(3S,4R)-3,4-dihydroxy-1-methyl-3-(3-methylbut-2-enyl)-4H-quinolin-2-one

Details

• Internal ID: a5a32936-aa0b-4944-af78-aab0431b6d8f
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Hydroquinolones
• IUPAC Name: (3S,4R)-3,4-dihydroxy-1-methyl-3-(3-methylbut-2-enyl)-4H-quinolin-2-one
• SMILES (Canonical): CC(=CCC1(C(C2=CC=CC=C2N(C1=O)C)O)O)C
• SMILES (Isomeric): CC(=CC[C@@]1([C@@H](C2=CC=CC=C2N(C1=O)C)O)O)C
• InChI: InChI=1S/C15H19NO3/c1-10(2)8-9-15(19)13(17)11-6-4-5-7-12(11)16(3)14(15)18/h4-8,13,17,19H,9H2,1-3H3/t13-,15+/m1/s1
• InChI Key: FEPKUMYKOJNXBH-HIFRSBDPSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₉NO₃
• Molecular Weight: 261.32 g/mol
• Exact Mass: 261.13649347 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.78
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9624	96.24%
Caco-2	+	0.7460	74.60%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5684	56.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	+	0.9467	94.67%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9143	91.43%
P-glycoprotein inhibitior	-	0.9422	94.22%
P-glycoprotein substrate	-	0.8002	80.02%
CYP3A4 substrate	+	0.5211	52.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7532	75.32%
CYP3A4 inhibition	-	0.8172	81.72%
CYP2C9 inhibition	-	0.7702	77.02%
CYP2C19 inhibition	-	0.7088	70.88%
CYP2D6 inhibition	-	0.8685	86.85%
CYP1A2 inhibition	+	0.5091	50.91%
CYP2C8 inhibition	-	0.9305	93.05%
CYP inhibitory promiscuity	-	0.7029	70.29%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5974	59.74%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.8276	82.76%
Skin irritation	-	0.7796	77.96%
Skin corrosion	-	0.9269	92.69%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6110	61.10%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.8677	86.77%
skin sensitisation	-	0.8308	83.08%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5442	54.42%
Acute Oral Toxicity (c)	III	0.5998	59.98%
Estrogen receptor binding	+	0.5327	53.27%
Androgen receptor binding	-	0.6052	60.52%
Thyroid receptor binding	+	0.6701	67.01%
Glucocorticoid receptor binding	+	0.5911	59.11%
Aromatase binding	-	0.7092	70.92%
PPAR gamma	+	0.6465	64.65%
Honey bee toxicity	-	0.9316	93.16%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.6908	69.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.20%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.63%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.26%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.20%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.11%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.66%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	85.50%	90.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.57%	82.69%

Plants that contains it

• Boronia pinnata

Cross-Links

• PubChem: 10515555
• LOTUS: LTS0250620
• wikiData: Q104994114