(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(1E,3S)-3-(4-hydroxyphenyl)penta-1,4-dienyl]phenoxy]oxane-3,4,5-triol

Details

• Internal ID: e9184a60-9115-47f8-bb10-e3d6005a3e01
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(1E,3S)-3-(4-hydroxyphenyl)penta-1,4-dienyl]phenoxy]oxane-3,4,5-triol
• SMILES (Canonical): C=CC(C=CC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O)C3=CC=C(C=C3)O
• SMILES (Isomeric): C=C[C@@H](/C=C/C1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C3=CC=C(C=C3)O
• InChI: InChI=1S/C23H26O7/c1-2-15(16-7-9-17(25)10-8-16)6-3-14-4-11-18(12-5-14)29-23-22(28)21(27)20(26)19(13-24)30-23/h2-12,15,19-28H,1,13H2/b6-3+/t15-,19+,20+,21-,22+,23+/m0/s1
• InChI Key: CUHXHQAEPUNRAQ-CYYOLSQCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₇
• Molecular Weight: 414.40 g/mol
• Exact Mass: 414.16785316 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7810	78.10%
Caco-2	-	0.8805	88.05%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6007	60.07%
OATP2B1 inhibitior	-	0.8506	85.06%
OATP1B1 inhibitior	+	0.8972	89.72%
OATP1B3 inhibitior	+	0.9594	95.94%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6559	65.59%
P-glycoprotein inhibitior	-	0.6536	65.36%
P-glycoprotein substrate	-	0.8840	88.40%
CYP3A4 substrate	+	0.5440	54.40%
CYP2C9 substrate	+	0.5829	58.29%
CYP2D6 substrate	-	0.8239	82.39%
CYP3A4 inhibition	-	0.6621	66.21%
CYP2C9 inhibition	-	0.8702	87.02%
CYP2C19 inhibition	-	0.8408	84.08%
CYP2D6 inhibition	-	0.9120	91.20%
CYP1A2 inhibition	-	0.9264	92.64%
CYP2C8 inhibition	+	0.5403	54.03%
CYP inhibitory promiscuity	-	0.6342	63.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6708	67.08%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9171	91.71%
Skin irritation	-	0.8399	83.99%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6935	69.35%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.7746	77.46%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.6997	69.97%
Acute Oral Toxicity (c)	III	0.6991	69.91%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.6482	64.82%
Thyroid receptor binding	+	0.5137	51.37%
Glucocorticoid receptor binding	+	0.5609	56.09%
Aromatase binding	+	0.5514	55.14%
PPAR gamma	+	0.7604	76.04%
Honey bee toxicity	-	0.5903	59.03%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9163	91.63%

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	99.04%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	96.81%	98.35%
CHEMBL226	P30542	Adenosine A1 receptor	94.49%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.11%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.86%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.12%	97.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	90.01%	89.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.92%	96.09%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	87.78%	94.97%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.54%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	86.85%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	85.76%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.64%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.68%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.50%	86.33%
CHEMBL4208	P20618	Proteasome component C5	83.15%	90.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.29%	85.00%
CHEMBL3194	P02766	Transthyretin	81.97%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.83%	89.00%
CHEMBL2581	P07339	Cathepsin D	81.72%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.67%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.27%	86.92%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.78%	89.62%

Plants that contains it

• Hypoxis nyasica

Cross-Links

• PubChem: 163192901
• LOTUS: LTS0025253
• wikiData: Q104970272