rel-(1R,2S)-1-(9,10-Dihydro-1-hydroxy-3,5,6-trimethoxy-9-oxo-2-acridinyl)-1,11-dihydro-5,9-dihydroxy-2-(1-hydroxy-1-methylethyl)-10-methoxy-11-methylfuro[2,3-c]acridin-6(2H)-one

Details

• Internal ID: b0761157-076c-44fc-9613-4fb2c2b98a57
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
• IUPAC Name: (1S,2R)-5,9-dihydroxy-2-(2-hydroxypropan-2-yl)-1-(1-hydroxy-3,5,6-trimethoxy-9-oxo-10H-acridin-2-yl)-10-methoxy-11-methyl-1,2-dihydrofuro[2,3-c]acridin-6-one
• SMILES (Canonical): CC(C)(C1C(C2=C(O1)C=C(C3=C2N(C4=C(C3=O)C=CC(=C4OC)O)C)O)C5=C(C=C6C(=C5O)C(=O)C7=C(N6)C(=C(C=C7)OC)OC)OC)O
• SMILES (Isomeric): CC(C)([C@H]1[C@@H](C2=C(O1)C=C(C3=C2N(C4=C(C3=O)C=CC(=C4OC)O)C)O)C5=C(C=C6C(=C5O)C(=O)C7=C(N6)C(=C(C=C7)OC)OC)OC)O
• InChI: InChI=1S/C36H34N2O11/c1-36(2,44)35-26(24-21(49-35)13-18(40)23-29(24)38(3)28-15(31(23)42)8-10-17(39)33(28)47-6)25-20(46-5)12-16-22(32(25)43)30(41)14-9-11-19(45-4)34(48-7)27(14)37-16/h8-13,26,35,39-40,43-44H,1-7H3,(H,37,41)/t26-,35+/m0/s1
• InChI Key: VNOSLNLEVFTHKG-OSPAZUARSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₄N₂O₁₁
• Molecular Weight: 670.70 g/mol
• Exact Mass: 670.21625990 g/mol
• Topological Polar Surface Area (TPSA): 176.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 4.50
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• rel-(1R,2S)-1-(9,10-Dihydro-1-hydroxy-3,5,6-trimethoxy-9-oxo-2-acridinyl)-1,11-dihydro-5,9-dihydroxy-2-(1-hydroxy-1-methylethyl)-10-methoxy-11-methylfuro[2,3-c]acridin-6(2H)-one
• rel-(1R,2S)-1-(9,10-Dihydro-1-hydroxy-3,5,6-trimethoxy-9-oxo-2-acridinyl)-1,11-dihydro-5,9-dihydroxy-2-(1-hydroxy-1-methylethyl)-10-methoxy-11-methylfuro(2,3-c)acridin-6(2H)-one
• RefChem:379059
• DTXSID201098901

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7464	74.64%
Caco-2	-	0.8370	83.70%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6311	63.11%
OATP2B1 inhibitior	-	0.5633	56.33%
OATP1B1 inhibitior	+	0.8901	89.01%
OATP1B3 inhibitior	+	0.9228	92.28%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8925	89.25%
P-glycoprotein inhibitior	+	0.7923	79.23%
P-glycoprotein substrate	+	0.6785	67.85%
CYP3A4 substrate	+	0.6838	68.38%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.7064	70.64%
CYP2C9 inhibition	-	0.5738	57.38%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.8209	82.09%
CYP1A2 inhibition	+	0.5707	57.07%
CYP2C8 inhibition	+	0.7234	72.34%
CYP inhibitory promiscuity	+	0.5435	54.35%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.3991	39.91%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.8979	89.79%
Skin irritation	-	0.8378	83.78%
Skin corrosion	-	0.9418	94.18%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6873	68.73%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.5336	53.36%
skin sensitisation	-	0.8979	89.79%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8448	84.48%
Acute Oral Toxicity (c)	III	0.6772	67.72%
Estrogen receptor binding	+	0.8163	81.63%
Androgen receptor binding	+	0.7560	75.60%
Thyroid receptor binding	+	0.6633	66.33%
Glucocorticoid receptor binding	+	0.8265	82.65%
Aromatase binding	+	0.7244	72.44%
PPAR gamma	+	0.7221	72.21%
Honey bee toxicity	-	0.8509	85.09%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.7472	74.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.14%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.07%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.99%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.97%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	96.41%	93.99%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.09%	91.11%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	95.30%	80.78%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.23%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	93.97%	91.49%
CHEMBL213	P08588	Beta-1 adrenergic receptor	93.94%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.56%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.43%	89.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.13%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.05%	96.09%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	90.91%	93.65%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.83%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.47%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	87.91%	94.75%
CHEMBL255	P29275	Adenosine A2b receptor	86.87%	98.59%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	86.52%	92.68%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.89%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.54%	95.78%
CHEMBL2535	P11166	Glucose transporter	84.88%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.47%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.66%	95.89%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	82.36%	96.86%

Plants that contains it

• Citrus × aurantium

Cross-Links

• PubChem: 10439455
• LOTUS: LTS0275074
• wikiData: Q105289821