4-Hydroxyquinoline

Details

• Internal ID: 66456d83-b66f-4012-93fe-b20a4c0b9ad3
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Hydroquinolones
• IUPAC Name: 1H-quinolin-4-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C=CN2
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)C=CN2
• InChI: InChI=1S/C9H7NO/c11-9-5-6-10-8-4-2-1-3-7(8)9/h1-6H,(H,10,11)
• InChI Key: PMZDQRJGMBOQBF-UHFFFAOYSA-N
• Popularity: 1,247 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16 g/mol
• Exact Mass: 145.052763847 g/mol
• Topological Polar Surface Area (TPSA): 29.10 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• Quinolin-4-ol
• 611-36-9
• 4-Quinolinol
• quinolin-4(1H)-one
• 529-37-3
• 4(1H)-Quinolinone
• Kynurine
• 1H-quinolin-4-one
• 4-Quinolone
• Quinoline, 4-hydroxy-
• 4-hydroxy quinoline
• MFCD00006777
• CCRIS 4329
• 4-Chinolinol
• NSC 3183
• MFCD00956391
• 1,4-dihydroquinolin-4-one
• M1O131WXFO
• CHEBI:15815
• NSC-3183
• 4-Oxoquinoline
• EINECS 210-268-2
• UNII-M1O131WXFO
• BRN 1524969
• 3kpu
• 1H-quinoline-4one
• 4(1H)-quinolone
• 4-hydroxy-quinoline
• 4-OXO-1,4-DIHYDROQUINOLINE
• 4-Quinolinol, 98%
• Oprea1_521432
• SCHEMBL10031
• 4-Quinolinol (8CI,9CI)
• HYDROXYQUINOLINE, 4-
• CHEMBL1232567
• BDBM14321
• DTXSID50209980
• NSC3183
• CHEBI:155900
• KUC100207N
• BCP27058
• CS-D1012
• AB4075
• AC-516
• KUC100207
• NSC263800
• AKOS000277429
• AKOS005738113
• 4,5-Dichloro-3-thiophenecarboxylicacid
• AM81187
• NSC-263800
• PB43148
• SB67475
• AS-10846
• HY-59208
• SY002846
• SY105850
• A8493
• AM20061372
• EU-0033653
• FT-0618750
• FT-0712331
• Q0029
• EN300-54449
• C06343
• J-512661
• J-650306
• W-105189
• Q27098240
• F0266-1090
• Z818727120
• InChI=1/C9H7NO/c11-9-5-6-10-8-4-2-1-3-7(8)9/h1-6H,(H,10,11

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8639	86.39%
Blood Brain Barrier	+	0.6879	68.79%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5445	54.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9541	95.41%
OATP1B3 inhibitior	+	0.9716	97.16%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8958	89.58%
P-glycoprotein inhibitior	-	0.9836	98.36%
P-glycoprotein substrate	-	0.9819	98.19%
CYP3A4 substrate	-	0.6155	61.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8330	83.30%
CYP3A4 inhibition	-	0.8727	87.27%
CYP2C9 inhibition	-	0.9513	95.13%
CYP2C19 inhibition	-	0.8853	88.53%
CYP2D6 inhibition	-	0.7505	75.05%
CYP1A2 inhibition	+	0.9166	91.66%
CYP2C8 inhibition	-	0.9535	95.35%
CYP inhibitory promiscuity	-	0.7297	72.97%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9123	91.23%
Carcinogenicity (trinary)	Non-required	0.6075	60.75%
Eye corrosion	-	0.9887	98.87%
Eye irritation	+	0.9955	99.55%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9822	98.22%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7701	77.01%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7516	75.16%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.8000	80.00%
Nephrotoxicity	+	0.4808	48.08%
Acute Oral Toxicity (c)	III	0.7318	73.18%
Estrogen receptor binding	-	0.8539	85.39%
Androgen receptor binding	-	0.7282	72.82%
Thyroid receptor binding	-	0.7331	73.31%
Glucocorticoid receptor binding	-	0.8746	87.46%
Aromatase binding	-	0.6086	60.86%
PPAR gamma	-	0.7358	73.58%
Honey bee toxicity	-	0.8283	82.83%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	-	0.7322	73.22%

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	95.74%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.53%	95.56%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	89.00%	92.67%
CHEMBL2581	P07339	Cathepsin D	86.81%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.53%	93.99%
CHEMBL3310	Q96DB2	Histone deacetylase 11	83.07%	88.56%
CHEMBL1937	Q92769	Histone deacetylase 2	81.69%	94.75%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	81.38%	81.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.00%	94.45%

Plants that contains it

• Glycosmis parviflora

Cross-Links

• PubChem: 69141
• LOTUS: LTS0261558
• wikiData: Q27098240