(2S,3R)-2-(4-{2-[(3S,4S)-3,4-Dimethylpyrrolidin-1-YL]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-OL

Details

• Internal ID: 61e91d97-e02a-4ac5-9837-442b82e7a507
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: (2S,3R)-2-[4-[2-[(3S,4S)-3,4-dimethylpyrrolidin-1-yl]ethoxy]phenyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol
• InChI: InChI=1S/C28H31NO4S/c1-18-16-29(17-19(18)2)13-14-32-24-10-5-20(6-11-24)27-28(21-3-7-22(30)8-4-21)34-26-15-23(31)9-12-25(26)33-27/h3-12,15,18-19,27-28,30-31H,13-14,16-17H2,1-2H3/t18-,19-,27+,28-/m1/s1
• InChI Key: COJFASLRENZFLP-FNZLKOBSSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₁NO₄S
• Molecular Weight: 477.60 g/mol
• Exact Mass: 477.19737964 g/mol
• Topological Polar Surface Area (TPSA): 87.50 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 6.03
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• (2S,3R)-2-(4-{2-[(3S,4S)-3,4-DIMETHYLPYRROLIDIN-1-YL]ETHOXY}PHENYL)-3-(4-HYDROXYPHENYL)-2,3-DIHYDRO-1,4-BENZOXATHIIN-6-OL
• 1xp6
• BDBM50157160
• Q27457289
• (2s,3r)-2-(4-2-[(3s,4s)-3,4-dimethylpyrrolidin-1-yl]ethoxyphenyl)-3-(4-hydroxyphenyl)-2,3dihydro-1,4-benzoxathiin-6-ol
• (2S,3R)-2-{4-[2-((S)-3,4-Dimethyl-pyrrolidin-1-yl)-ethoxy]-phenyl}-3-(4-hydroxy-phenyl)-2,3-dihydro-benzo[1,4]oxathiin-6-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9290	92.90%
Caco-2	-	0.6134	61.34%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5267	52.67%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8479	84.79%
OATP1B3 inhibitior	+	0.9297	92.97%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5054	50.54%
P-glycoprotein inhibitior	+	0.7950	79.50%
P-glycoprotein substrate	+	0.5424	54.24%
CYP3A4 substrate	+	0.6651	66.51%
CYP2C9 substrate	+	0.5969	59.69%
CYP2D6 substrate	+	0.6220	62.20%
CYP3A4 inhibition	+	0.6162	61.62%
CYP2C9 inhibition	-	0.8248	82.48%
CYP2C19 inhibition	+	0.6789	67.89%
CYP2D6 inhibition	+	0.5604	56.04%
CYP1A2 inhibition	-	0.6246	62.46%
CYP2C8 inhibition	+	0.6012	60.12%
CYP inhibitory promiscuity	+	0.7782	77.82%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6418	64.18%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9204	92.04%
Skin irritation	-	0.8053	80.53%
Skin corrosion	-	0.9375	93.75%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8575	85.75%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8466	84.66%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7588	75.88%
Acute Oral Toxicity (c)	III	0.6591	65.91%
Estrogen receptor binding	+	0.6113	61.13%
Androgen receptor binding	+	0.8504	85.04%
Thyroid receptor binding	+	0.6023	60.23%
Glucocorticoid receptor binding	+	0.5936	59.36%
Aromatase binding	+	0.5842	58.42%
PPAR gamma	+	0.6343	63.43%
Honey bee toxicity	-	0.8284	82.84%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9300	93.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL206	P03372	Estrogen receptor alpha	0.7 nM; 0.4 nM; 0.5 nM	IC50; IC50; IC50	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL242	Q92731	Estrogen receptor beta	73 nM; 22 nM; 37 nM	IC50; IC50; IC50	via Super-PRED; via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.49%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.61%	97.09%
CHEMBL2243	O00519	Anandamide amidohydrolase	95.35%	97.53%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.67%	91.11%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	94.17%	93.10%
CHEMBL4208	P20618	Proteasome component C5	93.95%	90.00%
CHEMBL2581	P07339	Cathepsin D	92.66%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.80%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.53%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.32%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.99%	99.17%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	89.09%	83.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.82%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.64%	94.73%
CHEMBL4330	Q9NS75	Cysteinyl leukotriene receptor 2	86.63%	98.00%
CHEMBL238	Q01959	Dopamine transporter	86.26%	95.88%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.99%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.81%	89.00%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	84.27%	96.25%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.48%	93.40%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.58%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	81.25%	91.49%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.83%	82.38%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.34%	94.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.09%	95.89%

Plants that contains it

• Dracaena angustifolia

Cross-Links

• PubChem: 449207
• LOTUS: LTS0135417
• wikiData: Q27457289