2,4-Quinolinediol

Details

• Internal ID: 2a76163d-1749-4d1a-af82-816e123ed241
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Hydroxyquinolones
• IUPAC Name: 4-hydroxy-1H-quinolin-2-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=CC(=O)N2)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=CC(=O)N2)O
• InChI: InChI=1S/C9H7NO2/c11-8-5-9(12)10-7-4-2-1-3-6(7)8/h1-5H,(H2,10,11,12)
• InChI Key: HDHQZCHIXUUSMK-UHFFFAOYSA-N
• Popularity: 360 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16 g/mol
• Exact Mass: 161.047678466 g/mol
• Topological Polar Surface Area (TPSA): 49.30 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.23
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 2,4-Dihydroxyquinoline
• 86-95-3
• 4-Hydroxyquinolin-2(1H)-one
• Quinoline-2,4-diol
• 2-Hydroxyquinolin-4(1H)-one
• 4-Hydroxy-2-quinolone
• 4-Hydroxycarbostyril
• 70254-44-3
• 2(1H)-Quinolinone, 4-hydroxy-
• 4-Hydroxy-2-quinolinone
• Hydroxycarbostyril
• 2-hydroxy-1H-quinolin-4-one
• CARBOSTYRIL, 4-HYDROXY-
• 70254-43-2
• 4-hydroxy-2(1H)-quinolone
• NSC 12465
• 4-hydroxy-1H-quinolin-2-one
• 4-hydroxy-1,2-dihydroquinolin-2-one
• 2.4-Quinolinediol
• N58HX8G9CN
• 2-hydroxy-4(1H)-quinolone
• CHEBI:75926
• MFCD00006744
• NSC-12465
• NSC-13962
• 4-Hydroxycarbostyril; 4-Hydroxyquinolin-2(1H)-one; 4-Hydroxyquinoline-2(1H)-one; NSC 13962
• NSC89729
• 2,4-Dihydroxy quinoline
• EINECS 201-711-0
• Dihydroxyquinoine
• DHQ quinolinol
• 4(1H)-Quinolinone, 2-hydroxy-
• NSC13962
• 2,4-Quinolinediol-
• 4-hydroxy quinolinone
• 2(1H)-QUINOLINONE, 4-HYDROXY
• 2.4-dihydroxy quinoline
• 4-hydroxyquinolin-2-one
• Maybridge1_006493
• 2, 4-Dihydroxyquinoline-
• UNII-N58HX8G9CN
• 2,4-Quinolinediol, 97%
• Oprea1_337514
• Oprea1_706175
• SCHEMBL64767
• MLS000716246
• 4-Hydroxy-2(1H)-quinolinone
• 4-hydroxy-2(l H)-quinolinone
• CHEMBL223449
• 4-hydroxy-quinolin-2(1H)-one
• DTXSID8058950
• HMS559P03
• 4-Hydroxy-2(1H)-quinolinone #
• HMS1693D10
• HMS2653O04
• BCP32971
• HY-Y1685
• NSC12465
• AM1202
• MFCD00277932
• MFCD18836846
• 2,4-Quinolinediol (mainly keto form)
• AKOS000115761
• AKOS000265236
• 4-HYDROXYQUINOLINE-2(1H)-ONE
• CS-W020079
• PS-4409
• SB67441
• SB67447
• NCGC00245100-01
• 2, 4-Dihydroxyquinoline, monosodium salt
• AC-22550
• SMR000277763
• SY037068
• TS-02141
• 4-Hydroxyquinolin-2(1H)-one, AldrichCPR
• CS-0166937
• D1753
• FT-0610128
• EN300-03079
• O10804
• AB00979379-01
• A841886
• AC-907/25014240
• J-650187
• W-104050
• Q27145638
• Z56781882
• F0722-1485
• 2,4-Dihydroxyquinoline;4-Hydroxyquinolin-2(1H)-one;Quinoline-2,4-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9945	99.45%
Caco-2	+	0.7933	79.33%
Blood Brain Barrier	+	0.8879	88.79%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5230	52.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9327	93.27%
OATP1B3 inhibitior	+	0.9570	95.70%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8348	83.48%
P-glycoprotein inhibitior	-	0.9843	98.43%
P-glycoprotein substrate	-	0.9856	98.56%
CYP3A4 substrate	-	0.6210	62.10%
CYP2C9 substrate	-	0.7947	79.47%
CYP2D6 substrate	-	0.8736	87.36%
CYP3A4 inhibition	-	0.8578	85.78%
CYP2C9 inhibition	-	0.9330	93.30%
CYP2C19 inhibition	-	0.8723	87.23%
CYP2D6 inhibition	-	0.8924	89.24%
CYP1A2 inhibition	+	0.9208	92.08%
CYP2C8 inhibition	-	0.8730	87.30%
CYP inhibitory promiscuity	-	0.8346	83.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9523	95.23%
Carcinogenicity (trinary)	Non-required	0.5753	57.53%
Eye corrosion	-	0.9962	99.62%
Eye irritation	+	1.0000	100.00%
Skin irritation	-	0.8056	80.56%
Skin corrosion	-	0.9831	98.31%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8163	81.63%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.6323	63.23%
skin sensitisation	-	0.7951	79.51%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.6263	62.63%
Acute Oral Toxicity (c)	III	0.6014	60.14%
Estrogen receptor binding	-	0.6827	68.27%
Androgen receptor binding	+	0.5552	55.52%
Thyroid receptor binding	-	0.4907	49.07%
Glucocorticoid receptor binding	-	0.7781	77.81%
Aromatase binding	-	0.5304	53.04%
PPAR gamma	+	0.6597	65.97%
Honey bee toxicity	-	0.9648	96.48%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.8628	86.28%

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	98.77%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.26%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	90.60%	91.49%
CHEMBL2581	P07339	Cathepsin D	90.11%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.59%	93.99%
CHEMBL2535	P11166	Glucose transporter	89.33%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.03%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	86.97%	94.75%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.12%	94.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.18%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.79%	99.23%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	84.45%	81.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.87%	99.15%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.26%	91.71%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.70%	94.23%

Plants that contains it

• Haplophyllum bucharicum

Cross-Links

• PubChem: 54680871
• LOTUS: LTS0243241
• wikiData: Q27145638