(S)-1-{2-[(Pyridine-2-carbonyl)-amino]-acryloyl}-pyrrolidine-2-carboxylic acid methyl ester

ID: ALA195116

PubChem CID: 44400797

Max Phase: Preclinical

Molecular Formula: C15H17N3O4

Molecular Weight: 303.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(NC(=O)c1ccccn1)C(=O)N1CCC[C@H]1C(=O)OC

Standard InChI:  InChI=1S/C15H17N3O4/c1-10(17-13(19)11-6-3-4-8-16-11)14(20)18-9-5-7-12(18)15(21)22-2/h3-4,6,8,12H,1,5,7,9H2,2H3,(H,17,19)/t12-/m0/s1

Standard InChI Key:  MBHZEWZWZLTCNR-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
   14.6125    1.2333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8917    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1750    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4542    0.8208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7375    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2792    1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0667    1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0167    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8917   -0.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0292    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7375    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1750    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6875    2.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9500    1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2167    0.6583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0375    2.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2042    2.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3167   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3042    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9917    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5917    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5917    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  1  1  0
  6  7  1  1
  8  5  1  0
  9  2  2  0
 10  8  1  0
 11  5  2  0
 12  3  2  0
 13  7  2  0
 14  1  1  0
 15  7  1  0
 16  6  1  0
 17 14  1  0
 18 10  2  0
 19  8  2  0
 20 15  1  0
 21 22  2  0
 22 19  1  0
 17 16  1  0
 21 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA195116

   methyl (2S)-1-[2-(pyridine-2-carbonylamino)prop-2-enoyl]pyrrolidine-2-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: 303.32

Molecular Weight (Monoisotopic): 303.1219

AlogP: 0.49

#Rotatable Bonds: 4

Polar Surface Area: 88.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.66

CX Basic pKa: 1.97

CX LogP: 0.10

CX LogD: 0.10

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.65

Np Likeness Score: -0.95

References

1. Ayida BK, Simonsen KB, Vourloumis D, Hermann T..  (2005)  Synthesis of dehydroalanine fragments as thiostrepton side chain mimetics.,  15  (10): [PMID:15863296] [10.1016/j.bmcl.2005.03.084]

Source

Source(1):

• Scientific Literature