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

ID: ALA1097594

PubChem CID: 44481930

Max Phase: Preclinical

Molecular Formula: C9H14ClN3O5

Molecular Weight: 243.22

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H13N3O5.ClH/c10-3-6(13)11-5-1-2-7(14)12(9(5)17)4-8(15)16;/h5H,1-4,10H2,(H,11,13)(H,15,16);1H/t5-;/m0./s1

Standard InChI Key:  FFWDIUIDCQFAFY-JEDNCBNOSA-N

Molfile:  

     RDKit          2D

 18 17  0  0  0  0  0  0  0  0999 V2000
    6.0114    2.4021    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3855    1.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6700    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010    2.0329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545    1.6222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6700    2.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2389    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    2.0278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851    2.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738    3.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2457    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687    0.7950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9021    3.2659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8949    1.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120    2.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3259    1.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    2.8480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  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
  3  6  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: 243.22

Molecular Weight (Monoisotopic): 243.0855

AlogP: -2.34

#Rotatable Bonds: 4

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: 3.30

CX Basic pKa: 7.84

CX LogP: -5.20

CX LogD: -5.32

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.47

Np Likeness Score: -0.44

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