Diethyl 2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate

Details

• Internal ID: 0870ab76-94be-4d6d-a585-8c2c5cfcaf92
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Phenylpyridines
• IUPAC Name: diethyl 2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate
• SMILES (Canonical): CCOC(=O)C1=C(N=C(C(=C1C2=CC=CC=C2)C(=O)OCC)C)C
• SMILES (Isomeric): CCOC(=O)C1=C(N=C(C(=C1C2=CC=CC=C2)C(=O)OCC)C)C
• InChI: InChI=1S/C19H21NO4/c1-5-23-18(21)15-12(3)20-13(4)16(19(22)24-6-2)17(15)14-10-8-7-9-11-14/h7-11H,5-6H2,1-4H3
• InChI Key: VQDKSJMDSZZJER-UHFFFAOYSA-N
• Popularity: 33 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.40 g/mol
• Exact Mass: 327.14705815 g/mol
• Topological Polar Surface Area (TPSA): 65.50 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.72
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• diethyl 2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate
• Diethyl 2,6-dimethyl-4-phenyl-3,5-pyridinedicarboxylate
• 3,5-Pyridinedicarboxylicacid, 2,6-dimethyl-4-phenyl-, 3,5-diethyl ester
• 3,5-diethyl 2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate
• SMR000185942
• CBMicro_021036
• Oprea1_647604
• MLS000576557
• CHEMBL1583690
• diethyl 4-phenyl-2,6-dimethyl-3,5-pyridinedicarboxylate
• SCHEMBL15976546
• DTXSID60348071
• HMS2459P20
• CCG-8762
• MFCD00980182
• STK791068
• AKOS001016678
• NS-00072
• BIM-0021095.P001
• EU-0084963
• AB00086266-01
• SR-01000518835
• SR-01000518835-1
• Z56791253
• 3,5-diethyl2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate
• 2,6-dimethyl-4-phenyl-pyridine-3,5-dicarboxylic acid diethyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9858	98.58%
Caco-2	+	0.8326	83.26%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.9414	94.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9496	94.96%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8530	85.30%
P-glycoprotein inhibitior	+	0.7345	73.45%
P-glycoprotein substrate	-	0.9831	98.31%
CYP3A4 substrate	-	0.5734	57.34%
CYP2C9 substrate	-	0.8338	83.38%
CYP2D6 substrate	-	0.9099	90.99%
CYP3A4 inhibition	-	0.5437	54.37%
CYP2C9 inhibition	+	0.7496	74.96%
CYP2C19 inhibition	+	0.6405	64.05%
CYP2D6 inhibition	-	0.9154	91.54%
CYP1A2 inhibition	+	0.7901	79.01%
CYP2C8 inhibition	+	0.7079	70.79%
CYP inhibitory promiscuity	+	0.8857	88.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6307	63.07%
Carcinogenicity (trinary)	Non-required	0.6215	62.15%
Eye corrosion	-	0.9901	99.01%
Eye irritation	+	0.5496	54.96%
Skin irritation	-	0.8166	81.66%
Skin corrosion	-	0.9758	97.58%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4661	46.61%
Micronuclear	+	0.5074	50.74%
Hepatotoxicity	+	0.6927	69.27%
skin sensitisation	-	0.9214	92.14%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6891	68.91%
Estrogen receptor binding	+	0.7082	70.82%
Androgen receptor binding	+	0.7840	78.40%
Thyroid receptor binding	+	0.5607	56.07%
Glucocorticoid receptor binding	+	0.7876	78.76%
Aromatase binding	+	0.7531	75.31%
PPAR gamma	+	0.5528	55.28%
Honey bee toxicity	-	0.9788	97.88%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6355	63.55%
Fish aquatic toxicity	+	0.9429	94.29%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	31622.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	19952.6 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	5623.4 nM	Potency	via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	25118.9 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	3981.1 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	6309.6 nM	Potency	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	2238.7 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	94.04%	90.17%
CHEMBL2581	P07339	Cathepsin D	93.28%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.15%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.63%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.98%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	88.10%	94.73%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	85.91%	93.65%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.81%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.55%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.07%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.25%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.92%	94.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.62%	96.67%
CHEMBL5028	O14672	ADAM10	80.60%	97.50%

Plants that contains it

• Jatropha elliptica
• Kadsura coccinea

Cross-Links

• PubChem: 629929
• NPASS: NPC191310
• ChEMBL: CHEMBL1583690
• LOTUS: LTS0031607
• wikiData: Q82122591