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

ID: ALA1097590

PubChem CID: 44481939

Max Phase: Preclinical

Molecular Formula: C12H21ClN4O5

Molecular Weight: 300.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H20N4O5.ClH/c1-6(2)10(13)11(19)14-7-3-4-9(18)16(12(7)20)5-8(17)15-21;/h6-7,10,21H,3-5,13H2,1-2H3,(H,14,19)(H,15,17);1H/t7-,10-;/m0./s1

Standard InChI Key:  WGAXZGOMIABRIU-YUWZRIFDSA-N

Molfile:  

     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
    5.9952   -4.3232    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5267   -5.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8112   -4.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422   -4.7588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0955   -5.1696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8112   -3.9332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3800   -4.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3306   -5.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0399   -4.7638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0441   -3.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -3.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3868   -3.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3276   -5.9968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7613   -3.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7539   -5.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710   -4.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1851   -5.1826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741   -3.9436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5267   -5.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2381   -6.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152   -6.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969   -4.7728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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  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
 19 21  1  0
  8  9  1  0
 17 22  1  0
  9 10  1  0
 10 11  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: 300.31

Molecular Weight (Monoisotopic): 300.1434

AlogP: -1.89

#Rotatable Bonds: 5

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: 8.10

CX LogP: -2.76

CX LogD: -3.16

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.27

Np Likeness Score: -0.27

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