Palmatine

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	62acdac8-a3c0-45a9-a98d-87268bd98d77
Taxonomy	Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name	2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium
SMILES (Canonical)	COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC
SMILES (Isomeric)	COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC
InChI	InChI=1S/C21H22NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,9-12H,7-8H2,1-4H3/q+1
InChI Key	QUCQEUCGKKTEBI-UHFFFAOYSA-N
Popularity	462 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₁H₂₂NO₄+
Molecular Weight	352.40 g/mol
Exact Mass	352.15488318 g/mol
Topological Polar Surface Area (TPSA)	40.80 Å²
XlogP	3.70
Atomic LogP (AlogP)	3.38
H-Bond Acceptor	4
H-Bond Donor	0
Rotatable Bonds	4

Synonyms

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3486-67-7

Berbericinine

Palmatin

O,O-Dimethyldemethyleneberberine

Burasaine

palmatine ion

palmatine cation

Dibenzo[a,g]quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy-

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium

7,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxyberbinium

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	+	0.7299	72.99%
Caco-2	+	0.9593	95.93%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5889	58.89%
OATP2B1 inhibitior	-	0.8900	89.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9524	95.24%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	+	0.8009	80.09%
P-glycoprotein inhibitior	+	0.7382	73.82%
P-glycoprotein substrate	-	0.5988	59.88%
CYP3A4 substrate	+	0.5332	53.32%
CYP2C9 substrate	-	0.8233	82.33%
CYP2D6 substrate	+	0.3791	37.91%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.6593	65.93%
CYP1A2 inhibition	-	0.8169	81.69%
CYP2C8 inhibition	-	0.5985	59.85%
CYP inhibitory promiscuity	-	0.5887	58.87%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5656	56.56%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9332	93.32%
Skin irritation	-	0.7680	76.80%
Skin corrosion	-	0.9485	94.85%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6499	64.99%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9187	91.87%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8304	83.04%
Acute Oral Toxicity (c)	III	0.7551	75.51%
Estrogen receptor binding	+	0.9416	94.16%
Androgen receptor binding	+	0.8055	80.55%
Thyroid receptor binding	+	0.5487	54.87%
Glucocorticoid receptor binding	+	0.8081	80.81%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.5327	53.27%
Honey bee toxicity	-	0.8983	89.83%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	-	0.7123	71.23%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL289	P10635	Cytochrome P450 2D6	12589.25 nM	AC50	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	12589.3 nM 12589.3 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	501.2 nM 501.2 nM	Potency Potency	via Super-PRED via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5747	Q92793	CREB-binding protein	94.86%	95.12%
CHEMBL1951	P21397	Monoamine oxidase A	93.90%	91.49%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.55%	93.99%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.64%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.35%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.11%	95.56%
CHEMBL2535	P11166	Glucose transporter	89.58%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.85%	94.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	88.09%	96.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.72%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.36%	86.33%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	86.27%	92.38%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	84.12%	94.03%
CHEMBL4302	P08183	P-glycoprotein 1	83.93%	92.98%
CHEMBL2581	P07339	Cathepsin D	83.67%	98.95%
CHEMBL2056	P21728	Dopamine D1 receptor	83.18%	91.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.57%	94.75%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	82.24%	85.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.99%	91.11%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.21%	96.67%
CHEMBL4158	P49327	Fatty acid synthase	80.46%	82.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.19%	96.00%
CHEMBL4581	P52732	Kinesin-like protein 1	80.09%	93.18%

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.

Achyrocline satureioides

Acorus calamus

Agathosma bisulca

Aloe microstigma subsp. microstigma

Anamirta cocculus

Androsace septentrionalis