1-(2-((Allyloxy)amino)-2-oxoethyl)-1H-pyrrole-3-carbonyl)-L-alanyl-L-leucine

ID: ALA5289757

Max Phase: Preclinical

Molecular Formula: C19H28N4O6

Molecular Weight: 408.46

Names and Identifiers

Canonical SMILES:  C=CCONC(=O)Cn1ccc(C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)O)c1

Standard InChI:  InChI=1S/C19H28N4O6/c1-5-8-29-22-16(24)11-23-7-6-14(10-23)18(26)20-13(4)17(25)21-15(19(27)28)9-12(2)3/h5-7,10,12-13,15H,1,8-9,11H2,2-4H3,(H,20,26)(H,21,25)(H,22,24)(H,27,28)/t13-,15-/m0/s1

Standard InChI Key:  BZIPDSRASNZMHR-ZFWWWQNUSA-N

Molfile:  

 
     RDKit          2D

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   -2.9223   -0.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9223    0.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2075   -0.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4928   -0.0982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7782   -0.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0635   -0.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7782   -1.3361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0225    0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295    0.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    0.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6899   -0.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0672    0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4799   -0.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050   -0.5354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0672   -1.2501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7177   -1.2501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430   -1.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9555   -1.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3515   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0662   -0.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7809   -0.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0662   -1.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3515    0.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0662    1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7809   -1.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2075   -1.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7809    0.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0662    1.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  9  7  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  7  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  1  6
 24 25  1  0
 26 19  2  0
  4 27  1  1
 25 28  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5289757

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 408.46

Molecular Weight (Monoisotopic): 408.2009

AlogP: 0.46

#Rotatable Bonds: 12

Polar Surface Area: 138.76

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.79

CX Basic pKa: ┄

CX LogP: 0.89

CX LogD: -3.27

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.23

Np Likeness Score: -0.65

References

1. Dak M, Šlachtová V, Šebela M, Bazgier V, Berka K, Smiejkowska N, Oorts L, Cappoen D, Brulíková L..  (2022)  Novel heterocyclic hydroxamates as inhibitors of the mycobacterial zinc metalloprotease Zmp1 to probe its mechanism of function.,  244  [PMID:36242986] [10.1016/j.ejmech.2022.114831]

Source

Source(1):

• Scientific Literature