Berberine

Details

• Internal ID: 250854e2-c8e7-47ec-847b-9ef6516b5319
• 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
• SMILES (Canonical): COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC
• SMILES (Isomeric): COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC
• InChI: InChI=1S/C20H18NO4/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/q+1
• InChI Key: YBHILYKTIRIUTE-UHFFFAOYSA-N
• Popularity: 4,134 references in papers

Physical and Chemical Properties

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

Synonyms

• 2086-83-1
• Umbellatine
• Berberin
• Berbericine
• Majarine
• Thalsine
• Umbellatin
• Berberone
• 0I8Y3P32UF
• CHEBI:16118
• EINECS 218-229-1
• BRN 3570374
• UNII-0I8Y3P32UF
• Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-
• DTXSID9043857
• C20H18NO4
• 9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetrahydroberbinium
• Berberal
• 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
• BERBERINE (MART.)
• BERBERINE [MART.]
• Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy-
• BERBINIUM, 7,8,13,13a-TETRAHYDRO-9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)-
• Berbamine sulphate acid
• CHEMBL12089
• 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
• 9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium
• 5,6-DIHYDRO-9,10-DIMETHOXY-1,3-BENZODIOXOLO(5,6-A)BENZO(G)QUINOLIZINIUM
• 5,6-DIHYDRO-9,10-DIMETHOXYBENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINIUM
• 9,10-DIMETHOXY-5,6-DIHYDRO(1,3)DIOXOLO(4,5-G)ISOQUINO(3,2-A)ISOQUINOLIN-7-IUM
• 9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium
• GNF-PF-4545
• BER
• NSC646666
• NCGC00016526-02
• NCGC00016526-07
• CAS-633-65-8
• Berbinium
• berberine dimer
• Coptis rhizome
• 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenebis(oxy))berbinium
• 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium
• Umbellatine (6CI)
• Spectrum_001110
• ST055798
• BERBERINE [MI]
• Prestwick0_000586
• Prestwick1_000586
• Prestwick2_000586
• Prestwick3_000586
• Spectrum2_000894
• Spectrum3_000618
• Spectrum4_000785
• Spectrum5_001458
• BERBERINE [VANDF]
• D0W8WB
• UPCMLD-DP032
• NCIMech_000354
• BERBERINE [WHO-DD]
• 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium
• SCHEMBL25632
• BSPBio_000432
• BSPBio_002156
• KBioGR_001230
• KBioSS_001590
• cid_12456
• DivK1c_000265
• inverted exclamation markY97%
• SPBio_000708
• SPBio_002651
• BPBio1_000476
• CHEMBL295124
• MEGxp0_001923
• DTXCID7023857
• UPCMLD-DP032:001
• ACon1_001957
• BCBcMAP01_000112
• GTPL11353
• KBio1_000265
• KBio2_001590
• KBio2_004158
• KBio2_006726
• KBio3_001656
• NINDS_000265
• YBHILYKTIRIUTE-UHFFFAOYSA-N
• 34MD1011DM
• HMS3561D13
• HY-N0716
• AC-117
• BBL029198
• BDBM50203126
• CCG-35898
• s9046
• STK870320
• 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium
• AKOS002141363
• DB04115
• SDCCGMLS-0066718.P001
• 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo-[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium
• IDI1_000265
• SMP1_000298
• NCGC00016526-01
• NCGC00016526-03
• NCGC00016526-04
• NCGC00016526-05
• NCGC00016526-06
• NCGC00016526-08
• NCGC00016526-11
• NCGC00091896-03
• LS-43472
• NCI60_001050
• NCI60_001224
• NCI60_004319
• SBI-0051613.P002
• BERBERINE (CONSTITUENT OF GOLDENSEAL)
• CS-0009734
• FT-0603587
• C00757
• A904183
• Q176525
• BERBERINE (CONSTITUENT OF GOLDENSEAL) [DSC]
• Q-200701
• Q-200702
• SR-01000711827-5
• BRD-K14796088-003-06-0
• BRD-K14796088-003-17-7
• Benzylpenicillin benzathine, Antibiotic for Culture Media Use Only
• 5,6-dihydro-9,10-dimethoxy-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
• Berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-
• 3,4-dimethoxy-6,7-dihydro-[1,3]dioxolo[4,5-g]pyrido[2,1-a]isoquinolin-5-ylium
• 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium
• 9,10-Dimethoxy-5,6-dihydro-7lambda~5~-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
• Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy- (9CI)
• 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
• 3-[3-(2-ethyl-1,3-thiazol-4-yl)phenyl]-5-{2-[(4-methylphenyl)sulfonyl]ethyl}-1,2,4-oxadiazole
• 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium chloride
• 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; chloride
• InChI=1/C20H18NO4/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/q+

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7454	74.54%
Caco-2	+	0.9418	94.18%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4894	48.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9399	93.99%
OATP1B3 inhibitior	+	0.9458	94.58%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.5348	53.48%
BSEP inhibitior	+	0.8318	83.18%
P-glycoprotein inhibitior	+	0.6872	68.72%
P-glycoprotein substrate	-	0.7450	74.50%
CYP3A4 substrate	+	0.5449	54.49%
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	-	0.6066	60.66%
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	-	0.9157	91.57%
Skin irritation	-	0.7800	78.00%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7260	72.60%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8664	86.64%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6482	64.82%
Acute Oral Toxicity (c)	III	0.6360	63.60%
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	-	0.8600	86.00%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	-	0.5793	57.93%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	100 nM; 100 nM	IC50; IC50	PMID: 26003344; via Super-PRED
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	44668.4 nM	Potency	via CMAUP
CHEMBL1914	P06276	Butyrylcholinesterase	1090 nM	IC50	PMID: 26003344
CHEMBL3356	P05177	Cytochrome P450 1A2	5011.87 nM	AC50	via CMAUP
CHEMBL4878	Q16678	Cytochrome P450 1B1	44 nM	Ki	via Super-PRED
CHEMBL289	P10635	Cytochrome P450 2D6	2511.89 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	2511.9 nM; 2511.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	12589.3 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	7079.5 nM	Potency	via CMAUP
CHEMBL2916	O14746	Telomerase reverse transcriptase	37000 nM	IC50	PMID: 22336246
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	12589.3 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	97.52%	96.77%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	93.51%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.47%	91.11%
CHEMBL261	P00915	Carbonic anhydrase I	92.69%	96.76%
CHEMBL5747	Q92793	CREB-binding protein	92.67%	95.12%
CHEMBL1951	P21397	Monoamine oxidase A	92.43%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.55%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.43%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.88%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.20%	92.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.94%	93.99%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.75%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.27%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.03%	94.45%
CHEMBL2581	P07339	Cathepsin D	85.98%	98.95%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.30%	95.78%
CHEMBL2535	P11166	Glucose transporter	85.19%	98.75%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.19%	82.67%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	85.13%	94.03%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.86%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.32%	100.00%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.58%	92.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.97%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	81.93%	83.82%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.45%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.39%	99.17%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.33%	90.95%

Plants that contains it

• Alhagi maurorum
• Aloe microstigma subsp. microstigma
• Anamirta cocculus
• Andira inermis
• Andira surinamensis
• Androsace septentrionalis
• Angelica dahurica
• Annona mucosa
• Aquilegia alpina
• Aquilegia jonesii
• Aralia hispida
• Arcangelisia flava
• Argemone albiflora
• Argemone mexicana
• Argemone polyanthemos
• Argemone subfusiformis
• Artabotrys maingayi
• Astragalus thracicus
• Baeckea frutescens
• Balanophora polyandra
• Berberis aggregata
• Berberis amurensis
• Berberis aquifolium
• Berberis aristata
• Berberis boliviana
• Berberis brandisiana
• Berberis canadensis
• Berberis chitria
• Berberis crataegina
• Berberis cretica
• Berberis darwinii
• Berberis empetrifolia
• Berberis fendleri
• Berberis fortunei
• Berberis glauca
• Berberis heteropoda
• Berberis ilicifolia
• Berberis iliensis
• Berberis integerrima
• Berberis microphylla
• Berberis nummularia
• Berberis oblonga
• Berberis polyodonta
• Berberis repens
• Berberis sibirica
• Berberis stolonifera
• Berberis thunbergii
• Berberis virgetorum
• Berberis vulgaris
• Berberis wilsoniae
• Boeberastrum anthemidifolium
• Calocephalus knappii
• Chelidonium majus
• Chenopodiastrum murale
• Chenopodium quinoa
• Cissampelos pareira
• Citrus medica
• Coleostephus myconis
• Coprosma foetidissima
• Coptis chinensis
• Coptis deltoidea
• Coptis japonica
• Coptis quinquefolia
• Coptis teeta
• Corydalis caucasica
• Corydalis decumbens
• Corydalis intermedia
• Corydalis ophiocarpa
• Corydalis pallida
• Corydalis solida
• Corydalis speciosa
• Corydalis ternata
• Corydalis turtschaninovii
• Corydalis yanhusuo
• Coscinium fenestratum
• Cryptocarya chinensis
• Cyperus nipponicus
• Dalbergia spruceana
• Davidsonia pruriens
• Dendrobium amplum
• Diospyros ebenum
• Echinochloa crus-galli
• Eriocephalus kingesii
• Erythrophleum suaveolens
• Eschscholzia californica
• Eupatorium album
• Euphorbia fortissima
• Festuca pratensis
• Fibraurea recisa
• Geranium collinum
• Girgensohnia oppositiflora
• Glaucium arabicum
• Glaucium squamigerum
• Haematocarpus subpeltatus
• Harpullia cupanioides
• Hemionitis schaffneri
• Horsfieldia glabra
• Hydrastis canadensis
• Isodon eriocalyx
• Isodon wikstroemioides
• Lappula squarrosa
• Ligularia nelumbifolia
• Ligularia sagitta
• Lilium brownii
• Lilium lancifolium
• Lilium pomponium
• Lilium pumilum
• Lychnophora pinaster
• Macrozamia spiralis
• Marrubium parviflorum
• Mezzettia parviflora
• Microglossa pyrifolia
• Nandina domestica
• Neocussonia longipedicellata
• Nuxia sphaerocephala
• Panax quinquefolius
• Papaver albiflorum
• Papaver cambricum
• Papaver dubium
• Papaver lapponicum
• Papaver pinnatifidum
• Papaver rhoeas
• Parabaena sagittata
• Parthenium confertum
• Penianthus zenkeri
• Phellodendron amurense
• Phellodendron chinense
• Phellodendron chinense var. glabriusculum
• Pilosocereus chrysacanthus
• Piper methysticum
• Piper retrofractum
• Plectranthus ernstii
• Polygonatum orientale
• Psacalium peltatum
• Psathyrotes ramosissima
• Radula voluta
• Sanguinaria canadensis
• Scleropyrum pentandrum
• Selliguea hastata
• Senna spectabilis
• Sideritis ferrensis
• Stachys plumosa
• Stylophorum diphyllum
• Stylophorum lasiocarpum
• Symphytum officinale
• Thalictrum alpinum
• Thalictrum atriplex
• Thalictrum baicalense
• Thalictrum cultratum
• Thalictrum delavayi
• Thalictrum dioicum
• Thalictrum foetidum
• Thalictrum foliolosum
• Thalictrum glandulosissimum
• Thalictrum hernandezii
• Thalictrum javanicum
• Thalictrum lankesteri
• Thalictrum lucidum
• Thalictrum minus
• Thalictrum orientale
• Thalictrum petaloideum
• Thalictrum przewalskii
• Thalictrum revolutum
• Thalictrum simplex
• Thalictrum tuberosum
• Thalictrum wangii
• Theobroma speciosum
• Thuja plicata
• Tinospora cordifolia
• Tinospora merrilliana
• Trifolium diffusum
• Trifolium dubium
• Ulex parviflorus subsp. airensis
• Vepris heterophylla
• Veronica stricta
• Xanthorhiza simplicissima
• Youngia japonica
• Zanthoxylum acuminatum subsp. juniperinum
• Zanthoxylum schreberi

Cross-Links

• PubChem: 2353
• NPASS: NPC53069
• ChEMBL: CHEMBL295124
• LOTUS: LTS0101484
• wikiData: Q176525