Berberine chloride

Details

• Internal ID: 651faa51-8942-4d39-8415-57056209d0a8
• 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-octaene;chloride
• SMILES (Canonical): COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.[Cl-]
• SMILES (Isomeric): COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.[Cl-]
• InChI: InChI=1S/C20H18NO4.ClH/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;/h3-4,7-10H,5-6,11H2,1-2H3;1H/q+1;/p-1
• InChI Key: VKJGBAJNNALVAV-UHFFFAOYSA-M
• Popularity: 622 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈ClNO₄
• Molecular Weight: 371.80 g/mol
• Exact Mass: 371.0924357 g/mol
• Topological Polar Surface Area (TPSA): 40.80 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.10
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Berberine hydrochloride
• 633-65-8
• Natural Yellow 18
• Berberinium chloride
• Benzodioxide
• Berberine HCl
• Berberine (chloride)
• Berberinum
• Berberine chloride [JAN]
• NSC-163088
• Berberin hydrochloride
• 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride
• EINECS 211-195-9
• UNII-UOT4O1BYV8
• MFCD00011939
• UOT4O1BYV8
• NSC 163088
• NSC-646666
• AI3-61834
• MLS002702530
• CCRIS 8656
• Natural Yellow 18 (chloride)
• DTXSID8024602
• CHEBI:31271
• NSC163088
• 633-65-8 (CHLORIDE)
• Berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-, chloride
• NSC 646666
• Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-, chloride
• DTXCID404602
• Berberinium chloride hydrate
• CHEMBL12089
• 5,6-Dihydro-9,10-dimethoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride hydrate
• 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium chloride
• GNF-PF-4545
• 16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium chloride
• 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-octaene;chloride
• SMR001233240
• NSC646666
• Berberine chloride form
• SR-01000711827
• NCGC00016526-02
• NCGC00016526-07
• CAS-633-65-8
• Berberine chloride, primary pharmaceutical reference standard
• C20H18NO4.Cl
• O(C)c1c(OC)ccc2cc3n(CCc4cc5OCOc5cc34)cc12
• 5,6-DIHYDRO-9,10-DIMETHOXYBENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINIUM CHLORIDE
• Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy-, chloride
• Prestwick_91
• dimethoxy[?] chloride
• Berberine chloride (TN)
• BERBERINUM [HPUS]
• Berberine Hydrochloride,(S)
• MLS002153890
• SCHEMBL153906
• SPECTRUM1500811
• HMS500N07
• CHEBI: 16118
• VKJGBAJNNALVAV-UHFFFAOYSA-M
• HMS1569F14
• HMS1921I18
• HMS2096F14
• HMS2210A06
• HMS2235H16
• HMS3336C05
• HMS3373L14
• HMS3655F20
• Pharmakon1600-01500811
• BERBERINE CHLORIDE [USP-RS]
• Tox21_110474
• Tox21_200348
• AC-118
• CCG-39622
• NSC757795
• s2271
• AKOS007930622
• Tox21_110474_1
• CS-3214
• KS-5294
• LS-1524
• NSC-757795
• Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-, chloride
• BERBERINE HYDROCHLORIDE [WHO-DD]
• NCGC00091896-01
• NCGC00094858-01
• NCGC00094858-02
• NCGC00257902-01
• HY-18258
• SY076593
• CAS: 638-65-8
• B0450
• FT-0622874
• SW196403-2
• EN300-116212
• A834344
• Berberine chloride hydrate, technical, >=90% (AT)
• Q-100261
• Q-100731
• SR-01000711827-4
• SR-01000711827-6
• BERBERINE CHLORIDE (BERBARINE(2086-73-1))
• Z1494829513
• Berberine chloride, British Pharmacopoeia (BP) Reference Standard
• Berberine chloride, European Pharmacopoeia (EP) Reference Standard
• Benzo[g]-1,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy-, chloride
• Berberine chloride, United States Pharmacopeia (USP) Reference Standard
• 5,6-dihydro-9,10-dimethoxy-1,3-benzodioxolo[5,6-a]benzo[g]quinolizinium chloride (1:1)
• Berberine Chloride, Pharmaceutical Secondary Standard; Certified Reference Material
• Berbinium,8,13,13a-tetradehydro-9.10-dimethoxy-2,3-(methylene dioxy)-, chloride
• 16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2(10),3,8,13,15(20),16,18-octaen-13-ylium chloride
• 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-iumchloride
• Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-, chloride (1:1)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8727	87.27%
Caco-2	+	0.9418	94.18%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Lysosomes	0.4132	41.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.5098	50.98%
BSEP inhibitior	+	0.8318	83.18%
P-glycoprotein inhibitior	+	0.6872	68.72%
P-glycoprotein substrate	-	0.6924	69.24%
CYP3A4 substrate	+	0.5449	54.49%
CYP2C9 substrate	-	0.8114	81.14%
CYP2D6 substrate	-	0.7718	77.18%
CYP3A4 inhibition	-	0.5297	52.97%
CYP2C9 inhibition	-	0.8576	85.76%
CYP2C19 inhibition	-	0.6263	62.63%
CYP2D6 inhibition	+	0.7986	79.86%
CYP1A2 inhibition	+	0.8831	88.31%
CYP2C8 inhibition	+	0.4443	44.43%
CYP inhibitory promiscuity	+	0.9059	90.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.4585	45.85%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.9157	91.57%
Skin irritation	-	0.7778	77.78%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7260	72.60%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8519	85.19%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6951	69.51%
Acute Oral Toxicity (c)	III	0.6389	63.89%
Estrogen receptor binding	+	0.9240	92.40%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.6855	68.55%
Glucocorticoid receptor binding	+	0.8556	85.56%
Aromatase binding	-	0.6449	64.49%
PPAR gamma	+	0.6935	69.35%
Honey bee toxicity	-	0.8583	85.83%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	-	0.4699	46.99%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	610 nM; 774 nM; 610 nM	IC50; IC50; IC50	PMID: 23062825; via CMAUP; via Super-PRED
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM	Potency	via CMAUP
CHEMBL1942	P18089	Alpha-2b adrenergic receptor	601 nM	IC50	via CMAUP
CHEMBL1916	P18825	Alpha-2c adrenergic receptor	2837 nM	IC50	via CMAUP
CHEMBL1914	P06276	Butyrylcholinesterase	18970 nM	IC50	PMID: 21924611
CHEMBL289	P10635	Cytochrome P450 2D6	4504.2 nM	IC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 12589.3 nM; 15848.9 nM; 12589.3 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL2362978	P43351	DNA repair protein RAD52 homolog	5690 nM; 2380 nM	AC50; AC50	via CMAUP; via CMAUP
CHEMBL5514	P42858	Huntingtin	10000 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	3080 nM	IC50	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	7079.5 nM; 11220.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	3437 nM	IC50	via CMAUP
CHEMBL287	Q99720	Sigma opioid receptor	1289 nM	IC50	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	4466.8 nM; 6309.6 nM; 7943.3 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.44%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.52%	91.11%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	93.75%	96.09%
CHEMBL5747	Q92793	CREB-binding protein	93.32%	95.12%
CHEMBL1951	P21397	Monoamine oxidase A	93.00%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.63%	89.62%
CHEMBL261	P00915	Carbonic anhydrase I	91.33%	96.76%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.88%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.43%	92.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.28%	93.99%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.00%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.75%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.63%	95.56%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	87.59%	94.03%
CHEMBL2581	P07339	Cathepsin D	87.43%	98.95%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.20%	82.67%
CHEMBL4040	P28482	MAP kinase ERK2	86.15%	83.82%
CHEMBL2535	P11166	Glucose transporter	85.54%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.50%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.32%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.62%	95.78%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.16%	96.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.35%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.88%	100.00%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.55%	92.38%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.05%	90.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.18%	89.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	80.28%	80.96%

Plants that contains it

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

Cross-Links

• PubChem: 12456
• NPASS: NPC296482
• ChEMBL: CHEMBL12089