Ethyl-2-((S)-2,6-dioxo-3-((S)-pyrrolidine-2-carboxamido)piperidin-1-yl)acetate hydrochloride

ID: ALA1096255

PubChem CID: 44482207

Max Phase: Preclinical

Molecular Formula: C15H25ClN4O5

Molecular Weight: 340.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN1C(=O)CC[C@H](NC(=O)[C@@H](N)C2CCCN2)C1=O.Cl

Standard InChI:  InChI=1S/C15H24N4O5.ClH/c1-2-24-12(21)8-19-11(20)6-5-10(15(19)23)18-14(22)13(16)9-4-3-7-17-9;/h9-10,13,17H,2-8,16H2,1H3,(H,18,22);1H/t9?,10-,13-;/m0./s1

Standard InChI Key:  IZNJMTLOUOBQBE-AHBWOGPESA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   17.2584   -7.8452    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8616   -8.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5771   -8.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1461   -8.2144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2927   -8.6251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5771   -7.3888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0082   -8.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7187   -8.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4279   -8.2194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4322   -7.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7210   -6.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0013   -7.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7157   -9.4522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1493   -6.9813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1419   -8.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8590   -8.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5730   -8.6382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8621   -7.3992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2900   -8.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0040   -8.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8616   -9.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1997   -9.9330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4535  -10.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2751  -10.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5288   -9.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 17 19  1  0
  3  6  2  0
 19 20  1  0
  7 12  1  0
  2 21  1  6
 21 22  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
  8 13  2  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: 340.38

Molecular Weight (Monoisotopic): 340.1747

AlogP: -1.74

#Rotatable Bonds: 6

Polar Surface Area: 130.83

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.32

CX Basic pKa: 10.16

CX LogP: -2.11

CX LogD: -4.76

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.39

Np Likeness Score: -0.19

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