(2R,3S,4R)-4-(3,4-dimethoxyphenyl)-2-hydroxy-6,7-dimethoxy-2,3-dimethyl-3,4-dihydronaphthalen-1-one

Details

• Internal ID: eccc3044-1241-4c60-9421-d339688a726a
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (2R,3S,4R)-4-(3,4-dimethoxyphenyl)-2-hydroxy-6,7-dimethoxy-2,3-dimethyl-3,4-dihydronaphthalen-1-one
• SMILES (Canonical): CC1C(C2=CC(=C(C=C2C(=O)C1(C)O)OC)OC)C3=CC(=C(C=C3)OC)OC
• SMILES (Isomeric): C[C@H]1[C@@H](C2=CC(=C(C=C2C(=O)[C@]1(C)O)OC)OC)C3=CC(=C(C=C3)OC)OC
• InChI: InChI=1S/C22H26O6/c1-12-20(13-7-8-16(25-3)17(9-13)26-4)14-10-18(27-5)19(28-6)11-15(14)21(23)22(12,2)24/h7-12,20,24H,1-6H3/t12-,20+,22+/m0/s1
• InChI Key: JSKWJJGGQAJPOM-IPLWYIACSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.40 g/mol
• Exact Mass: 386.17293854 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.44
• H-Bond Acceptor: 6
• 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	+	0.9956	99.56%
Caco-2	+	0.9147	91.47%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8722	87.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9160	91.60%
OATP1B3 inhibitior	+	0.9386	93.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7059	70.59%
P-glycoprotein inhibitior	+	0.7641	76.41%
P-glycoprotein substrate	-	0.8075	80.75%
CYP3A4 substrate	+	0.5835	58.35%
CYP2C9 substrate	-	0.7919	79.19%
CYP2D6 substrate	-	0.7883	78.83%
CYP3A4 inhibition	+	0.7924	79.24%
CYP2C9 inhibition	-	0.6473	64.73%
CYP2C19 inhibition	-	0.5496	54.96%
CYP2D6 inhibition	-	0.9169	91.69%
CYP1A2 inhibition	+	0.5498	54.98%
CYP2C8 inhibition	-	0.6541	65.41%
CYP inhibitory promiscuity	-	0.6339	63.39%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8930	89.30%
Carcinogenicity (trinary)	Non-required	0.4369	43.69%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.7637	76.37%
Skin irritation	-	0.7166	71.66%
Skin corrosion	-	0.9832	98.32%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4050	40.50%
Micronuclear	+	0.5359	53.59%
Hepatotoxicity	-	0.5289	52.89%
skin sensitisation	-	0.9490	94.90%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6068	60.68%
Acute Oral Toxicity (c)	III	0.6425	64.25%
Estrogen receptor binding	+	0.9154	91.54%
Androgen receptor binding	-	0.5183	51.83%
Thyroid receptor binding	+	0.8026	80.26%
Glucocorticoid receptor binding	+	0.7303	73.03%
Aromatase binding	+	0.6080	60.80%
PPAR gamma	+	0.7559	75.59%
Honey bee toxicity	-	0.8337	83.37%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9773	97.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.01%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.04%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.47%	92.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.47%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.14%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.50%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.43%	95.56%
CHEMBL4208	P20618	Proteasome component C5	85.49%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.07%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.15%	89.00%

Plants that contains it

• Aristolochia holostylis
• Salvia miltiorrhiza

Cross-Links

• PubChem: 102180985
• LOTUS: LTS0251597
• wikiData: Q105226869