(S)-Canadine

Details

• Internal ID: 5b8c79e4-4f8a-4e91-849d-dbaa70d734b1
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (1S)-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(C[C@H]3C4=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/t16-/m0/s1
• InChI Key: VZTUIEROBZXUFA-INIZCTEOSA-N
• Popularity: 60 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

• (S)-Canadine
• Canadine l-form
• (S)-Tetrahydroberberine
• (-)-Canadine
• (-)-Tetrahydroberberine
• (S)-(-)-Canadine
• (S)-(-)-Tetrahydroberberine
• Canadine, (-)-
• EINECS 225-815-0
• UNII-Q97V5BUT9D
• Q97V5BUT9D
• 9,10-Dimethoxy-2,3-(methylenedioxy)berbine
• CHEBI:16592
• NSC 36351
• 5,6,13,13a-Tetrahydro-9,10-dimethoxy-2,3-(methylenedioxy)-8H-dibenzo(a,g)quinolizine
• 6H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (S)-
• (1S)-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
• l-Canadine
• 13a-alpha-BERBINE, 9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)-
• (13aS)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine
• (13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
• alpha-canadine
• 6H-BENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINE, 5,8,13,13A-TETRAHYDRO-9,10-DIMETHOXY-, (13AS)-
• 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (13aS)-
• 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (S)-
• canadine, (S)-isomer
• .ALPHA.-CANADINE
• Canadine (Tetrahydroberberine)
• CANADINE L-FORM [MI]
• SCHEMBL432394
• CHEMBL490533
• DTXSID10110003
• HY-N1418
• BDBM50429047
• CCG-36046
• AKOS032962408
• LS-43450
• CS-0016842
• C03329
• Q4382087
• Z2216911272
• 13a.alpha.-Berbine, 9,10-dimethoxy-2,3-(methylenedioxy)-
• 9,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-benzo[g][1,3]benzodioxolo[5,6-a]quinolizine
• (13aS)-5, 8, 13, 13a-tetrahydro-9, 10-dimethoxy-6H-benzo[g] -1,3-benzodioxolo[5, 6-a]quinolizine
• (13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline

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	IC50	via Super-PRED
CHEMBL2056	P21728	Dopamine D1 receptor	66 nM; 48.6 nM	Ki; Ki	PMID: 23332346; via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	119 nM; 80.2 nM	Ki; Ki	PMID: 23332346; 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

• Angelica dahurica
• Argemone mexicana
• Artabotrys maingayi
• Chelidonium majus
• Corydalis cava
• Corydalis cheilanthifolia
• Corydalis ophiocarpa
• Corydalis solida
• Corydalis ternata
• Corydalis turtschaninovii
• Corydalis yanhusuo
• Coscinium fenestratum
• Diospyros ebenum
• Dovyalis hebecarpa
• Eremophila oppositifolia
• Eschscholzia californica
• Fibraurea recisa
• Hydrastis canadensis
• Ixeris repens
• Lappula squarrosa
• Ligularia sagitta
• Lindera glauca
• Mezzettia parviflora
• Phellodendron amurense
• Phellodendron chinense
• Piper methysticum
• Psacalium peltatum
• Senna spectabilis
• Stachys plumosa
• Symphytum officinale
• Taxillus sutchuenensis var. duclouxii
• Thuja plicata
• Ulex parviflorus subsp. airensis
• Vepris heterophylla
• Zanthoxylum ailanthoides
• Zanthoxylum integrifoliolum
• Zanthoxylum martinicense

Cross-Links

• PubChem: 21171
• NPASS: NPC216459
• ChEMBL: CHEMBL490533
• LOTUS: LTS0147391
• wikiData: Q4382087