(1R,2S,3S,4R)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol

Details

• Internal ID: 33075a0b-b082-4977-b305-636579ded4a7
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (1R,2S,3S,4R)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol
• SMILES (Canonical): CC1C(C(C2=CC(=C(C=C2C1C3=CC(=C(C=C3)OC)OC)OC)OC)O)C
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@H](C2=CC(=C(C=C2[C@H]1C3=CC(=C(C=C3)OC)OC)OC)OC)O)C
• InChI: InChI=1S/C22H28O5/c1-12-13(2)22(23)16-11-20(27-6)19(26-5)10-15(16)21(12)14-7-8-17(24-3)18(9-14)25-4/h7-13,21-23H,1-6H3/t12-,13+,21-,22-/m1/s1
• InChI Key: WBRPUFHEMGUPKR-YQJHHNQMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 372.50 g/mol
• Exact Mass: 372.19367399 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.17
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.8991	89.91%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8174	81.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9071	90.71%
OATP1B3 inhibitior	+	0.9371	93.71%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7469	74.69%
P-glycoprotein inhibitior	+	0.6164	61.64%
P-glycoprotein substrate	-	0.8038	80.38%
CYP3A4 substrate	-	0.5093	50.93%
CYP2C9 substrate	+	0.5862	58.62%
CYP2D6 substrate	+	0.4688	46.88%
CYP3A4 inhibition	+	0.5217	52.17%
CYP2C9 inhibition	-	0.6503	65.03%
CYP2C19 inhibition	+	0.6083	60.83%
CYP2D6 inhibition	-	0.8892	88.92%
CYP1A2 inhibition	+	0.8328	83.28%
CYP2C8 inhibition	+	0.4671	46.71%
CYP inhibitory promiscuity	+	0.5812	58.12%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8338	83.38%
Carcinogenicity (trinary)	Non-required	0.4406	44.06%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8278	82.78%
Skin irritation	-	0.7125	71.25%
Skin corrosion	-	0.9831	98.31%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7019	70.19%
Micronuclear	+	0.5918	59.18%
Hepatotoxicity	-	0.6914	69.14%
skin sensitisation	-	0.9121	91.21%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7668	76.68%
Acute Oral Toxicity (c)	III	0.6028	60.28%
Estrogen receptor binding	+	0.8251	82.51%
Androgen receptor binding	+	0.5766	57.66%
Thyroid receptor binding	+	0.8317	83.17%
Glucocorticoid receptor binding	+	0.6825	68.25%
Aromatase binding	+	0.6760	67.60%
PPAR gamma	+	0.6555	65.55%
Honey bee toxicity	-	0.9116	91.16%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9689	96.89%

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	97.82%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.78%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.62%	92.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.99%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.44%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.66%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.49%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.16%	99.17%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.95%	94.03%
CHEMBL2535	P11166	Glucose transporter	81.25%	98.75%
CHEMBL2581	P07339	Cathepsin D	81.16%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.71%	95.89%

Plants that contains it

• Aristolochia holostylis

Cross-Links

• PubChem: 102108255
• LOTUS: LTS0225014
• wikiData: Q105300996