1-[4-Hydroxy-3-(2-hydroxy-3-methyl-but-3-enyl)phenyl]ethanone

Details

• Internal ID: 72e5e0fc-afba-4220-9471-74ad198bd145
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 1-[4-hydroxy-3-(2-hydroxy-3-methylbut-3-enyl)phenyl]ethanone
• SMILES (Canonical): CC(=C)C(CC1=C(C=CC(=C1)C(=O)C)O)O
• SMILES (Isomeric): CC(=C)C(CC1=C(C=CC(=C1)C(=O)C)O)O
• InChI: InChI=1S/C13H16O3/c1-8(2)13(16)7-11-6-10(9(3)14)4-5-12(11)15/h4-6,13,15-16H,1,7H2,2-3H3
• InChI Key: BVZFRLZZCDLQQH-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.26 g/mol
• Exact Mass: 220.109944368 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• CHEMBL451274
• 3-(2-Hydroxyisopentenyl)-4-hydroxyacetophenone
• 1-[4-hydroxy-3-(2-hydroxy-3-methyl-but-3-enyl)phenyl]ethanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.5715	57.15%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8684	86.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9441	94.41%
OATP1B3 inhibitior	+	0.9604	96.04%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8984	89.84%
P-glycoprotein inhibitior	-	0.9627	96.27%
P-glycoprotein substrate	-	0.8803	88.03%
CYP3A4 substrate	-	0.6427	64.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7434	74.34%
CYP3A4 inhibition	-	0.5237	52.37%
CYP2C9 inhibition	-	0.6721	67.21%
CYP2C19 inhibition	+	0.5584	55.84%
CYP2D6 inhibition	-	0.7750	77.50%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.7509	75.09%
CYP inhibitory promiscuity	-	0.5168	51.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7080	70.80%
Carcinogenicity (trinary)	Non-required	0.7280	72.80%
Eye corrosion	-	0.9248	92.48%
Eye irritation	+	0.6366	63.66%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.7757	77.57%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6475	64.75%
Micronuclear	-	0.6108	61.08%
Hepatotoxicity	-	0.5216	52.16%
skin sensitisation	+	0.8978	89.78%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	+	0.4693	46.93%
Acute Oral Toxicity (c)	III	0.7529	75.29%
Estrogen receptor binding	-	0.7884	78.84%
Androgen receptor binding	-	0.7283	72.83%
Thyroid receptor binding	-	0.5205	52.05%
Glucocorticoid receptor binding	-	0.6009	60.09%
Aromatase binding	-	0.5950	59.50%
PPAR gamma	-	0.5904	59.04%
Honey bee toxicity	-	0.9541	95.41%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.8900	89.00%
Fish aquatic toxicity	+	0.9874	98.74%

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	96.62%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.83%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	90.80%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	90.55%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.81%	96.09%
CHEMBL4208	P20618	Proteasome component C5	89.12%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.47%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.62%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	84.19%	94.73%
CHEMBL1255126	O15151	Protein Mdm4	83.78%	90.20%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.41%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	82.45%	91.19%

Plants that contains it

• Helichrysum italicum
• Xenophyllum ciliolatum

Cross-Links

• PubChem: 455699
• LOTUS: LTS0200306
• wikiData: Q104947015