(2S,3R)-1-[4-[(1R,2R)-2-(1,3-benzodioxol-5-yl)-2-hydroxy-1-methyl-ethoxy]-3-methoxy-phenyl]-4-[4-[(1R,2R)-2-(3,4-dimethoxyphenyl)-2-hydroxy-1-methyl-ethoxy]-3-methoxy-phenyl]-2,3-dimethyl-butane-1,4-dione

Details

• Internal ID: eb1a1d35-3f62-4f60-9f2a-6a58e333335c
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: (2S,3R)-1-[4-[(1R,2R)-1-(1,3-benzodioxol-5-yl)-1-hydroxypropan-2-yl]oxy-3-methoxyphenyl]-4-[4-[(1R,2R)-1-(3,4-dimethoxyphenyl)-1-hydroxypropan-2-yl]oxy-3-methoxyphenyl]-2,3-dimethylbutane-1,4-dione
• SMILES (Canonical): CC(C(C)C(=O)C1=CC(=C(C=C1)OC(C)C(C2=CC(=C(C=C2)OC)OC)O)OC)C(=O)C3=CC(=C(C=C3)OC(C)C(C4=CC5=C(C=C4)OCO5)O)OC
• SMILES (Isomeric): C[C@@H]([C@@H](C)C(=O)C1=CC(=C(C=C1)O[C@H](C)[C@@H](C2=CC(=C(C=C2)OC)OC)O)OC)C(=O)C3=CC(=C(C=C3)O[C@H](C)[C@@H](C4=CC5=C(C=C4)OCO5)O)OC
• InChI: InChI=1S/C41H46O12/c1-22(38(42)26-11-15-32(35(17-26)48-7)52-24(3)40(44)28-9-13-30(46-5)34(19-28)47-6)23(2)39(43)27-12-16-33(36(18-27)49-8)53-25(4)41(45)29-10-14-31-37(20-29)51-21-50-31/h9-20,22-25,40-41,44-45H,21H2,1-8H3/t22-,23+,24-,25-,40+,41+/m1/s1
• InChI Key: APNXRQITXDDCJC-AAKSZLAOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₄₆O₁₂
• Molecular Weight: 730.80 g/mol
• Exact Mass: 730.29892690 g/mol
• Topological Polar Surface Area (TPSA): 148.00 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 6.79
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 17

Synonyms

• (2S,3R)-1-[4-[(1R,2R)-2-(1,3-benzodioxol-5-yl)-2-hydroxy-1-methyl-ethoxy]-3-methoxy-phenyl]-4-[4-[(1R,2R)-2-(3,4-dimethoxyphenyl)-2-hydroxy-1-methyl-ethoxy]-3-methoxy-phenyl]-2,3-dimethyl-butane-1,4-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9678	96.78%
Caco-2	-	0.8498	84.98%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7941	79.41%
OATP2B1 inhibitior	+	0.5795	57.95%
OATP1B1 inhibitior	+	0.9239	92.39%
OATP1B3 inhibitior	+	0.7984	79.84%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9434	94.34%
P-glycoprotein inhibitior	+	0.8160	81.60%
P-glycoprotein substrate	-	0.5645	56.45%
CYP3A4 substrate	+	0.5114	51.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7760	77.60%
CYP3A4 inhibition	+	0.6333	63.33%
CYP2C9 inhibition	+	0.9088	90.88%
CYP2C19 inhibition	+	0.7082	70.82%
CYP2D6 inhibition	-	0.6771	67.71%
CYP1A2 inhibition	-	0.5624	56.24%
CYP2C8 inhibition	-	0.7518	75.18%
CYP inhibitory promiscuity	+	0.6696	66.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.4323	43.23%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9017	90.17%
Skin irritation	-	0.8058	80.58%
Skin corrosion	-	0.9665	96.65%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3617	36.17%
Micronuclear	+	0.7674	76.74%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7939	79.39%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6612	66.12%
Acute Oral Toxicity (c)	III	0.6362	63.62%
Estrogen receptor binding	+	0.8391	83.91%
Androgen receptor binding	+	0.7722	77.22%
Thyroid receptor binding	+	0.6132	61.32%
Glucocorticoid receptor binding	+	0.7910	79.10%
Aromatase binding	+	0.6246	62.46%
PPAR gamma	+	0.7288	72.88%
Honey bee toxicity	-	0.8179	81.79%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7452	74.52%
Fish aquatic toxicity	+	0.9712	97.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.53%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.23%	85.14%
CHEMBL4208	P20618	Proteasome component C5	95.20%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.78%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.71%	94.80%
CHEMBL2581	P07339	Cathepsin D	92.55%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.43%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.76%	96.00%
CHEMBL2535	P11166	Glucose transporter	91.22%	98.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	91.15%	89.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.26%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	89.60%	90.20%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.14%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.87%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.68%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.59%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.44%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.27%	95.89%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	85.23%	80.96%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.06%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.33%	92.62%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.64%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.92%	95.89%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.68%	85.30%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.36%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.71%	97.14%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	80.28%	98.33%

Plants that contains it

• Saururus chinensis

Cross-Links

• PubChem: 76321153
• NPASS: NPC100425
• ChEMBL: CHEMBL3105546
• LOTUS: LTS0203485
• wikiData: Q104916444