(2S,3R)-2-allyl-N4-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-N1-hydroxy-3-isobutylsuccinamide

ID: ALA4785595

PubChem CID: 9855374

Max Phase: Preclinical

Molecular Formula: C18H33N3O4

Molecular Weight: 355.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC[C@H](C(=O)NO)[C@@H](CC(C)C)C(=O)N[C@H](C(=O)NC)C(C)(C)C

Standard InChI:  InChI=1S/C18H33N3O4/c1-8-9-12(16(23)21-25)13(10-11(2)3)15(22)20-14(17(24)19-7)18(4,5)6/h8,11-14,25H,1,9-10H2,2-7H3,(H,19,24)(H,20,22)(H,21,23)/t12-,13+,14+/m0/s1

Standard InChI Key:  DDRBOOUOUSFWET-BFHYXJOUSA-N

Molfile:  

 
     RDKit          2D

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   10.3625   -9.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0770   -8.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6481   -8.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9336   -9.2459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2191   -8.8334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6481   -8.0083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3625  -10.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6481  -10.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6481  -11.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7915   -9.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0758   -8.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7970   -7.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5087   -8.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8027   -6.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7915  -10.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5059   -8.8334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2205   -9.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9350   -8.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9350   -8.0083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2212  -10.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8798  -10.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6535   -9.2415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3651   -8.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4846  -10.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2168  -10.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  2  0
  1  7  1  6
  7  8  1  0
  8  9  2  0
  2 10  1  0
  2 11  1  1
 11 12  1  0
 12 13  1  0
 12 14  1  0
 10 15  2  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 17 20  1  6
 20 21  1  0
 18 22  1  0
 22 23  1  0
 20 24  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4785595

   (2R,3S)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N'-hydroxy-2-(2-methylpropyl)-3-prop-2-enylbutanediamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 355.48

Molecular Weight (Monoisotopic): 355.2471

AlogP: 1.62

#Rotatable Bonds: 9

Polar Surface Area: 107.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.86

CX Basic pKa: 0.13

CX LogP: 1.78

CX LogD: 1.77

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.29

Np Likeness Score: 0.55

References

1. Kumari S,Carmona AV,Tiwari AK,Trippier PC.  (2020)  Amide Bond Bioisosteres: Strategies, Synthesis, and Successes.,  63  (21.0): [PMID:32686940] [10.1021/acs.jmedchem.0c00530]

Source

Source(1):

• Scientific Literature