(2R,3R,4R,5S,6R)-5-[4-[(2R,3S,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-2,3,4-triol

Details

• Internal ID: ef17b4db-4590-4239-8647-efca440f1dae
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 7,9-epoxylignans
• IUPAC Name: (2R,3R,4R,5S,6R)-5-[4-[(2R,3S,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-2,3,4-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)CC2COC(C2CO)C3=CC(=C(C=C3)OC4C(OC(C(C4O)O)O)CO)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C[C@@H]2CO[C@H]([C@@H]2CO)C3=CC(=C(C=C3)O[C@@H]4[C@H](O[C@H]([C@@H]([C@H]4O)O)O)CO)OC)O
• InChI: InChI=1S/C26H34O11/c1-33-19-8-13(3-5-17(19)29)7-15-12-35-24(16(15)10-27)14-4-6-18(20(9-14)34-2)36-25-21(11-28)37-26(32)23(31)22(25)30/h3-6,8-9,15-16,21-32H,7,10-12H2,1-2H3/t15-,16-,21-,22-,23-,24+,25-,26-/m1/s1
• InChI Key: HLMUYOCDACORAV-NAHKDHJCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₁
• Molecular Weight: 522.50 g/mol
• Exact Mass: 522.21011190 g/mol
• Topological Polar Surface Area (TPSA): 168.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.13
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7142	71.42%
Caco-2	-	0.8238	82.38%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8117	81.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8283	82.83%
OATP1B3 inhibitior	+	0.9487	94.87%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4903	49.03%
P-glycoprotein inhibitior	-	0.4421	44.21%
P-glycoprotein substrate	-	0.6098	60.98%
CYP3A4 substrate	+	0.6558	65.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7860	78.60%
CYP3A4 inhibition	-	0.6159	61.59%
CYP2C9 inhibition	-	0.7885	78.85%
CYP2C19 inhibition	-	0.6807	68.07%
CYP2D6 inhibition	-	0.8669	86.69%
CYP1A2 inhibition	-	0.8524	85.24%
CYP2C8 inhibition	+	0.7498	74.98%
CYP inhibitory promiscuity	+	0.6997	69.97%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6240	62.40%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9316	93.16%
Skin irritation	-	0.8575	85.75%
Skin corrosion	-	0.9572	95.72%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7950	79.50%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8656	86.56%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9343	93.43%
Acute Oral Toxicity (c)	III	0.7164	71.64%
Estrogen receptor binding	+	0.7087	70.87%
Androgen receptor binding	+	0.5958	59.58%
Thyroid receptor binding	+	0.5957	59.57%
Glucocorticoid receptor binding	+	0.5956	59.56%
Aromatase binding	-	0.5146	51.46%
PPAR gamma	+	0.6030	60.30%
Honey bee toxicity	-	0.7807	78.07%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.8844	88.44%

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	99.15%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.61%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.17%	98.95%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	91.84%	85.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.02%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.02%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.95%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.28%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.12%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.38%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.65%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.44%	92.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.38%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.21%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.92%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.21%	97.14%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.33%	92.88%
CHEMBL4208	P20618	Proteasome component C5	83.31%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.30%	95.89%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	81.47%	97.31%
CHEMBL3438	Q05513	Protein kinase C zeta	80.92%	88.48%
CHEMBL226	P30542	Adenosine A1 receptor	80.54%	95.93%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.36%	97.33%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.22%	97.50%
CHEMBL3401	O75469	Pregnane X receptor	80.04%	94.73%

Plants that contains it

• Daphne feddei

Cross-Links

• PubChem: 45482324
• LOTUS: LTS0185276
• wikiData: Q105030215