Daphneolone

Details

• Internal ID: 1cfd8456-5602-4d33-8e26-9eb997484104
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 3-hydroxy-1-(4-hydroxyphenyl)-5-phenylpentan-1-one
• SMILES (Canonical): C1=CC=C(C=C1)CCC(CC(=O)C2=CC=C(C=C2)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)CCC(CC(=O)C2=CC=C(C=C2)O)O
• InChI: InChI=1S/C17H18O3/c18-15-10-7-14(8-11-15)17(20)12-16(19)9-6-13-4-2-1-3-5-13/h1-5,7-8,10-11,16,18-19H,6,9,12H2
• InChI Key: NNPDNNXUSPXBRO-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₃
• Molecular Weight: 270.32 g/mol
• Exact Mass: 270.125594432 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.96
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 54835-64-2
• 3-hydroxy-1-(4-hydroxyphenyl)-5-phenylpentan-1-one
• daphneolon
• MLS002472952
• CHEMBL1724888
• HMS2270K20
• AKOS040734761
• SMR001397060
• FT-0698570

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.5842	58.42%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.9092	90.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9109	91.09%
OATP1B3 inhibitior	+	0.9064	90.64%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6948	69.48%
P-glycoprotein inhibitior	-	0.9222	92.22%
P-glycoprotein substrate	-	0.6774	67.74%
CYP3A4 substrate	-	0.5664	56.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6852	68.52%
CYP3A4 inhibition	-	0.6450	64.50%
CYP2C9 inhibition	-	0.7785	77.85%
CYP2C19 inhibition	+	0.5883	58.83%
CYP2D6 inhibition	-	0.9135	91.35%
CYP1A2 inhibition	-	0.5650	56.50%
CYP2C8 inhibition	+	0.5546	55.46%
CYP inhibitory promiscuity	-	0.7110	71.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7811	78.11%
Carcinogenicity (trinary)	Non-required	0.5877	58.77%
Eye corrosion	-	0.9737	97.37%
Eye irritation	+	0.8661	86.61%
Skin irritation	-	0.5781	57.81%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5325	53.25%
Micronuclear	-	0.7782	77.82%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.6970	69.70%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6094	60.94%
Acute Oral Toxicity (c)	III	0.7087	70.87%
Estrogen receptor binding	+	0.8766	87.66%
Androgen receptor binding	+	0.8573	85.73%
Thyroid receptor binding	-	0.6115	61.15%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6304	63.04%
PPAR gamma	+	0.6771	67.71%
Honey bee toxicity	-	0.8372	83.72%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.8757	87.57%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL284	P27487	Dipeptidyl peptidase IV	38430 nM	IC50	DOI: 10.1039/C0MD00245C

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.89%	94.62%
CHEMBL2581	P07339	Cathepsin D	93.01%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	92.02%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.16%	99.17%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	90.30%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.73%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.20%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.90%	96.09%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	87.15%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.02%	95.50%
CHEMBL2535	P11166	Glucose transporter	85.73%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.20%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.60%	95.89%

Plants that contains it

• Daphne mezereum
• Daphne odora
• Salvia miltiorrhiza
• Thymelaea lythroides

Cross-Links

• PubChem: 5316300
• NPASS: NPC249435
• ChEMBL: CHEMBL1724888
• LOTUS: LTS0128940
• wikiData: Q105182233