5-[3-[4-Hydroxy-3-(3-methylbut-2-enyl)phenyl]propyl]benzene-1,3-diol

Details

• Internal ID: de8cda2d-680c-4570-943d-c670cae949ac
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Cinnamylphenols
• IUPAC Name: 5-[3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]propyl]benzene-1,3-diol
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1)CCCC2=CC(=CC(=C2)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1)CCCC2=CC(=CC(=C2)O)O)O)C
• InChI: InChI=1S/C20H24O3/c1-14(2)6-8-17-10-15(7-9-20(17)23)4-3-5-16-11-18(21)13-19(22)12-16/h6-7,9-13,21-23H,3-5,8H2,1-2H3
• InChI Key: HTNHTFRNGHVXBF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₃
• Molecular Weight: 312.40 g/mol
• Exact Mass: 312.17254462 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 4.49
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• DTXSID90718884
• AKOS032948239
• 5-[3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]propyl]benzene-1,3-diol
• 5-{3-[4-Hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propyl}benzene-1,3-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9911	99.11%
Caco-2	+	0.6455	64.55%
Blood Brain Barrier	-	0.5024	50.24%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8571	85.71%
OATP2B1 inhibitior	-	0.7056	70.56%
OATP1B1 inhibitior	+	0.9332	93.32%
OATP1B3 inhibitior	+	0.9520	95.20%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7588	75.88%
BSEP inhibitior	+	0.8245	82.45%
P-glycoprotein inhibitior	-	0.5584	55.84%
P-glycoprotein substrate	-	0.7678	76.78%
CYP3A4 substrate	-	0.5606	56.06%
CYP2C9 substrate	-	0.7887	78.87%
CYP2D6 substrate	+	0.3876	38.76%
CYP3A4 inhibition	+	0.5567	55.67%
CYP2C9 inhibition	+	0.8871	88.71%
CYP2C19 inhibition	+	0.8615	86.15%
CYP2D6 inhibition	-	0.6435	64.35%
CYP1A2 inhibition	+	0.8387	83.87%
CYP2C8 inhibition	+	0.4546	45.46%
CYP inhibitory promiscuity	+	0.9294	92.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8262	82.62%
Carcinogenicity (trinary)	Non-required	0.7472	74.72%
Eye corrosion	-	0.9776	97.76%
Eye irritation	+	0.6316	63.16%
Skin irritation	-	0.7345	73.45%
Skin corrosion	-	0.6500	65.00%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7233	72.33%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	+	0.5835	58.35%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6341	63.41%
Acute Oral Toxicity (c)	III	0.6435	64.35%
Estrogen receptor binding	+	0.9571	95.71%
Androgen receptor binding	+	0.8187	81.87%
Thyroid receptor binding	+	0.6710	67.10%
Glucocorticoid receptor binding	+	0.7048	70.48%
Aromatase binding	+	0.7102	71.02%
PPAR gamma	+	0.9181	91.81%
Honey bee toxicity	-	0.9256	92.56%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	98.25%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.12%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.29%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.90%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.78%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.24%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.95%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.74%	96.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	87.69%	90.24%
CHEMBL3194	P02766	Transthyretin	81.74%	90.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.82%	96.95%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.08%	83.57%

Plants that contains it

• Broussonetia papyrifera

Cross-Links

• PubChem: 56928073
• NPASS: NPC34525