(2S,3R,4S,5S,6R)-2-[5-[(3R,3aS,6S,6aR)-3-(1,3-benzodioxol-5-yl)-3a,6a-dihydroxy-1,3,4,6-tetrahydrofuro[3,4-c]furan-6-yl]-2-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 81cea6ad-b5c6-4db0-8f44-b1ae279ff0b7
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[5-[(3R,3aS,6S,6aR)-3-(1,3-benzodioxol-5-yl)-3a,6a-dihydroxy-1,3,4,6-tetrahydrofuro[3,4-c]furan-6-yl]-2-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1C2(C(OCC2(C(O1)C3=CC(=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC6=C(C=C5)OCO6)O
• SMILES (Isomeric): C1[C@@]2([C@H](OC[C@]2([C@@H](O1)C3=CC(=C(C=C3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC6=C(C=C5)OCO6)O
• InChI: InChI=1S/C25H28O13/c26-7-17-18(28)19(29)20(30)23(38-17)37-15-5-11(1-3-13(15)27)21-24(31)8-34-22(25(24,32)9-33-21)12-2-4-14-16(6-12)36-10-35-14/h1-6,17-23,26-32H,7-10H2/t17-,18-,19+,20-,21+,22-,23-,24-,25+/m1/s1
• InChI Key: HUVQMIPFAVBQIA-UEJHDFEVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₁₃
• Molecular Weight: 536.50 g/mol
• Exact Mass: 536.15299094 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -1.40
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6144	61.44%
Caco-2	-	0.8929	89.29%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6334	63.34%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.9214	92.14%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6702	67.02%
P-glycoprotein inhibitior	-	0.4797	47.97%
P-glycoprotein substrate	-	0.8609	86.09%
CYP3A4 substrate	+	0.5720	57.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	-	0.6844	68.44%
CYP2C9 inhibition	-	0.9043	90.43%
CYP2C19 inhibition	-	0.7530	75.30%
CYP2D6 inhibition	-	0.8203	82.03%
CYP1A2 inhibition	-	0.8903	89.03%
CYP2C8 inhibition	-	0.6592	65.92%
CYP inhibitory promiscuity	-	0.7646	76.46%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5306	53.06%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.8786	87.86%
Skin irritation	-	0.7938	79.38%
Skin corrosion	-	0.9491	94.91%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7524	75.24%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8797	87.97%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.5837	58.37%
Acute Oral Toxicity (c)	III	0.5251	52.51%
Estrogen receptor binding	+	0.7763	77.63%
Androgen receptor binding	+	0.6934	69.34%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5491	54.91%
Aromatase binding	+	0.5925	59.25%
PPAR gamma	+	0.7074	70.74%
Honey bee toxicity	-	0.7667	76.67%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9009	90.09%

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	99.86%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.76%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.83%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.68%	95.93%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.38%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.31%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.73%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.57%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.02%	92.62%
CHEMBL4208	P20618	Proteasome component C5	86.65%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.33%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.07%	94.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.73%	89.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.73%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.09%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.07%	96.77%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.95%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.68%	95.89%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.33%	89.67%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.38%	96.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.81%	97.36%

Plants that contains it

• Vitex glabrata

Cross-Links

• PubChem: 162943552
• LOTUS: LTS0239130
• wikiData: Q105034076