5,5'-Dimethoxysecoisolariciresinol

Details

• Internal ID: 78eccb45-47dd-4d87-8e25-c52574a28e87
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans > Dibenzylbutanediol lignans
• IUPAC Name: (2R,3R)-2,3-bis[(4-hydroxy-3,5-dimethoxyphenyl)methyl]butane-1,4-diol
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)CC(CO)C(CC2=CC(=C(C(=C2)OC)O)OC)CO
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C[C@@H](CO)[C@@H](CC2=CC(=C(C(=C2)OC)O)OC)CO
• InChI: InChI=1S/C22H30O8/c1-27-17-7-13(8-18(28-2)21(17)25)5-15(11-23)16(12-24)6-14-9-19(29-3)22(26)20(10-14)30-4/h7-10,15-16,23-26H,5-6,11-12H2,1-4H3/t15-,16-/m0/s1
• InChI Key: XTRARZPRFYUCGZ-HOTGVXAUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₈
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.19406791 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 11

Synonyms

• 1002106-91-3
• (2R,3R)-2,3-bis[(4-hydroxy-3,5-dimethoxyphenyl)methyl]butane-1,4-diol
• (2R,3R)-2,3-Bis(4-hydroxy-3,5-dimethoxybenzyl)butane-1,4-diol
• HY-N8581
• AKOS040761166
• CS-0148654

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9317	93.17%
Caco-2	-	0.5848	58.48%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8617	86.17%
OATP2B1 inhibitior	-	0.7125	71.25%
OATP1B1 inhibitior	+	0.7949	79.49%
OATP1B3 inhibitior	+	0.9253	92.53%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6558	65.58%
P-glycoprotein inhibitior	+	0.6039	60.39%
P-glycoprotein substrate	-	0.7637	76.37%
CYP3A4 substrate	-	0.6122	61.22%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	+	0.4255	42.55%
CYP3A4 inhibition	+	0.5342	53.42%
CYP2C9 inhibition	-	0.7330	73.30%
CYP2C19 inhibition	+	0.5527	55.27%
CYP2D6 inhibition	-	0.8642	86.42%
CYP1A2 inhibition	+	0.6244	62.44%
CYP2C8 inhibition	-	0.5856	58.56%
CYP inhibitory promiscuity	+	0.5413	54.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7743	77.43%
Carcinogenicity (trinary)	Non-required	0.6631	66.31%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.6941	69.41%
Skin irritation	-	0.8536	85.36%
Skin corrosion	-	0.9673	96.73%
Ames mutagenesis	-	0.7944	79.44%
Human Ether-a-go-go-Related Gene inhibition	+	0.6832	68.32%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.6528	65.28%
skin sensitisation	-	0.8011	80.11%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8212	82.12%
Acute Oral Toxicity (c)	III	0.7169	71.69%
Estrogen receptor binding	+	0.8343	83.43%
Androgen receptor binding	+	0.6117	61.17%
Thyroid receptor binding	+	0.6855	68.55%
Glucocorticoid receptor binding	+	0.6664	66.64%
Aromatase binding	+	0.6081	60.81%
PPAR gamma	+	0.6214	62.14%
Honey bee toxicity	-	0.8809	88.09%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6449	64.49%
Fish aquatic toxicity	+	0.9454	94.54%

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	96.52%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.84%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.79%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	91.79%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.72%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.82%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.69%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.00%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.91%	86.33%
CHEMBL2535	P11166	Glucose transporter	81.01%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.39%	89.62%

Plants that contains it

• Santalum album

Cross-Links

• PubChem: 10002343
• LOTUS: LTS0206843
• wikiData: Q105341798