(2S,3R)-3-Cyclopentylmethyl-N-hydroxy-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyramide

ID: ALA307192

PubChem CID: 193987

Max Phase: Preclinical

Molecular Formula: C22H36N4O5

Molecular Weight: 436.55

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ro-32-3555 | CHEMBL307192|Ro-32-3555|(2S,3R)-3-Cyclopentylmethyl-N-hydroxy-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyramide|SCHEMBL7297043|BDBM50290090|(2S,3R)-3-(cyclopentylmethyl)-N-hydroxy-4-oxo-4-piperidin-1-yl-2-[(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)methyl]butanamide|NS00121591|A815685|(2S,3R)-3-(cyclopentylmethyl)-4-oxo-4-(1-piperidyl)-2-[(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-yl)methyl]butanehydroxamic acid

Canonical SMILES:  CN1C(=O)N(C[C@@H](C(=O)NO)[C@@H](CC2CCCC2)C(=O)N2CCCCC2)C(=O)C1(C)C

Standard InChI:  InChI=1S/C22H36N4O5/c1-22(2)20(29)26(21(30)24(22)3)14-17(18(27)23-31)16(13-15-9-5-6-10-15)19(28)25-11-7-4-8-12-25/h15-17,31H,4-14H2,1-3H3,(H,23,27)/t16-,17-/m1/s1

Standard InChI Key:  GFUITADOEPNRML-IAGOWNOFSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  1  0  0  0  0  0999 V2000
   -1.9708   -0.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -2.9625   -1.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2583   -2.0625    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
   -0.5458    0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667    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
    0.8875    0.8875    0.0000 N   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
   -3.3375   -0.2292    0.0000 O   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
   -0.5458    1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667   -0.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708    1.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6833    0.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750   -2.6417    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
    1.6000    0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792    1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583    2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    3.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875    2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042    2.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708    3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458    3.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167    1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  9  1  1
  7  6  1  0
  8  7  1  0
  9  1  1  0
 10  8  1  0
 11  6  1  0
 12  2  2  0
 13  3  2  0
  7 14  1  1
 15  8  2  0
 16 11  2  0
 17 11  1  0
 18  4  1  0
 19  5  1  0
 20  5  1  0
 21 17  1  0
 22 10  1  0
 23 10  1  0
 24 14  1  0
 25 24  1  0
 26 24  1  0
 27 22  1  0
 28 23  1  0
 29 26  1  0
 30 25  1  0
 31 28  1  0
  4  5  1  0
 29 30  1  0
 31 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA307192

   (2S,3R)-3-(cyclopentylmethyl)-N-hydroxy-4-oxo-4-piperidin-1-yl-2-[(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)methyl]butanamide

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: 436.55

Molecular Weight (Monoisotopic): 436.2686

AlogP: 1.99

#Rotatable Bonds: 7

Polar Surface Area: 110.26

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.85

CX Basic pKa: 0.22

CX LogP: 1.21

CX LogD: 1.19

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: -0.28

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