(S)-3-tert-Butoxy-2-{2-[(pyrazine-2-carbonyl)-amino]-acryloylamino}-propionic acid methyl ester

ID: ALA194763

PubChem CID: 44400798

Max Phase: Preclinical

Molecular Formula: C16H22N4O5

Molecular Weight: 350.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(NC(=O)c1cnccn1)C(=O)N[C@@H](COC(C)(C)C)C(=O)OC

Standard InChI:  InChI=1S/C16H22N4O5/c1-10(19-14(22)11-8-17-6-7-18-11)13(21)20-12(15(23)24-5)9-25-16(2,3)4/h6-8,12H,1,9H2,2-5H3,(H,19,22)(H,20,21)/t12-/m0/s1

Standard InChI Key:  FXMPZIRZCNVUNQ-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  1  0  0  0  0  0999 V2000
    2.7042    2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500    2.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875    2.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417    2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250    2.7083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667    2.2875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708    2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542    2.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708    1.4708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500    3.5333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042    1.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417    1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417    3.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083    2.2958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875    3.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542    1.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833    2.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667    2.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833    1.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792    2.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  1  1  0
  4  5  1  0
  5  1  1  0
  6  3  1  0
  7  2  1  0
  8  4  1  0
  9  7  1  0
 10  2  2  0
 11  1  2  0
  4 12  1  6
 13  8  2  0
 14 18  1  0
 15  3  2  0
 16 12  1  0
 17 16  1  0
 18  7  2  0
 19  8  1  0
 20  9  2  0
 21 14  2  0
 22 17  1  0
 23 17  1  0
 24 17  1  0
 25 19  1  0
 21 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA194763

   pyrazinoyl-Dha-Ser(tBu)-OMe

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: 350.38

Molecular Weight (Monoisotopic): 350.1590

AlogP: 0.19

#Rotatable Bonds: 7

Polar Surface Area: 119.51

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.88

CX Basic pKa: ┄

CX LogP: -0.74

CX LogD: -0.74

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: -0.69

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