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

ID: ALA370425

PubChem CID: 44400791

Max Phase: Preclinical

Molecular Formula: C14H16N4O4

Molecular Weight: 304.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(NC(=O)c1cnccn1)C(=O)N1CCC[C@H]1C(=O)OC

Standard InChI:  InChI=1S/C14H16N4O4/c1-9(17-12(19)10-8-15-5-6-16-10)13(20)18-7-3-4-11(18)14(21)22-2/h5-6,8,11H,1,3-4,7H2,2H3,(H,17,19)/t11-/m0/s1

Standard InChI Key:  WHNVPWJRWVFJLA-NSHDSACASA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
   17.9250    1.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2042    1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4875    1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0500    1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7667    1.2250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5917    2.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3375    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3792    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3417    0.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2042    0.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0500    2.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4875    2.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0000    2.4208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9042    1.2333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2625    2.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6167    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5292    1.0583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3500    2.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5167    2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6292   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9042    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3042    0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  3  1  0
  6  1  1  0
  7  4  1  0
  6  8  1  1
  9  7  1  0
 10  2  2  0
 11  4  2  0
 12  3  2  0
 13  8  2  0
 14 16  1  0
 15  1  1  0
 16  7  2  0
 17  8  1  0
 18  6  1  0
 19 15  1  0
 20  9  2  0
 21 14  2  0
 22 17  1  0
 19 18  1  0
 21 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA370425

   methyl (2S)-1-[2-(pyrazine-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: 304.31

Molecular Weight (Monoisotopic): 304.1172

AlogP: -0.12

#Rotatable Bonds: 4

Polar Surface Area: 101.49

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.95

CX Basic pKa: ┄

CX LogP: -1.12

CX LogD: -1.12

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.61

Np Likeness Score: -1.02

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