(S)-N-((S)-1-(2-(Hydroxyamino)-2-oxoethyl)-2,6-dioxopiperidin-3-yl)pyrrolidine-2-carboxamide hydrochloride

ID: ALA1095253

PubChem CID: 44482218

Max Phase: Preclinical

Molecular Formula: C13H22ClN5O5

Molecular Weight: 327.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N[C@H](C(=O)N[C@H]1CCC(=O)N(CC(=O)NO)C1=O)C1CCCN1

Standard InChI:  InChI=1S/C13H21N5O5.ClH/c14-11(7-2-1-5-15-7)12(21)16-8-3-4-10(20)18(13(8)22)6-9(19)17-23;/h7-8,11,15,23H,1-6,14H2,(H,16,21)(H,17,19);1H/t7?,8-,11-;/m0./s1

Standard InChI Key:  TVWOSCGPORQZAP-KLUZNBEGSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   18.0645  -16.7202    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.6670  -17.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3826  -17.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9514  -17.0894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0981  -17.5002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3826  -16.2638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8137  -17.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5242  -17.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2336  -17.0945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2378  -16.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5265  -15.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8069  -16.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5214  -18.3273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9549  -15.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9476  -17.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6647  -17.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3787  -17.5133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6678  -16.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6670  -18.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0051  -18.8082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2590  -19.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0805  -19.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342  -18.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0907  -17.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8 13  2  0
  7  5  1  1
 10 14  2  0
  7  8  1  0
  9 15  1  0
  2  4  1  0
 15 16  1  0
 16 17  1  0
  3  5  1  0
 16 18  2  0
  2  3  1  0
  2 19  1  6
 19 20  1  0
  3  6  2  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 10 11  1  0
 17 24  1  0
 11 12  1  0
M  END

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: 327.34

Molecular Weight (Monoisotopic): 327.1543

AlogP: -2.80

#Rotatable Bonds: 5

Polar Surface Area: 153.86

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.73

CX Basic pKa: 10.16

CX LogP: -4.65

CX LogD: -5.75

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.21

Np Likeness Score: 0.00

References

1. Li Q, Fang H, Wang X, Xu W..  (2010)  Novel cyclic-imide peptidomimetics as aminopeptidase N inhibitors. Structure-based design, chemistry and activity evaluation. II.,  45  (4): [PMID:20129718] [10.1016/j.ejmech.2009.12.071]

2. Chen, H H, Noble, F F, Roques, B P BP and Fournié-Zaluski, M C MC.  2001-10-11  Long lasting antinociceptive properties of enkephalin degrading enzyme (NEP and APN) inhibitor prodrugs.  [PMID:11585456]

3. Vassiliou, Stamatia S and 7 more authors.  2014-10-09  Structure-guided, single-point modifications in the phosphinic dipeptide structure yield highly potent and selective inhibitors of neutral aminopeptidases.  [PMID:25192493]

4. Węglarz-Tomczak, Ewelina and 5 more authors.  2016-07-19  A structural insight into the P1S1 binding mode of diaminoethylphosphonic and phosphinic acids, selective inhibitors of alanine aminopeptidases.  [PMID:27100031]

5. Singh, Rohit R, Williams, Jessica J and Vince, Robert R.  2017-10-20  Puromycin based inhibitors of aminopeptidases for the potential treatment of hematologic malignancies.  [PMID:28803047]

6. Pascual, Isel and 10 more authors.  2017-11  Discovery of novel non-competitive inhibitors of mammalian neutral M1 aminopeptidase (APN).  [PMID:28964831]

Source

Source(1):

• Scientific Literature