2-Hydroxychalcone

Details

• Internal ID: b9850e91-cf39-4e67-a5f1-0983c5d8db18
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Retrochalcones
• IUPAC Name: (E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one
• InChI: InChI=1S/C15H12O2/c16-14-9-5-4-8-13(14)10-11-15(17)12-6-2-1-3-7-12/h1-11,16H/b11-10+
• InChI Key: UDOOPSJCRMKSGL-ZHACJKMWSA-N
• Popularity: 140 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₂
• Molecular Weight: 224.25 g/mol
• Exact Mass: 224.083729621 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.29
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 644-78-0
• 42224-53-3
• (E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one
• 2-Propen-1-one, 3-(2-hydroxyphenyl)-1-phenyl-
• 2-Hydroxybenzylidene acetophenone
• EINECS 211-422-1
• NSC 640539
• AI3-00855
• RefChem:87504
• 211-422-1
• 624-468-6
• 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one
• (E)-2-Hydroxychalcone
• (2E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one
• 2-(2-Hydroxybenzal)acetophenone
• MFCD00016449
• Salicylalacetophenone
• MLS002608038
• NSC640539
• 3-(2-hydroxyphenyl)-1-phenyl-2-propen-1-one
• (E)-3-(2-hydroxyphenyl)-1-phenyl-prop-2-en-1-one
• Chalcone, 1
• 2-Hydroxychalcone, 95%
• SCHEMBL626785
• ARONIS019357
• CHEMBL147067
• orb1299329
• BDBM86002
• HMS3078L22
• NSC37432
• 2-(2-Hydroxybenzylidene)acetophenone
• NSC-37432
• NSC170281
• SBB061939
• STK093271
• AKOS000486194
• AKOS025309995
• FH43279
• NSC-170281
• NSC-640539
• MS-10592
• SMR001526790
• SY057044
• SY113882
• HY-119931
• TL8004571
• CS-0078796
• CS-0311212
• H0234
• NS00042209
• ST45033206
• D90823
• AB-016/30005051
• F003115
• F996570
• SR-01000078236
• SR-01000078236-1
• trans-3-(O-Hydroxyphenyl)-1-phenyl-2-propen-1-one
• (2E)-3-(2-Hydroxyphenyl)-1-phenyl-2-propen-1-one #
• 6-[(1Z,2Z)-3-Hydroxy-3-phenyl-2-propene-1-ylidene]-2,4-cyclohexadiene-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7366	73.66%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8509	85.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9516	95.16%
OATP1B3 inhibitior	+	0.9464	94.64%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6057	60.57%
P-glycoprotein inhibitior	-	0.9452	94.52%
P-glycoprotein substrate	-	0.9728	97.28%
CYP3A4 substrate	-	0.7172	71.72%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8075	80.75%
CYP3A4 inhibition	-	0.8528	85.28%
CYP2C9 inhibition	-	0.7017	70.17%
CYP2C19 inhibition	+	0.8950	89.50%
CYP2D6 inhibition	-	0.8981	89.81%
CYP1A2 inhibition	+	0.8149	81.49%
CYP2C8 inhibition	-	0.5838	58.38%
CYP inhibitory promiscuity	+	0.6818	68.18%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.6581	65.81%
Carcinogenicity (trinary)	Non-required	0.6041	60.41%
Eye corrosion	-	0.9298	92.98%
Eye irritation	+	0.9922	99.22%
Skin irritation	+	0.7580	75.80%
Skin corrosion	-	0.9893	98.93%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8832	88.32%
Micronuclear	-	0.5718	57.18%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	+	0.9689	96.89%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	-	0.8750	87.50%
Nephrotoxicity	-	0.5798	57.98%
Acute Oral Toxicity (c)	III	0.7157	71.57%
Estrogen receptor binding	+	0.9234	92.34%
Androgen receptor binding	+	0.5424	54.24%
Thyroid receptor binding	-	0.5758	57.58%
Glucocorticoid receptor binding	+	0.5508	55.08%
Aromatase binding	+	0.9401	94.01%
PPAR gamma	+	0.6858	68.58%
Honey bee toxicity	-	0.9597	95.97%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
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
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.82%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.56%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	87.46%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.21%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.87%	94.62%
CHEMBL3194	P02766	Transthyretin	86.45%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.69%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.24%	99.23%
CHEMBL2581	P07339	Cathepsin D	80.81%	98.95%

Plants that contains it

• Sophora flavescens

Cross-Links

• PubChem: 5367146
• NPASS: NPC141523