(R)-N-Hydroxy-1-((4-(4-nitrobenzamido)phenyl)sulfonyl)pyrrolidine-2-carboxamide

ID: ALA4535400

PubChem CID: 155547834

Max Phase: Preclinical

Molecular Formula: C19H19N3O7S

Molecular Weight: 433.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(S(=O)(=O)C2CCC[C@@H]2C(=O)NO)cc1)c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C19H19N3O7S/c23-18(12-4-8-14(9-5-12)22(26)27)20-13-6-10-15(11-7-13)30(28,29)17-3-1-2-16(17)19(24)21-25/h4-11,16-17,25H,1-3H2,(H,20,23)(H,21,24)/t16-,17?/m0/s1

Standard InChI Key:  OIQMFKLUPFKRJF-BHWOMJMDSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   16.0467  -17.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3409  -17.8214    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.0512  -18.2262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0449  -17.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8621  -17.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1165  -16.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4535  -15.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7948  -16.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8974  -16.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5039  -16.6786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0684  -15.3319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8460  -15.0804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0084  -18.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1946  -18.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8613  -19.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3410  -20.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1578  -19.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4873  -19.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0088  -20.8034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1961  -20.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8638  -21.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7156  -20.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0505  -21.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7182  -22.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1988  -23.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0154  -23.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3440  -22.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8668  -23.8769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3481  -24.5373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0542  -23.9636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  9 10  2  0
  9 11  1  0
  6  9  1  6
 11 12  1  0
  5  2  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 21  1  0
 28 29  2  0
 28 30  1  0
 25 28  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4535400

   ---

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: 433.44

Molecular Weight (Monoisotopic): 433.0944

AlogP: 2.29

#Rotatable Bonds: 6

Polar Surface Area: 155.71

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.86

CX Basic pKa: ┄

CX LogP: 2.07

CX LogD: 2.06

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: -1.16

References

1. Lenci E, Innocenti R, Di Francescantonio T, Menchi G, Bianchini F, Contini A, Trabocchi A..  (2019)  Identification of highly potent and selective MMP2 inhibitors addressing the S1' subsite with d-proline-based compounds.,  27  (9): [PMID:30926311] [10.1016/j.bmc.2019.03.043]

Source

Source(1):

• Scientific Literature