5-[(6,7-Dimethoxyisoquinolin-1-yl)methyl]-2-methoxyphenol

Details

• Internal ID: 382d957b-a2b6-471c-b2eb-77f4ea8b50ad
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: 5-[(6,7-dimethoxyisoquinolin-1-yl)methyl]-2-methoxyphenol
• SMILES (Canonical): COC1=C(C=C(C=C1)CC2=NC=CC3=CC(=C(C=C32)OC)OC)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)CC2=NC=CC3=CC(=C(C=C32)OC)OC)O
• InChI: InChI=1S/C19H19NO4/c1-22-17-5-4-12(9-16(17)21)8-15-14-11-19(24-3)18(23-2)10-13(14)6-7-20-15/h4-7,9-11,21H,8H2,1-3H3
• InChI Key: MTJSWIPYMFUEPW-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.40 g/mol
• Exact Mass: 325.13140809 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.56
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 3'-Hydroxypapaverine
• 18694-10-5
• 5-[(6,7-dimethoxyisoquinolin-1-yl)methyl]-2-methoxyphenol
• 1-(3-Hydroxy-4-methoxybenzyl)-6,7-dimethoxyisoquinoline
• 3'-Desmethylpapaverine
• Phenol, 5-((6,7-dimethoxy-1-isoquinolinyl)methyl)-2-methoxy-
• DTXSID90171955
• CHEBI:175148
• FT-0665731

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9746	97.46%
Caco-2	+	0.8890	88.90%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4815	48.15%
OATP2B1 inhibitior	-	0.7295	72.95%
OATP1B1 inhibitior	+	0.9315	93.15%
OATP1B3 inhibitior	+	0.9622	96.22%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7191	71.91%
P-glycoprotein inhibitior	-	0.6204	62.04%
P-glycoprotein substrate	+	0.6973	69.73%
CYP3A4 substrate	-	0.5568	55.68%
CYP2C9 substrate	-	0.8374	83.74%
CYP2D6 substrate	+	0.4763	47.63%
CYP3A4 inhibition	+	0.6356	63.56%
CYP2C9 inhibition	-	0.8934	89.34%
CYP2C19 inhibition	+	0.5711	57.11%
CYP2D6 inhibition	+	0.8771	87.71%
CYP1A2 inhibition	+	0.7746	77.46%
CYP2C8 inhibition	+	0.8552	85.52%
CYP inhibitory promiscuity	+	0.7279	72.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9010	90.10%
Carcinogenicity (trinary)	Non-required	0.6456	64.56%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9383	93.83%
Skin irritation	-	0.7920	79.20%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.7346	73.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7218	72.18%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.9340	93.40%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8672	86.72%
Acute Oral Toxicity (c)	II	0.6504	65.04%
Estrogen receptor binding	+	0.9017	90.17%
Androgen receptor binding	+	0.6740	67.40%
Thyroid receptor binding	+	0.8065	80.65%
Glucocorticoid receptor binding	+	0.8048	80.48%
Aromatase binding	+	0.6908	69.08%
PPAR gamma	+	0.7367	73.67%
Honey bee toxicity	-	0.8795	87.95%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5451	54.51%
Fish aquatic toxicity	-	0.6222	62.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	97.59%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.75%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.78%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	93.84%	95.50%
CHEMBL5747	Q92793	CREB-binding protein	92.75%	95.12%
CHEMBL2535	P11166	Glucose transporter	92.18%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.79%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.55%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.28%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	88.76%	90.20%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.54%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.48%	99.15%
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	87.13%	95.39%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.98%	92.62%
CHEMBL4208	P20618	Proteasome component C5	84.98%	90.00%
CHEMBL2581	P07339	Cathepsin D	84.91%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.87%	94.45%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.95%	90.24%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.57%	92.38%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.41%	93.10%
CHEMBL4296013	Q5VWK5	Interleukin-23 receptor	81.97%	88.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.90%	94.03%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.87%	96.00%

Plants that contains it

• Aloe microstigma
• Chrozophora plicata
• Paeonia suffruticosa
• Papaver somniferum

Cross-Links

• PubChem: 167736
• NPASS: NPC285875