5-[(2R,3S)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2,3-dimethoxyphenol

Details

• Internal ID: 472ad4ad-5d4c-4447-b236-34c69ee1e1fa
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: 5-[(2R,3S)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2,3-dimethoxyphenol
• SMILES (Canonical): CC(CC1=CC2=C(C=C1)OCO2)C(C)CC3=CC(=C(C(=C3)OC)OC)O
• SMILES (Isomeric): C[C@@H](CC1=CC2=C(C=C1)OCO2)[C@H](C)CC3=CC(=C(C(=C3)OC)OC)O
• InChI: InChI=1S/C21H26O5/c1-13(7-15-5-6-18-19(10-15)26-12-25-18)14(2)8-16-9-17(22)21(24-4)20(11-16)23-3/h5-6,9-11,13-14,22H,7-8,12H2,1-4H3/t13-,14+/m0/s1
• InChI Key: ZGHOATLFXGBJGZ-UONOGXRCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.17802393 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.20
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9661	96.61%
Caco-2	+	0.8680	86.80%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6256	62.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9167	91.67%
OATP1B3 inhibitior	+	0.9144	91.44%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7711	77.11%
P-glycoprotein inhibitior	+	0.7789	77.89%
P-glycoprotein substrate	-	0.8790	87.90%
CYP3A4 substrate	-	0.5176	51.76%
CYP2C9 substrate	-	0.6107	61.07%
CYP2D6 substrate	+	0.4019	40.19%
CYP3A4 inhibition	+	0.8061	80.61%
CYP2C9 inhibition	+	0.7813	78.13%
CYP2C19 inhibition	+	0.7482	74.82%
CYP2D6 inhibition	+	0.5534	55.34%
CYP1A2 inhibition	+	0.5161	51.61%
CYP2C8 inhibition	+	0.4578	45.78%
CYP inhibitory promiscuity	+	0.7908	79.08%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9708	97.08%
Carcinogenicity (trinary)	Non-required	0.4432	44.32%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.8090	80.90%
Skin irritation	-	0.7790	77.90%
Skin corrosion	-	0.9602	96.02%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9276	92.76%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7804	78.04%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6928	69.28%
Acute Oral Toxicity (c)	III	0.5147	51.47%
Estrogen receptor binding	+	0.7228	72.28%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5852	58.52%
Glucocorticoid receptor binding	-	0.5057	50.57%
Aromatase binding	+	0.5332	53.32%
PPAR gamma	+	0.7509	75.09%
Honey bee toxicity	-	0.8859	88.59%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5051	50.51%
Fish aquatic toxicity	+	0.9919	99.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.22%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.48%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.16%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.13%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.55%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.69%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.50%	92.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.80%	85.14%
CHEMBL2535	P11166	Glucose transporter	89.32%	98.75%
CHEMBL4208	P20618	Proteasome component C5	89.23%	90.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	87.67%	90.24%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	87.51%	92.68%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.21%	94.80%
CHEMBL261	P00915	Carbonic anhydrase I	86.75%	96.76%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.56%	89.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.72%	95.89%
CHEMBL1255126	O15151	Protein Mdm4	83.22%	90.20%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.21%	95.89%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	82.97%	82.67%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.40%	89.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.32%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.40%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.39%	96.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	80.36%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.27%	86.33%

Plants that contains it

• Schisandra sphenanthera

Cross-Links

• PubChem: 102322866
• NPASS: NPC236426