(2R,3S)-2-(cyclopentylmethyl)-3-hydroxy-4-(hydroxyamino)-N-[(1S)-1-(3-isopropyl-1,2,4-oxadiazol-5-yl)-2,2-dimethyl-propyl]-4-oxo-butanamide

ID: ALA5285851

Max Phase: Preclinical

Molecular Formula: C20H34N4O5

Molecular Weight: 410.52

Names and Identifiers

Canonical SMILES:  CC(C)c1noc([C@@H](NC(=O)[C@H](CC2CCCC2)[C@H](O)C(=O)NO)C(C)(C)C)n1

Standard InChI:  InChI=1S/C20H34N4O5/c1-11(2)16-22-19(29-24-16)15(20(3,4)5)21-17(26)13(14(25)18(27)23-28)10-12-8-6-7-9-12/h11-15,25,28H,6-10H2,1-5H3,(H,21,26)(H,23,27)/t13-,14+,15-/m1/s1

Standard InChI Key:  DKICMBONSFPSLX-QLFBSQMISA-N

Molfile:  

 
     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -1.1269    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -0.6186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1269   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0162    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0162    1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    1.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    1.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0162    2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4835    0.5416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0352   -0.0710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230   -0.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8166   -0.6134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0354   -1.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8601   -1.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230   -2.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -1.8559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3017   -2.2682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412   -1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    1.4436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415   -0.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4479   -0.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8601   -0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085    0.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  5  4  2  0
  1  6  1  0
  6  5  1  0
  3  7  1  0
  7  8  1  0
  7  9  1  1
  9 10  1  0
  9 11  1  0
  9 12  1  0
 13  8  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  8  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
  5 20  1  0
 20 21  1  0
  6 22  1  1
  1 23  1  1
  2 24  2  0
 23 25  1  0
 26 25  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285851

   ---

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: 410.52

Molecular Weight (Monoisotopic): 410.2529

AlogP: 2.46

#Rotatable Bonds: 8

Polar Surface Area: 137.58

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.61

CX Basic pKa: ┄

CX LogP: 2.72

CX LogD: 2.70

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -0.50

References

1. Baidya SK, Amin SA, Jha T..  (2021)  Outline of gelatinase inhibitors as anti-cancer agents: A patent mini-review for 2010-present.,  213  [PMID:33279289] [10.1016/j.ejmech.2020.113044]

Source

Source(1):

• Scientific Literature