(S)-2-Amino-N-(1-(2-(hydroxyamino)-2-oxoethyl)-2,6-dioxopiperidin-3-yl)acetamide hydrochloride

ID: ALA1097214

PubChem CID: 44481934

Max Phase: Preclinical

Molecular Formula: C9H15ClN4O5

Molecular Weight: 258.23

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H14N4O5.ClH/c10-3-6(14)11-5-1-2-8(16)13(9(5)17)4-7(15)12-18;/h5,18H,1-4,10H2,(H,11,14)(H,12,15);1H/t5-;/m0./s1

Standard InChI Key:  VIRLQMUJUCSJCO-JEDNCBNOSA-N

Molfile:  

     RDKit          2D

 19 18  0  0  0  0  0  0  0  0999 V2000
    5.8994    0.9625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975    0.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    0.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131    0.5932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0665    0.1825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    1.4188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3509    0.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3596    0.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689    0.5882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730    1.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3618    1.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3577    1.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567   -0.6446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    1.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7829    0.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    0.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139    0.1695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5030    1.4084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9258    0.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 17 19  1  0
  3  6  2  0
  7 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: 258.23

Molecular Weight (Monoisotopic): 258.0964

AlogP: -2.92

#Rotatable Bonds: 4

Polar Surface Area: 141.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.75

CX Basic pKa: 7.79

CX LogP: -4.03

CX LogD: -4.33

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.24

Np Likeness Score: -0.47

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