(3R,4S)-3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-3,4-dihydropyrano[3,2-c]quinolin-5-one

Details

• Internal ID: 7c13f008-9abb-42b2-9ab8-739646e68a21
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Pyranoquinolines
• IUPAC Name: (3R,4S)-3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-3,4-dihydropyrano[3,2-c]quinolin-5-one
• SMILES (Canonical): CC1(C(C(C2=C(O1)C3=C(C(=CC=C3)OC)N(C2=O)C)O)O)C
• SMILES (Isomeric): CC1([C@@H]([C@H](C2=C(O1)C3=C(C(=CC=C3)OC)N(C2=O)C)O)O)C
• InChI: InChI=1S/C16H19NO5/c1-16(2)14(19)12(18)10-13(22-16)8-6-5-7-9(21-4)11(8)17(3)15(10)20/h5-7,12,14,18-19H,1-4H3/t12-,14+/m0/s1
• InChI Key: GQGXEILPTLCMFO-GXTWGEPZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₉NO₅
• Molecular Weight: 305.32 g/mol
• Exact Mass: 305.12632271 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 1.11
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5890	58.90%
Caco-2	+	0.6644	66.44%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5032	50.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9042	90.42%
OATP1B3 inhibitior	+	0.9524	95.24%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7873	78.73%
P-glycoprotein inhibitior	-	0.8187	81.87%
P-glycoprotein substrate	-	0.7061	70.61%
CYP3A4 substrate	+	0.6812	68.12%
CYP2C9 substrate	-	0.7936	79.36%
CYP2D6 substrate	-	0.8297	82.97%
CYP3A4 inhibition	-	0.8210	82.10%
CYP2C9 inhibition	-	0.8850	88.50%
CYP2C19 inhibition	-	0.6607	66.07%
CYP2D6 inhibition	-	0.9153	91.53%
CYP1A2 inhibition	+	0.7456	74.56%
CYP2C8 inhibition	-	0.8078	80.78%
CYP inhibitory promiscuity	-	0.8092	80.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5468	54.68%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8319	83.19%
Skin irritation	-	0.8326	83.26%
Skin corrosion	-	0.9496	94.96%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6456	64.56%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.6268	62.68%
skin sensitisation	-	0.8927	89.27%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6092	60.92%
Acute Oral Toxicity (c)	III	0.6940	69.40%
Estrogen receptor binding	+	0.6642	66.42%
Androgen receptor binding	-	0.5292	52.92%
Thyroid receptor binding	+	0.5360	53.60%
Glucocorticoid receptor binding	+	0.5964	59.64%
Aromatase binding	-	0.5545	55.45%
PPAR gamma	+	0.7781	77.81%
Honey bee toxicity	-	0.8338	83.38%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	-	0.4471	44.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.99%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.23%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.33%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.93%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.07%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.24%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.02%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.27%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.42%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.64%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.19%	97.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.92%	91.11%

Plants that contains it

• Zanthoxylum simulans

Cross-Links

• PubChem: 163025327
• LOTUS: LTS0270115
• wikiData: Q105015368