Epiberberine

Details

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	35b8c9fd-493c-4c52-9808-8374cc07cecc
Taxonomy	Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name	16,17-dimethoxy-5,7-dioxa-1-azoniapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,4(8),9,11,14,16,18-octaene
SMILES (Canonical)	COC1=C(C=C2C(=C1)CC[N+]3=C2C=C4C=CC5=C(C4=C3)OCO5)OC
SMILES (Isomeric)	COC1=C(C=C2C(=C1)CC[N+]3=C2C=C4C=CC5=C(C4=C3)OCO5)OC
InChI	InChI=1S/C20H18NO4/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
InChI Key	FPJQGFLUORYYPE-UHFFFAOYSA-N
Popularity	48 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₀H₁₈NO₄+
Molecular Weight	336.40 g/mol
Exact Mass	336.12358306 g/mol
Topological Polar Surface Area (TPSA)	40.80 Å²
XlogP	3.60
Atomic LogP (AlogP)	3.10
H-Bond Acceptor	4
H-Bond Donor	0
Rotatable Bonds	2

Synonyms

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6873-09-2

VWP9N35AYS

MLS000563434

SMR000232286

16,17-dimethoxy-5,7-dioxa-1-azoniapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,4(8),9,11,14,16,18-octaene

GNF-Pf-2355

DEHYDROSINACTINE

EPIBERBERINE ION

UNII-VWP9N35AYS

EPIBERBERINE CATION

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	+	0.7454	74.54%
Caco-2	+	0.9645	96.45%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4894	48.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9103	91.03%
OATP1B3 inhibitior	+	0.9458	94.58%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.5348	53.48%
BSEP inhibitior	+	0.8484	84.84%
P-glycoprotein inhibitior	+	0.7556	75.56%
P-glycoprotein substrate	-	0.6888	68.88%
CYP3A4 substrate	+	0.5663	56.63%
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	-	0.6354	63.54%
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	-	0.9201	92.01%
Skin irritation	-	0.7800	78.00%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5459	54.59%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8664	86.64%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4614	46.14%
Acute Oral Toxicity (c)	III	0.6360	63.60%
Estrogen receptor binding	+	0.9373	93.73%
Androgen receptor binding	+	0.8459	84.59%
Thyroid receptor binding	+	0.6661	66.61%
Glucocorticoid receptor binding	+	0.8513	85.13%
Aromatase binding	-	0.7470	74.70%
PPAR gamma	+	0.5719	57.19%
Honey bee toxicity	-	0.7848	78.48%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	-	0.5793	57.93%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	19952.6 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	39810.7 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	15848.9 nM	Potency	via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	12589.3 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	10000 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	14125.4 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.87%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.48%	95.56%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	93.14%	82.67%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.88%	93.99%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.06%	89.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.33%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.81%	92.94%
CHEMBL2581	P07339	Cathepsin D	89.83%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.75%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.34%	94.00%
CHEMBL5747	Q92793	CREB-binding protein	89.33%	95.12%
CHEMBL1951	P21397	Monoamine oxidase A	87.28%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.97%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.79%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.22%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.05%	94.80%
CHEMBL2535	P11166	Glucose transporter	84.58%	98.75%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	84.00%	92.38%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.74%	95.78%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.57%	96.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.33%	90.95%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.08%	85.49%

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.

Corydalis turtschaninovii

Corydalis yanhusuo

Fibraurea recisa

Nandina domestica

Phellodendron amurense