(5S,8R,9R)-9-(2,4-dibromo-5-methoxyphenyl)-8-hydroxy-7-methyl-1,7-diazaspiro[4.4]nonane-2,6-dione

Details

• Internal ID: 0a0ebb00-b9db-40cd-ad26-14e1ea9155ca
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines > Phenylpyrrolidines
• IUPAC Name: (5S,8R,9R)-9-(2,4-dibromo-5-methoxyphenyl)-8-hydroxy-7-methyl-1,7-diazaspiro[4.4]nonane-2,6-dione
• SMILES (Canonical): CN1C(C(C2(C1=O)CCC(=O)N2)C3=CC(=C(C=C3Br)Br)OC)O
• SMILES (Isomeric): CN1[C@@H]([C@@H]([C@]2(C1=O)CCC(=O)N2)C3=CC(=C(C=C3Br)Br)OC)O
• InChI: InChI=1S/C15H16Br2N2O4/c1-19-13(21)12(15(14(19)22)4-3-11(20)18-15)7-5-10(23-2)9(17)6-8(7)16/h5-6,12-13,21H,3-4H2,1-2H3,(H,18,20)/t12-,13+,15-/m0/s1
• InChI Key: MSSHNEUEONPAKC-GUTXKFCHSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆Br₂N₂O₄
• Molecular Weight: 448.11 g/mol
• Exact Mass: 447.94563 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.74
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9056	90.56%
Caco-2	+	0.5746	57.46%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6349	63.49%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.9255	92.55%
OATP1B3 inhibitior	+	0.9312	93.12%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8452	84.52%
BSEP inhibitior	-	0.6001	60.01%
P-glycoprotein inhibitior	-	0.9122	91.22%
P-glycoprotein substrate	-	0.6470	64.70%
CYP3A4 substrate	+	0.6336	63.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7801	78.01%
CYP3A4 inhibition	-	0.9014	90.14%
CYP2C9 inhibition	-	0.7455	74.55%
CYP2C19 inhibition	-	0.6859	68.59%
CYP2D6 inhibition	-	0.8547	85.47%
CYP1A2 inhibition	-	0.7584	75.84%
CYP2C8 inhibition	-	0.8192	81.92%
CYP inhibitory promiscuity	-	0.7555	75.55%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7222	72.22%
Carcinogenicity (trinary)	Non-required	0.5750	57.50%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9885	98.85%
Skin irritation	-	0.7927	79.27%
Skin corrosion	-	0.9228	92.28%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.5926	59.26%
skin sensitisation	-	0.8669	86.69%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8748	87.48%
Acute Oral Toxicity (c)	III	0.6110	61.10%
Estrogen receptor binding	+	0.5712	57.12%
Androgen receptor binding	+	0.6028	60.28%
Thyroid receptor binding	+	0.5831	58.31%
Glucocorticoid receptor binding	+	0.7705	77.05%
Aromatase binding	-	0.5711	57.11%
PPAR gamma	+	0.5906	59.06%
Honey bee toxicity	-	0.7928	79.28%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	-	0.4165	41.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.03%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	98.48%	93.99%
CHEMBL2581	P07339	Cathepsin D	98.35%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.19%	85.14%
CHEMBL1937	Q92769	Histone deacetylase 2	94.90%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.64%	95.56%
CHEMBL4208	P20618	Proteasome component C5	91.59%	90.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.47%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.01%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.78%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.03%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.11%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.74%	89.62%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	85.95%	90.24%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.85%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.63%	95.89%
CHEMBL2535	P11166	Glucose transporter	84.16%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.00%	89.00%
CHEMBL325	Q13547	Histone deacetylase 1	83.62%	95.92%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	83.48%	85.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.37%	86.33%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	81.71%	94.78%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.53%	95.53%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.51%	89.44%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.65%	91.07%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10527436
• LOTUS: LTS0226382
• wikiData: Q105171363