(7S,13aS)-2,10-dimethoxy-7-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-7-ium-3,9-diol

Details

• Internal ID: 8b838c84-cec9-4288-91fe-8f8d6d684ead
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (7S,13aS)-2,10-dimethoxy-7-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-7-ium-3,9-diol
• SMILES (Canonical): C[N+]12CCC3=CC(=C(C=C3C1CC4=C(C2)C(=C(C=C4)OC)O)OC)O
• SMILES (Isomeric): C[N@@+]12CCC3=CC(=C(C=C3[C@@H]1CC4=C(C2)C(=C(C=C4)OC)O)OC)O
• InChI: InChI=1S/C20H23NO4/c1-21-7-6-13-9-17(22)19(25-3)10-14(13)16(21)8-12-4-5-18(24-2)20(23)15(12)11-21/h4-5,9-10,16H,6-8,11H2,1-3H3,(H-,22,23)/p+1/t16-,21-/m0/s1
• InChI Key: JPZIEDNXIGBQCY-KKSFZXQISA-O
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄NO₄+
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.17053325 g/mol
• Topological Polar Surface Area (TPSA): 58.90 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.92
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9537	95.37%
Caco-2	+	0.7536	75.36%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4444	44.44%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.9142	91.42%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.5707	57.07%
P-glycoprotein inhibitior	-	0.6239	62.39%
P-glycoprotein substrate	-	0.6144	61.44%
CYP3A4 substrate	+	0.6158	61.58%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	-	0.8663	86.63%
CYP2C9 inhibition	-	0.8883	88.83%
CYP2C19 inhibition	-	0.8004	80.04%
CYP2D6 inhibition	-	0.5772	57.72%
CYP1A2 inhibition	-	0.6650	66.50%
CYP2C8 inhibition	+	0.6564	65.64%
CYP inhibitory promiscuity	-	0.9717	97.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6587	65.87%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.7570	75.70%
Skin irritation	-	0.7555	75.55%
Skin corrosion	-	0.9346	93.46%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6675	66.75%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8766	87.66%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8491	84.91%
Acute Oral Toxicity (c)	III	0.5960	59.60%
Estrogen receptor binding	+	0.7286	72.86%
Androgen receptor binding	+	0.6118	61.18%
Thyroid receptor binding	+	0.7322	73.22%
Glucocorticoid receptor binding	+	0.7125	71.25%
Aromatase binding	-	0.5408	54.08%
PPAR gamma	+	0.7258	72.58%
Honey bee toxicity	-	0.8245	82.45%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5651	56.51%
Fish aquatic toxicity	+	0.8848	88.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.44%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.38%	96.09%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	96.11%	91.79%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.51%	92.94%
CHEMBL261	P00915	Carbonic anhydrase I	94.38%	96.76%
CHEMBL217	P14416	Dopamine D2 receptor	92.93%	95.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.24%	94.45%
CHEMBL2535	P11166	Glucose transporter	91.10%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.34%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.12%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.82%	95.89%
CHEMBL3438	Q05513	Protein kinase C zeta	88.72%	88.48%
CHEMBL1951	P21397	Monoamine oxidase A	88.19%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.97%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.44%	99.17%
CHEMBL2056	P21728	Dopamine D1 receptor	87.33%	91.00%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	86.34%	95.70%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.21%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.99%	89.62%
CHEMBL205	P00918	Carbonic anhydrase II	83.51%	98.44%
CHEMBL2581	P07339	Cathepsin D	83.09%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.37%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.58%	93.40%
CHEMBL4208	P20618	Proteasome component C5	81.34%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.54%	92.62%

Plants that contains it

• Corydalis ternata
• Corydalis turtschaninovii
• Corydalis yanhusuo
• Cyclea racemosa
• Stephania cephalantha
• Stephania japonica

Cross-Links

• PubChem: 15432819
• NPASS: NPC92213
• LOTUS: LTS0064432
• wikiData: Q105133403