Canadine

Details

• Internal ID: ac3fdece-1bd6-4806-a094-78d5ac3dddb5
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene
• SMILES (Canonical): COC1=C(C2=C(CC3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
• SMILES (Isomeric): COC1=C(C2=C(CC3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
• InChI: InChI=1S/C20H21NO4/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/h3-4,8-9,16H,5-7,10-11H2,1-2H3
• InChI Key: VZTUIEROBZXUFA-UHFFFAOYSA-N
• Popularity: 319 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.40 g/mol
• Exact Mass: 339.14705815 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.09
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Tetrahydroberberine
• 522-97-4
• Xanthopuccine
• Canadin
• dl-Canadine
• 29074-38-2
• Canadine dl-form
• Berberine, tetrahydro-
• dl-Tetrahydroberberine
• NSC 94918
• (d,l)-Tetrahydroberberine
• EINECS 208-338-2
• (+-)-Tetrahydroberberine
• UNII-V2SSH085X8
• CHEMBL275097
• V2SSH085X8
• DTXSID5022724
• CHEBI:22998
• Berbine, 9,10-dimethoxy-2,3-(methylenedioxy)-
• NSC 36351
• NSC36351
• NSC-36351
• NSC-94918
• 5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo(g)benzo-1,3-dioxolo(5,6-a)quinolizine
• 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine,5,8,13,13a-tetrahydro-9,10-dimethoxy-
• 9,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
• canadine, (+-)-isomer
• 5,8,13,13a-tetrahydro-9,10-dimethoxy-6H-benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine
• 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-
• 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene
• DTXCID802724
• Berbine, 9,10-dimethoxy-2,3-(methylenedioxy)-, (+-)-
• 5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine
• 5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]benzo-1,3-dioxolo[5,6-a]quinolizine
• 6H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-
• Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (+-)-
• NCGC00016486-01
• CAS-522-97-4
• Prestwick_186
• (+-)-Canadine
• (+/-)-Canadine
• (.+-.)-Canadine
• Tetrahydroberberine THB
• Tetrahydroberberine,THB
• CANADINE [MI]
• (+-)-Tetrahydroberberin
• (.+/-.)-Canadine
• Prestwick0_000672
• Prestwick1_000672
• Prestwick2_000672
• Prestwick3_000672
• CANADINE (DL-)
• Canadine, (.+-.)-
• TimTec1_005946
• Oprea1_387569
• Oprea1_388593
• (.+-.)-Tetrahydroberberine
• BSPBio_000763
• MLS001202314
• CANADINE, (+-)-
• SCHEMBL232164
• SPBio_002684
• CANADINE DL-FORM [MI]
• BPBio1_000841
• CANADINE, (+/-)-
• VZTUIEROBZXUFA-UHFFFAOYSA-N
• HMS1550O06
• HMS1570G05
• HMS2097G05
• HMS2852B23
• HMS3358B11
• HMS3886O13
• HY-N0925
• NSC94918
• Tox21_110451
• BBL028121
• BDBM50203122
• MFCD00067284
• s5153
• STK722197
• AKOS000277103
• AKOS021856290
• Tox21_110451_1
• CCG-202815
• LS-2134
• NCGC00173359-04
• NCGC00173359-06
• NCGC00173359-08
• AC-34748
• NCI60_003328
• NCI60_042115
• SMR000393885
• VS-08674
• LS-175345
• Berbine,10-dimethoxy-2,3-(methylenedioxy)-
• FT-0659151
• FT-0664216
• BRD-A69950438-001-04-5
• BRD-A69950438-001-11-0
• Q27109653
• Berbine,10-dimethoxy-2,3-(methylenedioxy)-, (.+-.)-
• Berbine, 9,10-dimethoxy-2,3-(methylenedioxy)-, (.+.)-
• 6H-Benzo[g]-1,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-
• 6H-Benzo[g]-1,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10,dimethoxy-, (.+-.)-
• (1S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10.0^{4,8.0^{15,20]henicosa-2,4(8),9,15(20),16,18-hexaene
• 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0(2),(1)?.0?,?.0(1)?,(2)?]henicosa-2,4(8),9,15(20),16,18-hexaene
• 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10.0^{4,8.0^{15,20]henicosa-2,4(8),9,15(20),16,18-hexaene
• 6H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine, 5,8,13,13a-tetrahydro-9,10,dimethoxy-, (+-)-
• 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10,dimethoxy-, (.+.)-
• 9,10-bis(methyloxy)-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
• 9,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline #
• DL-CANADINE (GOLDENSEALRT;118-08-1;84603-60-1;2086-83-1;171869-95-7;5936-29-8)
• Isoquinolino[2,1-b]isoquinoline, 5,6,7,8,13,13a-hexahydro-2,3-methylenedioxy-9,10-dimethoxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9360	93.60%
Caco-2	+	0.8914	89.14%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.4940	49.40%
OATP2B1 inhibitior	-	0.8714	87.14%
OATP1B1 inhibitior	+	0.9469	94.69%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.8262	82.62%
P-glycoprotein inhibitior	-	0.5493	54.93%
P-glycoprotein substrate	-	0.7109	71.09%
CYP3A4 substrate	+	0.5963	59.63%
CYP2C9 substrate	-	0.6129	61.29%
CYP2D6 substrate	+	0.7342	73.42%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	-	0.9149	91.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	+	0.9236	92.36%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.6987	69.87%
CYP inhibitory promiscuity	+	0.8191	81.91%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5672	56.72%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9718	97.18%
Skin irritation	-	0.7945	79.45%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8173	81.73%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8548	85.48%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5421	54.21%
Estrogen receptor binding	+	0.6357	63.57%
Androgen receptor binding	+	0.5412	54.12%
Thyroid receptor binding	+	0.5639	56.39%
Glucocorticoid receptor binding	+	0.7210	72.10%
Aromatase binding	-	0.7645	76.45%
PPAR gamma	-	0.5220	52.20%
Honey bee toxicity	-	0.8401	84.01%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.7945	79.45%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4081	P13726	Coagulation factor III	8.35 nM; 8.35 nM	IC50; IC50	via Super-PRED; PMID: 23199480
CHEMBL2056	P21728	Dopamine D1 receptor	48.6 nM	Ki	via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	80.2 nM	Ki	via Super-PRED
CHEMBL234	P35462	Dopamine D3 receptor	433 nM	Ki	via Super-PRED
CHEMBL219	P21917	Dopamine D4 receptor	486 nM	Ki	via Super-PRED
CHEMBL1850	P21918	Dopamine D5 receptor	62.1 nM	Ki	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	354.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.45%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.68%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.96%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.34%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.34%	86.33%
CHEMBL261	P00915	Carbonic anhydrase I	93.15%	96.76%
CHEMBL5747	Q92793	CREB-binding protein	92.66%	95.12%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	89.78%	82.38%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.71%	89.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.91%	91.11%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	87.91%	90.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.88%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.80%	95.56%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	87.55%	96.86%
CHEMBL2535	P11166	Glucose transporter	87.25%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.21%	95.89%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	86.79%	82.67%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.24%	92.62%
CHEMBL240	Q12809	HERG	84.95%	89.76%
CHEMBL2581	P07339	Cathepsin D	84.39%	98.95%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.29%	89.05%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	84.06%	80.96%
CHEMBL3438	Q05513	Protein kinase C zeta	83.95%	88.48%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.30%	93.99%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.66%	95.78%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.58%	100.00%
CHEMBL4302	P08183	P-glycoprotein 1	81.01%	92.98%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.23%	90.71%

Plants that contains it

• Annona mucosa
• Argemone mexicana
• Berberis cretica
• Berberis heteropoda
• Chelidonium majus
• Corydalis ambigua
• Corydalis cava
• Corydalis intermedia
• Corydalis ophiocarpa
• Corydalis solida
• Corydalis ternata
• Corydalis turtschaninovii
• Corydalis yanhusuo
• Coscinium fenestratum
• Fibraurea recisa
• Glaucium arabicum
• Glaucium squamigerum
• Hydrastis canadensis
• Imperata cylindrica
• Lindera glauca
• Macleaya cordata
• Magnolia compressa
• Phellodendron amurense
• Phellodendron chinense
• Sanguinaria canadensis
• Zanthoxylum ailanthoides
• Zanthoxylum integrifoliolum
• Zanthoxylum rhetsa

Cross-Links

• PubChem: 34458
• NPASS: NPC41178
• ChEMBL: CHEMBL275097
• LOTUS: LTS0116620
• wikiData: Q27109653