2',5'-Dihydroxyacetophenone

Details

• Internal ID: 9283bba6-ceaf-451a-9ce5-e151aafcf09d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 1-(2,5-dihydroxyphenyl)ethanone
• SMILES (Canonical): CC(=O)C1=C(C=CC(=C1)O)O
• SMILES (Isomeric): CC(=O)C1=C(C=CC(=C1)O)O
• InChI: InChI=1S/C8H8O3/c1-5(9)7-4-6(10)2-3-8(7)11/h2-4,10-11H,1H3
• InChI Key: WLDWSGZHNBANIO-UHFFFAOYSA-N
• Popularity: 175 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15 g/mol
• Exact Mass: 152.047344113 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.30
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 2',5'-DIHYDROXYACETOPHENONE
• 1-(2,5-Dihydroxyphenyl)ethanone
• 2,5-Dihydroxyacetophenone
• 2-Acetylhydroquinone
• Quinacetophenone
• Acetylhydroquinone
• Ethanone, 1-(2,5-dihydroxyphenyl)-
• Acetylquinol
• 1-(2,5-dihydroxyphenyl)ethan-1-one
• MFCD00002343
• Acetophenone, 2',5'-dihydroxy-
• 1-Acetyl-2,5-dihydroxybenzene
• NSC 3759
• 2,5-Dihydroxy-1-acetylbenzene
• EINECS 207-716-4
• UNII-K1H7QH11ZH
• BRN 0637903
• K1H7QH11ZH
• ghl.PD_Mitscher_leg0.355
• 2', 5'-Dihydroxyacetophenone
• AI3-18221
• 2-Acetyl-1,4-dihydroxybenzene
• 2,5-Dihydroxyphenyl methyl ketone
• NSC-3759
• 4-08-00-01803 (Beilstein Handbook Reference)
• 2',5'-Dihydroxy acetophenone
• NSC3759
• 2-acetyl hydroquinone
• 2-acetyl-hydroquinone
• monoacetyl hydroquinone
• 2-5-dihydroxyacetophenone
• 2,5 -dihydroxyacetophenone
• WLN: QR CQ BV1
• 2,5-Dihydroxy acetophenone
• Acetophenone,5'-dihydroxy-
• 2`,5`-Dihydroxyacetophenone
• Ethanone,5-dihydroxyphenyl)-
• BIDD:ER0488
• SCHEMBL108053
• 2',5'-Dihydroxy-Acetophenone
• CHEMBL2348532
• DTXSID9060077
• CHEBI:173647
• 1-(2,5-dihydroxyphenyl)-ethanone
• 2-ACETYL-1,4-BENZENEDIOL
• 2-ACETYLHYDROQUINONE [INCI]
• AMY27936
• STR02363
• 1-(2,5-dihydroxy-phenyl)-ethanone
• 2',5'-Dihydroxyacetophenone, 97%
• BBL027378
• s9374
• STL199230
• AKOS000120785
• CCG-266221
• CS-W001174
• FS-3211
• HY-W001174
• 1-(2,5-Dihydroxyphenyl)ethanone, 9CI
• s12309
• AC-19701
• SY011591
• D1955
• DHAP, 2-Acetylhydroquinone, Quinacetophenone
• FT-0610380
• EN300-17127
• A827653
• AE-641/00693054
• Q-200196
• Q27281823
• Z56889030
• F3139-0239
• 2 inverted exclamation mark ,5 inverted exclamation mark -Dihydroxyacetophenone
• InChI=1/C8H8O3/c1-5(9)7-4-6(10)2-3-8(7)11/h2-4,10-11H,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.7391	73.91%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.9439	94.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9477	94.77%
OATP1B3 inhibitior	+	0.9873	98.73%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9393	93.93%
P-glycoprotein inhibitior	-	0.9818	98.18%
P-glycoprotein substrate	-	0.9436	94.36%
CYP3A4 substrate	-	0.7295	72.95%
CYP2C9 substrate	-	0.7996	79.96%
CYP2D6 substrate	-	0.8382	83.82%
CYP3A4 inhibition	-	0.8965	89.65%
CYP2C9 inhibition	-	0.7699	76.99%
CYP2C19 inhibition	-	0.5500	55.00%
CYP2D6 inhibition	-	0.9571	95.71%
CYP1A2 inhibition	-	0.5690	56.90%
CYP2C8 inhibition	-	0.8832	88.32%
CYP inhibitory promiscuity	-	0.7505	75.05%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.6568	65.68%
Carcinogenicity (trinary)	Non-required	0.6653	66.53%
Eye corrosion	+	0.9317	93.17%
Eye irritation	+	0.9942	99.42%
Skin irritation	+	0.9436	94.36%
Skin corrosion	-	0.5901	59.01%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7935	79.35%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.7190	71.90%
skin sensitisation	+	0.8670	86.70%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.7500	75.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.8066	80.66%
Estrogen receptor binding	-	0.9235	92.35%
Androgen receptor binding	-	0.5934	59.34%
Thyroid receptor binding	-	0.8047	80.47%
Glucocorticoid receptor binding	-	0.8261	82.61%
Aromatase binding	-	0.8713	87.13%
PPAR gamma	-	0.8018	80.18%
Honey bee toxicity	-	0.9693	96.93%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.9000	90.00%
Fish aquatic toxicity	+	0.8904	89.04%

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	95.96%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.73%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.37%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	85.00%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.49%	99.15%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.42%	93.10%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.76%	95.56%
CHEMBL2535	P11166	Glucose transporter	82.73%	98.75%
CHEMBL4208	P20618	Proteasome component C5	81.41%	90.00%

Plants that contains it

• Cynanchum wilfordii
• Flemingia prostrata
• Mesembryanthemum tortuosum

Cross-Links

• PubChem: 10279
• NPASS: NPC240163
• LOTUS: LTS0166352
• wikiData: Q27281823