(S)-pyrrolidin-2-ylmethyl 4-((4-(4-cyano-2-methylphenyl)piperidin-1-ylsulfonyl)methyl)-4-(hydroxycarbamoyl)piperidine-1-carboxylate

ID: ALA253021

PubChem CID: 11562986

Max Phase: Preclinical

Molecular Formula: C26H37N5O6S

Molecular Weight: 547.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C#N)ccc1C1CCN(S(=O)(=O)CC2(C(=O)NO)CCN(C(=O)OC[C@@H]3CCCN3)CC2)CC1

Standard InChI:  InChI=1S/C26H37N5O6S/c1-19-15-20(16-27)4-5-23(19)21-6-11-31(12-7-21)38(35,36)18-26(24(32)29-34)8-13-30(14-9-26)25(33)37-17-22-3-2-10-28-22/h4-5,15,21-22,28,34H,2-3,6-14,17-18H2,1H3,(H,29,32)/t22-/m0/s1

Standard InChI Key:  RMPKUSBLGZHQII-QFIPXVFZSA-N

Molfile:  

     RDKit          2D

 38 41  0  0  1  0  0  0  0  0999 V2000
    4.0905   -2.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5133   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3337   -3.4172    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4880   -2.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2232   -3.4884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6205   -2.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1930   -2.0597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4453   -2.7479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8704   -3.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6916   -3.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6665   -2.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -2.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1561   -3.4010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3479   -4.2421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3175   -2.5924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3128   -1.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0617   -1.2941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4603   -0.5718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5801   -4.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3990   -4.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000   -3.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3759   -2.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5509   -2.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6229   -3.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0461   -4.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8703   -4.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2722   -3.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8438   -2.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0211   -2.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5953   -1.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3984   -3.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011   -4.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202   -4.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9746   -5.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2515   -5.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3496   -4.9798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0957   -3.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9206   -3.3064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  1  4  1  0
  8 12  1  0
  9 10  1  0
 10  1  1  0
 13 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  1 11  1  0
 11 12  1  0
 24 25  2  0
  6  7  2  0
 25 26  1  0
  3 13  1  0
 26 27  2  0
  2  3  1  0
 27 28  1  0
  3 14  2  0
 28 29  2  0
 29 24  1  0
 21 24  1  0
  6  8  1  0
 29 30  1  0
  3 15  2  0
  5 31  1  0
  8  9  1  0
 32 31  1  1
 32 33  1  0
  4 16  2  0
  4 17  1  0
  1  2  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 32  1  0
 17 18  1  0
 13 19  1  0
 37 38  3  0
 27 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA253021

   (S)-pyrrolidin-2-ylmethyl 4-((4-(4-cyano-2-methylphenyl)piperidin-1-ylsulfonyl)methyl)-4-(hydroxycarbamoyl)piperidine-1-carboxylate

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: 547.68

Molecular Weight (Monoisotopic): 547.2465

AlogP: 1.85

#Rotatable Bonds: 7

Polar Surface Area: 152.07

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.81

CX Basic pKa: 10.31

CX LogP: -0.32

CX LogD: -1.50

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.35

Np Likeness Score: -0.78

References

1. Burns DM, He C, Li Y, Scherle P, Liu X, Marando CA, Covington MB, Yang G, Pan M, Turner S, Fridman JS, Hollis G, Vaddi K, Yeleswaram S, Newton R, Friedman S, Metcalf B, Yao W..  (2008)  Conversion of an MMP-potent scaffold to an MMP-selective HER-2 sheddase inhibitor via scaffold hybridization and subtle P1' permutations.,  18  (2): [PMID:18068976] [10.1016/j.bmcl.2007.11.086]

Source

Source(1):

• Scientific Literature