7H-Pyrano[2,3-c]acridin-7-one, 3,12-dihydro-6,11-dihydroxy-3,3,12-trimethyl-5-(3-methyl-2-butenyl)-

Details

• Internal ID: f6188f07-2647-4333-bd09-e4b625ad49a8
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
• IUPAC Name: 6,11-dihydroxy-3,3,12-trimethyl-5-(3-methylbut-2-enyl)pyrano[2,3-c]acridin-7-one
• SMILES (Canonical): CC(=CCC1=C2C(=C3C(=C1O)C(=O)C4=C(N3C)C(=CC=C4)O)C=CC(O2)(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C3C(=C1O)C(=O)C4=C(N3C)C(=CC=C4)O)C=CC(O2)(C)C)C
• InChI: InChI=1S/C24H25NO4/c1-13(2)9-10-16-22(28)18-20(15-11-12-24(3,4)29-23(15)16)25(5)19-14(21(18)27)7-6-8-17(19)26/h6-9,11-12,26,28H,10H2,1-5H3
• InChI Key: JLDLLLFQYFAMHX-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₅NO₄
• Molecular Weight: 391.50 g/mol
• Exact Mass: 391.17835828 g/mol
• Topological Polar Surface Area (TPSA): 70.00 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 4.80
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Alkaloid B from Atalantia ceylanica
• N-methylataphyllinine
• N-Methylatalaphyllinine
• 5-Hydroxy-N-methylseverifoline
• CHEMBL452222
• JLDLLLFQYFAMHX-UHFFFAOYSA-N
• 7H-Pyrano[2,3-c]acridin-7-one, 3,12-dihydro-6,11-dihydroxy-3,3,12-trimethyl-5-(3-methyl-2-butenyl)-
• 6,11-Dihydroxy-3,3,12-trimethyl-5-(3-methyl-2-butenyl)-3,12-dihydro-7H-pyrano[2,3-c]acridin-7-one #
• 6,11-dihydroxy-3,3,12-trimethyl-5-(3-methylbut-2-enyl)-3,12-dihydro- 7H-pyrano[2,3-c]acridin-7-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9578	95.78%
Caco-2	+	0.7459	74.59%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Nucleus	0.4942	49.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8604	86.04%
OATP1B3 inhibitior	+	0.9304	93.04%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8891	88.91%
P-glycoprotein inhibitior	-	0.4377	43.77%
P-glycoprotein substrate	+	0.5495	54.95%
CYP3A4 substrate	+	0.6788	67.88%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8329	83.29%
CYP3A4 inhibition	-	0.8985	89.85%
CYP2C9 inhibition	-	0.6249	62.49%
CYP2C19 inhibition	+	0.5413	54.13%
CYP2D6 inhibition	-	0.7362	73.62%
CYP1A2 inhibition	+	0.6576	65.76%
CYP2C8 inhibition	-	0.6139	61.39%
CYP inhibitory promiscuity	+	0.6182	61.82%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4572	45.72%
Eye corrosion	-	0.9897	98.97%
Eye irritation	+	0.6008	60.08%
Skin irritation	-	0.8060	80.60%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6751	67.51%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.5762	57.62%
skin sensitisation	-	0.8313	83.13%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8333	83.33%
Acute Oral Toxicity (c)	III	0.6396	63.96%
Estrogen receptor binding	+	0.8586	85.86%
Androgen receptor binding	+	0.5851	58.51%
Thyroid receptor binding	+	0.7725	77.25%
Glucocorticoid receptor binding	+	0.8488	84.88%
Aromatase binding	+	0.5953	59.53%
PPAR gamma	+	0.8260	82.60%
Honey bee toxicity	-	0.8497	84.97%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9113	91.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.66%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.32%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.87%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.06%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	97.65%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.98%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	94.87%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.81%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.21%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.35%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	92.14%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.43%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.79%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	86.52%	90.17%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.74%	90.08%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.45%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.28%	94.00%
CHEMBL1914	P06276	Butyrylcholinesterase	80.31%	95.00%

Plants that contains it

• Atalantia buxifolia
• Atalantia ceylanica
• Bosistoa transversa
• Citrus japonica
• Glycosmis parviflora

Cross-Links

• PubChem: 633176
• LOTUS: LTS0152115
• wikiData: Q105130653