(3S)-5-methoxy-2,2-dimethyl-3,4-dihydropyrano[2,3-b]quinolin-3-ol

Details

• Internal ID: ffd1ef65-053b-4b09-aa17-87cda49fada2
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Pyranoquinolines
• IUPAC Name: (3S)-5-methoxy-2,2-dimethyl-3,4-dihydropyrano[2,3-b]quinolin-3-ol
• SMILES (Canonical): CC1(C(CC2=C(C3=CC=CC=C3N=C2O1)OC)O)C
• SMILES (Isomeric): CC1([C@H](CC2=C(C3=CC=CC=C3N=C2O1)OC)O)C
• InChI: InChI=1S/C15H17NO3/c1-15(2)12(17)8-10-13(18-3)9-6-4-5-7-11(9)16-14(10)19-15/h4-7,12,17H,8H2,1-3H3/t12-/m0/s1
• InChI Key: SQJURFQZMPUMRB-LBPRGKRZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₇NO₃
• Molecular Weight: 259.30 g/mol
• Exact Mass: 259.12084340 g/mol
• Topological Polar Surface Area (TPSA): 51.60 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	+	0.6152	61.52%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5394	53.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9355	93.55%
OATP1B3 inhibitior	+	0.9598	95.98%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5668	56.68%
P-glycoprotein inhibitior	-	0.9460	94.60%
P-glycoprotein substrate	-	0.8895	88.95%
CYP3A4 substrate	+	0.5931	59.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4180	41.80%
CYP3A4 inhibition	-	0.9326	93.26%
CYP2C9 inhibition	-	0.9244	92.44%
CYP2C19 inhibition	-	0.6927	69.27%
CYP2D6 inhibition	-	0.9079	90.79%
CYP1A2 inhibition	+	0.7169	71.69%
CYP2C8 inhibition	+	0.7257	72.57%
CYP inhibitory promiscuity	-	0.8628	86.28%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5424	54.24%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.6144	61.44%
Skin irritation	-	0.8016	80.16%
Skin corrosion	-	0.9455	94.55%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7389	73.89%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8240	82.40%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.4726	47.26%
Acute Oral Toxicity (c)	III	0.5565	55.65%
Estrogen receptor binding	+	0.7977	79.77%
Androgen receptor binding	-	0.5115	51.15%
Thyroid receptor binding	+	0.7199	71.99%
Glucocorticoid receptor binding	+	0.6856	68.56%
Aromatase binding	-	0.5520	55.20%
PPAR gamma	+	0.7304	73.04%
Honey bee toxicity	-	0.9092	90.92%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	-	0.7107	71.07%

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	98.68%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.46%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.98%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.99%	86.33%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	91.92%	89.44%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.80%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	91.28%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.49%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.03%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.05%	94.00%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	82.48%	95.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.98%	94.62%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.26%	85.49%

Plants that contains it

• Citrus maxima
• Geijera balansae
• Melicope semecarpifolia

Cross-Links

• PubChem: 11086467
• LOTUS: LTS0049636
• wikiData: Q104402790