(2S,3R)-N*4*-((R)-2,2-Dimethyl-1-methylcarbamoyl-propyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-N*1*-hydroxy-3-isobutyl-succinamide

ID: ALA74670

PubChem CID: 44313736

Max Phase: Preclinical

Molecular Formula: C24H34N4O6

Molecular Weight: 474.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@H](NC(=O)[C@H](CC(C)C)[C@@H](CN1C(=O)c2ccccc2C1=O)C(=O)NO)C(C)(C)C

Standard InChI:  InChI=1S/C24H34N4O6/c1-13(2)11-16(19(29)26-18(21(31)25-6)24(3,4)5)17(20(30)27-34)12-28-22(32)14-9-7-8-10-15(14)23(28)33/h7-10,13,16-18,34H,11-12H2,1-6H3,(H,25,31)(H,26,29)(H,27,30)/t16-,17-,18+/m1/s1

Standard InChI Key:  KYOFVPKPPTUVKK-KURKYZTESA-N

Molfile:  

     RDKit          2D

 34 35  0  0  1  0  0  0  0  0999 V2000
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   -2.7875   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2583    0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2583   -0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2583   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8875    0.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458    0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6000    0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708    0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167    0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8375   -1.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3375   -0.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9708    1.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3167    1.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6833   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4833    0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667    2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500   -0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292    2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458    2.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792    2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6875   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9750   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  5  1  1
  5  1  1  0
  6 10  1  0
  7  2  1  0
  8  3  1  0
  9  6  1  0
 10  4  1  0
 11  9  1  0
 12  4  1  0
 13 11  1  0
 14  3  2  0
 15  2  2  0
 11 16  1  1
 17  6  2  0
 10 18  1  1
 19 12  2  0
 20 13  2  0
 21 12  1  0
 22 13  1  0
 23  8  1  0
 24  7  1  0
 25 21  1  0
 26 18  1  0
 27 16  1  0
 28 16  1  0
 29 16  1  0
 30 22  1  0
 31 26  1  0
 32 26  1  0
 33 24  2  0
 34 23  2  0
  7  8  2  0
 34 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA74670

   (2R,3S)-N-[(2R)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-3-[(1,3-dioxoisoindol-2-yl)methyl]-N'-hydroxy-2-(2-methylpropyl)butanediamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 474.56

Molecular Weight (Monoisotopic): 474.2478

AlogP: 1.34

#Rotatable Bonds: 9

Polar Surface Area: 144.91

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.85

CX Basic pKa: ┄

CX LogP: 1.35

CX LogD: 1.34

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.24

Np Likeness Score: -0.01

References

1. Broadhurst M, Brown P, Lawton G, Ballantyne N, Borkakoti N, Bottomley K, Cooper M, Eatherton A, Kilford I, Malsher P, Nixon J, Lewis E, Sutton B, Johnson W.  (1997)  Design and synthesis of the cartilage protective agent (CPA, Ro32-3555),  7  (17): [10.1016/S0960-894X(97)00416-2]

Source

Source(1):

• Scientific Literature