2,3-Dihydro-4,9-dihydroxy-2-(2-hydroxy-propan-2-yl)-11-methoxy-10-methylfuro[3,2-b]acridin-5(10h)-one

Details

• Internal ID: d8b57bba-4c76-4493-b304-1612835d35bc
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
• IUPAC Name: 4,9-dihydroxy-2-(2-hydroxypropan-2-yl)-11-methoxy-10-methyl-2,3-dihydrofuro[3,2-b]acridin-5-one
• InChI: InChI=1S/C20H21NO6/c1-20(2,25)12-8-10-17(24)13-15(19(26-4)18(10)27-12)21(3)14-9(16(13)23)6-5-7-11(14)22/h5-7,12,22,24-25H,8H2,1-4H3
• InChI Key: QHLDPWBFSQRVLN-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁NO₆
• Molecular Weight: 371.40 g/mol
• Exact Mass: 371.13688739 g/mol
• Topological Polar Surface Area (TPSA): 99.50 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.19
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• DTXSID201344356
• BDBM50336485
• 2,3-dihydro-4,9-dihydroxy-2-(2-hydroxy-propan-2-yl)-11-methoxy-10-methylfuro[3,2-b]acridin-5(10h)-one
• 935521-57-6
• 3,10-Dihydro-4,9-dihydroxy-2-(1-hydroxy-1-methylethyl)-11-methoxy-10-methylfuro[3,2-b]acridin-5(2H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9356	93.56%
Caco-2	+	0.6829	68.29%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4903	49.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8988	89.88%
OATP1B3 inhibitior	+	0.9352	93.52%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5755	57.55%
P-glycoprotein inhibitior	-	0.6479	64.79%
P-glycoprotein substrate	-	0.5847	58.47%
CYP3A4 substrate	+	0.6882	68.82%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8395	83.95%
CYP3A4 inhibition	-	0.8716	87.16%
CYP2C9 inhibition	-	0.8451	84.51%
CYP2C19 inhibition	-	0.6252	62.52%
CYP2D6 inhibition	-	0.7995	79.95%
CYP1A2 inhibition	+	0.6356	63.56%
CYP2C8 inhibition	+	0.4506	45.06%
CYP inhibitory promiscuity	-	0.7183	71.83%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4022	40.22%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.6486	64.86%
Skin irritation	-	0.8270	82.70%
Skin corrosion	-	0.9470	94.70%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4633	46.33%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.6586	65.86%
skin sensitisation	-	0.8663	86.63%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.9412	94.12%
Acute Oral Toxicity (c)	III	0.6744	67.44%
Estrogen receptor binding	+	0.8332	83.32%
Androgen receptor binding	+	0.5408	54.08%
Thyroid receptor binding	+	0.7227	72.27%
Glucocorticoid receptor binding	+	0.7460	74.60%
Aromatase binding	+	0.6458	64.58%
PPAR gamma	+	0.8229	82.29%
Honey bee toxicity	-	0.8788	87.88%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	-	0.4478	44.78%

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	98.99%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.73%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	97.71%	93.99%
CHEMBL2581	P07339	Cathepsin D	96.85%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.70%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.74%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.06%	94.45%
CHEMBL217	P14416	Dopamine D2 receptor	93.26%	95.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.83%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.71%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.20%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.81%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.61%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.17%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.74%	85.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.74%	93.56%
CHEMBL2535	P11166	Glucose transporter	86.03%	98.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.74%	97.25%
CHEMBL2056	P21728	Dopamine D1 receptor	84.18%	91.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.77%	92.62%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.41%	100.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.52%	99.15%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.35%	96.77%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.26%	93.65%

Plants that contains it

• Swinglea glutinosa

Cross-Links

• PubChem: 53326179
• LOTUS: LTS0273642
• wikiData: Q104195823