(4R)-7-[(1R,2R)-1,8-dihydroxy-6-methyl-4-oxo-2,3-dihydro-1H-naphthalen-2-yl]-4,8-dihydroxy-6-methyl-3,4-dihydro-2H-naphthalen-1-one

Details

• Internal ID: 9f47cb96-6197-4d5d-ab6a-11219de03511
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: (4R)-7-[(1R,2R)-1,8-dihydroxy-6-methyl-4-oxo-2,3-dihydro-1H-naphthalen-2-yl]-4,8-dihydroxy-6-methyl-3,4-dihydro-2H-naphthalen-1-one
• SMILES (Canonical): CC1=CC2=C(C(C(CC2=O)C3=C(C4=C(C=C3C)C(CCC4=O)O)O)O)C(=C1)O
• SMILES (Isomeric): CC1=CC2=C([C@@H]([C@H](CC2=O)C3=C(C4=C(C=C3C)[C@@H](CCC4=O)O)O)O)C(=C1)O
• InChI: InChI=1S/C22H22O6/c1-9-5-11-16(25)8-13(21(27)20(11)17(26)6-9)18-10(2)7-12-14(23)3-4-15(24)19(12)22(18)28/h5-7,13-14,21,23,26-28H,3-4,8H2,1-2H3/t13-,14-,21-/m1/s1
• InChI Key: XXBQCKGZTFHKKF-ZMOMAAQPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₆
• Molecular Weight: 382.40 g/mol
• Exact Mass: 382.14163842 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 3.13
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9701	97.01%
Caco-2	-	0.7184	71.84%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8628	86.28%
OATP2B1 inhibitior	-	0.7060	70.60%
OATP1B1 inhibitior	+	0.8748	87.48%
OATP1B3 inhibitior	+	0.9063	90.63%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9145	91.45%
BSEP inhibitior	-	0.5284	52.84%
P-glycoprotein inhibitior	-	0.7683	76.83%
P-glycoprotein substrate	-	0.6866	68.66%
CYP3A4 substrate	+	0.5933	59.33%
CYP2C9 substrate	-	0.5954	59.54%
CYP2D6 substrate	-	0.7971	79.71%
CYP3A4 inhibition	-	0.6238	62.38%
CYP2C9 inhibition	-	0.6577	65.77%
CYP2C19 inhibition	-	0.8146	81.46%
CYP2D6 inhibition	-	0.8757	87.57%
CYP1A2 inhibition	+	0.6560	65.60%
CYP2C8 inhibition	+	0.4795	47.95%
CYP inhibitory promiscuity	-	0.8118	81.18%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8611	86.11%
Carcinogenicity (trinary)	Non-required	0.6262	62.62%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9065	90.65%
Skin irritation	-	0.6670	66.70%
Skin corrosion	-	0.8520	85.20%
Ames mutagenesis	+	0.5128	51.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4356	43.56%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5553	55.53%
skin sensitisation	-	0.8568	85.68%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6174	61.74%
Acute Oral Toxicity (c)	III	0.5984	59.84%
Estrogen receptor binding	+	0.8063	80.63%
Androgen receptor binding	+	0.5380	53.80%
Thyroid receptor binding	-	0.5279	52.79%
Glucocorticoid receptor binding	+	0.7371	73.71%
Aromatase binding	-	0.6682	66.82%
PPAR gamma	+	0.5436	54.36%
Honey bee toxicity	-	0.8681	86.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9630	96.30%

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	97.20%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.24%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	94.77%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.75%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	91.59%	93.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.22%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.63%	90.71%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	90.44%	91.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.92%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.79%	99.23%
CHEMBL2056	P21728	Dopamine D1 receptor	88.97%	91.00%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	88.74%	95.70%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.29%	96.38%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.87%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.78%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.51%	100.00%
CHEMBL217	P14416	Dopamine D2 receptor	84.43%	95.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.79%	92.94%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.11%	93.04%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.55%	99.15%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.96%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.75%	85.14%
CHEMBL4208	P20618	Proteasome component C5	80.62%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.52%	96.21%
CHEMBL4530	P00488	Coagulation factor XIII	80.47%	96.00%

Plants that contains it

• Euclea natalensis

Cross-Links

• PubChem: 162957333
• LOTUS: LTS0113760
• wikiData: Q105343941