2',6'-Dihydroxyacetophenone

Details

• Internal ID: 4fe492c0-605f-4376-ae2d-b3afc72090ec
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 1-(2,6-dihydroxyphenyl)ethanone
• SMILES (Canonical): CC(=O)C1=C(C=CC=C1O)O
• SMILES (Isomeric): CC(=O)C1=C(C=CC=C1O)O
• InChI: InChI=1S/C8H8O3/c1-5(9)8-6(10)3-2-4-7(8)11/h2-4,10-11H,1H3
• InChI Key: YPTJKHVBDCRKNF-UHFFFAOYSA-N
• Popularity: 201 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: 1.40
• Atomic LogP (AlogP): 1.30
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 699-83-2
• 1-(2,6-Dihydroxyphenyl)ethanone
• 2,6-Dihydroxyacetophenone
• 2-Acetylresorcinol
• 1-(2,6-dihydroxyphenyl)ethan-1-one
• Ethanone, 1-(2,6-dihydroxyphenyl)-
• gamma-Resacetophenone
• 1,3-Benzenediol, 2-acetyl-
• Acetophenone, 2',6'-dihydroxy-
• NSC-615
• 88BO51G3Y2
• DTXSID00220185
• RefChem:80167
• DTXCID00142676
• 211-833-6
• Resorcinol, 2-acetyl-
• MFCD00002270
• .gamma.-Resacetophenone
• 2,6-dihydroxy acetophenone
• NSC 615
• 2, 6-Dihydroxyacetophenone
• Acetyl-2,6-dihydroxybenzene
• 2',6'-dihydroxy-acetophenone
• CHEMBL454739
• 2-Acetyl-1,3-dihydroxybenzene
• 1-(2,6-dihydroxyphenyl)-ethanone
• 1-(2,6-dihydroxy-phenyl)-ethanone
• 1-[2,6-bis(oxidanyl)phenyl]ethanone
• ACETOPHENONE, 2,6-DIHYDROXY-
• 1-acetyl-2,6-dihydroxybenzene
• 1-(2,6-Dihydroxyphenyl)ethanone (2',6'-Dihydroxyacetophenone)
• UNII-88BO51G3Y2
• Sodium Cromoglicate Imp. A (EP); 1-(2,6-Dihydroxyphenyl)ethanone; 2',6'-Dihydroxyacetophenone; Sodium Cromoglicate Impurity A
• EINECS 211-833-6
• 2-Acetyl-Resorcinol
• mono acetyl resorcinol
• 2-ACETYL RESORCINOL
• EC 211-833-6
• Acetophenone,6'-dihydroxy-
• 2-Acetyl-1,3-Benzenediol
• 2`,6`-Dihydroxyacetophenone
• Ethanone,6-dihydroxyphenyl)-
• BIDD:ER0607
• SCHEMBL105807
• 2',6'-Dihydroxyacetophenone;
• NSC615
• orb2663240
• (2',6'-dihydroxy)acetophenone
• 2'',6''-dihydroxyacetophenone
• 2\',6\'-Dihydroxyacetophenone
• Sodium Cromoglicate Impurity 17
• laquo gammaRaquo -resacetophenone
• YPTJKHVBDCRKNF-UHFFFAOYSA-
• CHEBI:173644
• AMY21894
• HY-Y0106
• 2',6'-Dihydroxyacetophenone, 97%
• BDBM50249071
• CK2557
• SBB063298
• STL195537
• AKOS000299253
• CS-W019984
• FD11049
• FS-2546
• TRA0041998
• 1-(2,6-Dihydroxyphenyl)ethanone, 9CI
• NCGC00166008-01
• AC-10724
• Acetophenone, 2',6'-dihydroxy- (8CI)
• PD158440
• SY001633
• DB-020214
• TL8004919
• D1716
• NS00001185
• ST50331349
• Ethanone, 1-(2,6-dihydroxyphenyl)- (9CI)
• KS-00000161
• 99D832
• EN300-114470
• M-3163
• AB-131/40185723
• F130800
• doi:10.14272/YPTJKHVBDCRKNF-UHFFFAOYSA-N.1
• SODIUM CROMOGLICATE IMPURITY A [EP IMPURITY]
• Q27269919
• Z1255485184
• 2',6'-Dihydroxyacetophenone, matrix substance for MALDI-MS, >=99.5%
• 2 inverted exclamation mark ,6 inverted exclamation mark -Dihydroxyacetophenone
• 2',6'-Dihydroxyacetophenone, matrix substance for MALDI-MS, >=99.5% (HPLC), Ultra pure
• InChI=1/C8H8O3/c1-5(9)8-6(10)3-2-4-7(8)11/h2-4,10-11H,1H3
• 9EQ

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	+	0.8681	86.81%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.9015	90.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9750	97.50%
OATP1B3 inhibitior	+	0.9809	98.09%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9532	95.32%
P-glycoprotein inhibitior	-	0.9829	98.29%
P-glycoprotein substrate	-	0.9803	98.03%
CYP3A4 substrate	-	0.7244	72.44%
CYP2C9 substrate	-	0.7996	79.96%
CYP2D6 substrate	-	0.8382	83.82%
CYP3A4 inhibition	-	0.6804	68.04%
CYP2C9 inhibition	-	0.5104	51.04%
CYP2C19 inhibition	+	0.5580	55.80%
CYP2D6 inhibition	-	0.9400	94.00%
CYP1A2 inhibition	+	0.5406	54.06%
CYP2C8 inhibition	-	0.9752	97.52%
CYP inhibitory promiscuity	-	0.6157	61.57%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7456	74.56%
Carcinogenicity (trinary)	Non-required	0.7621	76.21%
Eye corrosion	+	0.8839	88.39%
Eye irritation	+	0.9943	99.43%
Skin irritation	+	0.9237	92.37%
Skin corrosion	+	0.6998	69.98%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8225	82.25%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.8750	87.50%
skin sensitisation	+	0.9333	93.33%
Respiratory toxicity	-	0.9000	90.00%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	+	0.6040	60.40%
Acute Oral Toxicity (c)	III	0.8215	82.15%
Estrogen receptor binding	-	0.8484	84.84%
Androgen receptor binding	-	0.8408	84.08%
Thyroid receptor binding	-	0.7057	70.57%
Glucocorticoid receptor binding	-	0.8487	84.87%
Aromatase binding	-	0.9252	92.52%
PPAR gamma	-	0.7660	76.60%
Honey bee toxicity	-	0.9846	98.46%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.8613	86.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	92.62%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.29%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.63%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.71%	94.73%

Plants that contains it

• Aquilaria sinensis
• Myristica fragrans

Cross-Links

• PubChem: 69687
• NPASS: NPC118288
• ChEMBL: CHEMBL454739
• LOTUS: LTS0197806
• wikiData: Q27269919