%	94.45%
CHEMBL2056	P21728	Dopamine D1 receptor	82.54%	91.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.41%	99.17%
CHEMBL261	P00915	Carbonic anhydrase I	81.38%	96.76%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.29%	90.95%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.26%	82.38%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.69%	94.78%
CHEMBL3438	Q05513	Protein kinase C zeta	80.09%	88.48%

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.