(S)-4-((3S,4S)-2-Acetylamino-3-methyl-pentanoylamino)-5-[2-((S)-(S)-2-carboxy-1-formyl-ethylcarbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic acid

ID: ALA70602

PubChem CID: 44310132

Max Phase: Preclinical

Molecular Formula: C22H34N4O9

Molecular Weight: 498.53

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H34N4O9/c1-4-12(2)19(23-13(3)28)21(34)25-15(7-8-17(29)30)22(35)26-9-5-6-16(26)20(33)24-14(11-27)10-18(31)32/h11-12,14-16,19H,4-10H2,1-3H3,(H,23,28)(H,24,33)(H,25,34)(H,29,30)(H,31,32)/t12-,14-,15-,16-,19-/m0/s1

Standard InChI Key:  JFFGRTYAQZRQMF-RWBKLUSOSA-N

Molfile:  

     RDKit          2D

 35 35  0  0  1  0  0  0  0  0999 V2000
    3.4792   -0.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -0.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9042   -1.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -0.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3375   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458   -1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -1.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292    0.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6167   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -0.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833   -1.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    2.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -1.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1500   -1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3375    0.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292    2.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9000   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  5  4  1  1
  5  1  1  0
  6  7  1  0
  7  2  1  0
  8  3  1  0
  9  4  1  0
  8 10  1  6
 18 11  1  1
 12 11  1  0
 13 10  1  0
 14 25  1  0
 15  2  2  0
 16  3  2  0
 17  4  2  0
 18  9  1  0
  7 19  1  1
 20 12  2  0
 21 13  2  0
 22 14  2  0
 23 27  2  0
 24  1  1  0
 25 19  1  0
 26  8  1  0
 27 18  1  0
 28 12  1  0
 29 14  1  0
 30  5  1  0
 31 24  1  0
 32 13  1  0
 33 26  1  0
 26 34  1  1
 35 33  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA70602

   (S)-4-((3S,4S)-2-Acetylamino-3-methyl-pentanoylamino)-5-[2-((S)-(S)-2-carboxy-1-formyl-ethylcarbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic 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: 498.53

Molecular Weight (Monoisotopic): 498.2326

AlogP: -0.96

#Rotatable Bonds: 14

Polar Surface Area: 199.28

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.71

CX Basic pKa: ┄

CX LogP: -1.92

CX LogD: -8.21

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.19

Np Likeness Score: 0.27

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