3-Hydroxy-1-(4-hydroxyphenyl)propan-1-one

Details

• Internal ID: efbfcbad-2070-4459-90f0-bf9e5ea1ef40
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 3-hydroxy-1-(4-hydroxyphenyl)propan-1-one
• SMILES (Canonical): C1=CC(=CC=C1C(=O)CCO)O
• SMILES (Isomeric): C1=CC(=CC=C1C(=O)CCO)O
• InChI: InChI=1S/C9H10O3/c10-6-5-9(12)7-1-3-8(11)4-2-7/h1-4,10-11H,5-6H2
• InChI Key: LTEPZFZSPZASKJ-UHFFFAOYSA-N
• Popularity: 18 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17 g/mol
• Exact Mass: 166.062994177 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.96
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 53170-93-7
• 3-hydroxy-1-(4-hydroxyphenyl)propan-1-one
• 3-hydroxy-1-(4-hydroxyphenyl)-1-Propanone
• 1-propanone, 3-hydroxy-1-(4-hydroxyphenyl)-
• MLS000876963
• MFCD24688528
• SMR000440608
• 2-(p-Hydroxybenzoyl)ethanol
• 4-(3-Hydroxypropionyl)phenol
• beta,4'-Dihydroxypropiophenone
• cid_638759
• MEGxp0_000182
• SCHEMBL2991010
• CHEMBL1417159
• ACon1_000128
• BDBM50570
• DTXSID80348598
• CHEBI:173753
• HMS2270F23
• SB83926
• 2-(Hydroxyethyl) 4-hydroxyphenyl ketone
• NCGC00180853-01
• AS-32302
• SY027114
• CS-0313492
• FT-0763638
• 1-(4-hydroxyphenyl)-3-oxidanyl-propan-1-one
• A870803
• 3,4 inverted exclamation mark -Dihydroxypropiophenone
• 3,4'-Dihydroxypropiophenone, >=95% (LC/MS-ELSD)
• BRD-K75509313-001-01-5
• InChI=1/C9H10O3/c10-6-5-9(12)7-1-3-8(11)4-2-7/h1-4,10-11H,5-6H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.9162	91.62%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8962	89.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8615	86.15%
OATP1B3 inhibitior	+	0.9583	95.83%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9631	96.31%
P-glycoprotein inhibitior	-	0.9885	98.85%
P-glycoprotein substrate	-	0.9644	96.44%
CYP3A4 substrate	-	0.7485	74.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7274	72.74%
CYP3A4 inhibition	-	0.7705	77.05%
CYP2C9 inhibition	-	0.9313	93.13%
CYP2C19 inhibition	-	0.7426	74.26%
CYP2D6 inhibition	-	0.9537	95.37%
CYP1A2 inhibition	-	0.7216	72.16%
CYP2C8 inhibition	+	0.4926	49.26%
CYP inhibitory promiscuity	-	0.8878	88.78%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7810	78.10%
Carcinogenicity (trinary)	Non-required	0.6969	69.69%
Eye corrosion	-	0.8372	83.72%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.6202	62.02%
Skin corrosion	-	0.9289	92.89%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9254	92.54%
Micronuclear	-	0.8823	88.23%
Hepatotoxicity	+	0.6055	60.55%
skin sensitisation	-	0.5548	55.48%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	-	0.7889	78.89%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	+	0.6137	61.37%
Acute Oral Toxicity (c)	III	0.6628	66.28%
Estrogen receptor binding	-	0.8423	84.23%
Androgen receptor binding	-	0.6165	61.65%
Thyroid receptor binding	-	0.7587	75.87%
Glucocorticoid receptor binding	-	0.7852	78.52%
Aromatase binding	-	0.5866	58.66%
PPAR gamma	-	0.7002	70.02%
Honey bee toxicity	-	0.9722	97.22%
Biodegradation	+	0.9000	90.00%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	-	0.8267	82.67%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	37650.5 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	25118.9 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	25118.9 nM	Potency	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	1778.3 nM	Potency	via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	1258.9 nM	Potency	via CMAUP
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	5157.65 nM	IC50	via CMAUP
CHEMBL5573	P09923	Intestinal alkaline phosphatase	11300 nM	EC50	via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	3548.1 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	35481.3 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	44668.4 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	88.82%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.07%	91.11%
CHEMBL4208	P20618	Proteasome component C5	84.92%	90.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.79%	93.10%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.04%	85.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.52%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.66%	86.33%

Plants that contains it

• Acorus gramineus
• Carissa spinarum
• Citrullus colocynthis
• Isatis tinctoria
• Pseudolarix amabilis
• Xanthium strumarium

Cross-Links

• PubChem: 638759
• NPASS: NPC114682
• ChEMBL: CHEMBL1417159
• LOTUS: LTS0075622
• wikiData: Q82123562