(S)-3-{2-[3-((2S,3S)-2-Acetylamino-3-methyl-pentanoylamino)-2-oxo-2H-pyridin-1-yl]-acetylamino}-4-oxo-butyric acid

ID: ALA69482

PubChem CID: 44309888

Max Phase: Preclinical

Molecular Formula: C19H26N4O7

Molecular Weight: 422.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(C)=O)C(=O)Nc1cccn(CC(=O)N[C@H](C=O)CC(=O)O)c1=O

Standard InChI:  InChI=1S/C19H26N4O7/c1-4-11(2)17(20-12(3)25)18(29)22-14-6-5-7-23(19(14)30)9-15(26)21-13(10-24)8-16(27)28/h5-7,10-11,13,17H,4,8-9H2,1-3H3,(H,20,25)(H,21,26)(H,22,29)(H,27,28)/t11-,13-,17-/m0/s1

Standard InChI Key:  RDCICWNDKXBQAM-BNLOLNQZSA-N

Molfile:  

     RDKit          2D

 30 30  0  0  1  0  0  0  0  0999 V2000
    4.7625   -6.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375   -6.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875   -6.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -6.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -6.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625   -5.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3875   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250   -6.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -6.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -7.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -5.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -5.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625   -6.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9125   -5.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -7.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9125   -6.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -7.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792   -6.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3917   -4.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750   -6.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -7.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -7.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -8.3542    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  4  1  0
  7  9  1  0
  6  8  1  6
  9  1  1  0
 20 10  1  1
 11 10  1  0
 12  1  1  0
 13  8  1  0
 14 16  1  0
 15  7  1  0
 16 12  2  0
 17  2  2  0
 18  4  2  0
 19  7  2  0
 20 15  1  0
 21 11  2  0
 22 13  2  0
 23 25  2  0
 24  6  1  0
 25 20  1  0
 26 11  1  0
 27 13  1  0
 28 24  1  0
 24 29  1  1
 30 28  1  0
 14  3  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA69482

   (S)-3-{2-[3-((2S,3S)-2-Acetylamino-3-methyl-pentanoylamino)-2-oxo-2H-pyridin-1-yl]-acetylamino}-4-oxo-butyric acid

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: 422.44

Molecular Weight (Monoisotopic): 422.1801

AlogP: -0.50

#Rotatable Bonds: 11

Polar Surface Area: 163.67

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.90

CX Basic pKa: ┄

CX LogP: -1.89

CX LogD: -5.10

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.35

Np Likeness Score: -0.57

References

1. Willoughby CA, Bull HG, Garcia-Calvo M, Jiang J, Chapman KT, Thornberry NA..  (2002)  Discovery of potent, selective human granzyme B inhibitors that inhibit CTL mediated apoptosis.,  12  (16): [PMID:12127536] [10.1016/s0960-894x(02)00363-3]

Source

Source(1):

• Scientific Literature