Palmatine chloride

Details

• Internal ID: 9afef1b4-827b-4dc2-89e6-1d8a0f3f7428
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium;chloride
• SMILES (Canonical): COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC.[Cl-]
• SMILES (Isomeric): COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC.[Cl-]
• InChI: InChI=1S/C21H22NO4.ClH/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;1H/q+1;/p-1
• InChI Key: RLQYRXCUPVKSAW-UHFFFAOYSA-M
• Popularity: 363 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂ClNO₄
• Molecular Weight: 387.90 g/mol
• Exact Mass: 387.1237359 g/mol
• Topological Polar Surface Area (TPSA): 40.80 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.39
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 10605-02-4
• Palmatine hydrochloride
• Palmatine (chloride)
• Fibrauretin
• 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium chloride
• UNII-ZJ6W8881Z8
• ZJ6W8881Z8
• 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium chloride
• MFCD00016656
• NSC209407
• NSC 209407
• NSC-209407
• 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium;chloride
• 5,6-Dihydro-2,3,9,10-tetramethoxydibenzo[a,g]quinolizinium Chloride
• Dibenzo(a,g)quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy-, chloride
• CHEMBL274189
• SR-01000841226
• Dibenzo[a,g]quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy-, chloride
• Prestwick_374
• Palmatine Hydrochloride,(S)
• C21H22NO4.Cl
• MLS002153886
• SCHEMBL754702
• SPECTRUM1500872
• DTXSID40909881
• HMS1569D20
• HMS1921M10
• HMS2096D20
• HMS2234K10
• HMS3374O05
• HMS3651D03
• HMS3884P15
• BCP02274
• HY-N0110
• PALMATINE CHLORIDE [USP-RS]
• PALMATINE CHLORIDE [WHO-DD]
• AC-678
• CCG-38528
• s2397
• Palmatine chloride, >=98% (HPLC)
• AKOS015903832
• BCP9001048
• CS-5237
• NCGC00094871-01
• NCGC00094871-02
• AS-72876
• SMR001233237
• FT-0689390
• P2138
• SW196633-2
• Q-100041
• SR-01000841226-4
• Q27295608
• berbinium, 7,8,13,13a-tetradehydro-2,3,9,10-tetramethoxy-, chloride
• 3,4,10,11-TETRAMETHOXY-7,8-DIHYDRO-6??-AZATETRAPHEN-6-YLIUM CHLORIDE
• dibenzo(a,g)quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy-, chloride (1:1)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8617	86.17%
Caco-2	+	0.9593	95.93%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.3867	38.67%
OATP2B1 inhibitior	-	0.8900	89.00%
OATP1B1 inhibitior	+	0.9434	94.34%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	+	0.8009	80.09%
P-glycoprotein inhibitior	+	0.7382	73.82%
P-glycoprotein substrate	-	0.5315	53.15%
CYP3A4 substrate	+	0.5318	53.18%
CYP2C9 substrate	-	0.8149	81.49%
CYP2D6 substrate	-	0.7292	72.92%
CYP3A4 inhibition	-	0.7670	76.70%
CYP2C9 inhibition	-	0.8570	85.70%
CYP2C19 inhibition	-	0.7747	77.47%
CYP2D6 inhibition	+	0.5367	53.67%
CYP1A2 inhibition	-	0.7195	71.95%
CYP2C8 inhibition	+	0.4565	45.65%
CYP inhibitory promiscuity	-	0.5239	52.39%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5627	56.27%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9332	93.32%
Skin irritation	-	0.7730	77.30%
Skin corrosion	-	0.9340	93.40%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6499	64.99%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8971	89.71%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8572	85.72%
Acute Oral Toxicity (c)	III	0.7228	72.28%
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	-	0.8966	89.66%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7200	72.00%
Fish aquatic toxicity	-	0.6039	60.39%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	900 nM	IC50	PMID: 17994701
CHEMBL2362978	P43351	DNA repair protein RAD52 homolog	5190 nM	AC50	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	7.9 nM; 7.9 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5747	Q92793	CREB-binding protein	95.33%	95.12%
CHEMBL1951	P21397	Monoamine oxidase A	94.37%	91.49%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.85%	93.99%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.73%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.04%	92.94%
CHEMBL2535	P11166	Glucose transporter	89.84%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.30%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.85%	94.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	88.51%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.86%	86.33%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.72%	94.03%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	86.24%	92.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.82%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.32%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.59%	91.11%
CHEMBL2056	P21728	Dopamine D1 receptor	84.30%	91.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.62%	96.67%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	82.32%	85.49%
CHEMBL4302	P08183	P-glycoprotein 1	82.18%	92.98%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.11%	96.00%
CHEMBL4158	P49327	Fatty acid synthase	81.12%	82.50%
CHEMBL1937	Q92769	Histone deacetylase 2	80.55%	94.75%

Plants that contains it

• Coptis chinensis
• Coptis deltoidea
• Coptis japonica
• Coptis teeta
• Corydalis decumbens
• Phellodendron amurense
• Phellodendron chinense

Cross-Links

• PubChem: 73442
• NPASS: NPC36229
• ChEMBL: CHEMBL274189