3,3',4,5'-Tetrahydroxy-5-prenylbibenzyl

Details

• Internal ID: 6f36d555-544a-463a-b00e-951127008157
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 5-[2-(3,5-dihydroxyphenyl)ethyl]-3-(3-methylbut-2-enyl)benzene-1,2-diol
• SMILES (Canonical): CC(=CCC1=C(C(=CC(=C1)CCC2=CC(=CC(=C2)O)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC(=C1)CCC2=CC(=CC(=C2)O)O)O)O)C
• InChI: InChI=1S/C19H22O4/c1-12(2)3-6-15-7-13(10-18(22)19(15)23)4-5-14-8-16(20)11-17(21)9-14/h3,7-11,20-23H,4-6H2,1-2H3
• InChI Key: OLUUBKULUYLOQV-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₄
• Molecular Weight: 314.40 g/mol
• Exact Mass: 314.15180918 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 3.80
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9545	95.45%
Caco-2	+	0.6275	62.75%
Blood Brain Barrier	-	0.6024	60.24%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7935	79.35%
OATP2B1 inhibitior	-	0.5611	56.11%
OATP1B1 inhibitior	+	0.8806	88.06%
OATP1B3 inhibitior	+	0.9566	95.66%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7588	75.88%
BSEP inhibitior	+	0.8710	87.10%
P-glycoprotein inhibitior	-	0.7824	78.24%
P-glycoprotein substrate	-	0.8564	85.64%
CYP3A4 substrate	-	0.5763	57.63%
CYP2C9 substrate	-	0.7912	79.12%
CYP2D6 substrate	+	0.3482	34.82%
CYP3A4 inhibition	-	0.7129	71.29%
CYP2C9 inhibition	+	0.7950	79.50%
CYP2C19 inhibition	+	0.5789	57.89%
CYP2D6 inhibition	-	0.6789	67.89%
CYP1A2 inhibition	+	0.7678	76.78%
CYP2C8 inhibition	-	0.6139	61.39%
CYP inhibitory promiscuity	+	0.7239	72.39%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8323	83.23%
Carcinogenicity (trinary)	Non-required	0.7456	74.56%
Eye corrosion	-	0.9838	98.38%
Eye irritation	+	0.8704	87.04%
Skin irritation	-	0.7426	74.26%
Skin corrosion	-	0.7503	75.03%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7403	74.03%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	+	0.5336	53.36%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6851	68.51%
Acute Oral Toxicity (c)	III	0.6836	68.36%
Estrogen receptor binding	+	0.9204	92.04%
Androgen receptor binding	+	0.7275	72.75%
Thyroid receptor binding	+	0.6121	61.21%
Glucocorticoid receptor binding	+	0.6894	68.94%
Aromatase binding	+	0.7894	78.94%
PPAR gamma	+	0.9353	93.53%
Honey bee toxicity	-	0.9204	92.04%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.81%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	92.96%	94.73%
CHEMBL2581	P07339	Cathepsin D	91.82%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.85%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.34%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.64%	99.17%
CHEMBL3194	P02766	Transthyretin	85.42%	90.71%
CHEMBL4208	P20618	Proteasome component C5	85.05%	90.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.88%	83.57%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.31%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	83.43%	91.49%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.60%	96.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.26%	96.12%

Plants that contains it

• Glycyrrhiza glabra

Cross-Links

• PubChem: 10335780
• NPASS: NPC277588
• LOTUS: LTS0045025
• wikiData: Q105194153