(6As)-11-hydroxy-1,2,10-trimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinolinium

Details

• Internal ID: 6d34c771-b39c-42ab-ac6e-b062b462ec3e
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (6aS)-1,2,10-trimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium-11-ol
• SMILES (Canonical): C[N+]1(CCC2=CC(=C(C3=C2C1CC4=C3C(=C(C=C4)OC)O)OC)OC)C
• SMILES (Isomeric): C[N+]1(CCC2=CC(=C(C3=C2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC)OC)C
• InChI: InChI=1S/C21H25NO4/c1-22(2)9-8-13-11-16(25-4)21(26-5)19-17(13)14(22)10-12-6-7-15(24-3)20(23)18(12)19/h6-7,11,14H,8-10H2,1-5H3/p+1/t14-/m0/s1
• InChI Key: XQINTCORIZHGFD-AWEZNQCLSA-O
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆NO₄+
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.18618331 g/mol
• Topological Polar Surface Area (TPSA): 47.90 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.31
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• Chackranine
• 25342-82-9
• (6as)-11-hydroxy-1,2,10-trimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinolinium
• NIOSH/FL6698000
• FL66980000
• Isocorydine methochloride
• (6aS)-1,2,10-trimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium-11-ol
• CHEMBL1186240
• DTXSID70948187
• AKOS040735203
• NCI60_042007
• 11-Hydroxy-1,2,10-trimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium
• 4H-Dibenzo(de,g)quinolinium, 5,6,6a,7-tetrahydro-11-hydroxy-1,2,10-trimethoxy-6,6-dimethyl-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9450	94.50%
Caco-2	+	0.8674	86.74%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5336	53.36%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9233	92.33%
OATP1B3 inhibitior	+	0.9482	94.82%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	+	0.5519	55.19%
P-glycoprotein inhibitior	-	0.7531	75.31%
P-glycoprotein substrate	-	0.7650	76.50%
CYP3A4 substrate	+	0.6023	60.23%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	-	0.8857	88.57%
CYP2C9 inhibition	-	0.9052	90.52%
CYP2C19 inhibition	-	0.9115	91.15%
CYP2D6 inhibition	-	0.5483	54.83%
CYP1A2 inhibition	-	0.6854	68.54%
CYP2C8 inhibition	+	0.6592	65.92%
CYP inhibitory promiscuity	-	0.9647	96.47%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7138	71.38%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.8289	82.89%
Skin irritation	-	0.7642	76.42%
Skin corrosion	-	0.9240	92.40%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8063	80.63%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8785	87.85%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.9231	92.31%
Acute Oral Toxicity (c)	III	0.7308	73.08%
Estrogen receptor binding	+	0.7482	74.82%
Androgen receptor binding	+	0.6829	68.29%
Thyroid receptor binding	+	0.7227	72.27%
Glucocorticoid receptor binding	+	0.7927	79.27%
Aromatase binding	+	0.6092	60.92%
PPAR gamma	+	0.7773	77.73%
Honey bee toxicity	-	0.9023	90.23%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5651	56.51%
Fish aquatic toxicity	+	0.9286	92.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3192	Q9BY41	Histone deacetylase 8	98.67%	93.99%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.54%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.39%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.07%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	92.35%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.10%	92.94%
CHEMBL217	P14416	Dopamine D2 receptor	90.16%	95.62%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	89.85%	91.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.39%	95.56%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	89.12%	97.31%
CHEMBL3438	Q05513	Protein kinase C zeta	88.14%	88.48%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.04%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.00%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.38%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.57%	86.33%
CHEMBL2535	P11166	Glucose transporter	85.00%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.79%	89.62%
CHEMBL2056	P21728	Dopamine D1 receptor	84.39%	91.00%
CHEMBL2581	P07339	Cathepsin D	83.35%	98.95%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.14%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.77%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.31%	95.78%
CHEMBL261	P00915	Carbonic anhydrase I	81.30%	96.76%

Plants that contains it

• Coptis chinensis
• Coptis deltoidea
• Coptis japonica
• Coptis teeta
• Corydalis decumbens
• Magnolia grandiflora
• Manihot esculenta
• Menispermum dauricum
• Nandina domestica
• Penianthus zenkeri
• Phellodendron amurense
• Phellodendron chinense
• Rhigiocarya racemifera
• Sinomenium acutum
• Stephania cephalantha
• Stephania tetrandra
• Tinospora sagittata
• Xylopia parviflora
• Zanthoxylum nitidum

Cross-Links

• PubChem: 161487
• NPASS: NPC259732
• LOTUS: LTS0203896
• wikiData: Q82925967