(S)-3-tert-Butoxy-2-{2-[(2-pyridin-4-yl-thiazole-4-carbonyl)-amino]-acryloylamino}-propionic acid methyl ester

ID: ALA366175

PubChem CID: 44400652

Max Phase: Preclinical

Molecular Formula: C20H24N4O5S

Molecular Weight: 432.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(NC(=O)c1csc(-c2ccncc2)n1)C(=O)N[C@@H](COC(C)(C)C)C(=O)OC

Standard InChI:  InChI=1S/C20H24N4O5S/c1-12(16(25)23-14(19(27)28-5)10-29-20(2,3)4)22-17(26)15-11-30-18(24-15)13-6-8-21-9-7-13/h6-9,11,14H,1,10H2,2-5H3,(H,22,26)(H,23,25)/t14-/m0/s1

Standard InChI Key:  FCTXYJBDLIAVKP-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  1  0  0  0  0  0999 V2000
    2.9792    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    0.9083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667    0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000    0.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -0.4292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375    0.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5750    0.9833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167    0.5708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042    0.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000    1.8083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917    1.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000    0.5458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375    1.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -0.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7167    0.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3625   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    1.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7167   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5917   -0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4292    0.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  7  1  0
  6 11  1  0
  7 10  1  0
  8  9  1  0
  9  5  1  0
 10  4  1  0
 11  1  2  0
 12  8  1  0
 13  4  2  0
 14  3  1  0
  8 15  1  6
 16  5  2  0
 17 12  2  0
 18 24  2  0
 19  7  2  0
 20 15  1  0
 21 20  1  0
 22 12  1  0
 23 25  2  0
 24 26  1  0
 25 14  1  0
 26 14  2  0
 27 21  1  0
 28 21  1  0
 29 21  1  0
 30 22  1  0
  6  3  1  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA366175

   methyl (2S)-3-[(2-methylpropan-2-yl)oxy]-2-[2-[(2-pyridin-4-yl-1,3-thiazole-4-carbonyl)amino]prop-2-enoylamino]propanoate

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: 432.50

Molecular Weight (Monoisotopic): 432.1467

AlogP: 1.92

#Rotatable Bonds: 8

Polar Surface Area: 119.51

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.60

CX Basic pKa: 3.36

CX LogP: 1.16

CX LogD: 1.16

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.48

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