Isoaquiledine

Details

• Internal ID: e3be24c9-37be-4577-b7d3-7246af747b43
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
• IUPAC Name: 4-[(2S)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-8-yl]-1,3-diazepan-2-one
• SMILES (Canonical): C1CC(NC(=O)NC1)C2=C3C(=C(C=C2O)O)C(=O)CC(O3)C4=CC=CC=C4
• SMILES (Isomeric): C1CC(NC(=O)NC1)C2=C3C(=C(C=C2O)O)C(=O)C[C@H](O3)C4=CC=CC=C4
• InChI: InChI=1S/C20H20N2O5/c23-13-9-14(24)18-15(25)10-16(11-5-2-1-3-6-11)27-19(18)17(13)12-7-4-8-21-20(26)22-12/h1-3,5-6,9,12,16,23-24H,4,7-8,10H2,(H2,21,22,26)/t12?,16-/m0/s1
• InChI Key: OPODLFBNKXTLEX-INSVYWFGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀N₂O₅
• Molecular Weight: 368.40 g/mol
• Exact Mass: 368.13722174 g/mol
• Topological Polar Surface Area (TPSA): 108.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.94
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 4-[(2S)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-8-yl]-1,3-diazepan-2-one
• 321408-08-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9314	93.14%
Caco-2	-	0.8371	83.71%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5128	51.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9108	91.08%
OATP1B3 inhibitior	+	0.9411	94.11%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8898	88.98%
BSEP inhibitior	-	0.6159	61.59%
P-glycoprotein inhibitior	-	0.6117	61.17%
P-glycoprotein substrate	-	0.7690	76.90%
CYP3A4 substrate	+	0.5255	52.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7675	76.75%
CYP3A4 inhibition	-	0.8722	87.22%
CYP2C9 inhibition	-	0.8224	82.24%
CYP2C19 inhibition	-	0.7694	76.94%
CYP2D6 inhibition	-	0.8611	86.11%
CYP1A2 inhibition	-	0.7496	74.96%
CYP2C8 inhibition	+	0.4647	46.47%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6909	69.09%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9379	93.79%
Skin irritation	-	0.8078	80.78%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4689	46.89%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8838	88.38%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6022	60.22%
Acute Oral Toxicity (c)	III	0.5820	58.20%
Estrogen receptor binding	+	0.6066	60.66%
Androgen receptor binding	+	0.7747	77.47%
Thyroid receptor binding	-	0.5854	58.54%
Glucocorticoid receptor binding	-	0.5753	57.53%
Aromatase binding	-	0.6022	60.22%
PPAR gamma	+	0.7902	79.02%
Honey bee toxicity	-	0.8933	89.33%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.7781	77.81%

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	98.27%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.38%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.08%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.65%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.36%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.98%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	86.58%	83.82%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.49%	99.15%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.39%	93.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.41%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.53%	93.99%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.96%	83.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.94%	86.33%

Plants that contains it

• Aquilegia ecalcarata

Cross-Links

• PubChem: 10666709
• NPASS: NPC165940
• LOTUS: LTS0093669
• wikiData: Q105196465