4-[(2S)-2-[(1R,3R,5R)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione

Details

• Internal ID: 17777dcf-080f-4ed5-bc3a-e7b37ffe7b3a
• Taxonomy: Organoheterocyclic compounds > Piperidines > Piperidinones > Piperidinediones
• IUPAC Name: 4-[(2S)-2-[(1R,3R,5R)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
• SMILES (Canonical): CC1CC(C(=O)C(C1)C(CC2CC(=O)NC(=O)C2)O)C
• SMILES (Isomeric): C[C@@H]1C[C@H](C(=O)[C@H](C1)[C@H](CC2CC(=O)NC(=O)C2)O)C
• InChI: InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m1/s1
• InChI Key: YPHMISFOHDHNIV-IQIPOGNMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₃NO₄
• Molecular Weight: 281.35 g/mol
• Exact Mass: 281.16270821 g/mol
• Topological Polar Surface Area (TPSA): 83.50 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.04
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9371	93.71%
Caco-2	-	0.5983	59.83%
Blood Brain Barrier	+	0.5080	50.80%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7938	79.38%
OATP2B1 inhibitior	-	0.8485	84.85%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9604	96.04%
P-glycoprotein inhibitior	-	0.8887	88.87%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	-	0.5079	50.79%
CYP2C9 substrate	-	0.5969	59.69%
CYP2D6 substrate	-	0.8308	83.08%
CYP3A4 inhibition	-	0.9133	91.33%
CYP2C9 inhibition	-	0.9098	90.98%
CYP2C19 inhibition	-	0.9382	93.82%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9529	95.29%
CYP2C8 inhibition	-	0.9353	93.53%
CYP inhibitory promiscuity	-	0.9635	96.35%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8313	83.13%
Carcinogenicity (trinary)	Non-required	0.6136	61.36%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9294	92.94%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5383	53.83%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.5927	59.27%
skin sensitisation	-	0.9370	93.70%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.4619	46.19%
Acute Oral Toxicity (c)	I	0.8338	83.38%
Estrogen receptor binding	+	0.8905	89.05%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	-	0.4932	49.32%
Aromatase binding	-	0.7712	77.12%
PPAR gamma	+	0.8611	86.11%
Honey bee toxicity	-	0.7492	74.92%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.5122	51.22%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	251.2 nM	Potency	via Super-PRED
CHEMBL2052028	P60842	Eukaryotic initiation factor 4A-I	87 nM	IC50	via Super-PRED
CHEMBL5514	P42858	Huntingtin	354.8 nM	Potency	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	63.1 nM	Potency	via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	39.8 nM	Potency	via Super-PRED
CHEMBL1293277	O15118	Niemann-Pick C1 protein	446.7 nM; 316.2 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	316.2 nM; 316.2 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	446.7 nM; 891.3 nM	Potency; Potency	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.34%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.78%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.52%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	86.65%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.32%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.11%	96.61%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.30%	89.34%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.53%	90.08%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.37%	100.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.47%	95.56%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.12%	85.11%
CHEMBL3045	P05771	Protein kinase C beta	80.99%	97.63%
CHEMBL255	P29275	Adenosine A2b receptor	80.32%	98.59%

Plants that contains it

• Aglaia spectabilis
• Clibadium pentaneuron
• Coespeletia thyrsiformis f. marcanoi
• Croton bonplandianus
• Croton californicus
• Culcitium canescens
• Cymbopogon nardus
• Dendrobium rotundatum
• Malva verticillata
• Nolina erumpens
• Petasites paradoxus
• Philotheca fitzgeraldii
• Piptolepis leptospermoides
• Ratibida latipalearis
• Toxicodendron succedaneum
• Weddellina squamulosa

Cross-Links

• PubChem: 16757558
• NPASS: NPC311540