(2R)-2-[(2S)-1,2-dihydroxypropan-2-yl]-5-hydroxy-11-methyl-1,2-dihydrofuro[2,3-c]acridin-6-one

Details

• Internal ID: b8ee9e29-c133-46e7-9f50-4d4439058f9f
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
• IUPAC Name: (2R)-2-[(2S)-1,2-dihydroxypropan-2-yl]-5-hydroxy-11-methyl-1,2-dihydrofuro[2,3-c]acridin-6-one
• SMILES (Canonical): CC(CO)(C1CC2=C(O1)C=C(C3=C2N(C4=CC=CC=C4C3=O)C)O)O
• SMILES (Isomeric): C[C@](CO)([C@H]1CC2=C(O1)C=C(C3=C2N(C4=CC=CC=C4C3=O)C)O)O
• InChI: InChI=1S/C19H19NO5/c1-19(24,9-21)15-7-11-14(25-15)8-13(22)16-17(11)20(2)12-6-4-3-5-10(12)18(16)23/h3-6,8,15,21-22,24H,7,9H2,1-2H3/t15-,19+/m1/s1
• InChI Key: RQAGSTDFTGSIGB-BEFAXECRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₉NO₅
• Molecular Weight: 341.40 g/mol
• Exact Mass: 341.12632271 g/mol
• Topological Polar Surface Area (TPSA): 90.20 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8578	85.78%
Caco-2	-	0.5624	56.24%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.4901	49.01%
OATP2B1 inhibitior	-	0.8571	85.71%
OATP1B1 inhibitior	+	0.9009	90.09%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5899	58.99%
P-glycoprotein inhibitior	-	0.7575	75.75%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6305	63.05%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8460	84.60%
CYP3A4 inhibition	-	0.8686	86.86%
CYP2C9 inhibition	-	0.9160	91.60%
CYP2C19 inhibition	-	0.8462	84.62%
CYP2D6 inhibition	-	0.8842	88.42%
CYP1A2 inhibition	-	0.5110	51.10%
CYP2C8 inhibition	-	0.6932	69.32%
CYP inhibitory promiscuity	-	0.9244	92.44%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4888	48.88%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9466	94.66%
Skin irritation	-	0.8009	80.09%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	+	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4550	45.50%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.5161	51.61%
skin sensitisation	-	0.8450	84.50%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8718	87.18%
Acute Oral Toxicity (c)	III	0.6042	60.42%
Estrogen receptor binding	+	0.8159	81.59%
Androgen receptor binding	+	0.5917	59.17%
Thyroid receptor binding	+	0.6363	63.63%
Glucocorticoid receptor binding	+	0.7927	79.27%
Aromatase binding	+	0.8263	82.63%
PPAR gamma	+	0.8356	83.56%
Honey bee toxicity	-	0.9166	91.66%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.7138	71.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.27%	85.14%
CHEMBL2581	P07339	Cathepsin D	98.19%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.95%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	97.49%	93.99%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.31%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.89%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.68%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.61%	96.09%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	90.72%	93.65%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.34%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.87%	86.33%
CHEMBL3384	Q16512	Protein kinase N1	87.24%	80.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.10%	95.83%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.38%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	84.83%	94.73%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.85%	96.37%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.09%	93.40%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.89%	80.78%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	81.89%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	81.48%	91.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.17%	92.62%
CHEMBL2535	P11166	Glucose transporter	80.56%	98.75%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.39%	100.00%

Plants that contains it

• Ruta graveolens
• Thamnosma montana
• Thamnosma rhodesica

Cross-Links

• PubChem: 162890122
• LOTUS: LTS0038048
• wikiData: Q105243177