5,10-dihydroxy-2,2-dimethyl-12-(3-methylbut-2-enyl)-4,11-dihydro-3H-pyrano[3,2-b]acridin-6-one

Details

• Internal ID: f8409184-feb6-485b-987a-a067e8c6de21
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
• IUPAC Name: 5,10-dihydroxy-2,2-dimethyl-12-(3-methylbut-2-enyl)-4,11-dihydro-3H-pyrano[3,2-b]acridin-6-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C3=C1NC4=C(C3=O)C=CC=C4O)O)CCC(O2)(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C3=C1NC4=C(C3=O)C=CC=C4O)O)CCC(O2)(C)C)C
• InChI: InChI=1S/C23H25NO4/c1-12(2)8-9-14-19-17(20(26)13-6-5-7-16(25)18(13)24-19)21(27)15-10-11-23(3,4)28-22(14)15/h5-8,25,27H,9-11H2,1-4H3,(H,24,26)
• InChI Key: FLXKCCVEJAHWOT-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₅NO₄
• Molecular Weight: 379.40 g/mol
• Exact Mass: 379.17835828 g/mol
• Topological Polar Surface Area (TPSA): 78.80 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 4.70
• H-Bond Acceptor: 4
• 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	+	0.9519	95.19%
Caco-2	+	0.6277	62.77%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5828	58.28%
OATP2B1 inhibitior	-	0.7154	71.54%
OATP1B1 inhibitior	+	0.8686	86.86%
OATP1B3 inhibitior	+	0.9354	93.54%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7227	72.27%
P-glycoprotein inhibitior	-	0.5142	51.42%
P-glycoprotein substrate	-	0.5968	59.68%
CYP3A4 substrate	+	0.6526	65.26%
CYP2C9 substrate	+	0.5954	59.54%
CYP2D6 substrate	-	0.8135	81.35%
CYP3A4 inhibition	-	0.9433	94.33%
CYP2C9 inhibition	-	0.7616	76.16%
CYP2C19 inhibition	-	0.6935	69.35%
CYP2D6 inhibition	-	0.8703	87.03%
CYP1A2 inhibition	+	0.5074	50.74%
CYP2C8 inhibition	+	0.4561	45.61%
CYP inhibitory promiscuity	-	0.5518	55.18%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6494	64.94%
Eye corrosion	-	0.9892	98.92%
Eye irritation	+	0.7043	70.43%
Skin irritation	-	0.7817	78.17%
Skin corrosion	-	0.9266	92.66%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4344	43.44%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.5076	50.76%
skin sensitisation	-	0.7885	78.85%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8768	87.68%
Acute Oral Toxicity (c)	III	0.5881	58.81%
Estrogen receptor binding	+	0.8198	81.98%
Androgen receptor binding	+	0.7194	71.94%
Thyroid receptor binding	+	0.6368	63.68%
Glucocorticoid receptor binding	+	0.8904	89.04%
Aromatase binding	+	0.7281	72.81%
PPAR gamma	+	0.9176	91.76%
Honey bee toxicity	-	0.8183	81.83%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9235	92.35%

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	99.73%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	99.35%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.00%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	98.89%	93.99%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	97.74%	85.30%
CHEMBL2581	P07339	Cathepsin D	97.58%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.02%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	95.87%	90.08%
CHEMBL3401	O75469	Pregnane X receptor	94.47%	94.73%
CHEMBL3310	Q96DB2	Histone deacetylase 11	94.15%	88.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.71%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	92.15%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.68%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.62%	99.23%
CHEMBL255	P29275	Adenosine A2b receptor	88.51%	98.59%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.61%	86.33%
CHEMBL213	P08588	Beta-1 adrenergic receptor	85.77%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.20%	100.00%
CHEMBL1829	O15379	Histone deacetylase 3	83.67%	95.00%
CHEMBL2535	P11166	Glucose transporter	83.55%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.99%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.99%	95.89%
CHEMBL233	P35372	Mu opioid receptor	82.87%	97.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.78%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.11%	97.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.68%	91.71%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.29%	96.39%

Plants that contains it

• Citrus japonica

Cross-Links

• PubChem: 163011333
• LOTUS: LTS0029058
• wikiData: Q104997592