8-Benzyl-2-hexa-1,3-dienyl-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Details

• Internal ID: 6ee0c229-c100-4693-9807-55ef259ad671
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones
• IUPAC Name: 8-benzyl-2-hexa-1,3-dienyl-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
• SMILES (Canonical): CCC=CC=CC1=C(C(=O)C2(O1)C(C(NC2=O)(CC3=CC=CC=C3)O)O)C
• SMILES (Isomeric): CCC=CC=CC1=C(C(=O)C2(O1)C(C(NC2=O)(CC3=CC=CC=C3)O)O)C
• InChI: InChI=1S/C21H23NO5/c1-3-4-5-9-12-16-14(2)17(23)21(27-16)18(24)20(26,22-19(21)25)13-15-10-7-6-8-11-15/h4-12,18,24,26H,3,13H2,1-2H3,(H,22,25)
• InChI Key: QLKGRMRPKQNCRR-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.40 g/mol
• Exact Mass: 369.15762283 g/mol
• Topological Polar Surface Area (TPSA): 95.90 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.54
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9456	94.56%
Caco-2	-	0.7705	77.05%
Blood Brain Barrier	-	0.6379	63.79%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5681	56.81%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8134	81.34%
OATP1B3 inhibitior	+	0.9441	94.41%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.5790	57.90%
P-glycoprotein inhibitior	-	0.5208	52.08%
P-glycoprotein substrate	-	0.7007	70.07%
CYP3A4 substrate	+	0.5498	54.98%
CYP2C9 substrate	-	0.7985	79.85%
CYP2D6 substrate	-	0.8682	86.82%
CYP3A4 inhibition	-	0.9722	97.22%
CYP2C9 inhibition	-	0.8796	87.96%
CYP2C19 inhibition	-	0.8938	89.38%
CYP2D6 inhibition	-	0.9214	92.14%
CYP1A2 inhibition	-	0.9036	90.36%
CYP2C8 inhibition	-	0.5875	58.75%
CYP inhibitory promiscuity	-	0.9100	91.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.5638	56.38%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9615	96.15%
Skin irritation	-	0.7672	76.72%
Skin corrosion	-	0.9286	92.86%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4604	46.04%
Micronuclear	+	0.8159	81.59%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7877	78.77%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.5620	56.20%
Acute Oral Toxicity (c)	III	0.5197	51.97%
Estrogen receptor binding	+	0.6437	64.37%
Androgen receptor binding	+	0.5974	59.74%
Thyroid receptor binding	+	0.5350	53.50%
Glucocorticoid receptor binding	-	0.4748	47.48%
Aromatase binding	-	0.5110	51.10%
PPAR gamma	+	0.6953	69.53%
Honey bee toxicity	-	0.8451	84.51%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	-	0.6037	60.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.03%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.36%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	94.14%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.83%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.04%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.35%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.11%	94.62%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.59%	91.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.54%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.99%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	84.57%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.31%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 60122987
• LOTUS: LTS0038133
• wikiData: Q104195937