(5S,8R,9S)-2-benzyl-8-[(2S)-butan-2-yl]-8,9-dihydroxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Details

• Internal ID: e9722649-5b5d-4b2b-ab6d-ecee200d6e11
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones
• IUPAC Name: (5S,8R,9S)-2-benzyl-8-[(2S)-butan-2-yl]-8,9-dihydroxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
• SMILES (Canonical): CCC(C)C1(C(C2(C(=O)C=C(O2)CC3=CC=CC=C3)C(=O)N1)O)O
• SMILES (Isomeric): CC[C@H](C)[C@]1([C@H]([C@]2(C(=O)C=C(O2)CC3=CC=CC=C3)C(=O)N1)O)O
• InChI: InChI=1S/C18H21NO5/c1-3-11(2)18(23)15(21)17(16(22)19-18)14(20)10-13(24-17)9-12-7-5-4-6-8-12/h4-8,10-11,15,21,23H,3,9H2,1-2H3,(H,19,22)/t11-,15-,17+,18+/m0/s1
• InChI Key: XIINWDLLZRIJAK-DRCJMICCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₁NO₅
• Molecular Weight: 331.40 g/mol
• Exact Mass: 331.14197277 g/mol
• Topological Polar Surface Area (TPSA): 95.90 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 0.68
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8045	80.45%
Caco-2	-	0.7463	74.63%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5243	52.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8379	83.79%
OATP1B3 inhibitior	+	0.9412	94.12%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4666	46.66%
P-glycoprotein inhibitior	-	0.8556	85.56%
P-glycoprotein substrate	-	0.6908	69.08%
CYP3A4 substrate	+	0.5084	50.84%
CYP2C9 substrate	-	0.6033	60.33%
CYP2D6 substrate	-	0.8683	86.83%
CYP3A4 inhibition	-	0.9475	94.75%
CYP2C9 inhibition	-	0.8535	85.35%
CYP2C19 inhibition	-	0.8580	85.80%
CYP2D6 inhibition	-	0.9196	91.96%
CYP1A2 inhibition	-	0.8781	87.81%
CYP2C8 inhibition	-	0.8118	81.18%
CYP inhibitory promiscuity	-	0.8537	85.37%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8643	86.43%
Carcinogenicity (trinary)	Non-required	0.5739	57.39%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9900	99.00%
Skin irritation	-	0.7670	76.70%
Skin corrosion	-	0.9245	92.45%
Ames mutagenesis	-	0.6554	65.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4553	45.53%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.5145	51.45%
skin sensitisation	-	0.7929	79.29%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6133	61.33%
Acute Oral Toxicity (c)	III	0.4838	48.38%
Estrogen receptor binding	-	0.5053	50.53%
Androgen receptor binding	+	0.6634	66.34%
Thyroid receptor binding	-	0.5414	54.14%
Glucocorticoid receptor binding	-	0.5071	50.71%
Aromatase binding	+	0.6305	63.05%
PPAR gamma	+	0.6482	64.82%
Honey bee toxicity	-	0.8187	81.87%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.6963	69.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.91%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.85%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.63%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.58%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.56%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	89.20%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.12%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.10%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.53%	86.33%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	82.16%	95.00%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	82.11%	95.48%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163067847
• LOTUS: LTS0186928
• wikiData: Q105328504