methyl (5S,6R)-7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxylate

Details

• Internal ID: f585646a-884b-4070-8d20-fe9420bbe68c
• Taxonomy: Organoheterocyclic compounds > Azolines > Isoxazolines
• IUPAC Name: methyl (5S,6R)-7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxylate
• SMILES (Canonical): COC1=C(C(C2(CC(=NO2)C(=O)OC)C=C1Br)O)Br
• SMILES (Isomeric): COC1=C([C@@H]([C@]2(CC(=NO2)C(=O)OC)C=C1Br)O)Br
• InChI: InChI=1S/C11H11Br2NO5/c1-17-8-5(12)3-11(9(15)7(8)13)4-6(14-19-11)10(16)18-2/h3,9,15H,4H2,1-2H3/t9-,11+/m0/s1
• InChI Key: BWARHGMOCWYQHN-GXSJLCMTSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₁Br₂NO₅
• Molecular Weight: 397.02 g/mol
• Exact Mass: 396.89835 g/mol
• Topological Polar Surface Area (TPSA): 77.40 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.58
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9751	97.51%
Caco-2	-	0.6346	63.46%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4391	43.91%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9292	92.92%
OATP1B3 inhibitior	+	0.9349	93.49%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8159	81.59%
P-glycoprotein inhibitior	-	0.9547	95.47%
P-glycoprotein substrate	-	0.7914	79.14%
CYP3A4 substrate	+	0.6225	62.25%
CYP2C9 substrate	-	0.7923	79.23%
CYP2D6 substrate	-	0.8286	82.86%
CYP3A4 inhibition	-	0.8495	84.95%
CYP2C9 inhibition	-	0.8726	87.26%
CYP2C19 inhibition	-	0.8416	84.16%
CYP2D6 inhibition	-	0.9141	91.41%
CYP1A2 inhibition	-	0.6933	69.33%
CYP2C8 inhibition	-	0.5824	58.24%
CYP inhibitory promiscuity	-	0.7097	70.97%
UGT catelyzed	-	0.5841	58.41%
Carcinogenicity (binary)	-	0.7632	76.32%
Carcinogenicity (trinary)	Non-required	0.3815	38.15%
Eye corrosion	-	0.9744	97.44%
Eye irritation	+	0.6214	62.14%
Skin irritation	-	0.7565	75.65%
Skin corrosion	-	0.9190	91.90%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7390	73.90%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7898	78.98%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6483	64.83%
Acute Oral Toxicity (c)	III	0.5832	58.32%
Estrogen receptor binding	+	0.6538	65.38%
Androgen receptor binding	-	0.5756	57.56%
Thyroid receptor binding	+	0.5342	53.42%
Glucocorticoid receptor binding	+	0.7624	76.24%
Aromatase binding	+	0.5893	58.93%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9156	91.56%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.6472	64.72%

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	97.38%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.56%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	88.90%	90.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.80%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.25%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.28%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.69%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.44%	94.73%
CHEMBL5028	O14672	ADAM10	83.29%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.23%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.92%	95.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.71%	89.67%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.53%	92.62%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10572874
• LOTUS: LTS0175692
• wikiData: Q104947085