(2R,3R,4S,5S,6R)-2-[3-[4-[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-hydroxyphenyl]propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 09035b37-15e7-42a0-82b8-534b1421ca0d
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[3-[4-[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-hydroxyphenyl]propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)C(C(CO)OC2=C(C=C(C=C2)CCCOC3C(C(C(C(O3)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@H]([C@H](CO)OC2=C(C=C(C=C2)CCCO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
• InChI: InChI=1S/C25H34O12/c1-34-18-10-14(5-6-15(18)28)21(30)19(11-26)36-17-7-4-13(9-16(17)29)3-2-8-35-25-24(33)23(32)22(31)20(12-27)37-25/h4-7,9-10,19-33H,2-3,8,11-12H2,1H3/t19-,20+,21+,22+,23-,24+,25+/m0/s1
• InChI Key: UFXJPMNZQXNJAA-VQCHMSJISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₁₂
• Molecular Weight: 526.50 g/mol
• Exact Mass: 526.20502652 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.67
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8372	83.72%
Caco-2	-	0.8885	88.85%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7358	73.58%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.8399	83.99%
OATP1B3 inhibitior	+	0.9594	95.94%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5605	56.05%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6359	63.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7717	77.17%
CYP3A4 inhibition	-	0.9226	92.26%
CYP2C9 inhibition	-	0.6732	67.32%
CYP2C19 inhibition	-	0.8168	81.68%
CYP2D6 inhibition	-	0.9198	91.98%
CYP1A2 inhibition	-	0.8398	83.98%
CYP2C8 inhibition	+	0.6694	66.94%
CYP inhibitory promiscuity	-	0.7149	71.49%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6654	66.54%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9191	91.91%
Skin irritation	-	0.8318	83.18%
Skin corrosion	-	0.9526	95.26%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6891	68.91%
Micronuclear	-	0.6441	64.41%
Hepatotoxicity	-	0.8321	83.21%
skin sensitisation	-	0.8864	88.64%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.8992	89.92%
Acute Oral Toxicity (c)	III	0.7761	77.61%
Estrogen receptor binding	+	0.7442	74.42%
Androgen receptor binding	-	0.5182	51.82%
Thyroid receptor binding	+	0.5361	53.61%
Glucocorticoid receptor binding	-	0.5422	54.22%
Aromatase binding	-	0.5119	51.19%
PPAR gamma	+	0.6222	62.22%
Honey bee toxicity	-	0.8025	80.25%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.5977	59.77%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.29%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.05%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.54%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.22%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.38%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.84%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.15%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.78%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.97%	95.89%
CHEMBL1255126	O15151	Protein Mdm4	88.93%	90.20%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.22%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.60%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.80%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.16%	90.71%
CHEMBL3194	P02766	Transthyretin	82.97%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.79%	89.62%
CHEMBL4208	P20618	Proteasome component C5	82.63%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	82.51%	94.73%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.54%	97.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.28%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.82%	89.00%

Plants that contains it

• Iodes cirrhosa

Cross-Links

• PubChem: 24862425
• NPASS: NPC138738
• LOTUS: LTS0265022
• wikiData: Q105272200