3,3',5'-Trihydroxy-4-methoxy-5-prenylbibenzyl

Details

• Internal ID: 90a89586-bd12-48ec-8341-91ba5d2999f3
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 5-[2-[3-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]ethyl]benzene-1,3-diol
• SMILES (Canonical): CC(=CCC1=C(C(=CC(=C1)CCC2=CC(=CC(=C2)O)O)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC(=C1)CCC2=CC(=CC(=C2)O)O)O)OC)C
• InChI: InChI=1S/C20H24O4/c1-13(2)4-7-16-8-14(11-19(23)20(16)24-3)5-6-15-9-17(21)12-18(22)10-15/h4,8-12,21-23H,5-7H2,1-3H3
• InChI Key: CUVVBEWXVFROAW-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.16745924 g/mol
• Topological Polar Surface Area (TPSA): 69.90 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.11
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 3,3',5'-trihydroxy-4-methoxy-5-prenylbibenzyl
• alpha,beta-Dihydro-3,5,3'-trihydroxy-4'-methoxy-5'-isopentenylstilbene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9632	96.32%
Caco-2	+	0.8765	87.65%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7578	75.78%
OATP2B1 inhibitior	-	0.7181	71.81%
OATP1B1 inhibitior	+	0.9076	90.76%
OATP1B3 inhibitior	+	0.9221	92.21%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8280	82.80%
P-glycoprotein inhibitior	-	0.6021	60.21%
P-glycoprotein substrate	-	0.8500	85.00%
CYP3A4 substrate	-	0.5326	53.26%
CYP2C9 substrate	+	0.6000	60.00%
CYP2D6 substrate	+	0.4334	43.34%
CYP3A4 inhibition	-	0.6776	67.76%
CYP2C9 inhibition	+	0.7508	75.08%
CYP2C19 inhibition	+	0.8388	83.88%
CYP2D6 inhibition	-	0.6424	64.24%
CYP1A2 inhibition	+	0.7155	71.55%
CYP2C8 inhibition	-	0.5876	58.76%
CYP inhibitory promiscuity	+	0.8514	85.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8394	83.94%
Carcinogenicity (trinary)	Non-required	0.7595	75.95%
Eye corrosion	-	0.9881	98.81%
Eye irritation	+	0.6702	67.02%
Skin irritation	-	0.7606	76.06%
Skin corrosion	-	0.9066	90.66%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8900	89.00%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.5072	50.72%
skin sensitisation	-	0.6894	68.94%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6270	62.70%
Acute Oral Toxicity (c)	III	0.6530	65.30%
Estrogen receptor binding	+	0.8968	89.68%
Androgen receptor binding	-	0.5704	57.04%
Thyroid receptor binding	+	0.6356	63.56%
Glucocorticoid receptor binding	-	0.5129	51.29%
Aromatase binding	+	0.6032	60.32%
PPAR gamma	+	0.9024	90.24%
Honey bee toxicity	-	0.8408	84.08%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9942	99.42%

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	98.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.07%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.80%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.58%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.81%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.09%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	88.19%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.61%	96.95%
CHEMBL4208	P20618	Proteasome component C5	85.37%	90.00%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	84.57%	92.68%
CHEMBL2535	P11166	Glucose transporter	81.21%	98.75%
CHEMBL3194	P02766	Transthyretin	80.13%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.01%	95.89%

Plants that contains it

• Glycyrrhiza glabra

Cross-Links

• PubChem: 11023938
• NPASS: NPC252131
• LOTUS: LTS0271580
• wikiData: Q104970524