SID507515

ID: ALA1977154

Cas Number: 36422-59-0

PubChem CID: 376363

Max Phase: Preclinical

Molecular Formula: C20H25NO4

Molecular Weight: 343.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1ccc(C)cc1

Standard InChI:  InChI=1S/C20H25NO4/c1-6-24-19(22)16-13(4)21-14(5)17(20(23)25-7-2)18(16)15-10-8-12(3)9-11-15/h8-11,18,21H,6-7H2,1-5H3

Standard InChI Key:  YSDNGJONQCXVPU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -2.3273   -4.9665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852   -2.4915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7562   -4.9665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4707   -1.2540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3273   -2.4915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7562   -3.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417   -3.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7562   -2.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4707   -3.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3273   -3.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417   -2.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417   -4.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4707   -2.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4707   -4.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852   -3.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6128   -3.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417   -1.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852   -4.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8996   -3.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8996   -4.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3273   -5.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8996   -2.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6141   -4.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6128   -6.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8996   -1.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0
  1 21  1  0
  2 13  1  0
  2 22  1  0
  3 12  2  0
  4 13  2  0
  5 10  1  0
  5 11  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  7 10  2  0
  7 12  1  0
  8 11  2  0
  8 13  1  0
  9 14  2  0
  9 15  1  0
 10 16  1  0
 11 17  1  0
 14 18  1  0
 15 19  2  0
 18 20  2  0
 19 20  1  0
 20 23  1  0
 21 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1977154

   2,6-Dimethyl-4-p-tolyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 343.42

Molecular Weight (Monoisotopic): 343.1784

AlogP: 3.36

#Rotatable Bonds: 5

Polar Surface Area: 64.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.10

CX LogD: 3.10

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.56

References

1. PubChem BioAssay data set, 

2. Visentin S, Ermondi G, Medana C, Pedemonte N, Galietta L, Caron G..  (2012)  Ligand-based design, in silico ADME-Tox filtering, synthesis and biological evaluation to discover new soluble 1,4-DHP-based CFTR activators.,  55  [PMID:22889557] [10.1016/j.ejmech.2012.07.017]

3. Amgoth SN, Porika M, Abbagani S, Garlapati A, Vanga MR.  (2013)  Synthesis, anticancer and MRP1 inhibitory activities of 4-alkyl/aryl-3,5-bis(carboethoxy/carbomethoxy)-1,4-dihydro-2,6-dimethylpyridines,  22  (1): [10.1007/s00044-012-9994-0]

4. Niaz H, Kashtoh H, Khan JA, Khan A, Wahab AT, Alam MT, Khan KM, Perveen S, Choudhary MI..  (2015)  Synthesis of diethyl 4-substituted-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates as a new series of inhibitors against yeast α-glucosidase.,  95  [PMID:25817770] [10.1016/j.ejmech.2015.03.018]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays