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Berberine chloride
- Family: Plantae - Berberidaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid
| Canonical Smiles | COC1C(OC)CCC2C1CN1CCc3c(C1C2)cc1c(c3)OCO1 |
|---|---|
| InChI | InChI=1S/C20H27NO4/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/h8-9,12,15-17,20H,3-7,10-11H2,1-2H3 |
| InChIKey | NIQZJGTZVLTEBJ-UHFFFAOYSA-N |
| Formula | C20H27NO4 |
| HBA | 5 |
| HBD | 0 |
| MW | 345.44 |
| Rotatable Bonds | 2 |
| TPSA | 40.16 |
| LogP | 2.77 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 345.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Berberis hispanica | Berberidaceae | Plantae | 1491189 |
Showing of synonyms
Berberine chloride
Berberine hydrochloride
633-65-8
Berberinium chloride
Benzodioxide
Berberinum
Berberine chloride [JAN]
NSC-163088
UNII-UOT4O1BYV8
UOT4O1BYV8
EINECS 211-195-9
NSC 163088
NSC-646666
CCRIS 8656
DTXSID8024602
AI3-61834
BERBERINUM [HPUS]
NSC 646666
Berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-, chloride
DTXCID404602
GNF-PF-4545
BERBERINE CHLORIDE [USP-RS]
Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-, chloride
BERBERINE HYDROCHLORIDE [WHO-DD]
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
BERBERINE CHLORIDE (USP-RS)
UNII-266464AEJZ
5,6-DIHYDRO-9,10-DIMETHOXYBENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINIUM CHLORIDE
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
Berberine hydrochloride bihydrate
DTXSID5030820
BERBERINE CHLORIDE DIHYDRATE [MI]
Berberinum 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
Berbinium, 7,8,13,13a-tetradehydro-9.10-dimethoxy-2,3-(methylene dioxy)-, chloride
Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-, chloride, dihydrate
BENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINIUM, 5,6-DIHYDRO-9,10-DIMETHOXY-, CHLORIDE, HYDRATE (1:1:2)
DTXCID3010820
Iltrwwgsizfeiw-uhfffaoysa-n
Berberine (chloride)
Berberine HCl
Natural Yellow 18
Berberine chloride form
9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride
MFCD00011939
MLS002702530
Natural Yellow 18 (chloride)
CHEBI:31271
NSC163088
633-65-8 (CHLORIDE)
CHEMBL12089
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
SMR001233240
NSC646666
SR-01000711827
NCGC00016526-02
NCGC00016526-07
CAS-633-65-8
Prestwick_91
Umbellatine chloride
Dimethoxy[?] chloride
Berberine chloride (TN)
MLS002153890
SCHEMBL153906
SPECTRUM1500811
Berberine (chloride) (Standard)
HMS500N07
MSK40203A
CHEBI: 16118
GLXC-04320
HMS1569F14
HMS1921I18
HMS2096F14
HMS2210A06
HMS2235H16
HMS3336C05
HMS3373L14
HMS3655F20
Pharmakon1600-01500811
Tox21_110474
Tox21_200348
1ST40203A
AC-118
CCG-39622
HY-18258R
NSC757795
S2271
AKOS007930622
Tox21_110474_1
CS-3214
FB64955
KS-5294
NSC-757795
5,6-Dihydro-9,10-dimethoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride hydrate
NCGC00091896-01
NCGC00094858-01
NCGC00094858-02
NCGC00257902-01
HY-18258
SY076593
CAS: 638-65-8
B0450
SW196403-2
EN300-116212
Berberine chloride hydrate, technical, >=90% (AT)
SR-01000711827-4
SR-01000711827-6
Z1494829513
Berberine chloride, primary pharmaceutical reference standard
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
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
7,8,13,13a-Tetradehydro-9,1 0-dimethoxy-2,3-(methylenedioxy)berbinium 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)
- Boudjlida A, Kaci S, et al. (2019). Berberis hispanica alkaloids extract induced cell death and apoptosis in human laryngeal cancer cells Hep-2. South African Journal of Botany, 2019, 125, 134-141. [View]
Pubchem:
12456
Cas:
633-65-8
Gnps:
CCMSLIB00004711667
Kegg Ligand:
C12679
Chebi:
31271
Nmrshiftdb2:
60002118
Chembl:
CHEMBL12089
Comptox:
DTXSID8024602
Selleck:
Berberine-Hydrochloride
CPRiL:
410041
SMILES: O1COc(c12)cc3c(c2)C4N(CC3)CC5C(C4)CCCC5
Level: 0
Mol. Weight: 345.44 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.76
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.700
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.59
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.630
- Plasma Protein Binding
- 5.3
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.380
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- 1.070
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.010
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.760
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -4.580
- Rat (Acute)
- 2.800
- Rat (Chronic Oral)
- 1.040
- Fathead Minnow
- 4.330
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 408.890
- Hydration Free Energy
- -5.450
- Log(D) at pH=7.4
- 2.670
- Log(P)
- 2.98
- Log S
- -1.95
- Log(Vapor Pressure)
- -7.05
- Melting Point
- 120.78
- pKa Acid
- 12.07
- pKa Basic
- 8.13
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9458 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.9080 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.8736 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.8592 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8360 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.8026 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7982 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.7897 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7700 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7652 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 2 | 0.7618 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7613 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7540 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7434 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7408 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7404 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7394 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7379 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7321 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7317 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7173 |
| Diamine acetyltransferase 1 | P21673 | SAT1_HUMAN | Homo sapiens | 2 | 0.7160 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7158 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7155 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7130 |
| Orotidine 5'-phosphate decarboxylase | O26232 | PYRF_METTH | Methanothermobacter thermautotrophicus | 3 | 0.7114 |
| ADP compounds hydrolase NudE | P45799 | NUDE_ECOLI | Escherichia coli | 2 | 0.7100 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7068 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7048 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7038 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7028 |
| 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 | O50008 | METE1_ARATH | Arabidopsis thaliana | 2 | 0.7024 |