3-[((S)-{1-[(S)-2-((3S,4S)-2-Acetylamino-3-methyl-pentanoylamino)-acetyl]-pyrrolidin-2-yl}-oxo-methyl)-amino]-4-oxo-butyric acid

ID: ALA69424

PubChem CID: 44309881

Max Phase: Preclinical

Molecular Formula: C19H30N4O7

Molecular Weight: 426.47

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(C)=O)C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@H](C=O)CC(=O)O

Standard InChI:  InChI=1S/C19H30N4O7/c1-4-11(2)17(21-12(3)25)19(30)20-9-15(26)23-7-5-6-14(23)18(29)22-13(10-24)8-16(27)28/h10-11,13-14,17H,4-9H2,1-3H3,(H,20,30)(H,21,25)(H,22,29)(H,27,28)/t11-,13-,14-,17-/m0/s1

Standard InChI Key:  LTPPJOOHOLYSEP-MJFSBKNWSA-N

Molfile:  

     RDKit          2D

 30 30  0  0  1  0  0  0  0  0999 V2000
    6.1000   -2.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8125   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8125   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -4.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -2.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -2.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9542   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -4.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -3.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0500   -1.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6667   -2.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -4.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6667   -3.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9500   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9542   -1.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5250   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5292   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1
  3  1  1  0
  4  1  1  0
  5  9  1  0
  6  5  1  0
  7  2  1  0
  6  8  1  6
  9 13  1  0
 15 10  1  1
 11 10  1  0
 12  8  1  0
 13  4  1  0
 14  2  2  0
 15  7  1  0
 16  4  2  0
 17  5  2  0
 18 11  2  0
 19 12  2  0
 20 22  2  0
 21  6  1  0
 22 15  1  0
 23  1  1  0
 24 11  1  0
 25  3  1  0
 26 23  1  0
 27 12  1  0
 28 21  1  0
 21 29  1  1
 30 28  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA69424

   3-[((S)-{1-[(S)-2-((3S,4S)-2-Acetylamino-3-methyl-pentanoylamino)-acetyl]-pyrrolidin-2-yl}-oxo-methyl)-amino]-4-oxo-butyric acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 426.47

Molecular Weight (Monoisotopic): 426.2114

AlogP: -1.20

#Rotatable Bonds: 11

Polar Surface Area: 161.98

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.05

CX Basic pKa: ┄

CX LogP: -2.13

CX LogD: -5.27

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.30

Np Likeness Score: -0.24

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