(2S)-N-((1S)-2-((2S)-2-(5-cyano-4-(naphthalen-1-yl)thiazol-2-yl)pyrrolidin-1-yl)-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethyl)-2-(methylamino)propanamide

ID: ALA1091216

PubChem CID: 46884523

Max Phase: Preclinical

Molecular Formula: C29H33N5O3S

Molecular Weight: 531.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@@H](C)C(=O)N[C@H](C(=O)N1CCC[C@H]1c1nc(-c2cccc3ccccc23)c(C#N)s1)C1CCOCC1

Standard InChI:  InChI=1S/C29H33N5O3S/c1-18(31-2)27(35)32-25(20-12-15-37-16-13-20)29(36)34-14-6-11-23(34)28-33-26(24(17-30)38-28)22-10-5-8-19-7-3-4-9-21(19)22/h3-5,7-10,18,20,23,25,31H,6,11-16H2,1-2H3,(H,32,35)/t18-,23-,25-/m0/s1

Standard InChI Key:  AHPDFXKGRWZGMR-WYRQLCSISA-N

Molfile:  

     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
   17.9881  -12.2576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7036  -12.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9881  -11.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4190  -12.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7036  -13.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1345  -12.6683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4190  -11.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8499  -12.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5653  -12.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8499  -11.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5653  -13.4938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2766  -12.2576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0297  -12.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5835  -11.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1728  -11.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3653  -11.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2046  -13.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6512  -14.0132    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.0619  -14.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8695  -14.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9552  -13.7369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5796  -14.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2936  -14.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0073  -14.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0052  -15.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2877  -16.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5768  -15.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8595  -16.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8521  -17.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5678  -17.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2822  -17.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5635  -11.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5654  -10.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8524   -9.7859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1357  -10.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1320  -11.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7265  -15.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3944  -16.2256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  8 10  1  1
  1  3  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  2  0
  9 11  2  0
 22 27  2  0
 26 25  2  0
  4  6  1  0
 24 23  2  0
 23 22  1  0
 20 22  1  0
  9 12  1  0
 12 13  1  0
 24 25  1  0
  1  2  1  0
  4  7  2  0
 26 27  1  0
  2  4  1  0
 27 28  1  0
  6  8  1  0
 28 29  2  0
 13 14  1  0
 29 30  1  0
 14 15  1  0
 30 31  2  0
 31 26  1  0
 10 32  1  0
 15 16  1  0
 16 12  1  0
 13 17  1  1
 17 18  1  0
 10 36  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
  8  9  1  0
 19 37  1  0
  2  5  1  6
 37 38  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091216

   (2S)-N-((1S)-2-((2S)-2-(5-cyano-4-(naphthalen-1-yl)thiazol-2-yl)pyrrolidin-1-yl)-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethyl)-2-(methylamino)propanamide

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: 531.68

Molecular Weight (Monoisotopic): 531.2304

AlogP: 4.02

#Rotatable Bonds: 7

Polar Surface Area: 107.35

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.03

CX Basic pKa: 8.60

CX LogP: 3.11

CX LogD: 1.88

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.48

Np Likeness Score: -0.62

References

1. Cohen F, Koehler MF, Bergeron P, Elliott LO, Flygare JA, Franklin MC, Gazzard L, Keteltas SF, Lau K, Ly CQ, Tsui V, Fairbrother WJ..  (2010)  Antagonists of inhibitor of apoptosis proteins based on thiazole amide isosteres.,  20  (7): [PMID:20189383] [10.1016/j.bmcl.2010.02.021]

Source

Source(1):

• Scientific Literature