Atalaphillinine

Details

• Internal ID: f618fb6f-07a0-415a-bd91-593577bf4c0f
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
• IUPAC Name: 6,11-dihydroxy-3,3-dimethyl-5-(3-methylbut-2-enyl)-12H-pyrano[2,3-c]acridin-7-one
• SMILES (Canonical): CC(=CCC1=C2C(=C3C(=C1O)C(=O)C4=C(N3)C(=CC=C4)O)C=CC(O2)(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C3C(=C1O)C(=O)C4=C(N3)C(=CC=C4)O)C=CC(O2)(C)C)C
• InChI: InChI=1S/C23H23NO4/c1-12(2)8-9-15-21(27)17-19(14-10-11-23(3,4)28-22(14)15)24-18-13(20(17)26)6-5-7-16(18)25/h5-8,10-11,25,27H,9H2,1-4H3,(H,24,26)
• InChI Key: QJMYUQUOPGKBEZ-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₃NO₄
• Molecular Weight: 377.40 g/mol
• Exact Mass: 377.16270821 g/mol
• Topological Polar Surface Area (TPSA): 78.80 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 4.79
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• atalaphyllinine
• 56296-87-8
• 6,11-dihydroxy-3,3-dimethyl-5-(3-methylbut-2-enyl)-12H-pyrano[2,3-c]acridin-7-one
• 7H-Pyrano(2,3-c)acridin-7-one, 3,12-dihydro-6,11-dihydroxy-3,3-dimethyl-5-(3-methyl-2-butenyl)-
• CHEMBL508187
• DTXSID90204833
• AKOS040750615
• 5629-87-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9800	98.00%
Caco-2	+	0.5544	55.44%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4960	49.60%
OATP2B1 inhibitior	-	0.7154	71.54%
OATP1B1 inhibitior	+	0.8798	87.98%
OATP1B3 inhibitior	+	0.9496	94.96%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8954	89.54%
P-glycoprotein inhibitior	+	0.5814	58.14%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6468	64.68%
CYP2C9 substrate	+	0.5962	59.62%
CYP2D6 substrate	-	0.8144	81.44%
CYP3A4 inhibition	-	0.9250	92.50%
CYP2C9 inhibition	-	0.5346	53.46%
CYP2C19 inhibition	+	0.6203	62.03%
CYP2D6 inhibition	-	0.8278	82.78%
CYP1A2 inhibition	+	0.6204	62.04%
CYP2C8 inhibition	+	0.4680	46.80%
CYP inhibitory promiscuity	+	0.6541	65.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6391	63.91%
Eye corrosion	-	0.9914	99.14%
Eye irritation	+	0.6257	62.57%
Skin irritation	-	0.7969	79.69%
Skin corrosion	-	0.9309	93.09%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3908	39.08%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.5449	54.49%
skin sensitisation	-	0.7676	76.76%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7780	77.80%
Acute Oral Toxicity (c)	III	0.6209	62.09%
Estrogen receptor binding	+	0.9073	90.73%
Androgen receptor binding	+	0.7106	71.06%
Thyroid receptor binding	+	0.7293	72.93%
Glucocorticoid receptor binding	+	0.9128	91.28%
Aromatase binding	+	0.6861	68.61%
PPAR gamma	+	0.8810	88.10%
Honey bee toxicity	-	0.8351	83.51%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9352	93.52%

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	99.65%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.23%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	98.95%	94.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	98.47%	93.99%
CHEMBL1951	P21397	Monoamine oxidase A	98.00%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.84%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.09%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	95.03%	94.73%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	94.56%	85.30%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.28%	85.14%
CHEMBL5103	Q969S8	Histone deacetylase 10	94.03%	90.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.47%	89.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	93.12%	88.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.47%	99.23%
CHEMBL255	P29275	Adenosine A2b receptor	88.90%	98.59%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.35%	96.09%
CHEMBL213	P08588	Beta-1 adrenergic receptor	87.00%	95.56%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	85.85%	83.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.85%	86.33%
CHEMBL1829	O15379	Histone deacetylase 3	85.72%	95.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.82%	90.17%
CHEMBL2535	P11166	Glucose transporter	83.62%	98.75%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	82.32%	96.39%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.13%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.68%	94.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.41%	97.28%

Plants that contains it

• Atalantia buxifolia
• Atalantia macrophylla
• Citrus japonica

Cross-Links

• PubChem: 122681
• NPASS: NPC176113
• ChEMBL: CHEMBL508187
• LOTUS: LTS0013259
• wikiData: Q83078301