Ethyl 5-Cyano-2-methyl-6-(3-{[(phenylsulfonyl)amino]-carbonyl}azetidin-1-yl)nicotinate

ID: ALA2419500

PubChem CID: 11697626

Max Phase: Preclinical

Molecular Formula: C20H20N4O5S

Molecular Weight: 428.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc(C#N)c(N2CC(C(=O)NS(=O)(=O)c3ccccc3)C2)nc1C

Standard InChI:  InChI=1S/C20H20N4O5S/c1-3-29-20(26)17-9-14(10-21)18(22-13(17)2)24-11-15(12-24)19(25)23-30(27,28)16-7-5-4-6-8-16/h4-9,15H,3,11-12H2,1-2H3,(H,23,25)

Standard InChI Key:  ZOTDNPNVLACERX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.5776   -8.5269    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1686   -9.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263   -6.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3252   -7.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0332   -7.5473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7429   -7.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7401   -6.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0315   -5.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6185   -5.9103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4543   -7.5483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6671   -8.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8715   -8.1224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2869   -8.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6172   -7.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463   -5.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1525   -5.4954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9920   -8.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7009   -8.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7037   -7.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9919   -6.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2859   -7.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  7 15  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
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  2 22  1  0
  5 23  1  0
 24 25  3  0
  8 24  1  0
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 27 28  2  0
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 29 30  2  0
 30 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2419500

   Ethyl 6-[3-(benzenesulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate

Molecule Features

Natural Product: No

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: 428.47

Molecular Weight (Monoisotopic): 428.1154

AlogP: 1.38

#Rotatable Bonds: 6

Polar Surface Area: 129.46

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.18

CX Basic pKa: 1.90

CX LogP: 2.09

CX LogD: 1.15

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.68

Np Likeness Score: -1.51

References

1. Bach P, Antonsson T, Bylund R, Björkman JA, Österlund K, Giordanetto F, van Giezen JJ, Andersen SM, Zachrisson H, Zetterberg F..  (2013)  Lead optimization of ethyl 6-aminonicotinate acyl sulfonamides as antagonists of the P2Y12 receptor. separation of the antithrombotic effect and bleeding for candidate drug AZD1283.,  56  (17): [PMID:23899349] [10.1021/jm400820m]

Source

Source(1):

• Scientific Literature