6,11-dihydroxy-3,3-dimethyl-12H-pyrano[2,3-c]acridin-7-one

Details

• Internal ID: 53db4c9b-ced0-4e5d-ae3d-31e6ec4a2199
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
• IUPAC Name: 6,11-dihydroxy-3,3-dimethyl-12H-pyrano[2,3-c]acridin-7-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=C(C3=C2NC4=C(C3=O)C=CC=C4O)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=C(C3=C2NC4=C(C3=O)C=CC=C4O)O)C
• InChI: InChI=1S/C18H15NO4/c1-18(2)7-6-9-13(23-18)8-12(21)14-16(9)19-15-10(17(14)22)4-3-5-11(15)20/h3-8,20-21H,1-2H3,(H,19,22)
• InChI Key: QMIBOFBCPAGGAC-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₅NO₄
• Molecular Weight: 309.30 g/mol
• Exact Mass: 309.10010796 g/mol
• Topological Polar Surface Area (TPSA): 78.80 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.28
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• Atalaphyllidine
• CHEMBL452220
• 6,11-dihydroxy-3,3-dimethyl-12H-pyrano[2,3-c]acridin-7-one
• BDBM50021613
• 57959-88-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9682	96.82%
Caco-2	+	0.5952	59.52%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5864	58.64%
OATP2B1 inhibitior	-	0.7159	71.59%
OATP1B1 inhibitior	+	0.9323	93.23%
OATP1B3 inhibitior	+	0.9709	97.09%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6739	67.39%
P-glycoprotein inhibitior	-	0.6807	68.07%
P-glycoprotein substrate	-	0.6038	60.38%
CYP3A4 substrate	+	0.5969	59.69%
CYP2C9 substrate	-	0.6147	61.47%
CYP2D6 substrate	-	0.8369	83.69%
CYP3A4 inhibition	-	0.8138	81.38%
CYP2C9 inhibition	-	0.6847	68.47%
CYP2C19 inhibition	-	0.5052	50.52%
CYP2D6 inhibition	-	0.8701	87.01%
CYP1A2 inhibition	+	0.6467	64.67%
CYP2C8 inhibition	-	0.6550	65.50%
CYP inhibitory promiscuity	-	0.6312	63.12%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6049	60.49%
Eye corrosion	-	0.9932	99.32%
Eye irritation	+	0.8950	89.50%
Skin irritation	-	0.8211	82.11%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	+	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7287	72.87%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	0.5801	58.01%
skin sensitisation	-	0.7777	77.77%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7076	70.76%
Acute Oral Toxicity (c)	III	0.6881	68.81%
Estrogen receptor binding	+	0.8650	86.50%
Androgen receptor binding	+	0.7358	73.58%
Thyroid receptor binding	+	0.8426	84.26%
Glucocorticoid receptor binding	+	0.9584	95.84%
Aromatase binding	+	0.8278	82.78%
PPAR gamma	+	0.8251	82.51%
Honey bee toxicity	-	0.9209	92.09%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.7218	72.18%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	2200 nM	IC50	PMID: 24798019

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.17%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	98.67%	93.99%
CHEMBL1937	Q92769	Histone deacetylase 2	98.27%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.47%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.24%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.48%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.93%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.85%	89.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	92.30%	80.96%
CHEMBL3401	O75469	Pregnane X receptor	91.34%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.19%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	89.58%	91.49%
CHEMBL2535	P11166	Glucose transporter	89.09%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.04%	96.09%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.65%	85.30%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.61%	94.80%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.94%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.80%	94.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.76%	90.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.68%	86.33%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.93%	95.56%
CHEMBL3310	Q96DB2	Histone deacetylase 11	82.04%	88.56%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	80.30%	93.24%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	80.15%	85.00%

Plants that contains it

• Atalantia buxifolia
• Buchanania cochinchinensis
• Glycosmis macrantha
• Glycosmis parviflora
• Vepris glaberrima

Cross-Links

• PubChem: 5479542
• NPASS: NPC218303
• ChEMBL: CHEMBL452220
• LOTUS: LTS0104540
• wikiData: Q104395345