(3R)-7-[5-hydroxy-2-(hydroxymethyl)-4-methoxynaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol

Details

• Internal ID: 94a97da2-02a3-43b8-bc18-80cc8f04556b
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Naphthylisoquinolines
• IUPAC Name: (3R)-7-[5-hydroxy-2-(hydroxymethyl)-4-methoxynaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
• SMILES (Canonical): CC1CC2=C(C(N1)C)C(=C(C=C2)C3=C4C=CC=C(C4=C(C=C3CO)OC)O)O
• SMILES (Isomeric): C[C@@H]1CC2=C(C(N1)C)C(=C(C=C2)C3=C4C=CC=C(C4=C(C=C3CO)OC)O)O
• InChI: InChI=1S/C23H25NO4/c1-12-9-14-7-8-17(23(27)20(14)13(2)24-12)21-15(11-25)10-19(28-3)22-16(21)5-4-6-18(22)26/h4-8,10,12-13,24-27H,9,11H2,1-3H3/t12-,13?/m1/s1
• InChI Key: ZQSUAGVTKAZDJV-PZORYLMUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₅NO₄
• Molecular Weight: 379.40 g/mol
• Exact Mass: 379.17835828 g/mol
• Topological Polar Surface Area (TPSA): 82.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 4.01
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• NSC-656298

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9523	95.23%
Caco-2	-	0.5637	56.37%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4454	44.54%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8452	84.52%
OATP1B3 inhibitior	+	0.9225	92.25%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7861	78.61%
BSEP inhibitior	+	0.8721	87.21%
P-glycoprotein inhibitior	-	0.6286	62.86%
P-glycoprotein substrate	+	0.7692	76.92%
CYP3A4 substrate	+	0.6567	65.67%
CYP2C9 substrate	-	0.7850	78.50%
CYP2D6 substrate	+	0.6521	65.21%
CYP3A4 inhibition	+	0.5176	51.76%
CYP2C9 inhibition	-	0.5486	54.86%
CYP2C19 inhibition	-	0.5615	56.15%
CYP2D6 inhibition	-	0.6218	62.18%
CYP1A2 inhibition	-	0.6723	67.23%
CYP2C8 inhibition	+	0.5766	57.66%
CYP inhibitory promiscuity	+	0.6454	64.54%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6707	67.07%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9140	91.40%
Skin irritation	-	0.8251	82.51%
Skin corrosion	-	0.9247	92.47%
Ames mutagenesis	+	0.7063	70.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.8589	85.89%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8966	89.66%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.9002	90.02%
Acute Oral Toxicity (c)	III	0.6197	61.97%
Estrogen receptor binding	+	0.7688	76.88%
Androgen receptor binding	+	0.6472	64.72%
Thyroid receptor binding	+	0.7281	72.81%
Glucocorticoid receptor binding	+	0.8935	89.35%
Aromatase binding	+	0.5883	58.83%
PPAR gamma	+	0.8471	84.71%
Honey bee toxicity	-	0.8483	84.83%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5149	51.49%
Fish aquatic toxicity	-	0.5394	53.94%

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	99.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.85%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.58%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	97.58%	93.99%
CHEMBL1951	P21397	Monoamine oxidase A	96.36%	91.49%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	95.30%	91.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.83%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.40%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.62%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.20%	92.94%
CHEMBL2535	P11166	Glucose transporter	89.62%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.59%	94.00%
CHEMBL1907	P15144	Aminopeptidase N	88.92%	93.31%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.17%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.76%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.72%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.14%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	86.84%	94.75%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.82%	96.21%
CHEMBL4208	P20618	Proteasome component C5	86.65%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.36%	99.15%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.95%	96.95%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	84.52%	94.03%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.85%	89.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.84%	92.62%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.47%	91.71%

Plants that contains it

• Ancistrocladus barteri
• Ancistrocladus tanzaniensis
• Habropetalum dawei
• Triphyophyllum peltatum

Cross-Links

• PubChem: 375947
• LOTUS: LTS0015308
• wikiData: Q105381727