4-[(2S,3S,4S,5S)-5-(3-hydroxy-4-methoxyphenyl)-3,4-dimethyloxolan-2-yl]benzene-1,2-diol

Details

• Internal ID: 57153920-2678-4cf1-86d4-97722b655001
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 7,7-epoxylignans
• IUPAC Name: 4-[(2S,3S,4S,5S)-5-(3-hydroxy-4-methoxyphenyl)-3,4-dimethyloxolan-2-yl]benzene-1,2-diol
• SMILES (Canonical): CC1C(C(OC1C2=CC(=C(C=C2)O)O)C3=CC(=C(C=C3)OC)O)C
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H](O[C@@H]1C2=CC(=C(C=C2)O)O)C3=CC(=C(C=C3)OC)O)C
• InChI: InChI=1S/C19H22O5/c1-10-11(2)19(13-5-7-17(23-3)16(22)9-13)24-18(10)12-4-6-14(20)15(21)8-12/h4-11,18-22H,1-3H3/t10-,11-,18-,19-/m0/s1
• InChI Key: XEYABMSDSCEFHX-GTXVLXIYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.14672380 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.90
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9570	95.70%
Caco-2	+	0.5790	57.90%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8407	84.07%
OATP2B1 inhibitior	-	0.8489	84.89%
OATP1B1 inhibitior	+	0.9402	94.02%
OATP1B3 inhibitior	+	0.9274	92.74%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8591	85.91%
P-glycoprotein inhibitior	-	0.7281	72.81%
P-glycoprotein substrate	-	0.9507	95.07%
CYP3A4 substrate	-	0.5531	55.31%
CYP2C9 substrate	-	0.7552	75.52%
CYP2D6 substrate	-	0.6779	67.79%
CYP3A4 inhibition	-	0.6502	65.02%
CYP2C9 inhibition	-	0.5321	53.21%
CYP2C19 inhibition	+	0.7516	75.16%
CYP2D6 inhibition	-	0.8254	82.54%
CYP1A2 inhibition	+	0.6783	67.83%
CYP2C8 inhibition	+	0.4904	49.04%
CYP inhibitory promiscuity	+	0.9089	90.89%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8425	84.25%
Carcinogenicity (trinary)	Non-required	0.3619	36.19%
Eye corrosion	-	0.9844	98.44%
Eye irritation	-	0.8102	81.02%
Skin irritation	-	0.8219	82.19%
Skin corrosion	-	0.9570	95.70%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7623	76.23%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8814	88.14%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.6441	64.41%
Acute Oral Toxicity (c)	III	0.6684	66.84%
Estrogen receptor binding	+	0.7551	75.51%
Androgen receptor binding	+	0.5903	59.03%
Thyroid receptor binding	+	0.6853	68.53%
Glucocorticoid receptor binding	+	0.7763	77.63%
Aromatase binding	+	0.6839	68.39%
PPAR gamma	+	0.7000	70.00%
Honey bee toxicity	-	0.9304	93.04%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5751	57.51%
Fish aquatic toxicity	+	0.9520	95.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.84%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.62%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.93%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.52%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.45%	94.00%
CHEMBL4208	P20618	Proteasome component C5	83.44%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.24%	99.15%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.03%	92.94%
CHEMBL3401	O75469	Pregnane X receptor	82.89%	94.73%
CHEMBL3194	P02766	Transthyretin	82.53%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.31%	99.17%

Plants that contains it

• Larrea tridentata

Cross-Links

• PubChem: 11336474
• LOTUS: LTS0024065
• wikiData: Q105326824