4-[(2S,3S,4R,5R)-5-(4-hydroxy-3,5-dimethoxyphenyl)-3,4-bis(hydroxymethyl)oxolan-2-yl]-2,6-dimethoxyphenol

Details

• Internal ID: 3dbea169-303a-477c-884a-819d5ace25ae
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 7,7-epoxylignans
• IUPAC Name: 4-[(2S,3S,4R,5R)-5-(4-hydroxy-3,5-dimethoxyphenyl)-3,4-bis(hydroxymethyl)oxolan-2-yl]-2,6-dimethoxyphenol
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C(C(C(O2)C3=CC(=C(C(=C3)OC)O)OC)CO)CO
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)[C@@H]2[C@@H]([C@@H]([C@@H](O2)C3=CC(=C(C(=C3)OC)O)OC)CO)CO
• InChI: InChI=1S/C22H28O9/c1-27-15-5-11(6-16(28-2)19(15)25)21-13(9-23)14(10-24)22(31-21)12-7-17(29-3)20(26)18(8-12)30-4/h5-8,13-14,21-26H,9-10H2,1-4H3/t13-,14+,21-,22+
• InChI Key: WKDDUPJDCWIWAP-DQEHQXCCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₉
• Molecular Weight: 436.50 g/mol
• Exact Mass: 436.17333247 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.16
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9082	90.82%
Caco-2	-	0.6852	68.52%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8528	85.28%
OATP2B1 inhibitior	-	0.7133	71.33%
OATP1B1 inhibitior	+	0.7719	77.19%
OATP1B3 inhibitior	+	0.9260	92.60%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5775	57.75%
P-glycoprotein inhibitior	+	0.5775	57.75%
P-glycoprotein substrate	-	0.9327	93.27%
CYP3A4 substrate	-	0.6032	60.32%
CYP2C9 substrate	-	0.7853	78.53%
CYP2D6 substrate	+	0.3462	34.62%
CYP3A4 inhibition	+	0.7322	73.22%
CYP2C9 inhibition	+	0.6400	64.00%
CYP2C19 inhibition	+	0.7748	77.48%
CYP2D6 inhibition	-	0.8598	85.98%
CYP1A2 inhibition	+	0.5133	51.33%
CYP2C8 inhibition	-	0.6986	69.86%
CYP inhibitory promiscuity	+	0.9506	95.06%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8808	88.08%
Carcinogenicity (trinary)	Non-required	0.4868	48.68%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.7532	75.32%
Skin irritation	-	0.8457	84.57%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4634	46.34%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8405	84.05%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7694	76.94%
Acute Oral Toxicity (c)	III	0.6658	66.58%
Estrogen receptor binding	+	0.7230	72.30%
Androgen receptor binding	+	0.6744	67.44%
Thyroid receptor binding	+	0.7347	73.47%
Glucocorticoid receptor binding	+	0.5652	56.52%
Aromatase binding	-	0.5637	56.37%
PPAR gamma	+	0.6865	68.65%
Honey bee toxicity	-	0.9478	94.78%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9258	92.58%

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	98.99%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.25%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.53%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.26%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.31%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.39%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.52%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.42%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.80%	92.62%
CHEMBL2581	P07339	Cathepsin D	81.35%	98.95%

Plants that contains it

• Neoalsomitra clavigera
• Tetracentron sinense

Cross-Links

• PubChem: 124396485
• LOTUS: LTS0024850
• wikiData: Q105307247