2-((S)-3-((S)-2-Amino-3-phenylpropanamido)-2,6-dioxopiperidin-1-yl)acetic acid hydrochloride

ID: ALA1098908

PubChem CID: 44481932

Max Phase: Preclinical

Molecular Formula: C16H20ClN3O5

Molecular Weight: 333.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N[C@@H](Cc1ccccc1)C(=O)N[C@H]1CCC(=O)N(CC(=O)O)C1=O

Standard InChI:  InChI=1S/C16H19N3O5.ClH/c17-11(8-10-4-2-1-3-5-10)15(23)18-12-6-7-13(20)19(16(12)24)9-14(21)22;/h1-5,11-12H,6-9,17H2,(H,18,23)(H,21,22);1H/t11-,12-;/m0./s1

Standard InChI Key:  ZMSMVOSJPJUODG-FXMYHANSSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   17.8471  -10.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.7756  -10.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4924  -10.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0588  -10.2785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2093  -10.6900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4924   -9.4514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9261  -10.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6379  -10.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3484  -10.2835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3527   -9.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6402   -9.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9192   -9.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6349  -11.5186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0711   -9.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0637  -10.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7821  -10.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4975  -10.7030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7852   -9.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7756  -11.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0628  -11.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3517  -11.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6395  -11.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391  -12.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3568  -13.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0660  -12.7408    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  6
 15 16  1  0
 16 17  1  0
  3  5  1  0
 16 18  2  0
  2  3  1  0
  2 19  1  0
  3  6  2  0
 19 20  1  0
  7 12  1  0
 20 21  2  0
  8  9  1  0
 21 22  1  0
  9 10  1  0
 22 23  2  0
 10 11  1  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
 25 20  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: 333.34

Molecular Weight (Monoisotopic): 333.1325

AlogP: -0.73

#Rotatable Bonds: 6

Polar Surface Area: 129.80

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.31

CX Basic pKa: 7.71

CX LogP: -2.97

CX LogD: -3.13

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.59

Np Likeness Score: -0.13

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