6-hydroxy-4-[5-(hydroxymethyl)furan-2-yl]-1H-quinolin-2-one

Details

• Internal ID: 4581ec26-78a3-468a-b707-a776847a685e
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Hydroxyquinolines
• IUPAC Name: 6-hydroxy-4-[5-(hydroxymethyl)furan-2-yl]-1H-quinolin-2-one
• SMILES (Canonical): C1=CC2=C(C=C1O)C(=CC(=O)N2)C3=CC=C(O3)CO
• SMILES (Isomeric): C1=CC2=C(C=C1O)C(=CC(=O)N2)C3=CC=C(O3)CO
• InChI: InChI=1S/C14H11NO4/c16-7-9-2-4-13(19-9)11-6-14(18)15-12-3-1-8(17)5-10(11)12/h1-6,16-17H,7H2,(H,15,18)
• InChI Key: KSGGHUSLBXMWMY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₁NO₄
• Molecular Weight: 257.24 g/mol
• Exact Mass: 257.06880783 g/mol
• Topological Polar Surface Area (TPSA): 82.70 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 4-[5-(Hydroxymethyl)-2-furanyl]-6-hydroxy-1,2-dihydroquinoline-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9877	98.77%
Caco-2	-	0.7527	75.27%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6359	63.59%
OATP2B1 inhibitior	-	0.7135	71.35%
OATP1B1 inhibitior	+	0.7909	79.09%
OATP1B3 inhibitior	+	0.9318	93.18%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6935	69.35%
P-glycoprotein inhibitior	-	0.9275	92.75%
P-glycoprotein substrate	-	0.7104	71.04%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8110	81.10%
CYP2D6 substrate	-	0.8430	84.30%
CYP3A4 inhibition	-	0.8337	83.37%
CYP2C9 inhibition	-	0.7383	73.83%
CYP2C19 inhibition	-	0.9021	90.21%
CYP2D6 inhibition	-	0.8960	89.60%
CYP1A2 inhibition	+	0.7059	70.59%
CYP2C8 inhibition	+	0.5099	50.99%
CYP inhibitory promiscuity	-	0.6789	67.89%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5644	56.44%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.5960	59.60%
Skin irritation	-	0.8091	80.91%
Skin corrosion	-	0.9602	96.02%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7068	70.68%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8528	85.28%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6712	67.12%
Acute Oral Toxicity (c)	III	0.6071	60.71%
Estrogen receptor binding	+	0.6941	69.41%
Androgen receptor binding	+	0.8527	85.27%
Thyroid receptor binding	+	0.6085	60.85%
Glucocorticoid receptor binding	+	0.9118	91.18%
Aromatase binding	+	0.8720	87.20%
PPAR gamma	+	0.9412	94.12%
Honey bee toxicity	-	0.9186	91.86%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	-	0.8236	82.36%

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	98.69%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.91%	98.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	94.68%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.83%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.31%	93.99%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.58%	89.00%
CHEMBL242	Q92731	Estrogen receptor beta	90.29%	98.35%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.80%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.55%	94.45%
CHEMBL2535	P11166	Glucose transporter	87.18%	98.75%
CHEMBL1937	Q92769	Histone deacetylase 2	83.42%	94.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.34%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.87%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.44%	99.23%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.24%	88.56%

Plants that contains it

• Isatis tinctoria

Cross-Links

• PubChem: 60155952
• NPASS: NPC226680