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

Details

• Internal ID: 58b49b08-b9ae-44db-80d7-e53608f2e921
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (13aS)-3,10-dimethoxy-7-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-7-ium-2,9-diol
• SMILES (Canonical): C[N+]12CCC3=CC(=C(C=C3C1CC4=C(C2)C(=C(C=C4)OC)O)O)OC
• SMILES (Isomeric): C[N+]12CCC3=CC(=C(C=C3[C@@H]1CC4=C(C2)C(=C(C=C4)OC)O)O)OC
• InChI: InChI=1S/C20H23NO4/c1-21-7-6-13-9-19(25-3)17(22)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: LKLWVKCEYSPQHL-BJQOMGFOSA-O
• Popularity: 0 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	+	0.8007	80.07%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4444	44.44%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.9212	92.12%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.7189	71.89%
P-glycoprotein inhibitior	-	0.5121	51.21%
P-glycoprotein substrate	-	0.5286	52.86%
CYP3A4 substrate	+	0.6210	62.10%
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	+	0.6558	65.58%
CYP inhibitory promiscuity	-	0.9717	97.17%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6587	65.87%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8283	82.83%
Skin irritation	-	0.7555	75.55%
Skin corrosion	-	0.9346	93.46%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6411	64.11%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8766	87.66%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8561	85.61%
Acute Oral Toxicity (c)	III	0.5960	59.60%
Estrogen receptor binding	+	0.7224	72.24%
Androgen receptor binding	+	0.6118	61.18%
Thyroid receptor binding	+	0.7214	72.14%
Glucocorticoid receptor binding	+	0.6520	65.20%
Aromatase binding	-	0.5895	58.95%
PPAR gamma	+	0.6725	67.25%
Honey bee toxicity	-	0.8318	83.18%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.30%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.22%	91.11%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	96.09%	91.79%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.23%	92.94%
CHEMBL261	P00915	Carbonic anhydrase I	93.91%	96.76%
CHEMBL217	P14416	Dopamine D2 receptor	92.76%	95.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.53%	94.45%
CHEMBL2535	P11166	Glucose transporter	91.10%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.67%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.57%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.82%	95.89%
CHEMBL3438	Q05513	Protein kinase C zeta	89.15%	88.48%
CHEMBL2056	P21728	Dopamine D1 receptor	88.86%	91.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.91%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.44%	99.17%
CHEMBL2581	P07339	Cathepsin D	84.00%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.95%	89.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.69%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	82.53%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.37%	94.00%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	82.04%	95.70%
CHEMBL4208	P20618	Proteasome component C5	81.34%	90.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.24%	93.40%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.54%	92.62%

Plants that contains it

• Artemisia annua
• Artemisia capillaris
• Artemisia scoparia
• Cissampelos pareira
• Stephania tetrandra
• Tinospora hainanensis

Cross-Links

• PubChem: 9884460
• NPASS: NPC172204