(1R,3R)-5-[3-[4-[(1S,3S)-6,8-dihydroxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-1-hydroxy-8-methoxy-6-methylnaphthalen-2-yl]-4-hydroxy-5-methoxy-7-methylnaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol

Details

• Internal ID: ae4fe514-7639-41c7-b40e-85f14d7df707
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Naphthylisoquinolines
• IUPAC Name: (1R,3R)-5-[3-[4-[(1S,3S)-6,8-dihydroxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-1-hydroxy-8-methoxy-6-methylnaphthalen-2-yl]-4-hydroxy-5-methoxy-7-methylnaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol
• SMILES (Canonical): CC1CC2=C(C(=CC(=C2C(N1)C)O)O)C3=CC(=C(C4=C3C=C(C=C4OC)C)O)C5=C(C6=C(C=C(C=C6OC)C)C(=C5)C7=C8CC(NC(C8=C(C=C7O)O)C)C)O
• SMILES (Isomeric): C[C@@H]1CC2=C(C(=CC(=C2[C@H](N1)C)O)O)C3=CC(=C(C4=C3C=C(C=C4OC)C)O)C5=C(C6=C(C=C(C=C6OC)C)C(=C5)C7=C8C[C@@H](N[C@H](C8=C(C=C7O)O)C)C)O
• InChI: InChI=1S/C46H48N2O8/c1-19-9-25-27(41-31-13-21(3)47-23(5)39(31)33(49)17-35(41)51)15-29(45(53)43(25)37(11-19)55-7)30-16-28(26-10-20(2)12-38(56-8)44(26)46(30)54)42-32-14-22(4)48-24(6)40(32)34(50)18-36(42)52/h9-12,15-18,21-24,47-54H,13-14H2,1-8H3/t21-,22+,23-,24+
• InChI Key: GMLBVLXDRNJFGR-WAPCQROESA-N
• Popularity: 46 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₄₈N₂O₈
• Molecular Weight: 756.90 g/mol
• Exact Mass: 756.34106649 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 8.30
• Atomic LogP (AlogP): 9.05
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9481	94.81%
Caco-2	-	0.8310	83.10%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5737	57.37%
OATP2B1 inhibitior	-	0.7092	70.92%
OATP1B1 inhibitior	+	0.8668	86.68%
OATP1B3 inhibitior	+	0.9386	93.86%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8111	81.11%
BSEP inhibitior	+	0.9879	98.79%
P-glycoprotein inhibitior	+	0.7813	78.13%
P-glycoprotein substrate	+	0.5136	51.36%
CYP3A4 substrate	+	0.6240	62.40%
CYP2C9 substrate	-	0.7713	77.13%
CYP2D6 substrate	+	0.7329	73.29%
CYP3A4 inhibition	-	0.7273	72.73%
CYP2C9 inhibition	-	0.6566	65.66%
CYP2C19 inhibition	-	0.5430	54.30%
CYP2D6 inhibition	-	0.5331	53.31%
CYP1A2 inhibition	-	0.7286	72.86%
CYP2C8 inhibition	+	0.6446	64.46%
CYP inhibitory promiscuity	+	0.5906	59.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5385	53.85%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9031	90.31%
Skin irritation	-	0.8312	83.12%
Skin corrosion	-	0.9134	91.34%
Ames mutagenesis	-	0.5037	50.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8966	89.66%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9158	91.58%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.9015	90.15%
Acute Oral Toxicity (c)	III	0.5235	52.35%
Estrogen receptor binding	+	0.8198	81.98%
Androgen receptor binding	+	0.6906	69.06%
Thyroid receptor binding	+	0.6541	65.41%
Glucocorticoid receptor binding	+	0.6946	69.46%
Aromatase binding	+	0.6291	62.91%
PPAR gamma	+	0.6996	69.96%
Honey bee toxicity	-	0.7824	78.24%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	-	0.4155	41.55%

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	99.34%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.58%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	96.11%	92.94%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	94.11%	91.79%
CHEMBL1951	P21397	Monoamine oxidase A	93.46%	91.49%
CHEMBL213	P08588	Beta-1 adrenergic receptor	92.43%	95.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.15%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.14%	96.21%
CHEMBL2581	P07339	Cathepsin D	91.01%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.92%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.67%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.54%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.28%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.55%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.44%	93.03%
CHEMBL2535	P11166	Glucose transporter	86.29%	98.75%
CHEMBL4208	P20618	Proteasome component C5	85.81%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.76%	97.09%
CHEMBL3438	Q05513	Protein kinase C zeta	83.62%	88.48%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	82.40%	97.31%
CHEMBL2056	P21728	Dopamine D1 receptor	82.29%	91.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.98%	99.15%
CHEMBL5747	Q92793	CREB-binding protein	81.80%	95.12%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.20%	99.17%

Plants that contains it

• Ancistrocladus abbreviatus
• Ancistrocladus korupensis

Cross-Links

• PubChem: 44592719
• LOTUS: LTS0019012
• wikiData: Q104251368