(2R,3S)-3-hydroxy-3-methyl-2-[(E,4S)-4-methylhex-2-en-2-yl]-1-(2-methylpropyl)-5-propanoyl-2H-pyridin-4-one

Details

• Internal ID: d374f273-6810-4829-b4dd-51f0b8f314d4
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Hydropyridines > Tetrahydropyridines
• IUPAC Name: (2R,3S)-3-hydroxy-3-methyl-2-[(E,4S)-4-methylhex-2-en-2-yl]-1-(2-methylpropyl)-5-propanoyl-2H-pyridin-4-one
• SMILES (Canonical): CCC(C)C=C(C)C1C(C(=O)C(=CN1CC(C)C)C(=O)CC)(C)O
• SMILES (Isomeric): CC[C@H](C)/C=C(\C)/[C@@H]1[C@](C(=O)C(=CN1CC(C)C)C(=O)CC)(C)O
• InChI: InChI=1S/C20H33NO3/c1-8-14(5)10-15(6)18-20(7,24)19(23)16(17(22)9-2)12-21(18)11-13(3)4/h10,12-14,18,24H,8-9,11H2,1-7H3/b15-10+/t14-,18+,20-/m0/s1
• InChI Key: VNQQKAYJATZEJP-VLHFZGABSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₃NO₃
• Molecular Weight: 335.50 g/mol
• Exact Mass: 335.24604391 g/mol
• Topological Polar Surface Area (TPSA): 57.60 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7595	75.95%
Caco-2	+	0.7678	76.78%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7776	77.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8559	85.59%
OATP1B3 inhibitior	+	0.9452	94.52%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7372	73.72%
P-glycoprotein inhibitior	-	0.6571	65.71%
P-glycoprotein substrate	-	0.7080	70.80%
CYP3A4 substrate	+	0.5495	54.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7585	75.85%
CYP3A4 inhibition	-	0.8826	88.26%
CYP2C9 inhibition	-	0.8010	80.10%
CYP2C19 inhibition	-	0.7405	74.05%
CYP2D6 inhibition	-	0.8559	85.59%
CYP1A2 inhibition	-	0.7781	77.81%
CYP2C8 inhibition	-	0.8135	81.35%
CYP inhibitory promiscuity	-	0.7534	75.34%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4750	47.50%
Eye corrosion	-	0.9806	98.06%
Eye irritation	-	0.9779	97.79%
Skin irritation	-	0.7353	73.53%
Skin corrosion	-	0.8672	86.72%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7217	72.17%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7767	77.67%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.4928	49.28%
Acute Oral Toxicity (c)	III	0.7014	70.14%
Estrogen receptor binding	-	0.5835	58.35%
Androgen receptor binding	-	0.5059	50.59%
Thyroid receptor binding	+	0.6173	61.73%
Glucocorticoid receptor binding	-	0.6720	67.20%
Aromatase binding	-	0.5759	57.59%
PPAR gamma	+	0.6885	68.85%
Honey bee toxicity	-	0.8460	84.60%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	-	0.5433	54.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.30%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.69%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.77%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.79%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.72%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.99%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.96%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.84%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	83.70%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.51%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	81.18%	94.75%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.03%	93.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10759258
• LOTUS: LTS0238368
• wikiData: Q105289861