(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol; (2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

Details

• Internal ID: 15cd9fbf-c18e-49f9-ba11-d89610a56e90
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans > Dibenzylbutanediol lignans
• IUPAC Name: (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
• SMILES (Canonical): COC1=C(C=CC(=C1)CC(CO)C(CC2=CC(=C(C=C2)O)OC)CO)O.C(C1C(C(C(C(O1)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C[C@@H](CO)[C@@H](CC2=CC(=C(C=C2)O)OC)CO)O.C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)O)O)O)O
• InChI: InChI=1S/C20H26O6.C6H12O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2;7-1-2-3(8)4(9)5(10)6(11)12-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3;2-11H,1H2/t15-,16-;2-,3-,4+,5-,6-/m01/s1
• InChI Key: MJYQFWSXKFLTAY-OVEQLNGDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₈O₁₂
• Molecular Weight: 542.60 g/mol
• Exact Mass: 542.23632664 g/mol
• Topological Polar Surface Area (TPSA): 210.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.10
• H-Bond Acceptor: 12
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

• beta-D-Glucopyranose, diglycoside with (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol
• (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
• SCHEMBL5923772
• AKOS015901824
• (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol; (2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
• AS-74762

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7993	79.93%
Caco-2	-	0.7336	73.36%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6814	68.14%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8219	82.19%
OATP1B3 inhibitior	+	0.9550	95.50%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7113	71.13%
P-glycoprotein inhibitior	-	0.4867	48.67%
P-glycoprotein substrate	-	0.8134	81.34%
CYP3A4 substrate	+	0.5088	50.88%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.7761	77.61%
CYP3A4 inhibition	-	0.8280	82.80%
CYP2C9 inhibition	-	0.8739	87.39%
CYP2C19 inhibition	-	0.8071	80.71%
CYP2D6 inhibition	-	0.8962	89.62%
CYP1A2 inhibition	-	0.8526	85.26%
CYP2C8 inhibition	+	0.5810	58.10%
CYP inhibitory promiscuity	-	0.6956	69.56%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6756	67.56%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.8963	89.63%
Skin irritation	-	0.8532	85.32%
Skin corrosion	-	0.9544	95.44%
Ames mutagenesis	-	0.6944	69.44%
Human Ether-a-go-go-Related Gene inhibition	+	0.8522	85.22%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8750	87.50%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.8660	86.60%
Acute Oral Toxicity (c)	III	0.7497	74.97%
Estrogen receptor binding	+	0.6335	63.35%
Androgen receptor binding	+	0.6524	65.24%
Thyroid receptor binding	+	0.6449	64.49%
Glucocorticoid receptor binding	-	0.4887	48.87%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.4908	49.08%
Honey bee toxicity	-	0.8134	81.34%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5349	53.49%
Fish aquatic toxicity	+	0.7693	76.93%

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	98.11%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.67%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.92%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.69%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.45%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.60%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.57%	95.89%
CHEMBL1255126	O15151	Protein Mdm4	86.84%	90.20%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.59%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.52%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.17%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.49%	99.15%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.14%	89.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.84%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	82.09%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.93%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.97%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.30%	96.00%

Plants that contains it

• Linum usitatissimum

Cross-Links

• PubChem: 164475
• LOTUS: LTS0193828
• wikiData: Q72507267