(2S,4S)-1-acetyl-4-(4-(but-2-ynyloxy)phenylsulfonyl)-N-hydroxypyrrolidine-2-carboxamide

ID: ALA4096921

PubChem CID: 137653882

Max Phase: Preclinical

Molecular Formula: C17H20N2O6S

Molecular Weight: 380.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC#CCOc1ccc(S(=O)(=O)[C@H]2C[C@@H](C(=O)NO)N(C(C)=O)C2)cc1

Standard InChI:  InChI=1S/C17H20N2O6S/c1-3-4-9-25-13-5-7-14(8-6-13)26(23,24)15-10-16(17(21)18-22)19(11-15)12(2)20/h5-8,15-16,22H,9-11H2,1-2H3,(H,18,21)/t15-,16-/m0/s1

Standard InChI Key:  YLKPSGUOQSEIGJ-HOTGVXAUSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   15.1161   -1.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5327   -2.4999    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.9450   -1.7808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8193   -2.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2482   -2.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2434   -3.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9581   -4.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6777   -3.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6781   -2.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9629   -2.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3911   -4.1651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3891   -4.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1025   -5.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0695   -2.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5184   -3.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9309   -3.9053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7369   -3.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6979   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3619   -2.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2134   -3.7739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3930   -3.6882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5960   -4.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7755   -4.7460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0814   -5.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8159   -5.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5293   -6.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  2  1  6
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  4  1  0
 15 18  1  6
 18 19  2  0
 18 20  1  0
 20 21  1  0
 16 22  1  0
 22 23  2  0
 22 24  1  0
 13 25  3  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096921

   ---

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: 380.42

Molecular Weight (Monoisotopic): 380.1042

AlogP: 0.36

#Rotatable Bonds: 5

Polar Surface Area: 113.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.72

CX Basic pKa: ┄

CX LogP: 0.10

CX LogD: 0.08

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.43

Np Likeness Score: -0.64

References

1. Ouvry G, Berton Y, Bhurruth-Alcor Y, Bonnary L, Bouix-Peter C, Bouquet K, Bourotte M, Chambon S, Comino C, Deprez B, Duvert D, Duvert G, Hacini-Rachinel F, Harris CS, Luzy AP, Mathieu A, Millois C, Pascau J, Pinto A, Polge G, Reitz A, Reversé K, Rosignoli C, Taquet N, Hennequin LF..  (2017)  Identification of novel TACE inhibitors compatible with topical application.,  27  (8): [PMID:28274635] [10.1016/j.bmcl.2017.02.035]

Source

Source(1):

• Scientific Literature